Bioinspired Synthesis of Bridged Isochromane Fused Pyrazoles by a Silver Catalyzed Cascade Reaction and Its Application for Antibacterial Activity
Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide 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.
Source: JACS Au
Authors: Bhuvnesh Singh, Shreya Tewari, Manleen Kaur, Himanshu Sharma, Kumar Vanka, Neetu Singh, Ravi P. Singh
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $3,500
Funders: Department of Science and Technology, Ministry of Science and Technology, India, Council of Scientific and Industrial Research, India, University Grants Commission, Ministry of Education, India, Indian Institute of Science Education and Research Pune, Indian Institute of Science Education and Research Mohali, Science and Engineering Research Board
OpenAlex ID: W4413623197