Hissana Ather, Aysha A. Ali Theban, Fareeaa Ashar, Boshra Yahya A. Mohammad Essa, Yomna Ali A. Albarqi, Ghadah Saad A. Alshehri, and Renad Abdulhadi M. Almodawi
{"title":"1,3-取代吡唑类亚甲基衍生物的合成、表征、分子对接研究及抗菌活性研究","authors":"Hissana Ather, Aysha A. Ali Theban, Fareeaa Ashar, Boshra Yahya A. Mohammad Essa, Yomna Ali A. Albarqi, Ghadah Saad A. Alshehri, and Renad Abdulhadi M. Almodawi","doi":"10.3987/com-23-14877","DOIUrl":null,"url":null,"abstract":"<span>Two different series of azomethine derivatives of 1,3-substitued pyrazoles were synthesized from the intermediates 3-(4-chlorophenyl)-1-phenyl-1</span><span>H</span><span>-pyrazole-4-carbaldehyde (</span><span>3a</span><span>) and 3-(furan-2-yl)-1-phenyl-1</span><span>H</span><span>-pyrazole-4-carbaldehyde (</span><span>3b</span><span>) by the condensation of various substituted anilines. The intermediates were obtained from the appropriate phenylhydrazones via Vilsmeier–Haack reaction. The synthesized compounds were characterized by IR, </span><span>1</span><span>H NMR and MASS spectral studies. Molecular docking studies results revealed that </span><span>4a7</span><span> and </span><span>4a8</span><span> showed highest binding affinity against fungal target secreted aspartic proteinase (Sap) 1 (</span><span>2QZW</span><span>) and compounds </span><span>4a8</span><span> and </span><span>4a5</span><span> showed highest binding affinity against bacterial target glucosamine-6-phosphate synthase </span><span>(2VF5</span><span>). </span><span>In vitro</span><span> antimicrobial activity of corresponding azomethine derivatives were assessed on Gram-positive and Gram-negative bacteria. Antifungal activity was assessed on </span><span>Candida albicans</span><span>. The results revealed that six out of fifteen compounds screened have shown good antimicrobial activity. Among them, </span><span>4a1</span><span>,</span><span> 4a4</span><span>,</span><span> 4a6 </span><span>and</span><span> 4a7</span><span> shown good inhibition against </span><span>Candida albicans</span><span>.</span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis, Characterization, Molecular Docking Studies and Antimicrobial Activity of Azomethine Derivatives of 1,3-Substituted Pyrazoles\",\"authors\":\"Hissana Ather, Aysha A. Ali Theban, Fareeaa Ashar, Boshra Yahya A. Mohammad Essa, Yomna Ali A. Albarqi, Ghadah Saad A. Alshehri, and Renad Abdulhadi M. Almodawi\",\"doi\":\"10.3987/com-23-14877\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<span>Two different series of azomethine derivatives of 1,3-substitued pyrazoles were synthesized from the intermediates 3-(4-chlorophenyl)-1-phenyl-1</span><span>H</span><span>-pyrazole-4-carbaldehyde (</span><span>3a</span><span>) and 3-(furan-2-yl)-1-phenyl-1</span><span>H</span><span>-pyrazole-4-carbaldehyde (</span><span>3b</span><span>) by the condensation of various substituted anilines. The intermediates were obtained from the appropriate phenylhydrazones via Vilsmeier–Haack reaction. The synthesized compounds were characterized by IR, </span><span>1</span><span>H NMR and MASS spectral studies. Molecular docking studies results revealed that </span><span>4a7</span><span> and </span><span>4a8</span><span> showed highest binding affinity against fungal target secreted aspartic proteinase (Sap) 1 (</span><span>2QZW</span><span>) and compounds </span><span>4a8</span><span> and </span><span>4a5</span><span> showed highest binding affinity against bacterial target glucosamine-6-phosphate synthase </span><span>(2VF5</span><span>). </span><span>In vitro</span><span> antimicrobial activity of corresponding azomethine derivatives were assessed on Gram-positive and Gram-negative bacteria. Antifungal activity was assessed on </span><span>Candida albicans</span><span>. The results revealed that six out of fifteen compounds screened have shown good antimicrobial activity. Among them, </span><span>4a1</span><span>,</span><span> 4a4</span><span>,</span><span> 4a6 </span><span>and</span><span> 4a7</span><span> shown good inhibition against </span><span>Candida albicans</span><span>.</span>\",\"PeriodicalId\":13166,\"journal\":{\"name\":\"Heterocycles\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.8000,\"publicationDate\":\"2023-11-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Heterocycles\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.3987/com-23-14877\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Heterocycles","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3987/com-23-14877","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis, Characterization, Molecular Docking Studies and Antimicrobial Activity of Azomethine Derivatives of 1,3-Substituted Pyrazoles
Two different series of azomethine derivatives of 1,3-substitued pyrazoles were synthesized from the intermediates 3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (3a) and 3-(furan-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (3b) by the condensation of various substituted anilines. The intermediates were obtained from the appropriate phenylhydrazones via Vilsmeier–Haack reaction. The synthesized compounds were characterized by IR, 1H NMR and MASS spectral studies. Molecular docking studies results revealed that 4a7 and 4a8 showed highest binding affinity against fungal target secreted aspartic proteinase (Sap) 1 (2QZW) and compounds 4a8 and 4a5 showed highest binding affinity against bacterial target glucosamine-6-phosphate synthase (2VF5). In vitro antimicrobial activity of corresponding azomethine derivatives were assessed on Gram-positive and Gram-negative bacteria. Antifungal activity was assessed on Candida albicans. The results revealed that six out of fifteen compounds screened have shown good antimicrobial activity. Among them, 4a1, 4a4, 4a6 and 4a7 shown good inhibition against Candida albicans.
期刊介绍:
Since its inception in 1973 HETEROCYCLES has provided a platform for the rapid exchange of research in the areas of organic, pharmaceutical, analytical, and medicinal chemistry of heterocyclic compounds in addition to communications, papers, reviews, a special section of the journal presents newly-discovered natural products whose structure has recently been established.
Another section is devoted to the total synthesis of previously documented natural products with heterocyclic ring systems.
Due to the fact that the journal is able to publish articles within two months of receipt of the manuscripts, researchers in this field can obtain up-to-date information on heterocyclic research by reading Heterocycles regularly.
Audience: Organic and Physical Organic Chemists, Biochemists, Pharmacologists and Scientists studying heterocyclic compounds