5-(5-methyl-4-nitro-2-thienyl)-1,3,4-oxathiazol-2-one | 36050-10-9

• 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: 5-(5-methyl-4-nitro-2-thienyl)-1,3,4-oxathiazol-2-one
• 英文别名: 5-Methyl-4-nitrothiophene-2-carboxamide
• CAS: 36050-10-9
• 化学式: C₆H₆N₂O₃S
• 分子量: 186.191
• InChiKey: DFQLMQGFILOBCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  295.5±40.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯羰基亚磺酰氯 、 5-(5-methyl-4-nitro-2-thienyl)-1,3,4-oxathiazol-2-one 以 甲苯 为溶剂， 反应 20.0h， 以70%的产率得到HT1171
  参考文献：
  名称：

  Cycloaddition of C60 fullerene to stable 2-RSO2-benzonitrile oxides

  摘要：

  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.

  DOI：

  10.1007/bf02495359
• 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 10.0h， 生成 5-(5-methyl-4-nitro-2-thienyl)-1,3,4-oxathiazol-2-one
  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

• [EN] THIENOPYRROLE DERIVATIVES AS ITK INHIBITORS<br/>[FR] COMPOSÉS THIÉNOPYRROLE COMME INHIBITEURS DE L'ITK
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2014041518A1

  公开（公告）日：2014-03-20

  The present invention is directed to thienopyrrole compounds of formula (I) as Tec kinase inhibitors, in particular ITK (interleukin-2 inducible tyrosine kinase) inhibitors. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders mediated by ITK.

  本发明涉及一种化合物，其化学式为(I)，作为Tec激酶抑制剂，特别是ITK（白细胞介素-2诱导酪氨酸激酶）抑制剂。本文还提供了制备所述化合物的方法、用于合成的中间体、药物组合物以及治疗或预防由ITK介导的疾病、症状和/或障碍的方法。
• 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.
• 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.