Synthesis and biological activity of 2-hydroxynicotinoyl-serine-butyl esters related to antibiotic UK-3A

Ade Arsianti; Muhammad Hanafi; Endang Saepudin; Tsumoru Morimoto; Kiyomi Kakiuchi

doi:10.1016/j.bmcl.2010.05.104

Synthesis and biological activity of 2-hydroxynicotinoyl-serine-butyl esters related to antibiotic UK-3A

Bioorg Med Chem Lett. 2010 Jul 15;20(14):4018-20. doi: 10.1016/j.bmcl.2010.05.104. Epub 2010 Jun 2.

Authors

Ade Arsianti¹, Muhammad Hanafi, Endang Saepudin, Tsumoru Morimoto, Kiyomi Kakiuchi

Affiliation

¹ Graduate School of Materials Science, Nara Institute of Science and Technology, Takayama-cho, Ikoma, Nara 630-0192, Japan. a-arsianti@ms.naist.jp

PMID: 20621723
DOI: 10.1016/j.bmcl.2010.05.104

Abstract

Novel 2-hydroxynicotinoyl-serine-butyl esters have been synthesized. Three-step reactions from L-serine by esterification with n-butanol, amidation with 2-hydroxynicotinic acid and esterification with the corresponding carboxylic acids gave AD-1, AD-2 and AD-3. The toxicity level of esters were determined by Brine shrimp assay, and antibiotic activity was tested against Escherichia coli, Bacillus subtilis, Staphylococcus aureus and Candida albicans. AD-3 showed greater activity as a growth inhibitor of B. subtilis and S. aureus compared to Antimycin A(3).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Infective Agents / chemical synthesis*
Anti-Infective Agents / pharmacology*
Bacillus subtilis / drug effects
Candida albicans / drug effects
Crustacea
Escherichia coli / drug effects
Esters
Lactones / chemical synthesis*
Lactones / pharmacology*
Microbial Sensitivity Tests
Nicotinic Acids / chemical synthesis*
Nicotinic Acids / pharmacology*
Pyridines / chemical synthesis*
Pyridines / pharmacology*
Staphylococcus aureus / drug effects

Substances

Anti-Infective Agents
Esters
Lactones
Nicotinic Acids
Pyridines
UK-3A
2-hydroxynicotinic acid