Bhuvnesh Singh, Shreya Tewari, Manleen Kaur, Himanshu Sharma, Kumar Vanka, Neetu Singh, Ravi P Singh
{"title":"银催化级联反应合成桥接等铬胺融合吡唑及其抗菌活性研究。","authors":"Bhuvnesh Singh, Shreya Tewari, Manleen Kaur, Himanshu Sharma, Kumar Vanka, Neetu Singh, Ravi P Singh","doi":"10.1021/jacsau.5c00105","DOIUrl":null,"url":null,"abstract":"<p><p>A stereoselective silver catalyzed one pot vinylogous aldol addition followed by a cascade [4+2] cycloaddition reaction of α-arylidene pyrazolinones to <i>in situ</i> generated isochromenylium ions has been developed, which provides an unprecedented bridged [2.2.2] [3.3.1] pentacyclic [5-6-6-6-6] skeleton consisting of an isochroman, chroman, and a pyrazole unit in one molecule with good to high yields as a single diastereomer. This method offers mild reaction conditions, wide substrate compatibility, excellent scalability and easy derivatization. A DFT study was carried out to clarify the reaction mechanism. It was exciting to observe that the unprecedented bridged isochromans synthesized here have shown excellent selectivity toward Gram-positive and Gram-negative bacteria. We demonstrate that while some structures are broad spectrum antibacterial there are two distinct structures that can be explored for selective activity.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"5 9","pages":"4184-4195"},"PeriodicalIF":8.7000,"publicationDate":"2025-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12458016/pdf/","citationCount":"0","resultStr":"{\"title\":\"Bioinspired Synthesis of Bridged Isochromane Fused Pyrazoles by a Silver Catalyzed Cascade Reaction and Its Application for Antibacterial Activity.\",\"authors\":\"Bhuvnesh Singh, Shreya Tewari, Manleen Kaur, Himanshu Sharma, Kumar Vanka, Neetu Singh, Ravi P Singh\",\"doi\":\"10.1021/jacsau.5c00105\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A stereoselective silver catalyzed one pot vinylogous aldol addition followed by a cascade [4+2] cycloaddition reaction of α-arylidene pyrazolinones to <i>in situ</i> generated isochromenylium ions has been developed, which provides an unprecedented bridged [2.2.2] [3.3.1] pentacyclic [5-6-6-6-6] skeleton consisting of an isochroman, chroman, and a pyrazole unit in one molecule with good to high yields as a single diastereomer. This method offers mild reaction conditions, wide substrate compatibility, excellent scalability and easy derivatization. A DFT study was carried out to clarify the reaction mechanism. It was exciting to observe that the unprecedented bridged isochromans synthesized here have shown excellent selectivity toward Gram-positive and Gram-negative bacteria. We demonstrate that while some structures are broad spectrum antibacterial there are two distinct structures that can be explored for selective activity.</p>\",\"PeriodicalId\":94060,\"journal\":{\"name\":\"JACS Au\",\"volume\":\"5 9\",\"pages\":\"4184-4195\"},\"PeriodicalIF\":8.7000,\"publicationDate\":\"2025-08-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12458016/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"JACS Au\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1021/jacsau.5c00105\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/9/22 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"JACS Au","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1021/jacsau.5c00105","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/9/22 0:00:00","PubModel":"eCollection","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Bioinspired Synthesis of Bridged Isochromane Fused Pyrazoles by a Silver Catalyzed Cascade Reaction and Its Application for Antibacterial Activity.
A stereoselective silver catalyzed one pot vinylogous aldol addition followed by a cascade [4+2] cycloaddition reaction of α-arylidene pyrazolinones to in situ generated isochromenylium ions has been developed, which provides an unprecedented bridged [2.2.2] [3.3.1] pentacyclic [5-6-6-6-6] skeleton consisting of an isochroman, chroman, and a pyrazole unit in one molecule with good to high yields as a single diastereomer. This method offers mild reaction conditions, wide substrate compatibility, excellent scalability and easy derivatization. A DFT study was carried out to clarify the reaction mechanism. It was exciting to observe that the unprecedented bridged isochromans synthesized here have shown excellent selectivity toward Gram-positive and Gram-negative bacteria. We demonstrate that while some structures are broad spectrum antibacterial there are two distinct structures that can be explored for selective activity.