Macozinone: Revised synthesis and crystal structure of a promising new drug for treating drug-sensitive and drug-resistant tuberculosis

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Mycobacterium tuberculosis (Mtb), the principal etiological agent of tuberculosis (TB), infects over one-quarter of humanity and is now the leading cause of infectious disease mortality by a single pathogen. Macozinone {2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluorometh yl)-4H-1,3-benzo thia zin-4-one, C20H23F3N4O3S} is a promising new drug for treating drug-sensitive and drug-resistant TB that has successfully completed phase I clinical trials. We report the complete spectroscopic and structural characterization by 1H NMR, 13C NMR, HRMS, IR, and X-ray crystallography. The cyclo hexyl moiety is observed to be nearly perpendicular to the core formed by the 1,3-benzo thia zin-4-one and piperazine groups. The central piperazine ring adopts a slightly distorted chair conformation caused by sp 2-hybridization of the nitro N atom, which donates into the electron-deficient 1,3-benzo thia zin-4-one group.

Original languageEnglish (US)
Pages (from-to)1031-1035
Number of pages5
JournalActa Crystallographica Section C: Structural Chemistry
Volume75
DOIs
StatePublished - Aug 1 2019

Keywords

  • Crystal structure
  • Drug resistant
  • Drug sensitive
  • Macozinone
  • Synthesis
  • Tuberculosis.

PubMed: MeSH publication types

  • Journal Article
  • Research Support, Non-U.S. Gov't
  • Video-Audio Media

Fingerprint Dive into the research topics of 'Macozinone: Revised synthesis and crystal structure of a promising new drug for treating drug-sensitive and drug-resistant tuberculosis'. Together they form a unique fingerprint.

Cite this