Pub Date : 2024-11-19DOI: 10.1016/j.molstruc.2024.140772
Saliha Begeç
In this study, described the synthesis on a cyclotriphosphazene containing the spirocyclic 2,2′-dioxybiphenyl group and 2-mercapto-1-methylimidazole (methimazole) or 2-mercaptothiazoline (MTZ) moieties. These spiro(in difunctional ligands, both ends are bound to the same phosphorus) cyclotriphosphazene derivatives (6, 7a) were synthesized in two steps. In first step; mono substituted phosphazene compounds 2,4,4,6,6-pentachloro-2-(2-mercapto-1-methylimidazolyl) cyclo2λ5, 4λ5, 6λ5, triphosphazatriene; N4P3Cl5C3S2H5 (4), and 2,4,4,6,6-pentachloro-2-(2-mercapto-tiyazolinyl) cyclo2λ5, 4λ5, 6λ5, triphosphazatriene; N4P3Cl5C4S2H4 (5)] were prepared from the reaction of hexachlorocyclotriphosphazatriene (trimer, N3P3Cl6, 1), with methimazole (2) or MTZ (3) in tetrahydrofurane (THF) in the presence of metallic sodium under an argon atmosphere.
In second step; monospiro2-mercaptothiazolinyl (7a) and dispiro2-mercapto-1-methylimidazolyl sübstituted (6) phosphazene derivatives were obtained from the reactions of 4 and 5 with 2,2′-dihydroxybiphenyl (8) in acetone in the presence of potassium carbonate (K2CO3). Structural characterizations of all obtained compounds were made using by elemental analysis, FT-IR, 1H, 13C and 31P NMR spectroscopies. Compounds 5–7a are reported for the first time in this study.
{"title":"Design, synthesis and spectral characterization of cyclotriphosphazenes including heterocyclic rings","authors":"Saliha Begeç","doi":"10.1016/j.molstruc.2024.140772","DOIUrl":"10.1016/j.molstruc.2024.140772","url":null,"abstract":"<div><div>In this study, described the synthesis on a cyclotriphosphazene containing the spirocyclic 2,2′-dioxybiphenyl group and 2-mercapto-1-methylimidazole (methimazole) or 2-mercaptothiazoline (MTZ) moieties. These spiro(in difunctional ligands, both ends are bound to the same phosphorus) cyclotriphosphazene derivatives (<strong>6, 7a</strong>) were synthesized in two steps. In first step; mono substituted phosphazene compounds 2,4,4,6,6-pentachloro-2-(2-mercapto-1-methylimidazolyl) cyclo2<em>λ</em><sup>5</sup><em>,</em> 4<em>λ</em><sup>5</sup><em>,</em> 6<em>λ</em><sup>5</sup>, triphosphazatriene; N<sub>4</sub>P<sub>3</sub>Cl<sub>5</sub>C<sub>3</sub>S<sub>2</sub>H<sub>5</sub> (<strong>4</strong>), and 2,4,4,6,6-pentachloro-2-(2-mercapto-tiyazolinyl) cyclo2<em>λ</em><sup>5</sup><em>,</em> 4<em>λ</em><sup>5</sup><em>,</em> 6<em>λ</em><sup>5</sup>, triphosphazatriene; N<sub>4</sub>P<sub>3</sub>Cl<sub>5</sub>C<sub>4</sub>S<sub>2</sub>H<sub>4</sub> (<strong>5</strong>)] were prepared from the reaction of hexachlorocyclotriphosphazatriene (trimer, N<sub>3</sub>P<sub>3</sub>Cl<sub>6</sub>, <strong>1),</strong> with methimazole (<strong>2</strong>) or MTZ (<strong>3</strong>) in tetrahydrofurane (THF) in the presence of metallic sodium under an argon atmosphere.</div><div>In second step; monospiro2-mercaptothiazolinyl (<strong>7a</strong>) and dispiro2-mercapto-1-methylimidazolyl sübstituted (<strong>6)</strong> phosphazene derivatives were obtained from the reactions of <strong>4</strong> and <strong>5</strong> with 2,2′-dihydroxybiphenyl <strong>(8)</strong> in acetone in the presence of potassium carbonate (K<sub>2</sub>CO<sub>3</sub>). Structural characterizations of all obtained compounds were made using by elemental analysis, FT-IR, <sup>1</sup>H, <sup>13</sup>C and <sup>31</sup>P NMR spectroscopies. Compounds <strong>5–7a</strong> are reported for the first time in this study.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140772"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720827","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.molstruc.2024.140800
Oztekin Algul , Burak Mete , Burcin Turkmenoglu , Ruya Saglamtas , M.Abdullah Alagoz , Aylin Dogen , Ilhami Gulcin , Serdar Burmaoglu
This study presents the synthesis and bioactivity screening of a series of substituted bisbenzimidazoles (3a–l), assessed for their inhibitory effects on α-glycosidase, α-amylase, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), as well as their antibacterial activities and metal chelation properties. Compound 3e exhibited the most significant inhibitory activity against intestinal α-glycosidase and α-amylase, showing IC50 values of 15.51 µM and 18.18 µM, respectively. All bisbenzimidazole derivatives demonstrated significant inhibitory activities, with Ki values between 0.99 and 2.98 nM for AChE and 0.40 to 2.18 nM for BChE. Antimicrobial analyses revealed significant antibacterial efficacy in compounds 3c and 3f, with IC50 values ranging from 10.75 to 12.83 μg/μL. This article presents a thorough evaluation of the pharmacological activities associated with bisbenzimidazole compounds 3a–l. To validate experimental results, selected compounds exhibiting notable enzyme inhibitory potential were subjected to molecular docking studies, which demonstrated their binding interactions within the active sites of target enzymes. Molecular dynamics simulation studies were carried out for 100 ns to determine the stability of the compounds in target proteins. During the simulation, it was observed that 3h, 3 g, 3l, and 3e were stable in 4EY7, 4BDS, 3TOP, and 2QV4, respectively. Compounds 3h, 3 g, 3e, and 3l have been identified as promising candidates for the inhibition of AChE, BChE, α-glycosidase, and α-amylase, respectively.
{"title":"Substituted bisbenzimidazole derivatives as multiple targeting agents to treat Alzheimer's disease, diabetes, and microbial infections","authors":"Oztekin Algul , Burak Mete , Burcin Turkmenoglu , Ruya Saglamtas , M.Abdullah Alagoz , Aylin Dogen , Ilhami Gulcin , Serdar Burmaoglu","doi":"10.1016/j.molstruc.2024.140800","DOIUrl":"10.1016/j.molstruc.2024.140800","url":null,"abstract":"<div><div>This study presents the synthesis and bioactivity screening of a series of substituted bisbenzimidazoles (<strong>3a–l</strong>), assessed for their inhibitory effects on α-glycosidase, α-amylase, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), as well as their antibacterial activities and metal chelation properties. Compound <strong>3e</strong> exhibited the most significant inhibitory activity against intestinal α-glycosidase and α-amylase, showing IC<sub>50</sub> values of 15.51 µM and 18.18 µM, respectively. All bisbenzimidazole derivatives demonstrated significant inhibitory activities, with Ki values between 0.99 and 2.98 nM for AChE and 0.40 to 2.18 nM for BChE. Antimicrobial analyses revealed significant antibacterial efficacy in compounds <strong>3c</strong> and <strong>3f</strong>, with IC<sub>50</sub> values ranging from 10.75 to 12.83 μg/μL. This article presents a thorough evaluation of the pharmacological activities associated with bisbenzimidazole compounds <strong>3a–l</strong>. To validate experimental results, selected compounds exhibiting notable enzyme inhibitory potential were subjected to molecular docking studies, which demonstrated their binding interactions within the active sites of target enzymes. Molecular dynamics simulation studies were carried out for 100 ns to determine the stability of the compounds in target proteins. During the simulation, it was observed that <strong>3</strong> <strong>h, 3 g, 3l</strong>, and <strong>3e</strong> were stable in 4EY7, 4BDS, 3TOP, and 2QV4, respectively. Compounds <strong>3</strong> <strong>h, 3 g, 3e</strong>, and <strong>3l</strong> have been identified as promising candidates for the inhibition of AChE, BChE, α-glycosidase, and α-amylase, respectively.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140800"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720344","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.molstruc.2024.140759
S. Sowmiya, M. Hemalatha, M. Joseph
This study involves the synthesis of encapsulated herbicides to improve herbicide efficacy and activity assays, to reduce their environmental impact. The synthesized pyrazosulfuron ethyl and pretilachlor entrapped with zeolite, polycaprolactone and water-soluble polymer were characterized using a Particle size analyzer and Scanning Electron Microscope to interpret the size and morphology. Among the encapsulated herbicides, pyrazosulfuron ethyl entrapped zeolite shows a 12,950 nm in diameter and a typical morphology of a uniform, regular cubical-like structure, with a higher herbicide encapsulation efficiency of 86 % and activity assay results in better rice growth. It was on par with the pyrazosulfuron ethyl encapsulated with polycaprolactone, which has a 3679 nm diameter and an irregular shape. The Aqueous release studies show the controlled release of encapsulated herbicide, among them pyrazosulfuron ethyl entrapped with zeolite shows better performance with low leaching potential in the soil column. Thus, Controlled release herbicide formulation with zeolite, polycaprolactone and water soluble polymer was used to release herbicide in target species and reduces the leaching potential to the soil which acts as a tool for agroecotoxicity.
{"title":"Controlled release formulations of encapsulated herbicide enhances herbicide activity as a tool for agro-ecotoxicity","authors":"S. Sowmiya, M. Hemalatha, M. Joseph","doi":"10.1016/j.molstruc.2024.140759","DOIUrl":"10.1016/j.molstruc.2024.140759","url":null,"abstract":"<div><div>This study involves the synthesis of encapsulated herbicides to improve herbicide efficacy and activity assays, to reduce their environmental impact. The synthesized pyrazosulfuron ethyl and pretilachlor entrapped with zeolite, polycaprolactone and water-soluble polymer were characterized using a Particle size analyzer and Scanning Electron Microscope to interpret the size and morphology. Among the encapsulated herbicides, pyrazosulfuron ethyl entrapped zeolite shows a 12,950 nm in diameter and a typical morphology of a uniform, regular cubical-like structure, with a higher herbicide encapsulation efficiency of 86 % and activity assay results in better rice growth. It was on par with the pyrazosulfuron ethyl encapsulated with polycaprolactone, which has a 3679 nm diameter and an irregular shape. The Aqueous release studies show the controlled release of encapsulated herbicide, among them pyrazosulfuron ethyl entrapped with zeolite shows better performance with low leaching potential in the soil column. Thus, Controlled release herbicide formulation with zeolite, polycaprolactone and water soluble polymer was used to release herbicide in target species and reduces the leaching potential to the soil which acts as a tool for agroecotoxicity.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1324 ","pages":"Article 140759"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720937","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this study a new series of isatin-1,3,5-triazine-benzylamine hybrids (6a-k) were designed, synthesized and evaluated for in vitro anti-Alzheimer's disease(AD) properties. These molecules were tested for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes inhibition and biometal chelation effect. Results revealed these molecules to be very potent AChE inhibitors with IC50 values in the range of 0.86–36.30nM. BChE inhibition potencies were also good and IC50 values for active compounds were from 0.66 to 3.88 μM. Molecule 6c had the highest activity against both enzymes and further studies showed that it kinetically inhibited AChE and BChE with non-competitive and competitive mechanisms, respectively. This compound could effectively inhibit amyloid beta self/Cu2+ induced aggregation in 10μM. These compounds could significantly chelate to Cu2+ as an important biometal involved in AD andin silico simulations demonstrated that these molecules had key interactions with both ChE enzymes. It was concluded that these compounds had high potency to be used in future evaluations as anti-AD lead compounds.
{"title":"Evaluation of isatin-1,3,5-triazine-benzylamine hybrids as multi-target directed ligands against Alzheimer's disease","authors":"Yasaman Tamaddon-Abibigloo , Siavoush Dastmalchi , Nima Razzaghi-Asl , Tuba Tüylü üKüçükkılınç , Javid Shahbazi Mojarrad","doi":"10.1016/j.molstruc.2024.140717","DOIUrl":"10.1016/j.molstruc.2024.140717","url":null,"abstract":"<div><div>In this study a new series of isatin-1,3,5-triazine-benzylamine hybrids (<strong>6a-k</strong>) were designed, synthesized and evaluated for in vitro anti-Alzheimer's disease(AD) properties. These molecules were tested for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes inhibition and biometal chelation effect. Results revealed these molecules to be very potent AChE inhibitors with IC<sub>50</sub> values in the range of <strong>0.86–36.30</strong> <strong>nM</strong>. BChE inhibition potencies were also good and IC<sub>50</sub> values for active compounds were from <strong>0.66 to 3.88 μM</strong>. Molecule <strong>6c</strong> had the highest activity against both enzymes and further studies showed that it kinetically inhibited AChE and BChE with non-competitive and competitive mechanisms, respectively. This compound could effectively inhibit amyloid beta self/Cu<sup>2+</sup> induced aggregation in 10μM. These compounds could significantly chelate to Cu<sup>2+</sup> as an important biometal involved in AD andin silico simulations demonstrated that these molecules had key interactions with both ChE enzymes. It was concluded that these compounds had high potency to be used in future evaluations as anti-AD lead compounds.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1324 ","pages":"Article 140717"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142748108","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.molstruc.2024.140805
Bo Zhang , Shuchun Qin , Jiamin Wang , Xiaoteng Ma , Ruiqi Han , Minghao Ruan , Weili Zhao , Jian Zhang
Alcoholic liver disease (ALD) is a liver disease which caused by excessive drinking. It is deeply associated with liver inflammation and brings about up-regulation of reactive oxygen species including peroxynitrite (ONOO−). In this work, we developed a near-infrared (NIR) ONOO−-activated fluorescent probe BDP-NIR-ONOO for real-time visualizing of alcoholic liver disease. BDP-NIR-ONOO showed excellent response to ONOO− in vitro tests, with NIR emitting wavelength (700 nm), good specificity, fast response speed (80 s), and high signal to noise ratio (252-fold). BDP-NIR-ONOO could detect the up-regulation of ONOO− content in the mouse peritonitis model and realize the diagnosis of inflammation in mice. Meanwhile, BDP-NIR-ONOO could image endogenous ONOO− in mice tumor. Most importantly, one mimic risky drinking ALD mice models and one mimic excessive drinking ALD mice models were established, BDP-NIR-ONOO could visualize the alcoholic liver injury of mice by imaging the ONOO− fluctuation in ALD mice, which providing a powerful tool for the diagnosis of ALD. Finally, BDP-NIR-ONOO was further utilized to dynamically trace the therapeutic effect of N-acetylcysteine on ALD.
{"title":"A near-infrared ONOO−-activated fluorescent probe for real-time visualizing of alcoholic liver disease","authors":"Bo Zhang , Shuchun Qin , Jiamin Wang , Xiaoteng Ma , Ruiqi Han , Minghao Ruan , Weili Zhao , Jian Zhang","doi":"10.1016/j.molstruc.2024.140805","DOIUrl":"10.1016/j.molstruc.2024.140805","url":null,"abstract":"<div><div>Alcoholic liver disease (ALD) is a liver disease which caused by excessive drinking. It is deeply associated with liver inflammation and brings about up-regulation of reactive oxygen species including peroxynitrite (ONOO<sup>−</sup>). In this work, we developed a near-infrared (NIR) ONOO<sup>−</sup>-activated fluorescent probe BDP-NIR-ONOO for real-time visualizing of alcoholic liver disease. BDP-NIR-ONOO showed excellent response to ONOO<sup>−</sup> in <em>vitro</em> tests, with NIR emitting wavelength (700 nm), good specificity, fast response speed (80 s), and high signal to noise ratio (252-fold). BDP-NIR-ONOO could detect the up-regulation of ONOO<sup>−</sup> content in the mouse peritonitis model and realize the diagnosis of inflammation in mice. Meanwhile, BDP-NIR-ONOO could image endogenous ONOO<sup>−</sup> in mice tumor. Most importantly, one mimic risky drinking ALD mice models and one mimic excessive drinking ALD mice models were established, BDP-NIR-ONOO could visualize the alcoholic liver injury of mice by imaging the ONOO<sup>−</sup> fluctuation in ALD mice, which providing a powerful tool for the diagnosis of ALD. Finally, BDP-NIR-ONOO was further utilized to dynamically trace the therapeutic effect of N-acetylcysteine on ALD.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140805"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720409","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lanthanide (Er, Yb) doped lead-free halide perovskites (Cs3Bi2Cl9) have been developed, which crystallise into an orthorhombic structure with a Pnma space group. The material shows both direct (3.06 eV) and indirect (2.96 eV) bandgap. Theoretical calculation using DFT also predicts a direct bandgap at the Г position (3.12 eV) and a low-lying indirect bandgap from the Г point to a point between Г and Z point (3.08 eV), which are in close match with the experimentally observed values. The optimised Er/Yb: Cs3Bi2Cl9 demonstrated an intense upconversion (UC) emission (λexc= 980 nm), which shows an unusual negative thermal quenching effect, where the intensities of both the red and the green emissions increased with temperature. This effect is attributed to the efficient energy transfer from the sensitiser Yb3+ ions to the activator Er3+ ions due to the negative thermal expansion (NTE) of the lattice and the removal of moisture from the sample after heating. This unique optical feature has been used for optical temperature sensing applications using the fluorescence intensity ratio method. The observed absolute and relative temperature sensitivities of Er/Yb: Cs3Bi2Cl9 are 1.07 % K−1 and 0.98 % K−1, respectively, which is reasonably good. This work provides new insights for designing optical temperature sensors using lead-free halide perovskites at high temperatures and exploration of more halides showing NTE.
{"title":"Negative thermal quenching in Er/Yb codoped lead-free halide perovskite Cs3Bi2Cl9","authors":"Shanas Fatima , Santosh Kachhap , Zubair Nabi Ganaie , Priya Johari , Neeraj Kumar Mishra , Kaushal Kumar , Sunil Kumar Singh","doi":"10.1016/j.molstruc.2024.140762","DOIUrl":"10.1016/j.molstruc.2024.140762","url":null,"abstract":"<div><div>Lanthanide (Er, Yb) doped lead-free halide perovskites (Cs<sub>3</sub>Bi<sub>2</sub>Cl<sub>9</sub>) have been developed, which crystallise into an orthorhombic structure with a <em>Pnma</em> space group. The material shows both direct (3.06 eV) and indirect (2.96 eV) bandgap. Theoretical calculation using DFT also predicts a direct bandgap at the Г position (3.12 eV) and a low-lying indirect bandgap from the Г point to a point between Г and Z point (3.08 eV), which are in close match with the experimentally observed values. The optimised Er/Yb: Cs<sub>3</sub>Bi<sub>2</sub>Cl<sub>9</sub> demonstrated an intense upconversion (UC) emission (λ<sub>exc</sub>= 980 nm), which shows an unusual negative thermal quenching effect, where the intensities of both the red and the green emissions increased with temperature. This effect is attributed to the efficient energy transfer from the sensitiser Yb<sup>3+</sup> ions to the activator Er<sup>3+</sup> ions due to the negative thermal expansion (NTE) of the lattice and the removal of moisture from the sample after heating. This unique optical feature has been used for optical temperature sensing applications using the fluorescence intensity ratio method. The observed absolute and relative temperature sensitivities of Er/Yb: Cs<sub>3</sub>Bi<sub>2</sub>Cl<sub>9</sub> are 1.07 % K<sup>−1</sup> and 0.98 % K<sup>−1</sup>, respectively, which is reasonably good. This work provides new insights for designing optical temperature sensors using lead-free halide perovskites at high temperatures and exploration of more halides showing NTE.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1324 ","pages":"Article 140762"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142748111","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Detailed structural and non-covalent interactions in the novel thiazole derivative benzyl 4-(4-chlorophenyl)thiazole-2-carboxylate (6a) has been synthesized and characterized by spectroscopic characterizations like 1H NMR and 13C NMR, and single crystal structure analysis. Its results were compared with the previously reported similar thiazole derivative (4-methoxyphenyl)methyl 4-(4-chlorophenyl)-1,3-thiazole-2-carboxylate (6b). The crystal structure analysis revealed that C–H……O, hydrogen bonds involved in stabilizing the crystal packing. The differences and similarities in the relative contribution of non-covalent interactions in 6a and 6b compounds are compared using the Hirshfeld surface analysis and 2D fingerprint plots. The binding energies of specific molecular pairs and dimers have been investigated using pair-wise interaction energy calculation. The hierarchy and supramolecular architecture of intermolecular interactions are visualized through energy frameworks. Geometric parameters of the optimized structure were determined using DFT calculations on the B3LYP/6–311++G(d,p) basis set and compared to X-ray diffraction data. Molecular docking with the 6FS1 protein revealed a binding score of 6a is -6.7 kcal/mol, and 6b is -6.5kcal/mol indicating potential anticancer action for the thiazole compound. Furthermore, the binding interaction was investigated using dynamics modelling simulations. Further in vitro and in vivo analysis will help in the exploration of the inhibition activity of the ligand with the protein.
{"title":"Structural elucidation, Hirshfeld surface, DFT, molecular docking and molecular dynamics studies of a novel thiazole derivative as anti-cancer drug","authors":"Neetha S․ , Santhosh C․ , Lohith T․N․ , Sharath K․ , Sridhar M․A․ , Sadashiva M․P․","doi":"10.1016/j.molstruc.2024.140793","DOIUrl":"10.1016/j.molstruc.2024.140793","url":null,"abstract":"<div><div>Detailed structural and non-covalent interactions in the novel thiazole derivative <em>benzyl 4-(4-chlorophenyl)thiazole-2-carboxylate (</em><strong><em>6a</em></strong><em>)</em> has been synthesized and characterized by spectroscopic characterizations like <sup>1</sup>H NMR and <sup>13</sup>C NMR, and single crystal structure analysis. Its results were compared with the previously reported similar thiazole derivative <em>(4-methoxyphenyl)methyl 4-(4-chlorophenyl)-1,3-thiazole-2-carboxylate (</em><strong><em>6b</em></strong><em>)</em>. The crystal structure analysis revealed that C–H……O, hydrogen bonds involved in stabilizing the crystal packing. The differences and similarities in the relative contribution of non-covalent interactions in <strong>6a</strong> and <strong>6b</strong> compounds are compared using the Hirshfeld surface analysis and 2D fingerprint plots. The binding energies of specific molecular pairs and dimers have been investigated using pair-wise interaction energy calculation. The hierarchy and supramolecular architecture of intermolecular interactions are visualized through energy frameworks. Geometric parameters of the optimized structure were determined using DFT calculations on the B3LYP/6–311++<em>G</em>(d,p) basis set and compared to X-ray diffraction data. Molecular docking with the 6FS1 protein revealed a binding score of <strong>6a</strong> is -6.7 kcal/mol, and <strong>6b</strong> is -6.5kcal/mol indicating potential anticancer action for the thiazole compound. Furthermore, the binding interaction was investigated using dynamics modelling simulations. Further in vitro and in vivo analysis will help in the exploration of the inhibition activity of the ligand with the protein.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1324 ","pages":"Article 140793"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142748202","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.molstruc.2024.140804
Tuba Ashraf , Afifa Maryam , Riaz Hussain , Sadia Rani , Bakhat Ali , Muhammad Imran , Shafaq Ashraf , Usman Rahim , Sajjad H. Sumrra
In current research work, new hydrazone ligands (HL1-HL2) and their copper(II), nickel(II), and cobalt(II) complexes were prepared and categorized by various spectroscopic (FT-IR, proton NMR, carbon NMR and UV–vis) and physical techniques. To compare the theoretical and experimental findings, density functional theory calculations were executed at the B3LYP/6-31G (d,p) level for the following parameters: molecular electrostatic potential (MEP), global reactivity parameters, frontier molecular orbital (FMO) analysis, natural bond orbital (NBO) analysis and first hyperpolarizability analysis. The FMO analysis of the synthesized compounds has shown the potential for charge transfer in the newly synthesized compounds. The GRPs observed that all the synthesized compounds exhibited increased hardness and decreased softness, suggesting reduced reactivity and enhanced stability. The NLO properties of the complexes (1–6) are shown more polarized than their corresponding hydrazone Schiff-base ligands HL1-HL2. Various parameters were studied in ADME/T analysis. Our theoretical study shows that the synthesized compounds are potential applicants for NLO applications with properties similar to those of common NLO materials used in different technological fields.
{"title":"Synthesis, characterization, natural bond orbital and nonlinear optical exploration of Cu(II), Co(II) and Ni(II) complexes derived from hydrazone Schiff base ligands","authors":"Tuba Ashraf , Afifa Maryam , Riaz Hussain , Sadia Rani , Bakhat Ali , Muhammad Imran , Shafaq Ashraf , Usman Rahim , Sajjad H. Sumrra","doi":"10.1016/j.molstruc.2024.140804","DOIUrl":"10.1016/j.molstruc.2024.140804","url":null,"abstract":"<div><div>In current research work, new hydrazone ligands (<strong>HL<sub>1</sub>-HL<sub>2</sub>)</strong> and their copper(II), nickel(II), and cobalt(II) complexes were prepared and categorized by various spectroscopic (FT-IR, proton NMR, carbon NMR and UV–vis) and physical techniques. To compare the theoretical and experimental findings, density functional theory calculations were executed at the B3LYP/6-31G (d,p) level for the following parameters: molecular electrostatic potential (MEP), global reactivity parameters, frontier molecular orbital (FMO) analysis, natural bond orbital (NBO) analysis and first hyperpolarizability analysis. The FMO analysis of the synthesized compounds has shown the potential for charge transfer in the newly synthesized compounds. The GRPs observed that all the synthesized compounds exhibited increased hardness and decreased softness, suggesting reduced reactivity and enhanced stability. The NLO properties of the complexes (<strong>1–6</strong>) are shown more polarized than their corresponding hydrazone Schiff-base ligands <strong>HL<sub>1</sub></strong>-<strong>HL<sub>2</sub></strong>. Various parameters were studied in ADME/T analysis. Our theoretical study shows that the synthesized compounds are potential applicants for NLO applications with properties similar to those of common NLO materials used in different technological fields.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140804"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720291","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.molstruc.2024.140749
Anas AlAli , Khalil Shalalin , Ahmed Abu-Rayyan , Hussien Khamees , Mohammad K. Al-Sadoon , Abdelkader Zarrouk , Mousa Al-Noaimi , Ismail Warad , Shaukath Ara Khanum
Treating of Cu(NO3)2·3H2O with di(pyridin-2-yl)methanone (Py2CO) ligand resulted the [CuII(Py2CO)2](NO3)2 intermediate complex was first introduced the diol [CuII(Py2C(OH)2](NO3)2·H2O dicationic complex in a significant yield. In situ py2CO hydrolysis while coordinating the Cu(II) center, forming di(pyridin-2-yl)methanediol Py2C(OH)2, via incidental water solvent. Accordingly, the [CuII(Py2C(OH)2](NO3)2·H2O formula was confirmed using a range of analytical tools, including XRD-crystallography. The XRD analysis revealed that the [CuII(Py2C(OH)2](NO3)2·H2O had a highly distorted octahedral Cu(II) core that was surrounded by four N-pyridines occupying the square planar CuN4 arrangement. The 2‑hydroxyl group of Py2C(OH)2 occupied the trans-Z-axial position of the Cu(II) center, representing a significantly elongated Jahn Teller distortion octahedral geometry. The presence of the 4‑hydroxyl and 2-nitro functional groups, in addition to one water molecule, played an interesting role in building the interconnected and compact lattice since several 2D-S12/S9/S7 synthons constructed via a numerous number of H-bonds have been recorded. Moreover, the presence of such synthons reflected positively in the stability of the complex, as it demonstrated high thermal stability. Lipoxygenase (LOX) and cyclooxygenase (COX-1 and 2) inhibition were used to evaluate the desired complex as anti-inflammatory inhibitory, moreover, in silico docking was used to clarify theoretically the COX/LOX anti-inflammatory result.
{"title":"SC-XRD investigation of Oh dicationic [CuII(Py2C(OH)2)2]2+: A significant Jahn Teller distortion, 2D-S12/S9/S7 synthons, XRD/HSA-interactions, thermal, spectroscopic, anti-inflammatory and docking potential","authors":"Anas AlAli , Khalil Shalalin , Ahmed Abu-Rayyan , Hussien Khamees , Mohammad K. Al-Sadoon , Abdelkader Zarrouk , Mousa Al-Noaimi , Ismail Warad , Shaukath Ara Khanum","doi":"10.1016/j.molstruc.2024.140749","DOIUrl":"10.1016/j.molstruc.2024.140749","url":null,"abstract":"<div><div>Treating of Cu(NO<sub>3</sub>)<sub>2</sub>·3H<sub>2</sub>O with di(pyridin-2-yl)methanone (Py<sub>2</sub>C<img>O) ligand resulted the [Cu<sup>II</sup>(Py<sub>2</sub>CO)<sub>2</sub>](NO<sub>3</sub>)<sub>2</sub> intermediate complex was first introduced the diol [Cu<sup>II</sup>(Py<sub>2</sub>C(OH)<sub>2</sub>](NO<sub>3</sub>)<sub>2</sub>·H<sub>2</sub>O dicationic complex in a significant yield. In situ py<sub>2</sub>C<img>O hydrolysis while coordinating the Cu(II) center, forming di(pyridin-2-yl)methanediol Py<sub>2</sub>C(OH)<sub>2</sub>, via incidental water solvent. Accordingly, the [Cu<sup>II</sup>(Py<sub>2</sub>C(OH)<sub>2</sub>](NO<sub>3</sub>)<sub>2</sub>·H<sub>2</sub>O formula was confirmed using a range of analytical tools, including XRD-crystallography. The XRD analysis revealed that the [Cu<sup>II</sup>(Py<sub>2</sub>C(OH)<sub>2</sub>](NO<sub>3</sub>)<sub>2</sub>·H<sub>2</sub>O had a highly distorted octahedral Cu(II) core that was surrounded by four N-pyridines occupying the square planar CuN<sub>4</sub> arrangement. The 2‑hydroxyl group of Py<sub>2</sub>C(OH)<sub>2</sub> occupied the <em>trans</em>-Z-axial position of the Cu(II) center, representing a significantly elongated Jahn Teller distortion octahedral geometry. The presence of the 4‑hydroxyl and 2-nitro functional groups, in addition to one water molecule, played an interesting role in building the interconnected and compact lattice since several 2D-S12/S9/S7 synthons constructed <em>via</em> a numerous number of H-bonds have been recorded. Moreover, the presence of such synthons reflected positively in the stability of the complex, as it demonstrated high thermal stability. Lipoxygenase (LOX) and cyclooxygenase (COX-1 and 2) inhibition were used to evaluate the desired complex as anti-inflammatory inhibitory, moreover, in silico docking was used to clarify theoretically the COX/LOX anti-inflammatory result.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140749"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720304","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-19DOI: 10.1016/j.molstruc.2024.140784
Halla Abdelbaki , Amar Djemoui , Mohammed Ridha Ouahrani , Mohammed Messaoudi , Ilham Ben Amor , Huda Alsaeedi , David CORNU , Mikhael Bechelany , Ahmed Barhoum
This study focuses on the design, synthesis and evaluation of antibacterial and antioxidant properties of 1,4-disubstituted 1,2,3-triazole-linked thiosemicarbazone derivatives.The synthesis involved a multistep process, beginning with the preparation of alkyne derivatives from three benzaldehyde derivatives (4-hydroxybenzaldehyde, vanillin, and salicylaldehyde) and using flower-like Cu2O microbeads as a catalyst. The synthesized compounds were evaluated for antibacterial activity against four bacterial strains: Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa), Bacillus subtilis (B. subtilis), and Staphylococcus aureus (S. aureus), at concentrations ranging from 10 to 80 mg/mL, using ciprofloxacin (CIP) as a reference. Among the derivatives, Compound 3c, (Z)-2-(4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxybenzylidene)hydrazine-1-carbothioamide,exhibited the most potent antibacterial activity against E. coli, with a zone of inhibition of 22±0.1 mm at 80 mg/mL. Compound 3a, (Z)-2-(4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)benzylidene)hydrazine-1-carbothioamide, showed the highest efficacy against B. subtilis, with an inhibition zone of 21±0.4 mm. Antioxidant assays, including DPPH and ABTS, revealed Compound 3c to have the lowest IC50 values (2 ± 0.4 μg/mL and 160±0.1 μg/mL, respectively), indicating strong antioxidant activity. These results demonstrate that Cu2O-catalyzed synthesis and chemical substitution in 1,4-disubstituted 1,2,3-triazole-linked thiosemicarbazone derivatives significantly enhance their antibacterial and antioxidant activities, making them promising candidates for therapeutic development.
{"title":"Synthesis of bioactive 1,4-disubstituted 1,2,3-triazole-linked Thiosemicarbazone derivatives using Cu2O microbeads catalysis for enhanced antibacterial and antioxidant activities","authors":"Halla Abdelbaki , Amar Djemoui , Mohammed Ridha Ouahrani , Mohammed Messaoudi , Ilham Ben Amor , Huda Alsaeedi , David CORNU , Mikhael Bechelany , Ahmed Barhoum","doi":"10.1016/j.molstruc.2024.140784","DOIUrl":"10.1016/j.molstruc.2024.140784","url":null,"abstract":"<div><div>This study focuses on the design, synthesis and evaluation of antibacterial and antioxidant properties of 1,4-disubstituted 1,2,3-triazole-linked thiosemicarbazone derivatives.The synthesis involved a multistep process, beginning with the preparation of alkyne derivatives from three benzaldehyde derivatives (4-hydroxybenzaldehyde, vanillin, and salicylaldehyde) and using flower-like Cu<sub>2</sub>O microbeads as a catalyst. The synthesized compounds were evaluated for antibacterial activity against four bacterial strains: <em>Escherichia coli</em> (<em>E. coli</em>), <em>Pseudomonas aeruginosa</em> (<em>P. aeruginosa</em>), <em>Bacillus subtilis</em> (<em>B. subtilis</em>), and <em>Staphylococcus aureus</em> (<em>S. aureus</em>), at concentrations ranging from 10 to 80 mg/mL, using ciprofloxacin (CIP) as a reference. Among the derivatives, Compound <strong>3c</strong>, (Z)-2-(4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxybenzylidene)hydrazine-1-carbothioamide,exhibited the most potent antibacterial activity against <em>E. coli</em>, with a zone of inhibition of 22±0.1 mm at 80 mg/mL. Compound <strong>3a</strong>, (Z)-2-(4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)benzylidene)hydrazine-1-carbothioamide, showed the highest efficacy against <em>B. subtilis</em>, with an inhibition zone of 21±0.4 mm. Antioxidant assays, including DPPH and ABTS, revealed Compound <strong>3c</strong> to have the lowest IC50 values (2 ± 0.4 μg/mL and 160±0.1 μg/mL, respectively), indicating strong antioxidant activity. These results demonstrate that Cu<sub>2</sub>O-catalyzed synthesis and chemical substitution in 1,4-disubstituted 1,2,3-triazole-linked thiosemicarbazone derivatives significantly enhance their antibacterial and antioxidant activities, making them promising candidates for therapeutic development.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1324 ","pages":"Article 140784"},"PeriodicalIF":4.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720933","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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