6-[5-(2-Aminomethyl-phenyl)-oxazol-2-ylamino]-1-methyl-1H-indole-3-carbonitrile | 625116-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-[5-(2-Aminomethyl-phenyl)-oxazol-2-ylamino]-1-methyl-1H-indole-3-carbonitrile
• 英文别名: 6-[[5-[2-(aminomethyl)phenyl]-1,3-oxazol-2-yl]amino]-1-methylindole-3-carbonitrile
• CAS: 625116-12-3
• 化学式: C₂₀H₁₇N₅O
• 分子量: 343.388
• InChiKey: LFDQDCYGGJMWEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  92.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-羟基丙腈 、 N,N'-羰基二咪唑 、 6-[5-(2-Aminomethyl-phenyl)-oxazol-2-ylamino]-1-methyl-1H-indole-3-carbonitrile 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以85%的产率得到{2-[2-(3-Cyano-1-methyl-1H-indol-6-ylamino)-oxazol-5-yl]-benzyl}-carbamic acid 2-cyano-ethyl ester
  参考文献：
  名称：

  3-Cyanoindole-based inhibitors of inosine monophosphate dehydrogenase: synthesis and initial structure–Activity relationships

  摘要：

  A series of novel small molecule inhibitors of inosine monophosphate dehydrogenase (IMPDH), based upon a 3-cyanoindole core, were explored. IMPDH catalyzes the rate determining step in guanine nucleotide biosynthesis and is a target for anticancer, immunosuppressive and antiviral therapy. The synthesis and the structure-activity relationships (SAR), derived from in vitro studies, for this new series of inhibitors is given. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00757-1
• 作为产物：
  描述：

  1-methyl-6-nitro-1H-indole-3-carbonitrile 在 palladium on activated charcoal 氢气 、 三苯基膦 、 肼 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0~100.0 ℃ 、103.42 kPa 条件下， 反应 3.17h， 生成 6-[5-(2-Aminomethyl-phenyl)-oxazol-2-ylamino]-1-methyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  3-Cyanoindole-based inhibitors of inosine monophosphate dehydrogenase: synthesis and initial structure–Activity relationships

  摘要：

  A series of novel small molecule inhibitors of inosine monophosphate dehydrogenase (IMPDH), based upon a 3-cyanoindole core, were explored. IMPDH catalyzes the rate determining step in guanine nucleotide biosynthesis and is a target for anticancer, immunosuppressive and antiviral therapy. The synthesis and the structure-activity relationships (SAR), derived from in vitro studies, for this new series of inhibitors is given. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00757-1