5-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1-(4-methylphenyl)-1H-tetrazole | 1571901-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1-(4-methylphenyl)-1H-tetrazole
• 英文别名: 6-[1-(4-Methylphenyl)tetrazol-5-yl]-1,2lambda6-benzoxathiine 2,2-dioxide；6-[1-(4-methylphenyl)tetrazol-5-yl]-1,2λ6-benzoxathiine 2,2-dioxide
• CAS: 1571901-98-8
• 化学式: C₁₆H₁₂N₄O₃S
• 分子量: 340.362
• InChiKey: GVYPZNRMXFBYJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-formyl-4-iodophenyl methanesulfonate 在 copper(l) iodide 、 三(2-呋喃基)膦 、 palladium diacetate 、 caesium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 5-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1-(4-methylphenyl)-1H-tetrazole
  参考文献：
  名称：

  Synthesis of 6-tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor-associated carbonic anhydrase isoforms IX and XII

  摘要：

  A series of 6-substituted sulfocoumarins incorporating substituted-1,2,3,4-tetrazol-5-yl moieties were synthesized by reaction of 6-iodo-sulfocoumarin and the corresponding tetrazole via the CH activation reaction. The new sulfocoumarins incorporating alkyl and substituted aryl moieties at the 1-position of the tetrazole, 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 tetrazole-substituted sulfocoumarins did not inhibit the ubiquitous, off-target cytosolic isoforms (K(I)s > 10 mu M) but showed effective inhibition against the two transmembrane CAs, with KIs ranging from 6.5 to 68.6 nM against hCA IX, and between 4.3 and 59.8 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.bmc.2014.01.043