1,1-Diphenyl-3-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)urea

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-Diphenyl-3-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)urea
• 化学式: C₁₅H₁₃N₅O₃S₂
• 分子量: 375.432
• InChiKey: AKNQQMWAXRCKIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-氨基-1,3,4-噻二唑-2-磺酰胺 、 二苯氨基甲酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以59%的产率得到1,1-Diphenyl-3-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)urea
  参考文献：
  名称：

  Carbonic anhydrase inhibitors - Part 94. 1,3,4-Thiadiazole-2-sulfonamide derivatives as antitumor agents?

  摘要：

  Potent sulfonamide inhibitors of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), derivatives of 1,3,4-thiadiazole-2-sulfonamide,sing inhibition constants in the range of 10(-8)-10(-9) M against isozymes II and IV, were shown to act as efficient in vitro tumour cell growth inhibitors with GI,, (molarity of inhibitor producing a 50% inhibition of tumour cell growth) values typically in the range of 0.1-30 mu M against several leukaemia, non-small cell lung cancer, ovarian, melanoma, colon, CNS, renal, prostate and breast cancer cell lines. The mechanism of antitumour action with the new sulfonamides reported here is unknown, but it might involve either inhibition of several CA isozymes (such as CA IX, CA XIII CA XIV) present predominantly in tumour cell membranes, acidification of the intracellular environment as a consequence of CA inhibition, uncoupling of mitochondria and/or strong CA V inhibition, or a combination of several such mechanisms. Such derivatives might lead to the developement of effective novel types of anticancer agents/therapies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00169-0

文献信息

• Carbonic anhydrase inhibitors - Part 94. 1,3,4-Thiadiazole-2-sulfonamide derivatives as antitumor agents?
  作者：C Supuran

  DOI：10.1016/s0223-5234(00)00169-0

  日期：2000.9

  Potent sulfonamide inhibitors of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), derivatives of 1,3,4-thiadiazole-2-sulfonamide,sing inhibition constants in the range of 10(-8)-10(-9) M against isozymes II and IV, were shown to act as efficient in vitro tumour cell growth inhibitors with GI,, (molarity of inhibitor producing a 50% inhibition of tumour cell growth) values typically in the range of 0.1-30 mu M against several leukaemia, non-small cell lung cancer, ovarian, melanoma, colon, CNS, renal, prostate and breast cancer cell lines. The mechanism of antitumour action with the new sulfonamides reported here is unknown, but it might involve either inhibition of several CA isozymes (such as CA IX, CA XIII CA XIV) present predominantly in tumour cell membranes, acidification of the intracellular environment as a consequence of CA inhibition, uncoupling of mitochondria and/or strong CA V inhibition, or a combination of several such mechanisms. Such derivatives might lead to the developement of effective novel types of anticancer agents/therapies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.