Novel synthetic methods of dibenzo a_d cycloheptanoids and triazol_3_ylidene derivatives from 1_3_Indanediones including Carbamyl and#946;_Lactam Hybrids and evaluation of their anticancer activity

Abstract

The thesis entitled Novel synthetic methods of dibenzo[a,d]cycloheptanoids and triazol-3- ylidene derivatives from 1,3-Indanediones including Carbamyl and#946;-Lactam Hybrids and evaluation of their anticancer activity has been divided into five chapters. newline newlineCHAPTER-1 newlineThe chapter outlines the importance and biological applications of and#946;-lactam (2-azetidinone), general methods for the synthesis of dibenzocycloheptanes and their biological activities. Introduction and general methods for the synthesis of 1,2,4-Triazoles and their biological activities were explained in detail. newlineCHAPTER-2 newlineThis chapter describes a simple and practical protocol for the direct synthesis of a series of new hybrid molecules of carbamyl and#946;-lactam derivatives bearing quinone moiety via [2and#8201;+and#8201;2] cycloaddition of Staudinger reaction. The and#946;-lactam ring is tolerating carbamylation and further leads to a variety of quinone hybrid derivatives. The structures of the compounds were characterized by IR, NMR, and HRMS analysis. All the new synthesized compounds were screened for theirin vitro antiproliferative activity using an MTT assay analysis. Out of fourteen derivatives synthesized in the current study, compounds 2.9h, 2.9k, 2.9iand2.9b exhibited the very good anticancer activities in B16F10 cell line. newlineCHAPTER-3 newlineThis chapter represents novel and unexpected insertion reaction of 2-arylidene-1,3-indandiones onto arynes via [2 + 2]-cycloaddition followed by ring expansion (retro [2 + 2]-cycloaddition) is developed to afford dibenzo[a,d]cycloheptanoid derivatives in good yields with single diastereomer. This reaction represents a rare instance of cyclic enone C-C bond insertion (Acyl- Alkenylation) in aryne chemistry. Interestingly, 2-arylidene-1,3-indandiones bearing electron rich functional groups provided dibenz[a,c]anthracene-9,14-dione derivatives via [4 + 2] cycloaddition followed by ring expansion. newline newline newline