HT1171 | 192880-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: HT1171
• 英文别名: 5-(2-methyl-3-nitrothiophen-5-yl)-1,3,4-oxathiazol-2-one；5-(5-Methyl-4-nitro-2-thienyl)-1,3,4-oxathiazol-2-one；5-(5-methyl-4-nitrothiophen-2-yl)-1,3,4-oxathiazol-2-one
• CAS: 192880-96-9
• 化学式: C₇H₄N₂O₄S₂
• 分子量: 244.252
• InChiKey: ILBBOKHACYTXRK-UHFFFAOYSA-N

物化性质

• 溶解度：
  二甲基亚砜：>10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基-3-硝基-5-噻吩甲酸 在 ammonium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 26.0h， 生成 HT1171
  参考文献：
  名称：

  3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents

  摘要：

  Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guerin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 mu g/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 mu M, indicating its better safety profile. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.065

文献信息

• Cycloaddition of C60 fullerene to stable 2-RSO2-benzonitrile oxides
  作者：V. N. Drozd、V. N. Knyazev、F. M. Stoyanovich、F. M. Dolgushin、A. I. Yanovsky

  DOI：10.1007/bf02495359

  日期：1997.1

  The interaction of stable 2-RSO2-benzonitrile oxides 1a-c (R = Ph, Bu-t, or PhMeN) with C-60 fullerene proceeds at the double (6,6)-bond of fullerene as the [3+2] cycloaddition to form the corresponding isoxazolines 2a-c. The molecular structure of compound 2b was established by X-ray structural analysis. The interaction of C-60 fullerene with 2-(5-methyl-4-nitrothiophene)carbonitrile sulfide, which was obtained by thermolysis of 5-(5'-methyl-4'-nitro-2'-thienyl)-1,3,4-oxathiazol-2-one, affords only unstable products.
• 3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents
  作者：Jianzhong Yang、Weiyi Pi、Li Xiong、Wei Ang、Tao Yang、Jun He、Yuanyuan Liu、Ying Chang、Weiwei Ye、Zhenling Wang、Youfu Luo、Yuquan Wei

  DOI：10.1016/j.bmcl.2012.12.065

  日期：2013.3

  Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guerin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 mu g/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 mu M, indicating its better safety profile. (C) 2012 Elsevier Ltd. All rights reserved.