8-methoxy-4,5-dimethyl-N-(3-pyrrolidin-1-ylpropyl)pyrido[4,3-b]indol-1-amine | 111380-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 8-methoxy-4,5-dimethyl-N-(3-pyrrolidin-1-ylpropyl)pyrido[4,3-b]indol-1-amine
• CAS: 111380-68-8
• 化学式: C₂₁H₂₈N₄O
• 分子量: 352.48
• InChiKey: JPIHFCZKWVYKMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  42.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-methoxy-4,5-dimethyl-N-(3-pyrrolidin-1-ylpropyl)pyrido[4,3-b]indol-1-amine 在 氢溴酸 作用下， 以75%的产率得到4,5-Dimethyl-1-((3-(1-pyrrolidinyl)propyl)amino)-5H-pyrido(4,3-b)indol-8-ol
  参考文献：
  名称：

  1-Amino-substituted 4-methyl-5H-pyrido[4,3-b]indoles (.gamma.-carbolines) as tricyclic analogs of ellipticines: a new class of antineoplastic agents

  摘要：

  A series of 1-amino-substituted 4-methyl-5H-pyrido[4,3-b]indoles that are structurally related to ellipticines by deletion of a ring have been synthesized in order to evaluate their DNA affinity, their in vitro cytotoxicity on L1210 cultured cells, and their in vivo antitumor activity. Among 24 derivatives that have been prepared and studied for the structure-activity relationship in this new class of antineoplastic agents, those that have a NH(CH2)3N(R)2 side chain (R = CH3 or C2H5) at their 1-position, a 4-methyl group, and an 8-OH substituent, either with a 5-NH or with a 5-NCH3 group, show the most potent cytotoxicities on L1210 cultured cells and in vivo antitumor properties in P388 and L1210 leukemia systems. In vivo antineoplastic activity of the most potent products was confirmed in P388 and L1210 leukemia systems. In vivo antineoplastic activity of the most potent products was confirmed on other mouse experimental tumors from the standard NCI screening:B16 melanoma and C38 adenocarcinoma.

  DOI：

  10.1021/jm00397a023
• 作为产物：
  描述：

  4-methyl-8-methoxy-2H,5H-pyrido<4,3-b>indol-1-one 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 8-methoxy-4,5-dimethyl-N-(3-pyrrolidin-1-ylpropyl)pyrido[4,3-b]indol-1-amine
  参考文献：
  名称：

  1-Amino-substituted 4-methyl-5H-pyrido[4,3-b]indoles (.gamma.-carbolines) as tricyclic analogs of ellipticines: a new class of antineoplastic agents

  摘要：

  A series of 1-amino-substituted 4-methyl-5H-pyrido[4,3-b]indoles that are structurally related to ellipticines by deletion of a ring have been synthesized in order to evaluate their DNA affinity, their in vitro cytotoxicity on L1210 cultured cells, and their in vivo antitumor activity. Among 24 derivatives that have been prepared and studied for the structure-activity relationship in this new class of antineoplastic agents, those that have a NH(CH2)3N(R)2 side chain (R = CH3 or C2H5) at their 1-position, a 4-methyl group, and an 8-OH substituent, either with a 5-NH or with a 5-NCH3 group, show the most potent cytotoxicities on L1210 cultured cells and in vivo antitumor properties in P388 and L1210 leukemia systems. In vivo antineoplastic activity of the most potent products was confirmed in P388 and L1210 leukemia systems. In vivo antineoplastic activity of the most potent products was confirmed on other mouse experimental tumors from the standard NCI screening:B16 melanoma and C38 adenocarcinoma.

  DOI：

  10.1021/jm00397a023