The ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (S1) was chosen for this investigation due to its important biological and pharmacological activities. Detailed infrared and Raman spectra have been investigated in both theoretical and experimental. Frontier molecular orbitals and the electronic properties of the S1 are explained. The titled compound S1 calculated HOMO-LUMO energy gap is 4.60 eV In molecular electrostatic potential (MEP) map the NO2 group exhibits a blue color, indicating the presence of nucleophilic sites. The density of state (DOS), non-covalent interaction (NCI), electron localized function (ELF), localized orbital locator (LOL), Mulliken atomic charges, and reactive sites have been investigated. The anti-bacterial, antifungal, antitoxin, antiviral, and antimycobacterial studies have been investigated. The molecular docking investigations of the compound were also conducted. Using the Auto-dock program, the compound S1 molecular docking study has been conducted. The molecular docking study's lowest binding energy is -7.91, -5.62, -6.92, and -5.85 kcal/mol for 4XGK, 4ATO, 3U9 G, and 2DP4 respectively.
{"title":"Computational investigation and antimicrobial activity prediction of potential antiviral drug","authors":"Vaithilingam Sasikala , Vadivelu Balachandran , Natarajan Elangovan , Natarajan Arumugam , Abdulrahman I. Almansour","doi":"10.1016/j.molstruc.2024.140711","DOIUrl":"10.1016/j.molstruc.2024.140711","url":null,"abstract":"<div><div>The ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (S1) was chosen for this investigation due to its important biological and pharmacological activities. Detailed infrared and Raman spectra have been investigated in both theoretical and experimental. Frontier molecular orbitals and the electronic properties of the S1 are explained. The titled compound S1 calculated HOMO-LUMO energy gap is 4.60 eV In molecular electrostatic potential (MEP) map the NO<sub>2</sub> group exhibits a blue color, indicating the presence of nucleophilic sites. The density of state (DOS), non-covalent interaction (NCI), electron localized function (ELF), localized orbital locator (LOL), Mulliken atomic charges, and reactive sites have been investigated. The anti-bacterial, antifungal, antitoxin, antiviral, and antimycobacterial studies have been investigated. The molecular docking investigations of the compound were also conducted. Using the Auto-dock program, the compound S1 molecular docking study has been conducted. The molecular docking study's lowest binding energy is -7.91, -5.62, -6.92, and -5.85 kcal/mol for 4XGK, 4ATO, 3U9 G, and 2DP4 respectively.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140711"},"PeriodicalIF":4.0,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142651625","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 : 2024-11-09DOI: 10.1016/j.molstruc.2024.140608
Sathish Kumar J, Fateh V. Singh
A simple and convenient metal-free approach for synthesizing p-terphenyls 7a–f is presented through a carbanion-induced ring transformation reaction involving 6-biphenyl-2H-pyran-2-ones 5 with pyruvic acetyl dimethyl aldehyde 6. Further the prepared dimethoxy p-terphenyls 7b-c,f were converted into diethoxy p-terphenyls 8a-c. The base-mediated ring transformation reactions proceeded smoothly under mild reaction conditions, resulting the formation of ring transformation products 7a-f and 8a-c in good to excellent yields. This synthetic approach allows the incorporation of both electron-withdrawing and electron-donating functionalities into p-terphenyl framework. Moreover, the structure of compound 7a was confirmed by its single crystal X-ray analysis. Additionally, the photophysical properties of synthesized p-terphenyls were analysed using UV-visible and fluorescence spectroscopy. Interestingly, the synthesized p-terphenyls 7a–f showed blue fluorescence in chloroform. The solvatochromic behaviour and concentration studies of compound 7d was also perforemd. Additionally, the thermal stability characteristics of compound 7d was also studied using TG and DTA analysis.
{"title":"Metal-free synthesis, single crystal analysis and photophysical behavior of p-terphenyls","authors":"Sathish Kumar J, Fateh V. Singh","doi":"10.1016/j.molstruc.2024.140608","DOIUrl":"10.1016/j.molstruc.2024.140608","url":null,"abstract":"<div><div>A simple and convenient metal-free approach for synthesizing <em>p</em>-terphenyls <strong>7a–f</strong> is presented through a carbanion-induced ring transformation reaction involving 6-biphenyl-2<em>H</em>-pyran-2-ones <strong>5</strong> with pyruvic acetyl dimethyl aldehyde <strong>6</strong>. Further the prepared dimethoxy <em>p</em>-terphenyls <strong>7b-c,f</strong> were converted into diethoxy <em>p</em>-terphenyls <strong>8a-c</strong>. The base-mediated ring transformation reactions proceeded smoothly under mild reaction conditions, resulting the formation of ring transformation products <strong>7a-f</strong> and <strong>8a-c</strong> in good to excellent yields. This synthetic approach allows the incorporation of both electron-withdrawing and electron-donating functionalities into <em>p</em>-terphenyl framework. Moreover, the structure of compound <strong>7a</strong> was confirmed by its single crystal X-ray analysis. Additionally, the photophysical properties of synthesized <em>p</em>-terphenyls were analysed using UV-visible and fluorescence spectroscopy. Interestingly, the synthesized <em>p</em>-terphenyls <strong>7a–f</strong> showed blue fluorescence in chloroform. The solvatochromic behaviour and concentration studies of compound <strong>7d</strong> was also perforemd. Additionally, the thermal stability characteristics of compound <strong>7d</strong> was also studied using TG and DTA analysis.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140608"},"PeriodicalIF":4.0,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142659571","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 : 2024-11-09DOI: 10.1016/j.molstruc.2024.140697
Yuxing Tan , Zhijian Zhang , Jiazi Liu , Yujun Tan , Wujiu Jiang
Six organotin carboxylates based on the Alrestatin ligand (HL) were synthesized and characterized using elemental analysis, IR spectroscopy, NMR spectroscopy, and TGA techniques. The molecular structure of complexes a-f was confirmed through single-crystal X-ray crystallography. Alrestatin demonstrated a tendency to adopt various coordination modes, leading to the formation of diverse molecular configurations in the organotin carboxylates. Hirshfeld surface analysis indicated that the six complexes exhibited similar contributions of different contacts to the Hirshfeld surfaces, with reciprocal H···H/C/O contacts dominating over 91 % of the total Hirshfeld surface. The in vitro anticancer activities of all the complexes were evaluated by a CCK8 assay against three human cancer cell lines (NCI-H460, HepG2, and MCF7). The anticancer activity of Alrestatin was effectively increased by introducing the butyl tin group, and exhibited excellent anticancer activity in vitro, significantly superior to cisplatin. The DNA binding of complex d was studied by UV–visible absorption spectrometry and fluorescence competitive assays.
利用元素分析、红外光谱、核磁共振光谱和热重分析技术合成并表征了六种基于阿司他丁配体（HL）的有机锡羧酸盐。通过单晶 X 射线晶体学研究证实了 a-f 复合物的分子结构。阿司他丁显示出采用各种配位模式的趋势，从而在有机锡羧酸盐中形成了不同的分子构型。Hirshfeld表面分析表明，六种复合物的Hirshfeld表面呈现出类似的不同接触，其中H--H/C/O相互接触占Hirshfeld总表面的91%以上。针对三种人类癌细胞系（NCI-H460、HepG2 和 MCF7）的 CCK8 试验评估了所有复合物的体外抗癌活性。通过引入丁基锡基，阿司他丁的抗癌活性得到了有效提高，并在体外表现出卓越的抗癌活性，明显优于顺铂。通过紫外可见吸收光谱法和荧光竞争法研究了复合物 d 的 DNA 结合情况。
{"title":"Syntheses, crystal structures, and anticancer activities of organotin carboxylates based on Alrestatin","authors":"Yuxing Tan , Zhijian Zhang , Jiazi Liu , Yujun Tan , Wujiu Jiang","doi":"10.1016/j.molstruc.2024.140697","DOIUrl":"10.1016/j.molstruc.2024.140697","url":null,"abstract":"<div><div>Six organotin carboxylates based on the Alrestatin ligand (<strong>HL</strong>) were synthesized and characterized using elemental analysis, IR spectroscopy, NMR spectroscopy, and TGA techniques. The molecular structure of complexes <strong>a-f</strong> was confirmed through single-crystal X-ray crystallography. Alrestatin demonstrated a tendency to adopt various coordination modes, leading to the formation of diverse molecular configurations in the organotin carboxylates. Hirshfeld surface analysis indicated that the six complexes exhibited similar contributions of different contacts to the Hirshfeld surfaces, with reciprocal H···H/C/O contacts dominating over 91 % of the total Hirshfeld surface. The <em>in vitro</em> anticancer activities of all the complexes were evaluated by a CCK8 assay against three human cancer cell lines (NCI-H460, HepG2, and MCF7). The anticancer activity of Alrestatin was effectively increased by introducing the butyl tin group, and exhibited excellent anticancer activity <em>in vitro</em>, significantly superior to cisplatin. The DNA binding of complex <strong>d</strong> was studied by UV–visible absorption spectrometry and fluorescence competitive assays.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140697"},"PeriodicalIF":4.0,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142659607","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}
This report presents an application of simple and convenient grindstone chemistry to construct a library of pharmaceutically valuable hydrazinyl thiazole moieties using biomass-derived furfurals as key synthons. Significantly, the current green process avoids the use of catalysts and solvents for the desired conversion, achieving good to excellent product yields in a short reaction time. The synthesized compounds were evaluated for their anti-cancer activity against the human breast cancer cell line (MCF-7) using an in vitro MTT assay, which revealed significant antiproliferative activity of compounds 4d and 4e, with IC50 values of 41.06±0.06 and 38.39±0.90 μg/mL, respectively.
Further, the in vitro antibacterial activity of the newly synthesized thiazole derivatives and reference drugs was assessed against both gram-negative bacteria, including Escherichia coli, and gram-positive bacteria such as Bacillus subtilis. The current research demonstrates that compounds 4d and 4e exhibit significantly enhanced antibacterial efficacy against pathogenic bacteria, with MIC values >25 μg/mL and >6.25 μg/mL for E. coli, and >25 μg/mL for Bacillus subtilis for both compounds. The DPPH assay revealed that compounds 4a, 4d, and 4e were the most significant, displaying comparatively higher IC50 values of 41.58±1.28, 42.36±0.45 and 42.31±0.73 μg/mL respectively.
Furthermore, the synthesized compounds were investigated through molecular docking studies, which were consistent with the in vitro results. The findings were further supported by a structure-activity relationship (SAR) study.
本报告介绍了一种简单方便的磨石化学应用，它以生物质衍生的呋喃为关键合成物，构建了一个具有医药价值的肼基噻唑分子库。值得注意的是，当前的绿色工艺避免了催化剂和溶剂的使用，从而在短时间内实现了所需的转化，并获得了良好甚至卓越的产品收率。利用体外 MTT 试验评估了合成化合物对人类乳腺癌细胞系（MCF-7）的抗癌活性，结果显示化合物 4d 和 4e 具有显著的抗增殖活性，其 IC50 值分别为 41.06±0.06 和 38.此外，还评估了新合成的噻唑衍生物和参考药物对大肠杆菌等革兰氏阴性菌和枯草杆菌等革兰氏阳性菌的体外抗菌活性。目前的研究表明，化合物 4d 和 4e 对病原菌的抗菌效果显著增强，对大肠杆菌的 MIC 值分别为 >25 μg/mL 和 >6.25 μg/mL，对枯草杆菌的 MIC 值分别为 >25 μg/mL。DPPH 试验显示，化合物 4a、4d 和 4e 的作用最为显著，其 IC50 值相对较高，分别为 41.58±1.28、42.36±0.45 和 42.31±0.73 μg/mL。结构-活性关系（SAR）研究进一步证实了上述结论。
{"title":"Design and synthesis of novel hydrazinyl thiazoles from biomass derived furfurals: Their molecular docking, anti-cancer, anti-oxidant, and anti-bacterial study","authors":"Akshay Gurav , Rutikesh Gurav , Prakash N. Chavan , Nisha Nerlekar , Padma Dandge , Sandeep Sankpal , Shankar Hangirgekar","doi":"10.1016/j.molstruc.2024.140541","DOIUrl":"10.1016/j.molstruc.2024.140541","url":null,"abstract":"<div><div>This report presents an application of simple and convenient grindstone chemistry to construct a library of pharmaceutically valuable hydrazinyl thiazole moieties using biomass-derived furfurals as key synthons. Significantly, the current green process avoids the use of catalysts and solvents for the desired conversion, achieving good to excellent product yields in a short reaction time. The synthesized compounds were evaluated for their anti-cancer activity against the human breast cancer cell line (MCF-7) using an <em>in vitro</em> MTT assay, which revealed significant antiproliferative activity of compounds 4d and 4e, with IC<sub>50</sub> values of 41.06±0.06 and 38.39±0.90 μg/mL, respectively.</div><div>Further, the <em>in vitro</em> antibacterial activity of the newly synthesized thiazole derivatives and reference drugs was assessed against both gram-negative bacteria, including Escherichia coli, and gram-positive bacteria such as Bacillus subtilis. The current research demonstrates that compounds 4d and 4e exhibit significantly enhanced antibacterial efficacy against pathogenic bacteria, with MIC values >25 μg/mL and >6.25 μg/mL for E. coli, and >25 μg/mL for Bacillus subtilis for both compounds. The DPPH assay revealed that compounds 4a, 4d, and 4e were the most significant, displaying comparatively higher IC<sub>50</sub> values of 41.58±1.28, 42.36±0.45 and 42.31±0.73 μg/mL respectively.</div><div>Furthermore, the synthesized compounds were investigated through molecular docking studies, which were consistent with the <em>in vitro</em> results. The findings were further supported by a structure-activity relationship (SAR) study.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140541"},"PeriodicalIF":4.0,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142651782","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 : 2024-11-09DOI: 10.1016/j.molstruc.2024.140620
Siqi Shen , Haiyan Qi , Tonghui Yi , Tao Jing , Jun Li , Yang Gao , Qingxin Zeng , Hongxu Zhao
Bacterial infections pose a significant threat to global health, necessitating the development of novel antibacterial materials. Tetracycline antibiotics (CTC, OTC, TC) are low-cost and widely abused in recent years. However, they were easily absorbed by the human body and long-term exposure to tetracycline could contribute to some adverse reactions and diseases. So there is a need for novel antimicrobial agents and a rapid, sensitive detection method of tetracycline antibiotics. In this study, we synthesized three carbon dots (CDs1, CDs2, CDs3) from quaternary ammonium salts via a hydrothermal method. Antibacterial assays against Staphylococcus aureus and Escherichia coli demonstrated their potent antibacterial activity with minimum inhibitory concentrations(MIC) determined as 39 μg/mL, 78 μg/mL, and 9.8 μg/mL, respectively. Notably, CDs3 exhibited the highest antibacterial effectiveness, attributed to its smaller size and higher chlorine content compared to CDs1 and CDs2. Additionally, CDs1, characterized by its high fluorescence quantum yield and stability, demonstrated remarkable specificity and robust anti-interference capabilities in detecting tetracycline antibiotics, including chlortetracycline (CTC), oxytetracycline (OTC), and tetracycline (TC). Leveraging the internal filtration effect mechanism, CDs1 exhibited detection limits of 0.18 μmol/L for CTC, 0.15 μmol/L for OTC, and 0.13 μmol/L for TC, respectively. The effectiveness of this detection method was further confirmed through validation in real milk samples, confirming the practical utility of CDs1 in food safety testing. The low toxicity of carbon dots were synthesized using a simple one-step hydrothermal method, which was fast, cost-effective, and easy to achieve large-scale production. Our findings underscore the potential of CDs derived from quaternary ammonium salts, demonstrating promising performance in antibacterial applications and providing insights into food safety testing methodologies.
{"title":"Quaternary ammonium salt-derived carbon dots for antibacterial efficacy and tetracycline sensing","authors":"Siqi Shen , Haiyan Qi , Tonghui Yi , Tao Jing , Jun Li , Yang Gao , Qingxin Zeng , Hongxu Zhao","doi":"10.1016/j.molstruc.2024.140620","DOIUrl":"10.1016/j.molstruc.2024.140620","url":null,"abstract":"<div><div>Bacterial infections pose a significant threat to global health, necessitating the development of novel antibacterial materials. Tetracycline antibiotics (CTC, OTC, TC) are low-cost and widely abused in recent years. However, they were easily absorbed by the human body and long-term exposure to tetracycline could contribute to some adverse reactions and diseases. So there is a need for novel antimicrobial agents and a rapid, sensitive detection method of tetracycline antibiotics. In this study, we synthesized three carbon dots (CDs1, CDs2, CDs3) from quaternary ammonium salts via a hydrothermal method. Antibacterial assays against <em>Staphylococcus aureus</em> and <em>Escherichia coli</em> demonstrated their potent antibacterial activity with minimum inhibitory concentrations(MIC) determined as 39 μg/mL, 78 μg/mL, and 9.8 μg/mL, respectively. Notably, CDs3 exhibited the highest antibacterial effectiveness, attributed to its smaller size and higher chlorine content compared to CDs1 and CDs2. Additionally, CDs1, characterized by its high fluorescence quantum yield and stability, demonstrated remarkable specificity and robust anti-interference capabilities in detecting tetracycline antibiotics, including chlortetracycline (CTC), oxytetracycline (OTC), and tetracycline (TC). Leveraging the internal filtration effect mechanism, CDs1 exhibited detection limits of 0.18 μmol/L for CTC, 0.15 μmol/L for OTC, and 0.13 μmol/L for TC, respectively. The effectiveness of this detection method was further confirmed through validation in real milk samples, confirming the practical utility of CDs1 in food safety testing. The low toxicity of carbon dots were synthesized using a simple one-step hydrothermal method, which was fast, cost-effective, and easy to achieve large-scale production. Our findings underscore the potential of CDs derived from quaternary ammonium salts, demonstrating promising performance in antibacterial applications and providing insights into food safety testing methodologies.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140620"},"PeriodicalIF":4.0,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142659576","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 : 2024-11-09DOI: 10.1016/j.molstruc.2024.140695
Ya-Chen Wang, Feng Zhu, Jun Pan, Tong-Mou Geng
Recently, flexible covalent organic frameworks (COFs) prepared with nitrogen-rich building units have become targets for selective detection of pollutants to serve a clean environment. To meet the requirements of the practical applications, a series of novel flexible covalent organic frameworks containing polyethylene polyamine units (the flexible PEPA-based COFs, remember as TEDA, TDETA, TTETA, TTEPA, and TPEHA) were designed and developed to create fluorescence sensors. The flexible PEPA-based COFs were found to be excellently fluorescent properties in presence of some solvents under irradiation with UV light and can sense some nitrophenols with good sensitivity for DNP, o-NP, or TNP by fluorescence quenching with high S-V constants (KSV) of 5.01 × 104, 6.92 × 103, 7.42 × 104, 7.37 × 103, and 1.59 × 104 L mol−1, respectively. Theoretical calculations and experimental studies show that the fluorescence quenching in the presence of nitrophenols is put down to photoinduced electron transfer, energy resonance transfer, and the difference between nitrophenols binding sites to the flexible PEPA-based COFs. In addition, TEDA, TDETA, TTETA, TTEPA, and TPEHA can fluorescently sense iodide ions with high KSV of 2.28 × 104, 1.09 × 104, 6.88 × 103, 8.81 × 103, and 1.82 × 104 L mol−1, which are the most sensitive among POP materials.
{"title":"Application of the flexible polyethylene polyamine-based covalent organic frameworks for fluorescence sensing nitrophenols and iodide ions","authors":"Ya-Chen Wang, Feng Zhu, Jun Pan, Tong-Mou Geng","doi":"10.1016/j.molstruc.2024.140695","DOIUrl":"10.1016/j.molstruc.2024.140695","url":null,"abstract":"<div><div>Recently, flexible covalent organic frameworks (COFs) prepared with nitrogen-rich building units have become targets for selective detection of pollutants to serve a clean environment. To meet the requirements of the practical applications, a series of novel flexible covalent organic frameworks containing polyethylene polyamine units (the flexible PEPA-based COFs, remember as TEDA, TDETA, TTETA, TTEPA, and TPEHA) were designed and developed to create fluorescence sensors. The flexible PEPA-based COFs were found to be excellently fluorescent properties in presence of some solvents under irradiation with UV light and can sense some nitrophenols with good sensitivity for DNP, o-NP, or TNP by fluorescence quenching with high S-V constants (K<sub>SV</sub>) of 5.01 × 10<sup>4</sup>, 6.92 × 10<sup>3</sup>, 7.42 × 10<sup>4</sup>, 7.37 × 10<sup>3</sup>, and 1.59 × 10<sup>4</sup> L mol<sup>−1</sup>, respectively. Theoretical calculations and experimental studies show that the fluorescence quenching in the presence of nitrophenols is put down to photoinduced electron transfer, energy resonance transfer, and the difference between nitrophenols binding sites to the flexible PEPA-based COFs. In addition, TEDA, TDETA, TTETA, TTEPA, and TPEHA can fluorescently sense iodide ions with high K<sub>SV</sub> of 2.28 × 10<sup>4</sup>, 1.09 × 10<sup>4</sup>, 6.88 × 10<sup>3</sup>, 8.81 × 10<sup>3</sup>, and 1.82 × 10<sup>4</sup> L mol<sup>−1</sup>, which are the most sensitive among POP materials.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140695"},"PeriodicalIF":4.0,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142651780","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}
A facile, efficient and green photo-catalyzed amination of benzylic C(sp3)−H bonds via C−N coupling for the synthesis of novel N-benzylaniline derivatives starting from readily available toluene derivative and aniline derivative under irradiation of UV LEDs (365 nm) with catalyst Fe(III), without using any bases, strong oxidants, complex ligands, or precious metals is reported. The N-benzylaniline products could be obtained under UV LEDs irradiation at room temperature in 12 h with definite compatibilities with functional groups. To discuss the characteristic pattern of armatic protons and carbons, to identify its structure, NMR spectra analysis (1D and 2D-NMR) was carried out in details by the chemical shifts, couplings and correlations. The energy levels of molecular orbitals (HOMO and LUMO) for N-benzylaniline product (3a) were investigated.
{"title":"Photocatalyzed amination of benzylic C(sp3)−H bonds via C−N coupling: Green synthesis and NMR analysis of N-benzylanilines","authors":"Hong-bo Tan , Chang-qiu Lin , Si-ying Ren , Yu-han Peng , Meng-qi Zhang , Zhi-gang Xu , Dian-yong Tang , Zhong-zhu Chen","doi":"10.1016/j.molstruc.2024.140699","DOIUrl":"10.1016/j.molstruc.2024.140699","url":null,"abstract":"<div><div>A facile, efficient and green photo-catalyzed amination of benzylic C(sp<sup>3</sup>)−H bonds via C−N coupling for the synthesis of novel <em>N</em>-benzylaniline derivatives starting from readily available toluene derivative and aniline derivative under irradiation of UV LEDs (365 nm) with catalyst Fe(III), without using any bases, strong oxidants, complex ligands, or precious metals is reported. The <em>N</em>-benzylaniline products could be obtained under UV LEDs irradiation at room temperature in 12 h with definite compatibilities with functional groups. To discuss the characteristic pattern of armatic protons and carbons, to identify its structure, NMR spectra analysis (1D and 2D-NMR) was carried out in details by the chemical shifts, couplings and correlations. The energy levels of molecular orbitals (HOMO and LUMO) for <em>N</em>-benzylaniline product (<strong>3a</strong>) were investigated.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140699"},"PeriodicalIF":4.0,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142659664","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 : 2024-11-09DOI: 10.1016/j.molstruc.2024.140686
Safia Iqbal , Mohd Kamil Hussain , Roohi Ansari , Bhoomika Singh , Farhanaz , Insha Akbar , Mohammad Rehan Zaheer , Mohammad Faheem Khan , Anamika Gupta
Green synthesis of biologically active molecules is essential for environmental sustainability, resource efficiency, reduced environmental impact, and compliance with regulations. It ensures a safer working environment, and fosters innovation in sustainable chemistry practices. In this context, we introduce an electron donor-acceptor (EDA)-mediated visible light-promoted, catalyst-free (VLCF) scalable synthesis of isoniazid azomethines. This synthesis encompasses the drug salizide and its analogues, which were subsequently evaluated for their antioxidant activities. Isoniazid azomethines 3e demonstrated superior activity compared to salizide and ascorbic acid, with an IC50 of 0.078 mg/mL in the hydrogen peroxide antioxidant assay. Specifically, 3e exhibited greater antioxidant properties (79.02 %) than isoniazid azomethine 3b (75.82 %), isoniazid azomethine 3d (62.2 %), isoniazid azomethine 3c (59.86 %), and isoniazid azomethine 3a (54.62 %). In the superoxide dismutase antioxidant assay, 3e was also identified as the most active, with a SOD activity level of 650 U/mg of protein, surpassing other compounds (3a-d) with SOD activity levels of 330, 560, 350, and 420 U/mg of protein, respectively. Molecular docking against horseradish peroxidase (1W4Y) showed compound 3e with the best binding energy (-6.561 kcal/mol), forming key hydrogen bonds (Asn135, Pro139) and a π-cation interaction with Arg38. These interactions suggest 3e may effectively inhibit hydrogen peroxide catalysis. The in silico assessment of the physicochemical properties, pharmacokinetics, and toxicology of synthesized compounds suggests that these compounds exhibit promising ADMET characteristics, with no identified toxicological concerns.
{"title":"Visible light-promoted, catalyst-free synthesis of isoniazid azomethines: In vitro antioxidant activity, molecular docking, ADME and toxicity prediction","authors":"Safia Iqbal , Mohd Kamil Hussain , Roohi Ansari , Bhoomika Singh , Farhanaz , Insha Akbar , Mohammad Rehan Zaheer , Mohammad Faheem Khan , Anamika Gupta","doi":"10.1016/j.molstruc.2024.140686","DOIUrl":"10.1016/j.molstruc.2024.140686","url":null,"abstract":"<div><div>Green synthesis of biologically active molecules is essential for environmental sustainability, resource efficiency, reduced environmental impact, and compliance with regulations. It ensures a safer working environment, and fosters innovation in sustainable chemistry practices. In this context, we introduce an electron donor-acceptor (EDA)-mediated visible light-promoted, catalyst-free (VLCF) scalable synthesis of isoniazid azomethines. This synthesis encompasses the drug salizide and its analogues, which were subsequently evaluated for their antioxidant activities. Isoniazid azomethines 3e demonstrated superior activity compared to salizide and ascorbic acid, with an IC<sub>50</sub> of 0.078 mg/mL in the hydrogen peroxide antioxidant assay. Specifically, 3e exhibited greater antioxidant properties (79.02 %) than isoniazid azomethine 3b (75.82 %), isoniazid azomethine 3d (62.2 %), isoniazid azomethine 3c (59.86 %), and isoniazid azomethine 3a (54.62 %). In the superoxide dismutase antioxidant assay, 3e was also identified as the most active, with a SOD activity level of 650 U/mg of protein, surpassing other compounds (3a-d) with SOD activity levels of 330, 560, 350, and 420 U/mg of protein, respectively. Molecular docking against horseradish peroxidase (1W4Y) showed compound 3e with the best binding energy (-6.561 kcal/mol), forming key hydrogen bonds (Asn135, Pro139) and a π-cation interaction with Arg38. These interactions suggest 3e may effectively inhibit hydrogen peroxide catalysis. The in silico assessment of the physicochemical properties, pharmacokinetics, and toxicology of synthesized compounds suggests that these compounds exhibit promising ADMET characteristics, with no identified toxicological concerns.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140686"},"PeriodicalIF":4.0,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142659604","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 : 2024-11-09DOI: 10.1016/j.molstruc.2024.140690
Yongkang Lyu , Yonglin Cui , Xiaolin Chen , Hao Shen , He Xu , Changzhe Zhang , Qingtian Meng
Ganglioside GM1 is a crucial glycolipid in neuronal cells, playing significant roles in various biological processes such as pathogen recognition, signal transduction, and protein sorting. Poly-arginine, widely used as a template for cell-penetrating peptides design, is highly valuable for molecular cargo delivery and information transmission. Investigating the interaction mechanisms and physicochemical principles of poly-arginine with GM1-containing cell membranes is essential for understanding the functions of specific cellular components and for developing novel drugs. In this study, we employed coarse-grained molecular dynamics simulations to explore the interaction processes between poly-arginine of varying concentrations and polymerization degrees with model membranes of human brain neuronal cells. Our findings reveal that poly-arginines preferentially adsorb onto GM1 and aggregate into clusters on the membrane, primarily driven by electrostatic interactions, which contributes to membrane stabilization. Additionally, poly-arginine shows a higher affinity for membranes with elevated GM1 concentrations, highlighting its potential for targeting specific membrane compositions. These insights are crucial for designing molecular targets and understanding the biophysical mechanisms in lipidomics using high-performance computational simulation methods.
{"title":"Mechanics of poly-arginine adsorption onto cell membrane by GM1 and their cluster forming: Coarse-grained molecular dynamics study","authors":"Yongkang Lyu , Yonglin Cui , Xiaolin Chen , Hao Shen , He Xu , Changzhe Zhang , Qingtian Meng","doi":"10.1016/j.molstruc.2024.140690","DOIUrl":"10.1016/j.molstruc.2024.140690","url":null,"abstract":"<div><div>Ganglioside GM1 is a crucial glycolipid in neuronal cells, playing significant roles in various biological processes such as pathogen recognition, signal transduction, and protein sorting. Poly-arginine, widely used as a template for cell-penetrating peptides design, is highly valuable for molecular cargo delivery and information transmission. Investigating the interaction mechanisms and physicochemical principles of poly-arginine with GM1-containing cell membranes is essential for understanding the functions of specific cellular components and for developing novel drugs. In this study, we employed coarse-grained molecular dynamics simulations to explore the interaction processes between poly-arginine of varying concentrations and polymerization degrees with model membranes of human brain neuronal cells. Our findings reveal that poly-arginines preferentially adsorb onto GM1 and aggregate into clusters on the membrane, primarily driven by electrostatic interactions, which contributes to membrane stabilization. Additionally, poly-arginine shows a higher affinity for membranes with elevated GM1 concentrations, highlighting its potential for targeting specific membrane compositions. These insights are crucial for designing molecular targets and understanding the biophysical mechanisms in lipidomics using high-performance computational simulation methods.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140690"},"PeriodicalIF":4.0,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142659672","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 : 2024-11-08DOI: 10.1016/j.molstruc.2024.140691
Xin Wang , Manaswini Ray , Like Zou , Jing Xu , Lipeeka Rout , Yu Wu , Mohd Afzal , Abdullah Alarifi , Aurobinda Mohanty
A new Cd(II) metal-organic framework (Cd-MOF), namely [Cd2(L)(H2O)3·3·4H2O]n (1) (H4L = (3-(2,4-dicarboxylphenyl)-2,6-dicarboxylpyridine)) was effectively produced. 1 shows a new 3D 3,5-connected network with gra topology built by the multi-carboxylate linker through (κ2)-(κ1)-μ2, (κ1)-(κ1)-μ1 and (κ0)-(κ1)-μ1 coordination modes. The sensing results showed that 1 would be a viable possibility for developing luminous sensors to sensitively probe nitrofurazone (NFZ), Fe3+, and CrO42-. The limits of detection (LODs) for Fe3+, CrO42−and NFZ were calculated to be 1.17 × 10–7 M-1, 1.63 × 10–7 M-1 and 7.03 × 10–8M-1, respectively. Density functional theory (DFT), UV–vis spectroscopy, and PXRD research have reinforced the understanding of luminescence sensing mechanisms.
{"title":"A new 3D Cd(II)-based metal-organic framework as dual-function luminescent sensor to ions and antibiotic: Mechanism and theoretical studies","authors":"Xin Wang , Manaswini Ray , Like Zou , Jing Xu , Lipeeka Rout , Yu Wu , Mohd Afzal , Abdullah Alarifi , Aurobinda Mohanty","doi":"10.1016/j.molstruc.2024.140691","DOIUrl":"10.1016/j.molstruc.2024.140691","url":null,"abstract":"<div><div>A new Cd(II) metal-organic framework (Cd-MOF), namely [Cd<sub>2</sub>(L)(H<sub>2</sub>O)<sub>3</sub>·3·4H<sub>2</sub>O]<sub>n</sub> (<strong>1</strong>) (H<sub>4</sub>L = (3-(2,4-dicarboxylphenyl)-2,6-dicarboxylpyridine)) was effectively produced. <strong>1</strong> shows a new 3D 3,5-connected network with <strong><em>gra</em></strong> topology built by the multi-carboxylate linker through (<em>κ</em><sup>2</sup>)-(<em>κ</em><sup>1</sup>)-<em>μ</em><sub>2</sub>, (<em>κ</em><sup>1</sup>)-(<em>κ</em><sup>1</sup>)-<em>μ</em><sub>1</sub> and (<em>κ</em><sup>0</sup>)-(<em>κ</em><sup>1</sup>)-<em>μ</em><sub>1</sub> coordination modes. The sensing results showed that <strong>1</strong> would be a viable possibility for developing luminous sensors to sensitively probe nitrofurazone (NFZ), Fe<sup>3+</sup>, and CrO<sub>4</sub><sup>2-</sup>. The limits of detection (LODs) for Fe<sup>3+</sup>, CrO<sub>4</sub><sup>2−</sup>and NFZ were calculated to be 1.17 × 10<sup>–7</sup> M<sup>-1</sup>, 1.63 × 10<sup>–7</sup> M<sup>-1</sup> and 7.03 × 10<sup>–8</sup>M<sup>-1</sup>, respectively. Density functional theory (DFT), UV–vis spectroscopy, and PXRD research have reinforced the understanding of luminescence sensing mechanisms.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140691"},"PeriodicalIF":4.0,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142659669","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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