methyl (3S)-3-methyl-8-[8-nitro-4-oxo-6-(trifluoromethyl)-1,3-benzothiazin-2-yl]-1,4-dioxa-8-azaspiro[4.5]decane-10-carboxylate | 1396842-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: methyl (3S)-3-methyl-8-[8-nitro-4-oxo-6-(trifluoromethyl)-1,3-benzothiazin-2-yl]-1,4-dioxa-8-azaspiro[4.5]decane-10-carboxylate
• 英文别名: methyl (3S)-3-methyl-8-[8-nitro-4-oxo-6-(trifluoromethyl)-1,3-benzothiazin-2-yl]-1,4-dioxa-8-azaspiro[4.5]decane-6-carboxylate
• CAS: 1396842-57-1
• 化学式: C₁₉H₁₈F₃N₃O₇S
• 分子量: 489.429
• InChiKey: TUHYXNFWDMPTTO-ZSZQOMGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  、 甲基 (2R,3S)-(+)-2,3-二羟基-3-苯基丙酸盐 在 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以39%的产率得到methyl (3S)-3-methyl-8-[8-nitro-4-oxo-6-(trifluoromethyl)-1,3-benzothiazin-2-yl]-1,4-dioxa-8-azaspiro[4.5]decane-10-carboxylate
  参考文献：
  名称：

  Identification of Antitubercular Benzothiazinone Compounds by Ligand-Based Design

  摘要：

  1,3-Benzothiazin-4-ones (BTZs) are a novel class of TB drug candidates with potent activity against M. tuberculosis. An in silico ligand-based model based on structure-activity data from 170 BTZ compounds was used to design a new series. Compounds were tested against a panel of mycobacterial strains and were profiled for cytotoxicity, stability, and antiproliferative effects. Several of the compounds showed improved activity against MDR-TB while retaining low toxicity with higher microsomal, metabolic, and plasma stability.

  DOI：

  10.1021/jm3008882

文献信息

• Identification of Antitubercular Benzothiazinone Compounds by Ligand-Based Design
  作者：Tomislav Karoli、Bernd Becker、Johannes Zuegg、Ute Möllmann、Soumya Ramu、Johnny X. Huang、Matthew A. Cooper

  DOI：10.1021/jm3008882

  日期：2012.9.13

  1,3-Benzothiazin-4-ones (BTZs) are a novel class of TB drug candidates with potent activity against M. tuberculosis. An in silico ligand-based model based on structure-activity data from 170 BTZ compounds was used to design a new series. Compounds were tested against a panel of mycobacterial strains and were profiled for cytotoxicity, stability, and antiproliferative effects. Several of the compounds showed improved activity against MDR-TB while retaining low toxicity with higher microsomal, metabolic, and plasma stability.