2,4- and 2,5-disubstituted arylthiazoles: Rapid synthesis by C-H coupling and biological evaluation

Lilia Lohrey, Takahiro N. Uehara, Satoshi Tani, Junichiro Yamaguchi, Hans Ulrich Humpf, Kenichiro Itami

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Life-threatening infections caused by bacteria that have developed resistance to common antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA), have become a serious problem in hospitals and other areas all over the world. Thus, the development of an effective class of antibiotics against these bacteria is an urgent subject. Herein, we report a step-economical and diversity-oriented synthesis of a series of 2-arylidenehydrazinyl-4- arylthiazole and 2-arylidenehydrazinyl-5-arylthiazole analogues that utilizes C-H coupling methodologies. A library of 54 new congeners were synthesized and tested for their biological potential. Moreover, new knowledge regarding the structure-activity relationships (SARs) of these heterobiaryl compounds was collected.

Original languageEnglish
Pages (from-to)3387-3394
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number16
DOIs
Publication statusPublished - 2014 Jun
Externally publishedYes

Keywords

  • Antibiotics
  • C-H arylation
  • Cross-coupling
  • Structure-activity relationships
  • Thiazoles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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