Zhang Gang, Aldrich Courtney C
State Key Laboratory of Bioactive Substances and Function of Natural Medicine, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, People's Republic of China.
Acta Crystallogr C Struct Chem. 2019 Aug 1;75(Pt 8):1031-1035. doi: 10.1107/S2053229619009185. Epub 2019 Jul 5.
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-(trifluoromethyl)-4H-1,3-benzothiazin-4-one, CHFNOS} 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 H NMR, C NMR, HRMS, IR, and X-ray crystallography. The cyclohexyl moiety is observed to be nearly perpendicular to the core formed by the 1,3-benzothiazin-4-one and piperazine groups. The central piperazine ring adopts a slightly distorted chair conformation caused by sp-hybridization of the nitro N atom, which donates into the electron-deficient 1,3-benzothiazin-4-one group.
结核分枝杆菌（Mtb）是结核病（TB）的主要病原体，感染了超过四分之一的人类，目前是单一病原体导致传染病死亡的主要原因。马佐酮{2-[4-(环己基甲基)哌嗪-1-基]-8-硝基-6-(三氟甲基)-4H-1,3-苯并噻嗪-4-酮，CHFNOS}是一种有前景的新型药物，用于治疗敏感和耐药结核病，已成功完成I期临床试验。我们通过1H NMR、13C NMR、HRMS、IR和X射线晶体学报告了其完整的光谱和结构表征。观察到环己基部分几乎垂直于由1,3-苯并噻嗪-4-酮和哌嗪基团形成的核心。中心哌嗪环由于硝基N原子的sp杂化而呈现出略微扭曲的椅式构象，该硝基N原子向缺电子的1,3-苯并噻嗪-4-酮基团供电子。
