A structure-activity relationship of some derivatives of 2-phenylsubstituted- 3-hydroxyquinolin-4(1H)-one-7-carboxamides was systematically studied using combinatorial solid-phase synthesis and in vitro cytotoxic activity screening on representative cancer lines. The effect of substituent type in position 2 as well as of the carboxamide group was investigated via synthesis of generic libraries constructed with respect to polarity and bulkiness of appropriate substituents. The process of development afforded a set of compounds with significant cytotoxic activity. Subsequently, corresponding 2-phenylsubstituted-3-hydroxyquinolin-4(1H)-one-6-carboxamides and 2-phenylsubstituted-3-hydroxyquinolin-4(1H)-one-8-carboxamides were prepared to evaluate the influence of the carboxamide group position on the resulting biological activity.
A simple pathway leading to 3-hydroxyquinoline-4(1H)-one-5-carboxamides was developed. Target compounds were identified as potential anticancer agents and fluorescent labels.
4-Chloro-2-fluoro-5-nitrobenzoic acid is a commercially available multireactive building block that can serve as a starting material in heterocyclic oriented synthesis (HOS) leading to various condensed nitrogenous cycles. This work describes its ability for the preparation of substituted nitrogenous heterocycles having 5-7-membered cycles via polymer-supported o-phenylendiamines. Immobilization of this compound on Rink resin followed by further chlorine substitution, reduction of a nitro group and appropriate cyclization afforded benzimidazoles, benzotriazoles, quinoxalinones, benzodiazepinediones and succinimides. The method developed is suitable for the synthesis of diverse libraries including the mentioned types of heterocycles, which have significant importance in current drug discovery. In this paper, we also report limitation of these method and unsuccessful attempt to prepare an 8-membered benzodiazocine cycle.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.