4-(3-Cyano-1H-indol-7-ylsulfamoyl)-benzoic acid | 247186-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3-Cyano-1H-indol-7-ylsulfamoyl)-benzoic acid
• 英文别名: 4-[(3-cyano-1H-indol-7-yl)sulfamoyl]benzoic acid
• CAS: 247186-91-0
• 化学式: C₁₆H₁₁N₃O₄S
• 分子量: 341.347
• InChiKey: WCJRLNLIYKBEBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3-Cyano-1H-indol-7-ylsulfamoyl)-benzoic acid 在 二苯基磷酸 、 碳酸氢铵 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以79%的产率得到4-(3-cyano-1H-indol-7-ylsulfamoyl)-benzamide
  参考文献：
  名称：

  Discovery of Novel Antitumor Sulfonamides Targeting G1 Phase of the Cell Cycle

  摘要：

  Described herein is the discovery of a novel series of antitumor sulfonamides targeting G1 phase of the cell cycle. Cell cycle control in G1 phase has attracted considerable attention in recent cancer research, because many of the important proteins involved in G1 progression or G1/S transition have been found to play a crucial role in proliferation, differentiation, transformation, and programmed cell death (apoptosis). We previously reported our first antitumor sulfonamide E7010 as a novel tubulin polymerization inhibitor. Interestingly enough, continuous research on structurally related compounds led us to the finding of another class of antitumor sulfonamides that block cell cycle progression of P388 murine leukemia cells in GI phase, but not in M phase. Of the compounds examined, N-(3-chloro-7-indolyl)-1,4-benzenedisulfonamide (E7070) showed significant antitumor activity against HCT116 human colon carcinoma both in vitro (IC50 0.11 mu g/mL in cell proliferation assay) and in vivo (not only growth suppression but also a marked reduction of tumor size in nude mice). Because of its promising efficacy against human tumor xenografts and its unique mode of action, E7070 is currently undergoing phase I clinical trials in European countries.

  DOI：

  10.1021/jm9902638
• 作为产物：
  描述：

  7-硝基吲哚-3-甲醛 在 palladium on activated charcoal 吡啶 、 selenium(IV) oxide 、 盐酸羟胺 、 氢气 、 magnesium sulfate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 9.5h， 生成 4-(3-Cyano-1H-indol-7-ylsulfamoyl)-benzoic acid
  参考文献：
  名称：

  Discovery of Novel Antitumor Sulfonamides Targeting G1 Phase of the Cell Cycle

  摘要：

  Described herein is the discovery of a novel series of antitumor sulfonamides targeting G1 phase of the cell cycle. Cell cycle control in G1 phase has attracted considerable attention in recent cancer research, because many of the important proteins involved in G1 progression or G1/S transition have been found to play a crucial role in proliferation, differentiation, transformation, and programmed cell death (apoptosis). We previously reported our first antitumor sulfonamide E7010 as a novel tubulin polymerization inhibitor. Interestingly enough, continuous research on structurally related compounds led us to the finding of another class of antitumor sulfonamides that block cell cycle progression of P388 murine leukemia cells in GI phase, but not in M phase. Of the compounds examined, N-(3-chloro-7-indolyl)-1,4-benzenedisulfonamide (E7070) showed significant antitumor activity against HCT116 human colon carcinoma both in vitro (IC50 0.11 mu g/mL in cell proliferation assay) and in vivo (not only growth suppression but also a marked reduction of tumor size in nude mice). Because of its promising efficacy against human tumor xenografts and its unique mode of action, E7070 is currently undergoing phase I clinical trials in European countries.

  DOI：

  10.1021/jm9902638