alexa Abstract | DESIGN AND SYNTHESIS OF 4-[2’-(5’- NITRO)] IMIDAZOLYL BENZOYL (N-METHYL) AMINO ACIDS AND PEPTIDES

International Journal of Drug Development and Research
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Abstract

In the past two decades, a wide variety of bioactive peptides have been discovered. Condensation of heterocyclic moieties viz nicotinic acid, thiazole coumarin, quinolin, furan, imidazole etc. with amino acids and peptides resulted in compounds with potent biological activities. Many of the heterocyclic found to exhibit antifungal, antibacterial, cytotoxic, antineoplastic, insectisidal, antiinflammatory, anthelmintic, tyrosinase inhibitory and melanin production inhibitory activities. Metronidazole, serconidazole, flucanazole are well known marketed drugs. Introduction of D-amino acids and N-methylation of amino acids like tyrosine, valine, alanine etc enhanced antimicrobial activity. Hence an attempt is made towards the synthesis of 5-nitroimidazolyl-benzoic acid derivative of N-methylamino acids and peptide using solution phase technique of peptide synthesis. The method includes the introduction of tert-butyloxy carboxyl group (Boc) to amino acids to protect the amino group forming Boc-amino acids .The protection of carboxyl group was done by converting the amino acids into corresponding methyl ester. The protected amino acids were coupled using diisopropylcarbodimide and triethylamine to get protected dipeptides. N-methylation was done by treating with methyl iodide and sodium hydride. The ester group was then removed by lithium hydroxide. The Boc(N-methyl)dipetide were coupled to amino acids or Boc(Nmethyl) dipeptide were coupled to 4-[2-(5-nitro)imidazoly]benzoic acids.

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Author(s): PARAMITA DAS AND MHIMAJA

Keywords

Imidazole, N-Methylation, Antibacterial, Antifungal, Anthelmintic

 
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