4-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide hydrochloride | 1613266-95-7

• 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-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide hydrochloride
• 英文别名: 4-(4-aminomethyl[1,2,3]triazol-1-yl)benzenesulfonamide hydrochloride
• CAS: 1613266-95-7
• 化学式: C₉H₁₁N₅O₂S*ClH
• 分子量: 289.746
• InChiKey: BZUKOVREMZWHFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  116.89
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide hydrochloride 、 Fluorescein isothiocyanate 在 三乙胺 作用下， 以38%的产率得到2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-5-{3-[1-(4-sulfamoylphenyl)-1H-[1,2,3]triazol-4-ylmethyl]thioureido}benzoic acid
  参考文献：
  名称：

  Fluorescent sulfonamide carbonic anhydrase inhibitors incorporating 1,2,3-triazole moieties: Kinetic and X-ray crystallographic studies

  摘要：

  Fluorescent sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors (CAIs) were essential for demonstrating the role played by the tumor-associated isoform CA IX in acidification of tumors, cancer progression towards metastasis and for the development of imaging and therapeutic strategies for the management of hypoxic tumors which overexpress CA IX. However, the presently available such compounds are poorly water soluble which limits their use. Here we report new fluorescent sulfonamides 7, 8 and 10 with increased water solubility. The new derivatives showed poor hCA I inhibitory properties, but were effective inhibitors against the hCA II (K(I)s of 366-127 nM), CA IX (K(I)s of 8.1-36.9 nM), CA XII (K(I)s of 4.1-20.5 nM) and CA XIV (K(I)s of 12.8-53.6 nM). A high resolution X-ray crystal structure of one of these compounds bound to hCA II revealed the factors associated with the good inhibitory properties. Furthermore, this compound showed a three-fold increase of water solubility compared to a similar derivative devoid of the triazole moiety, making it an interesting candidate for ex vivo/in vivo studies. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.031
• 作为产物：
  描述：

  4-azidobenzenesulfonamide 在 盐酸 、 铜 、 三乙胺盐酸盐 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 20.5h， 生成 4-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide hydrochloride
  参考文献：
  名称：

  Carbonic Anhydrase Inhibition with Benzenesulfonamides and Tetrafluorobenzenesulfonamides Obtained via Click Chemistry

  摘要：

  A series of novel benzene- and 2,3,5,6-tetrafluorobenzenesulfonamide was synthesized by using a click chemistry approach starting from azido-substituted sulfonamides and alkynes, incorporating aryl, alkyl, cycloalkyl, and amino-/hydroxy-/halogenoalkyl moieties. The new compounds were medium potency inhibitors of the cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isoforms I and II and low nanomolar/subnanomolar inhibitors of the tumor-associated hCA IX and XII isoforms. The X-ray crystal structure of two such sulfonamides in adduct with hCA II allowed us to understand the factors governing inhibitory power.

  DOI：

  10.1021/ml500196t