Synthesis of New DNA Gyrase Inhibitors: Application of the DMSO Oxidation to the Conversion of the Amine into the Imine

Yoshikazu Jinbo, Hirosato Kondo, Masahiro Taguchi, Fumio Sakamoto, Goro Tsukamoto

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27 Citations (Scopus)

Abstract

A novel type of pyridonecarboxylic acid with a planar thiazolopyrazine-incorporated tetracyclic skeleton, 4,9b-diaza-8,9b-dihydro-6-fluoro-5-(4-methyl-1-piperazinyl)-8-oxo-1-thia-1H-cyclopenta-[cd]phenalene-9-carboxylic acid (3), was prepared. Compound 3 was a potent inhibitor of DNA gyrase and exhibited attractive antibacterial activity against both Gram-positive and Gram-negative bacteria. In the course of the synthetic studies, we have found a new oxidation method of the amine 4 to the imine 5 with DMSO activated by trifluoroacetic anhydride or oxalyl chloride. The DMSO/trifluoroacetic anhydride method gave the byproduct 8, an unusual (methylthio)methyl adduct. The DMSO/oxalyl chloride method gave the byproducts 9 and 10, a (methylthio)methyl ester, and a halogen adduct, respectively. The mechanisms of these oxidations are also discussed.

Original languageEnglish
Pages (from-to)6057-6062
Number of pages6
JournalJournal of Organic Chemistry
Volume59
Issue number20
DOIs
Publication statusPublished - Oct 1 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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