A series of new pyridine-malonate derivatives were synthesized and fully characterized by 1HNMR, 13CNMR, FTIR, and elemental analysis. Their molecular geometry and chemical reactivity have been investigated using DFT calculations. The cytotoxicity of all synthesized compounds was assessed against two human cancer cell lines (MCF-7 and A-2780) using the MTT assay. Among them, compounds 2a, 2c, 2e, and 2g showed comparable or more potent cytotoxicity toward the MCF-7 cells than the reference drug docetaxel (IC50 = 0.34–0.47 vs. 0.50 µM). In contrast, only compound 2g showed more potent cytotoxicity against the A-2780 cell line compared to the standard (IC50 = 0.36 vs. 0.42 µM). The docking study revealed a good affinity for the active site of the human topoisomerase-IIβ enzyme, which may explain the promising cytotoxicity of these classes of molecules. The radical scavenging activity of the respective compounds was studied using DPPH radical scavenging assay and it was found that most of the compounds are moderate DPPH radical scavengers compared to the standard drugs BHA and BHT.
{"title":"Synthesis, Cytotoxicity, Antioxidant Activity, DFT Calculations, and Docking Studies of New Pyridine-Malonate Derivatives as Potential Anticancer Agents","authors":"Ibtissem Kadi , Şekerci Güldeniz , Houssem Boulebd , Zineddine Zebbiche , Tekin Suat , Küçükbay Fatümetüzzehra , Zeynep Gönül , Hasan Küçükbay , Taoues Boumoud","doi":"10.1080/10406638.2023.2281468","DOIUrl":"10.1080/10406638.2023.2281468","url":null,"abstract":"<div><div>A series of new pyridine-malonate derivatives were synthesized and fully characterized by <sup>1</sup>HNMR, <sup>13</sup>CNMR, FTIR, and elemental analysis. Their molecular geometry and chemical reactivity have been investigated using DFT calculations. The cytotoxicity of all synthesized compounds was assessed against two human cancer cell lines (MCF-7 and A-2780) using the MTT assay. Among them, compounds <strong>2a, 2c, 2e,</strong> and <strong>2g</strong> showed comparable or more potent cytotoxicity toward the MCF-7 cells than the reference drug docetaxel (IC<sub>50</sub> = 0.34–0.47 vs. 0.50 µM). In contrast, only compound <strong>2g</strong> showed more potent cytotoxicity against the A-2780 cell line compared to the standard (IC<sub>50</sub> = 0.36 vs. 0.42 µM). The docking study revealed a good affinity for the active site of the human topoisomerase-IIβ enzyme, which may explain the promising cytotoxicity of these classes of molecules. The radical scavenging activity of the respective compounds was studied using DPPH radical scavenging assay and it was found that most of the compounds are moderate DPPH radical scavengers compared to the standard drugs BHA and BHT.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 6615-6629"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138504144","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-25DOI: 10.1080/10406638.2024.2351388
Eman Mansour , Ahmed M. Sayed , Safaa I. Elewa
Some of the interesting pyrido[2,3-d] pyrimidines (3a, 3b), 4, (5a–d), (6a, b), 7–13, and (15a–c) based on uracil moiety were synthesized efficiently using a conventional method and ultrasonic irradiation. Heterocyclic scaffolds such as pyrido[2,3-d] pyrimidines are vital structural elements in drug discovery. Their interactions with different viral mechanistic pathways will be leveraged in future research to create heterocycle-based antivirals. Therefore, the purpose of this work is to demonstrate the anticipated contribution of heterocyclic scaffolds to the advancement and identification of SARS CoV-2 treatment, The newly synthesized compounds were characterized by spectral data, and screened for their binding activity toward the main protease of COVID-19 utilizing a molecular docking study, according to the outcome of our initial screening and docking study, the produced compounds 3a, 4, 6a, 13, 15b, and 15c achieved an evaluation in vitro using the SARS-CoV-2 Mpro utilizing the main protease assay, the results of the evaluation showed that the hydrazinylpyridopyrimidine 4 (IC50 value: 10.69 µM) and triazolopyrimidin 15c (IC50 value 8.723 µM) had the greatest inhibitory effects on SARS-CoV-2 Mpro. Additionally, this study was conducted to assess the inhibitory efficacy of the synthesized compounds 4 and 15c, which show moderate inhibition for the replication of SARS CoV-2. Additional molecular dynamics and docking simulations were performed to prove the binding mechanism of 15c.
{"title":"Design, Synthesis of Novel Pyrido[2,3-d] pyrimidine Derivatives as SARS-CoV-2 Mpro Inhibitors for COVID-19 Therapy","authors":"Eman Mansour , Ahmed M. Sayed , Safaa I. Elewa","doi":"10.1080/10406638.2024.2351388","DOIUrl":"10.1080/10406638.2024.2351388","url":null,"abstract":"<div><div>Some of the interesting pyrido[2,3-d] pyrimidines <strong>(3a, 3b), 4, (5a–d</strong>), <strong>(6a, b)</strong>, <strong>7–13</strong>, and <strong>(15a–c)</strong> based on uracil moiety were synthesized efficiently using a conventional method and ultrasonic irradiation. Heterocyclic scaffolds such as pyrido[2,3-d] pyrimidines are vital structural elements in drug discovery. Their interactions with different viral mechanistic pathways will be leveraged in future research to create heterocycle-based antivirals. Therefore, the purpose of this work is to demonstrate the anticipated contribution of heterocyclic scaffolds to the advancement and identification of SARS CoV-2 treatment, The newly synthesized compounds were characterized by spectral data, and screened for their binding activity toward the main protease of COVID-19 utilizing a molecular docking study, according to the outcome of our initial screening and docking study, the produced compounds <strong>3a</strong>, <strong>4</strong>, <strong>6a</strong>, <strong>13</strong>, <strong>15b</strong>, and <strong>15c</strong> achieved an evaluation <em>in vitro</em> using the SARS-CoV-2 Mpro utilizing the main protease assay, the results of the evaluation showed that the hydrazinylpyridopyrimidine <strong>4</strong> (IC<sub>50</sub> value: 10.69 µM) and triazolopyrimidin <strong>15c</strong> (IC<sub>50</sub> value 8.723 µM) had the greatest inhibitory effects on SARS-CoV-2 Mpro. Additionally, this study was conducted to assess the inhibitory efficacy of the synthesized compounds <strong>4</strong> and <strong>15c</strong>, which show moderate inhibition for the replication of SARS CoV-2. Additional molecular dynamics and docking simulations were performed to prove the binding mechanism of <strong>15c</strong>.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 7061-7086"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141102492","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-25DOI: 10.1080/10406638.2023.2287029
Abdelwahed R. Sayed , Olivia McNair , Jeffrey S. Wiggins
The present work describes the preparation and characterization of new polyazothiazole and polyacetyltrazine polymers in good yields from new bis-(α-ketohydrazonoyl) dichlorides. Synthesis of the new polyazothiazole proceeds through the reaction of bis-(α-ketohydrazonoyl) dichlorides with 1,4-phenylene[bis(carbothioamide)] in a basic medium to afford novel polyazothiazole derivatives. Additionally, the self-polymerization reaction to synthesize polydiacetyltetrazine derivatives based on bis-(α-ketohydrazonoyl) dichlorides is described. The new polyazothiazole and polyacetyltetrazine derivatives were characterized using spectral and thermal techniques.
{"title":"Synthesis and Characterization of Polyazothiazole and Polyacetyltetrazine from Novel Bis-Ketohydrazonoyl Dichlorides","authors":"Abdelwahed R. Sayed , Olivia McNair , Jeffrey S. Wiggins","doi":"10.1080/10406638.2023.2287029","DOIUrl":"10.1080/10406638.2023.2287029","url":null,"abstract":"<div><div>The present work describes the preparation and characterization of new polyazothiazole and polyacetyltrazine polymers in good yields from new <em>bis</em>-(α-ketohydrazonoyl) dichlorides. Synthesis of the new polyazothiazole proceeds through the reaction of <em>bis</em>-(α-ketohydrazonoyl) dichlorides with 1,4-phenylene[<em>bis</em>(carbothioamide)] in a basic medium to afford novel polyazothiazole derivatives. Additionally, the self-polymerization reaction to synthesize polydiacetyltetrazine derivatives based on <em>bis</em>-(α-ketohydrazonoyl) dichlorides is described. The new polyazothiazole and polyacetyltetrazine derivatives were characterized using spectral and thermal techniques.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 6834-6844"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138577337","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-25DOI: 10.1080/10406638.2023.2290178
Mona H. Alhalafi
During the last decade quinazolinones derivatives have been shown to be useful building blocks for the synthesis of a variety of functionalized polynuclear heterocyclic systems. This review presents the recent systematic and comprehensive literature survey of fused quinazolinones synthesis. These fused heterocycles are classified according to the ring volume starting from three membered up to seven membered cycles and divided according to the number of heteroatoms and type or position of these heteroatoms.
过去十年间，喹唑啉酮衍生物已被证明是合成各种功能化多核杂环系统的有用构件。本综述介绍了...
{"title":"Recent Advances on Diversity Oriented Heterocycle Synthesis of Fused Quinazolinones","authors":"Mona H. Alhalafi","doi":"10.1080/10406638.2023.2290178","DOIUrl":"10.1080/10406638.2023.2290178","url":null,"abstract":"<div><div>During the last decade quinazolinones derivatives have been shown to be useful building blocks for the synthesis of a variety of functionalized polynuclear heterocyclic systems. This review presents the recent systematic and comprehensive literature survey of fused quinazolinones synthesis. These fused heterocycles are classified according to the ring volume starting from three membered up to seven membered cycles and divided according to the number of heteroatoms and type or position of these heteroatoms.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 7109-7167"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138715877","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-25DOI: 10.1080/10406638.2023.2283626
Infant Deepthi S. , Sangavi P. , Priyanka G. , Kirubhanand C. , Nachammai KT. , Gowtham Kumar S. , Langeswaran K.
Cancer is a complicated and diverse family of diseases characterized by the body’s aberrant cells growing and spreading out of control. It is one of the major causes of mortality in the world and may affect almost every organ or tissue in the body. One of the most prevalent forms of malignant tumors that affect both men and women is bone cancer. The study introduces the soluble frizzled-related protein SFRP3 as a significant participant. It functions as a tumor suppressor and regulator as well as an antagonist of the Wnt signaling pathway. It interacts directly with Wnts, regulating Wnt signaling and directing cell proliferation and differentiation in certain cell types. The study focuses on SFRP3 as a possible target for bone cancer therapy. The purpose is to find prospective medication candidates. Several databases are listed as possible drug compound sources, including NCI_Natural Products, Enamine, and specifications. Potent drugs from the selected databases are scrutinized and identified using ligand-based pharmacophore modeling. The binding affinity and interactions between the selected compounds and the SFRP3-modeled protein are evaluated using virtual screening and molecular docking approaches. The selection of lead compounds is based on their scores, binding affinity, and interactions, which indicate their potential as therapeutic candidates. To ensure that the contacts stay stable throughout time, molecular dynamics modeling is used to analyze the stability of the Protein-Ligand complex. The investigation leads to the identification of the top three compounds from each of the three databases that show potential against the target protein, SFRP3.
{"title":"Discovery of Potential Inhibitors for SFRP3: Ligand-Based 3D Pharmacophore, Virtual Screening, Molecular Docking, and Dynamics Studies","authors":"Infant Deepthi S. , Sangavi P. , Priyanka G. , Kirubhanand C. , Nachammai KT. , Gowtham Kumar S. , Langeswaran K.","doi":"10.1080/10406638.2023.2283626","DOIUrl":"10.1080/10406638.2023.2283626","url":null,"abstract":"<div><div>Cancer is a complicated and diverse family of diseases characterized by the body’s aberrant cells growing and spreading out of control. It is one of the major causes of mortality in the world and may affect almost every organ or tissue in the body. One of the most prevalent forms of malignant tumors that affect both men and women is bone cancer. The study introduces the soluble frizzled-related protein SFRP3 as a significant participant. It functions as a tumor suppressor and regulator as well as an antagonist of the Wnt signaling pathway. It interacts directly with Wnts, regulating Wnt signaling and directing cell proliferation and differentiation in certain cell types. The study focuses on SFRP3 as a possible target for bone cancer therapy. The purpose is to find prospective medication candidates. Several databases are listed as possible drug compound sources, including NCI_Natural Products, Enamine, and specifications. Potent drugs from the selected databases are scrutinized and identified using ligand-based pharmacophore modeling. The binding affinity and interactions between the selected compounds and the SFRP3-modeled protein are evaluated using virtual screening and molecular docking approaches. The selection of lead compounds is based on their scores, binding affinity, and interactions, which indicate their potential as therapeutic candidates. To ensure that the contacts stay stable throughout time, molecular dynamics modeling is used to analyze the stability of the Protein-Ligand complex. The investigation leads to the identification of the top three compounds from each of the three databases that show potential against the target protein, SFRP3.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 6714-6736"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138826567","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-25DOI: 10.1080/10406638.2023.2276864
Neda Ehtemae , Navid Ghanavati , Ahad Nazarpour , Teimour Babaeinejad , Michael James Watts
A total of 25 Ilam street dust specimens were sampled to investigate the possible ecological and health risks of heavy metal(loid)s and polycyclic aromatic hydrocarbons (PAHs). We found that the average concentrations of heavy metal(loid)s, namely Pb, Zn, Cu, Cr, Cd, Ni, V, and As, were 52, 213, 63, 46, 0.4, 44, 31, and 5 mg/kg, respectively. The average concentration of all heavy metal(loid)s except for Cr and V was several times higher than the baseline values. We evaluated Zn and Pb in the region using the average enrichment factor (EF) and pollution index (PI); the Nemerow integrated pollution index (NIPI) indicated that 76% of the samples had high degrees of pollution. According to principal component analysis (PCA), three principle components are involved in the heavy metal(loid) pollution of Ilam street dust. For example, the pollution sources of Cu, Cr, Cd, and Ni likely originated from anthropogenetic origins, including traffic, tire depreciation, and gasoline use. The sources of Pb and Zn were other anthropogenic activities, such as metal corroding and the combustion of garbage and gases from industries, while V and As were probably from natural sources. The range of sum over 11 PAHs was 167–11,497 μg/kg with a mean of 2242 μg/kg. The concentration of low molecular weight (LMW) PAHs averaged 1471 μg/kg, accounting for 66% of the total PAHs; their sources were mainly associated with combustion and pyrogenic emissions. The PCA also revealed that PAHs mainly originated from burning fossil fuels. The values of RQ∑PAHs (MPCs) and RQ∑PAHs (NCs) were respectively >1 and ≥800, indicating a high ecosystem risk for PAHs. Mean values for RQ∑PAHs (MPCs) and RQ∑PAHs (NCs) were 4 and 1021, respectively, implying that Ilam street dust poses a relatively high ecosystem risk of PAHs. Street dust PAHs’ toxic equivalency quotient (TEQ) varied from 26 to 199 μg/kg. The total cancer risk was 3.92 × 10−4 and 4.06 × 10−4 for adults and children, respectively, indicating that the potential for cancer risk is very high through dust dermal contact and ingestion.
{"title":"Status, Source, and Risk Assessment of Heavy Metal(Loid)s and Polycyclic Aromatic Hydrocarbons (PAHs) in the Street Dust of Ilam, Iran","authors":"Neda Ehtemae , Navid Ghanavati , Ahad Nazarpour , Teimour Babaeinejad , Michael James Watts","doi":"10.1080/10406638.2023.2276864","DOIUrl":"10.1080/10406638.2023.2276864","url":null,"abstract":"<div><div>A total of 25 Ilam street dust specimens were sampled to investigate the possible ecological and health risks of heavy metal(loid)s and polycyclic aromatic hydrocarbons (PAHs). We found that the average concentrations of heavy metal(loid)s, namely Pb, Zn, Cu, Cr, Cd, Ni, V, and As, were 52, 213, 63, 46, 0.4, 44, 31, and 5 mg/kg, respectively. The average concentration of all heavy metal(loid)s except for Cr and V was several times higher than the baseline values. We evaluated Zn and Pb in the region using the average enrichment factor (EF) and pollution index (PI); the Nemerow integrated pollution index (NIPI) indicated that 76% of the samples had high degrees of pollution. According to principal component analysis (PCA), three principle components are involved in the heavy metal(loid) pollution of Ilam street dust. For example, the pollution sources of Cu, Cr, Cd, and Ni likely originated from anthropogenetic origins, including traffic, tire depreciation, and gasoline use. The sources of Pb and Zn were other anthropogenic activities, such as metal corroding and the combustion of garbage and gases from industries, while V and As were probably from natural sources. The range of sum over 11 PAHs was 167–11,497 μg/kg with a mean of 2242 μg/kg. The concentration of low molecular weight (LMW) PAHs averaged 1471 μg/kg, accounting for 66% of the total PAHs; their sources were mainly associated with combustion and pyrogenic emissions. The PCA also revealed that PAHs mainly originated from burning fossil fuels. The values of RQ<sub>∑PAHs (MPCs)</sub> and RQ<sub>∑PAHs (NCs)</sub> were respectively >1 and ≥800, indicating a high ecosystem risk for PAHs. Mean values for RQ<sub>∑PAHs (MPCs)</sub> and RQ<sub>∑PAHs (NCs)</sub> were 4 and 1021, respectively, implying that Ilam street dust poses a relatively high ecosystem risk of PAHs. Street dust PAHs’ toxic equivalency quotient (TEQ) varied from 26 to 199 μg/kg. The total cancer risk was 3.92 × 10<sup>−4</sup> and 4.06 × 10<sup>−4</sup> for adults and children, respectively, indicating that the potential for cancer risk is very high through dust dermal contact and ingestion.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 6475-6500"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135480475","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-25DOI: 10.1080/10406638.2024.2309358
Smita P. Khare , Tejshri R. Deshmukh , Jaiprakash N. Sangshetti , Vijay M. Khedkar , Bapurao B. Shingate
An efficient, ultrasound assisted catalyst-free, green protocol has been developed for the synthesis of 1,2,3-triazolyl phenylhydrazone derivatives under environmentally benign condition. The antioxidant activity for all the synthesized derivatives were evaluated in vitro by using 1,1-diphenylpicrylhydrazyl (DPPH) radical scavenging method. The compounds 6a, 6e, 6f, and 6i were shows an excellent antioxidant activity than the standard drug butylated hydroxy toluene with IC50 values in the range 12.03 ± 0.11–14.07 ± 0.31 µg/mL. Molecular docking study was also performed to elaborate their possible interactions with Myeloperoxidase enzyme. Furthermore, in silico ADME properties for all the compounds were also studied.
{"title":"1,2,3-Triazolyl Phenylhydrazones as Antioxidant Agents: An Ultrasound Promoted Catalyst-Free Synthesis and Molecular Docking Study","authors":"Smita P. Khare , Tejshri R. Deshmukh , Jaiprakash N. Sangshetti , Vijay M. Khedkar , Bapurao B. Shingate","doi":"10.1080/10406638.2024.2309358","DOIUrl":"10.1080/10406638.2024.2309358","url":null,"abstract":"<div><div>An efficient, ultrasound assisted catalyst-free, green protocol has been developed for the synthesis of 1,2,3-triazolyl phenylhydrazone derivatives under environmentally benign condition. The antioxidant activity for all the synthesized derivatives were evaluated <em>in vitro</em> by using 1,1-diphenylpicrylhydrazyl (DPPH) radical scavenging method. The compounds <strong>6a</strong>, <strong>6e</strong>, <strong>6f</strong>, and <strong>6i</strong> were shows an excellent antioxidant activity than the standard drug butylated hydroxy toluene with IC<sub>50</sub> values in the range 12.03 ± 0.11–14.07 ± 0.31 µg/mL. Molecular docking study was also performed to elaborate their possible interactions with <em>Myeloperoxidase</em> enzyme. Furthermore, <em>in silico</em> ADME properties for all the compounds were also studied.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 6885-6902"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139751542","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The reaction of 6-hydroxypyridine-3-carboxylic acid with guanidine bicarbonate and aminoguanidine hydrogen carbonate, in different molar ratios (1:1, 1:2, and 2:1) yield salts of composition[GunH][C6H4NO3]. H2O(1),[GunH][C6H4NO3][C6H5NO3](2),[GunH]2[C6H3NO3]. H2O(3),[AmguH][C6H4NO3](4),[AmguH][C6H4NO3][C6H5NO3](5),[AmguH]2[C6H3NO3](6). The physicochemical techniques like elemental, spectral and thermal studies were employed to characterize the compounds. All the six as prepared compounds were found to be polycrystalline in nature. The N-N stretching frequency of aminoguanidine moiety appear in the range of 989–914 cm−1. Proton nuclear magnetic resonance (1H NMR) results show signals at7.5–7.9 δ for NH2 protons (1–6). Thermal data of all the as prepared salts exhibit continuous decomposition to produce carbon residue as end products. Density functional theoretical studies were carried out to optimize the structure of the compounds theoretically. The lower molecular orbital energy reveal, the high biological activity of the compounds. The broth disk diffusion method was used to examine the antibacterial activities of compounds (1–6) against Gram-negative and Gram-positive bacterial pathogens. The compound 3 showed potential antibacterial activity against Escherichia coli and Staphylococcus aureus bacteria showing 24 and 20 mm, zone of inhibition respectively. Molecular docking (MD) studies were performed for the compounds, with protein structures of Staphylococcus aureus (5CZZ) and Escherichia coli (3T88). The results were consistent with the experimental data obtained from the antibacterial activity.
{"title":"Synthesis, Characterization and Biological Applications of New Guanidinium and Aminoguanidinium Salts of 6-Hydroxypyridine-3-Carboxylic Acid","authors":"Prabha Devi Balakrishnan , Sangeedha Appusamy , Kanchana Ponnusamy","doi":"10.1080/10406638.2024.2311699","DOIUrl":"10.1080/10406638.2024.2311699","url":null,"abstract":"<div><div>The reaction of 6-hydroxypyridine-3-carboxylic acid with guanidine bicarbonate and aminoguanidine hydrogen carbonate, in different molar ratios (1:1, 1:2, and 2:1) yield salts of composition[GunH][C<sub>6</sub>H<sub>4</sub>NO<sub>3</sub>]. H<sub>2</sub>O(<strong>1</strong>),[GunH][C<sub>6</sub>H<sub>4</sub>NO<sub>3</sub>][C<sub>6</sub>H<sub>5</sub>NO<sub>3</sub>](<strong>2</strong>),[GunH]<sub>2</sub>[C<sub>6</sub>H<sub>3</sub>NO<sub>3</sub>]. H<sub>2</sub>O(<strong>3</strong>),[AmguH][C<sub>6</sub>H<sub>4</sub>NO<sub>3</sub>](<strong>4</strong>),[AmguH][C<sub>6</sub>H<sub>4</sub>NO<sub>3</sub>][C<sub>6</sub>H<sub>5</sub>NO<sub>3</sub>](<strong>5</strong>),[AmguH]<sub>2</sub>[C<sub>6</sub>H<sub>3</sub>NO<sub>3</sub>](<strong>6</strong>). The physicochemical techniques like elemental, spectral and thermal studies were employed to characterize the compounds. All the six as prepared compounds were found to be polycrystalline in nature. The N-N stretching frequency of aminoguanidine moiety appear in the range of 989–914 cm<sup>−1</sup>. Proton nuclear magnetic resonance (<sup>1</sup>H NMR) results show signals at7.5–7.9 δ for NH<sub>2</sub> protons (<strong>1–6</strong>). Thermal data of all the as prepared salts exhibit continuous decomposition to produce carbon residue as end products. Density functional theoretical studies were carried out to optimize the structure of the compounds theoretically. The lower molecular orbital energy reveal, the high biological activity of the compounds. The broth disk diffusion method was used to examine the antibacterial activities of compounds (<strong>1–6</strong>) against Gram-negative and Gram-positive bacterial pathogens. The compound <strong>3</strong> showed potential antibacterial activity against <em>Escherichia coli</em> and <em>Staphylococcus aureus</em> bacteria showing 24 and 20 mm, zone of inhibition respectively. Molecular docking (MD) studies were performed for the compounds, with protein structures of <em>Staphylococcus aureus</em> (5CZZ) and <em>Escherichia coli</em> (3T88). The results were consistent with the experimental data obtained from the antibacterial activity.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 6903-6921"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139948732","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2271647
Coronavirus is a family of viruses that cause upper respiratory infections in humans. Drug properties can be obtained by studying the molecular structure of corresponding drugs. The calculation of the topological index of a drug structure enables scientists to have a better understanding of the physical chemistry and biological characteristics of drugs. In this paper, we study topological indices and find the exact formulas for general topological indices and By the appropriate choice of parameters γ and η, several new/old inequalities that reveal topological indices are obtained.
冠状病毒是导致人类上呼吸道感染的病毒家族。药物特性可以通过研究相应药物的分子结构来获得。通过计算药物结构的拓扑指数，科学家可以更好地了解药物的物理化学和生物学特性。本文对拓扑指数进行了研究，并找到了一般拓扑指数 mSOγ(G) 和 KA(γ,η)1(G) 的精确公式。通过对参数 γ 和 η 的适当选择，可以得到几个揭示拓扑指数的新/旧不等式。
{"title":"On the Molecular Structure of Remdesivir Compound Applied for the Treatment of Corona Virus","authors":"","doi":"10.1080/10406638.2023.2271647","DOIUrl":"10.1080/10406638.2023.2271647","url":null,"abstract":"<div><div>Coronavirus is a family of viruses that cause upper respiratory infections in humans. Drug properties can be obtained by studying the molecular structure of corresponding drugs. The calculation of the topological index of a drug structure enables scientists to have a better understanding of the physical chemistry and biological characteristics of drugs. In this paper, we study topological indices and find the exact formulas for general topological indices <span><math><mrow><mi>m</mi><mi>S</mi><mrow><msub><mrow><mi>O</mi></mrow><mi>γ</mi></msub></mrow><mo>(</mo><mi>G</mi><mo>)</mo></mrow></math></span> and <span><math><mrow><mi>K</mi><mrow><msubsup><mrow><mi>A</mi></mrow><mrow><mo>(</mo><mi>γ</mi><mo>,</mo><mi>η</mi><mo>)</mo></mrow><mn>1</mn></msubsup></mrow><mo>(</mo><mi>G</mi><mo>)</mo></mrow><mo>.</mo></math></span> By the appropriate choice of parameters <em>γ</em> and <em>η</em>, several new/old inequalities that reveal topological indices are obtained.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 6014-6023"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134973799","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-10-20DOI: 10.1080/10406638.2023.2276241
(E)-1-benzyl-3-(2-pyridine-2-yl)hydrazono)indolin-2-one (BPHI), an aromatic moiety, were subjected to a collection of theoretical studies with the help of the Gaussian 09, GaussView 6.0, and Multiwfn-3.8 packages of software. Its molecular geometry, bond angle, and bond length are computed theoretically. Vibrational assignments and PED values are calculated theoretically and were corroborated with experimental IR spectra to gain insight and knowledge about the structural details of BPHI. The theoretical determination of the electronic transitions along with photophysical properties for various mediums (viz., gas, acetonitrile, DMSO), including HOMO and LUMO energy gap are theoretically found from time-dependent—density functional theory (TD-DFT). Interpretation of the Fukui function helps in identifying the active sites in BPHI. To study the topology of BPHI, ELF maps (electron localization function) have been utilized. Alongside, detailed analyses of RDG (reduced density gradient) as well as LOL (localized orbital locator) are also carried out. Interactions pertaining to donor and acceptor moiety in BPHI are computed through natural bond analysis. MEP analysis is used to determine the bioactive site of BPHI. 4F5S crystal structure with respect to BSA protein was used for molecular docking with the help of the CB-dock software and docked results are visualized by Molegro molecular view software.
{"title":"Computational, Reactivity, Fukui Function, Molecular Docking, and Spectroscopic Studies of a Novel (E)-1-Benzyl-3-(2-(Pyrindin-2-yl)Hydrazono)Indolin-2-One","authors":"","doi":"10.1080/10406638.2023.2276241","DOIUrl":"10.1080/10406638.2023.2276241","url":null,"abstract":"<div><div>(E)-1-benzyl-3-(2-pyridine-2-yl)hydrazono)indolin-2-one (<strong>BPHI</strong>), an aromatic moiety, were subjected to a collection of theoretical studies with the help of the Gaussian 09, GaussView 6.0, and Multiwfn-3.8 packages of software. Its molecular geometry, bond angle, and bond length are computed theoretically. Vibrational assignments and PED values are calculated theoretically and were corroborated with experimental IR spectra to gain insight and knowledge about the structural details of <strong>BPHI</strong>. The theoretical determination of the electronic transitions along with photophysical properties for various mediums (viz., gas, acetonitrile, DMSO), including HOMO and LUMO energy gap are theoretically found from time-dependent—density functional theory (TD-DFT). Interpretation of the Fukui function helps in identifying the active sites in <strong>BPHI</strong>. To study the topology of <strong>BPHI</strong>, ELF maps (electron localization function) have been utilized. Alongside, detailed analyses of RDG (reduced density gradient) as well as LOL (localized orbital locator) are also carried out. Interactions pertaining to donor and acceptor moiety in <strong>BPHI</strong> are computed through natural bond analysis. MEP analysis is used to determine the bioactive site of <strong>BPHI</strong>. 4F5S crystal structure with respect to BSA protein was used for molecular docking with the help of the CB-dock software and docked results are visualized by Molegro molecular view software.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 9","pages":"Pages 6263-6283"},"PeriodicalIF":2.4,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135678832","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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