methyl α-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetate

• 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: methyl α-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetate
• 英文别名: Methyl 2-[[5-(5-nitro-2-thienyl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetate；methyl 2-[[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]acetate
• 化学式: C₉H₇N₃O₄S₃
• 分子量: 317.37
• InChiKey: FYHVSPKEBHDLJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  180
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-((5-nitrothiophen-2-yl)methylene)hydrazinecarbothioamide 在 盐酸 、 氢氧化钾 、 ammonium ferric sulfate 、 铜 、 硫脲 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 8.5h， 生成 methyl α-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetate
  参考文献：
  名称：

  Antituberculosis agents VIII

  摘要：

  A series of alkyl alpha-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetic acid esters 6a-e were synthesized and evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis strain H(37)Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The antituberculosis data indicated that methyl, propyl, buthyl and benzyl esters showed a significant in vitro antimycobacterium tuberculosis activity (MIC=0.39-0.78 microg/ml) and the ethyl analogue did not show a good activity (MIC>6.25 microg/ml, %inhibition=58). The most active compound of the series was n-propyl alpha-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetate (6c) with MIC value of 0.39 microg/ml.

  DOI：

  10.1016/s0014-827x(03)00158-7

文献信息

• Antituberculosis agents VIII
  作者：Alireza Foroumadi、Zahra Kiani、Fatemeh Soltani

  DOI：10.1016/s0014-827x(03)00158-7

  日期：2003.11

  A series of alkyl alpha-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetic acid esters 6a-e were synthesized and evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis strain H(37)Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The antituberculosis data indicated that methyl, propyl, buthyl and benzyl esters showed a significant in vitro antimycobacterium tuberculosis activity (MIC=0.39-0.78 microg/ml) and the ethyl analogue did not show a good activity (MIC>6.25 microg/ml, %inhibition=58). The most active compound of the series was n-propyl alpha-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetate (6c) with MIC value of 0.39 microg/ml.