4-(2-(6-methyl-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene)hydrazinyl)benzenesulfonamide | 1529774-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-(6-methyl-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene)hydrazinyl)benzenesulfonamide
• CAS: 1529774-39-7
• 化学式: C₁₇H₁₅N₇O₂S₂
• 分子量: 413.484
• InChiKey: AOAVAXUIUIEVSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  127.63
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2-oxo-N'-(4-sulfamoylphenyl)propanehydrazonoyl chloride 、 4-氨基-5-苯基-4H-1,2,4-三唑-3-硫醇 以 乙醇 为溶剂， 反应 10.0h， 以68%的产率得到4-(2-(6-methyl-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-ylidene)hydrazinyl)benzenesulfonamide
  参考文献：
  名称：

  Inhibition of carbonic anhydrases from the extremophilic bacteria Sulfurihydrogenibium yellostonense (SspCA) and S. azorense (SazCA) with a new series of sulfonamides incorporating aroylhydrazone-, [1,2,4]triazolo[3,4-b][1,3,4]thiadiazinyl- or 2-(cyanophenylmethylene)-1,3,4-thiadiazol-3(2H)-yl moieties

  摘要：

  A series of new sulfonamides was prepared starting from 2-oxo-N'-(4-sulfamoylphenyl)-propanehydrazonoyl chloride, a sulfanilamide derivative, which was reacted with aroylhydrazides, amines, or thiols. A library of derivatives incorporating aroylhydrazone, [1,2,4] triazolo[3,4-b][1,3,4]thiadiazinyl- or 2-(cyanophenyl-methylene)-1,3,4-thiadiazol-3(2H)-yl moieties was thus synthesized. The new compounds were investigated as inhibitors of four alpha-carbonic anhydrases (CAs, EC 4.2.1.1), the human (h) isoforms hCA I and II, and the bacterial ones recently isolated from the extremophilic bacteria Sulfurihydrogenibium yellostonense (SspCA) and Sulfurihydrogenibium azorense (SazCA). Low nanomolar activity was observed against hCA II (K(I)s of 0.56-17.1 nM) whereas hCA I was less inhibited by these compounds (K(I)s of 86.4 nM-32.8 mu M). The bacterial CAs were also effectively inhibited by these derivatives (K(I)s in the range of 0.77-234 nM against SazCA, and of 6.2-89.1 against SspCA, respectively), with several low nanomolar/subnanomolar inhibitors detected against both of them. As SspCA and SazCA are among the most thermostable and catalytically active CAs, it is of interest to find modulators of their activity for potential biotechnologic applications. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.042