4-tert-butyl-1-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1H-1,2,3-triazole | 1571151-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环己烯
• 英文名称: 4-tert-butyl-1-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1H-1,2,3-triazole
• 英文别名: AG2-433；6-(4-Tert-butyltriazol-1-yl)-1,2lambda6-benzoxathiine 2,2-dioxide；6-(4-tert-butyltriazol-1-yl)-1,2λ6-benzoxathiine 2,2-dioxide
• CAS: 1571151-55-7
• 化学式: C₁₄H₁₅N₃O₃S
• 分子量: 305.357
• InChiKey: FUZSGZMZUBIEFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.08
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  6-amino sulfocoumarin 在 copper(l) iodide 、 sodium azide 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.0h， 生成 4-tert-butyl-1-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  6-Triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrases IX and XII

  摘要：

  A series of 6-substituted sulfocoumarins incorporating substituted-1,2,3-triazol-4-yl-/5-yl moieties were synthesized by employing click chemistry. The new sulfocoumarins incorporated cycloalkyl, tert-butyl and substituted aryl moieties at the triazole ring, and were investigated for the inhibition of four human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, the cytosolic hCA I and II; and the transmembrane, tumor-associated hCA IX and XII. The triazole-substituted sulfocoumarins did not inhibit the ubiquitous, off-target cytosolic isoforms hCA I and II (K(I)s > 10 mu M) but showed effective inhibition against the two transmembrane CAs, with KIs ranging from 7.2 to 10.5 nM against hCA IX, and between 5.5 and 17.7 nM against hCA XII. As hCA IX and XII are validated anti-tumor targets, such prodrug, isoform-selective inhibitors as the sulfocoumarins reported here, may be useful for identifying suitable drug candidates for clinical trials. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.076

文献信息

• 6-Triazolyl-substituted sulfocoumarins are potent, selective inhibitors of the tumor-associated carbonic anhydrases IX and XII
  作者：Aiga Grandane、Muhammet Tanc、Raivis Zalubovskis、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2014.01.076

  日期：2014.3

  A series of 6-substituted sulfocoumarins incorporating substituted-1,2,3-triazol-4-yl-/5-yl moieties were synthesized by employing click chemistry. The new sulfocoumarins incorporated cycloalkyl, tert-butyl and substituted aryl moieties at the triazole ring, and were investigated for the inhibition of four human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, the cytosolic hCA I and II; and the transmembrane, tumor-associated hCA IX and XII. The triazole-substituted sulfocoumarins did not inhibit the ubiquitous, off-target cytosolic isoforms hCA I and II (K(I)s > 10 mu M) but showed effective inhibition against the two transmembrane CAs, with KIs ranging from 7.2 to 10.5 nM against hCA IX, and between 5.5 and 17.7 nM against hCA XII. As hCA IX and XII are validated anti-tumor targets, such prodrug, isoform-selective inhibitors as the sulfocoumarins reported here, may be useful for identifying suitable drug candidates for clinical trials. (c) 2014 Elsevier Ltd. All rights reserved.