Synthesis and antibacterial activity of Schiff bases and amines derived from alkyl 2-2-formyl-4-nitrophenoxyalkanoatesReport as inadecuate




Synthesis and antibacterial activity of Schiff bases and amines derived from alkyl 2-2-formyl-4-nitrophenoxyalkanoates - Download this document for free, or read online. Document in PDF available to download.

Medicinal Chemistry Research

, Volume 24, Issue 9, pp 3561–3577

First Online: 15 July 2015Received: 27 November 2014Accepted: 27 June 2015

Abstract

A series of novel Schiff bases and secondary amines were obtained in good yields, as a result of the reductive amination of alkyl 2-2-formyl-4-nitrophenoxyalkanoates with both aniline and 4-methoxyaniline under established mild reaction conditions. Sodium triacetoxyborohydride as well as hydrogen in the presence of palladium on carbon were used as efficient reducing agents of the Schiff bases, in both direct and stepwise reductive amination processes. The Schiff bases, amines, and amine hydrochlorides were designed as potential antibacterial agents, and structure–activity relationship could be established following in vitro assays against Gram-positive and Gram-negative bacteria. The minimal inhibitory concentration and zone of inhibition were also determined. In these tests, some of Schiff bases and secondary amine hydrochlorides showed moderate-to-good activity against Gram-positive bacteria, including S. aureus, M. luteus, and S. mutans.

KeywordsAmines Antibacterial activities Esters 2-2-Formylphenoxyalkanoic acids Reduction Reductive amination Schiff bases Electronic supplementary materialThe online version of this article doi:10.1007-s00044-015-1397-6 contains supplementary material, which is available to authorized users.

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Author: Agata Goszczyńska - Halina Kwiecień - Karol Fijałkowski

Source: https://link.springer.com/







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