N-(3-chloro-1H-indol-7-yl)-4-methoxy-benzenesulfonamide | 247186-96-5

• 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: N-(3-chloro-1H-indol-7-yl)-4-methoxy-benzenesulfonamide
• 英文别名: N-(3-chloro-1H-indol-7-yl)-4-methoxybenzenesulfonamide
• CAS: 247186-96-5
• 化学式: C₁₅H₁₃ClN₂O₃S
• 分子量: 336.799
• InChiKey: UEIFSFBNRBJSCK-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  556.4±60.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(1H-indol-7-yl)-4-methoxybenzenesulfonamide 在 盐酸 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(3-chloro-1H-indol-7-yl)-4-methoxy-benzenesulfonamide
  参考文献：
  名称：

  新型N-（7-吲哚基）苯磺酰胺的聚焦化合物库，用于发现有效的细胞周期抑制剂。

  摘要：

  合成了一系列含有N-（7-吲哚基）苯磺酰胺药效基团的化合物，并将其作为潜在的抗肿瘤药进行了评估。用P388鼠白血病细胞进行的细胞周期分析表明，有两种不同类型的有效细胞周期抑制剂。一个破坏有丝分裂，另一个导致G1积累。本文描述了该药效团模板上取代基图案的SAR总结。

  DOI：

  10.1016/s0960-894x(00)00219-5

文献信息

• Discovery of Novel Antitumor Sulfonamides Targeting G1 Phase of the Cell Cycle
  作者：Takashi Owa、Hiroshi Yoshino、Tatsuo Okauchi、Kentaro Yoshimatsu、Yoichi Ozawa、Naoko Hata Sugi、Takeshi Nagasu、Nozomu Koyanagi、Kyosuke Kitoh

  DOI：10.1021/jm9902638

  日期：1999.9.1

  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.
• A focused compound library of novel N -(7-indolyl)benzenesulfonamides for the discovery of potent cell cycle inhibitors
  作者：Takashi Owa、Tatsuo Okauchi、Kentaro Yoshimatsu、Naoko Hata Sugi、Yoichi Ozawa、Takeshi Nagasu、Nozomu Koyanagi、Tadashi Okabe、Kyosuke Kitoh、Hiroshi Yoshino

  DOI：10.1016/s0960-894x(00)00219-5

  日期：2000.6

  A series of compounds containing an N-(7-indolyl)benzenesulfonamide pharmacophore was synthesized and evaluated as a potential antitumor agent. Cell cycle analysis with P388 murine leukemia cells revealed that there were two different classes of potent cell cycle inhibitors; one disrupted mitosis and the other caused G1 accumulation. Herein described is the SAR summary of the substituent patterns on

  合成了一系列含有N-（7-吲哚基）苯磺酰胺药效基团的化合物，并将其作为潜在的抗肿瘤药进行了评估。用P388鼠白血病细胞进行的细胞周期分析表明，有两种不同类型的有效细胞周期抑制剂。一个破坏有丝分裂，另一个导致G1积累。本文描述了该药效团模板上取代基图案的SAR总结。