1-amino-3-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)urea | 955132-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-amino-3-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)urea
• CAS: 955132-20-4
• 化学式: C₃H₅N₅OS₂
• 分子量: 191.238
• InChiKey: TWYZXRQRSYNTBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-溴靛红 、 1-amino-3-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)urea 在 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到4-(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)-1-(5-bromo-2-oxoindolin-3-ylidene)semicarbazide
  参考文献：
  名称：

  Design, synthesis, and docking studies of new 1,3,4-thiadiazole-2-thione derivatives with carbonic anhydrase inhibitory activity

  摘要：

  A new series of 1,3,4-thiadiazole-2-thione derivatives have been prepared and assayed for the inhibition of three physiologically relevant carbonic anhydrase (CA, EC 4.2. 1. 1) isozymes, the cytosolic human isozymes I and II, and the transmembrane, tumor-associated hCA IX. Against hCA I the investigated thiones, showed inhibition constants in the range of 2.55-222 mu M, against hCA II in the range of 2.0-433 mu M, and against hCA IX in the range of 1.25-148 mu M. Compound 5c, 4-(4,5-dihydro-5-thioxo-1,3,4thiadi izol-2-yl)-1-(5-nitro-2-oxoindolin-3-ylidene)semicarbazide showed interesting inhibition of the turnor-associated hCA IX with K-1 value of 1.25 mu M, being the first non-sulforiamide type inhibitor of such activity. This result is rather important taking into consideration the known antitumor activity of thiones. In addition, docking of the tested compounds into CA II active site was performed in order to predict the affinity and orientation of these compounds at the isozyme active site. The results showed similar orientation of the target compounds at CA II active site compared with reported sulfonamide type CAls with the thione group acting as a zinc-binding moiety. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.044
• 作为产物：
  描述：

  (5-thioxo-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-carbamic acid ethyl ester 在 一水合肼 作用下， 以 水 为溶剂， 反应 48.0h， 以84%的产率得到1-amino-3-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)urea
  参考文献：
  名称：

  Design, synthesis, and docking studies of new 1,3,4-thiadiazole-2-thione derivatives with carbonic anhydrase inhibitory activity

  摘要：

  A new series of 1,3,4-thiadiazole-2-thione derivatives have been prepared and assayed for the inhibition of three physiologically relevant carbonic anhydrase (CA, EC 4.2. 1. 1) isozymes, the cytosolic human isozymes I and II, and the transmembrane, tumor-associated hCA IX. Against hCA I the investigated thiones, showed inhibition constants in the range of 2.55-222 mu M, against hCA II in the range of 2.0-433 mu M, and against hCA IX in the range of 1.25-148 mu M. Compound 5c, 4-(4,5-dihydro-5-thioxo-1,3,4thiadi izol-2-yl)-1-(5-nitro-2-oxoindolin-3-ylidene)semicarbazide showed interesting inhibition of the turnor-associated hCA IX with K-1 value of 1.25 mu M, being the first non-sulforiamide type inhibitor of such activity. This result is rather important taking into consideration the known antitumor activity of thiones. In addition, docking of the tested compounds into CA II active site was performed in order to predict the affinity and orientation of these compounds at the isozyme active site. The results showed similar orientation of the target compounds at CA II active site compared with reported sulfonamide type CAls with the thione group acting as a zinc-binding moiety. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.044