Manjula Kavala , Raja Rajeswari Tiruveedula , Subramanyam Chennamsetty
{"title":"通过纳米氧化锌催化微波法合成新型铬烯基膦酸盐:通过分子对接、ADMET 分析和 α 淀粉酶抑制作用探索潜在的抗糖尿病药物","authors":"Manjula Kavala , Raja Rajeswari Tiruveedula , Subramanyam Chennamsetty","doi":"10.1080/00397911.2024.2388799","DOIUrl":null,"url":null,"abstract":"<div><p>A more efficient and environmentally friendly approach has been developed for synthesizing phosphonates through the Michaelis-Arbuzov reaction, catalyzed by nano-ZnO in a solvent-free environment, utilizing microwave irradiation. Before synthesis, each compound underwent <em>in silico</em> ADMET analysis and molecular docking to assess drug-like characteristics and their potential to inhibit <em>α</em>-amylase. The structure of the newly synthesized compounds was validated using spectroscopic analysis, and their <em>in vitro</em> inhibitory effects on <em>α</em>-amylase were assessed. Among the compounds, dimethyl 2-(anthracen-10-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6j</strong>), dimethyl 2-(naphthalen-1-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6h</strong>), and dimethyl 2-(1-methyl-1H-indol-3-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6e</strong>) displayed the highest inhibitory activity compared to the reference substance, acarbose. Additionally, compounds dimethyl 2-(benzo[d][1,3]dioxol-4-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6i</strong>), dimethyl 4-oxo-2-phenyl-4H-chromen-6-yl-6-phosphonate (<strong>6a</strong>), and dimethyl 2-(1H-indol-5-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6g</strong>) exhibited nearly equivalent effective inhibitory activity when compared to the standard. The remaining compounds demonstrated moderate to good enzyme inhibition.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":1.8000,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of novel chromenyl phosphonates via nano-ZnO-catalyzed microwave method: Exploring potential anti-diabetic agents through molecular docking, ADMET analysis, and α-amylase inhibition\",\"authors\":\"Manjula Kavala , Raja Rajeswari Tiruveedula , Subramanyam Chennamsetty\",\"doi\":\"10.1080/00397911.2024.2388799\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A more efficient and environmentally friendly approach has been developed for synthesizing phosphonates through the Michaelis-Arbuzov reaction, catalyzed by nano-ZnO in a solvent-free environment, utilizing microwave irradiation. Before synthesis, each compound underwent <em>in silico</em> ADMET analysis and molecular docking to assess drug-like characteristics and their potential to inhibit <em>α</em>-amylase. The structure of the newly synthesized compounds was validated using spectroscopic analysis, and their <em>in vitro</em> inhibitory effects on <em>α</em>-amylase were assessed. Among the compounds, dimethyl 2-(anthracen-10-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6j</strong>), dimethyl 2-(naphthalen-1-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6h</strong>), and dimethyl 2-(1-methyl-1H-indol-3-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6e</strong>) displayed the highest inhibitory activity compared to the reference substance, acarbose. Additionally, compounds dimethyl 2-(benzo[d][1,3]dioxol-4-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6i</strong>), dimethyl 4-oxo-2-phenyl-4H-chromen-6-yl-6-phosphonate (<strong>6a</strong>), and dimethyl 2-(1H-indol-5-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (<strong>6g</strong>) exhibited nearly equivalent effective inhibitory activity when compared to the standard. The remaining compounds demonstrated moderate to good enzyme inhibition.</p></div>\",\"PeriodicalId\":22119,\"journal\":{\"name\":\"Synthetic Communications\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-08-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthetic Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S0039791124000870\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124000870","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis of novel chromenyl phosphonates via nano-ZnO-catalyzed microwave method: Exploring potential anti-diabetic agents through molecular docking, ADMET analysis, and α-amylase inhibition
A more efficient and environmentally friendly approach has been developed for synthesizing phosphonates through the Michaelis-Arbuzov reaction, catalyzed by nano-ZnO in a solvent-free environment, utilizing microwave irradiation. Before synthesis, each compound underwent in silico ADMET analysis and molecular docking to assess drug-like characteristics and their potential to inhibit α-amylase. The structure of the newly synthesized compounds was validated using spectroscopic analysis, and their in vitro inhibitory effects on α-amylase were assessed. Among the compounds, dimethyl 2-(anthracen-10-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6j), dimethyl 2-(naphthalen-1-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6h), and dimethyl 2-(1-methyl-1H-indol-3-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6e) displayed the highest inhibitory activity compared to the reference substance, acarbose. Additionally, compounds dimethyl 2-(benzo[d][1,3]dioxol-4-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6i), dimethyl 4-oxo-2-phenyl-4H-chromen-6-yl-6-phosphonate (6a), and dimethyl 2-(1H-indol-5-yl)-4-oxo-4H-chromen-6-yl-6-phosphonate (6g) exhibited nearly equivalent effective inhibitory activity when compared to the standard. The remaining compounds demonstrated moderate to good enzyme inhibition.
期刊介绍:
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.