1,6-bis[3-ethoxycarbonyl-1-(pyridyl-3-yl)-β-carboline-9-yl]hexane | 1415723-69-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1,6-bis[3-ethoxycarbonyl-1-(pyridyl-3-yl)-β-carboline-9-yl]hexane
• 英文别名: Ethyl 9-[6-(3-ethoxycarbonyl-1-pyridin-3-ylpyrido[3,4-b]indol-9-yl)hexyl]-1-pyridin-3-ylpyrido[3,4-b]indole-3-carboxylate；ethyl 9-[6-(3-ethoxycarbonyl-1-pyridin-3-ylpyrido[3,4-b]indol-9-yl)hexyl]-1-pyridin-3-ylpyrido[3,4-b]indole-3-carboxylate
• CAS: 1415723-69-1
• 化学式: C₄₄H₄₀N₆O₄
• 分子量: 716.839
• InChiKey: IYJCFIVDXHMVCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3S)-1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid 在 氯化亚砜 、 sodium hydride 、 sulfur 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 1,6-bis[3-ethoxycarbonyl-1-(pyridyl-3-yl)-β-carboline-9-yl]hexane
  参考文献：
  名称：

  Design, synthesis and in vitro and in vivo antitumor activities of novel bivalent β-carbolines

  摘要：

  A series of bivalent beta-carbolines with a spacer of three to ten methylene units between the indole nitrogen was synthesized and evaluated as antitumor agents. The results demonstrated that compounds 18c, 21b, 25a and 31b exhibited strong cytotoxic activities with IC50 value of lower than 20 mu M against four tumor cell lines. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, compounds 18b, 21b, 26a and 31b exhibited potent antitumor activities with tumor inhibition rate of over 40% in animal models. Preliminary structure-activity relationships analysis indicated that (1) the spacer length affected antitumor potencies, and four to six methylene units were more favorable; (2) the introduction of appropriate substituent into position-1 of beta-carboline facilitated antitumor potencies. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.033

文献信息

• Design, synthesis and in vitro and in vivo antitumor activities of novel bivalent β-carbolines
  作者：Buxi Shi、Rihui Cao、Wenxi Fan、Liang Guo、Qin Ma、Xuemei Chen、Guoxian Zhang、Liqin Qiu、Huacan Song

  DOI：10.1016/j.ejmech.2012.11.033

  日期：2013.2

  A series of bivalent beta-carbolines with a spacer of three to ten methylene units between the indole nitrogen was synthesized and evaluated as antitumor agents. The results demonstrated that compounds 18c, 21b, 25a and 31b exhibited strong cytotoxic activities with IC50 value of lower than 20 mu M against four tumor cell lines. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, compounds 18b, 21b, 26a and 31b exhibited potent antitumor activities with tumor inhibition rate of over 40% in animal models. Preliminary structure-activity relationships analysis indicated that (1) the spacer length affected antitumor potencies, and four to six methylene units were more favorable; (2) the introduction of appropriate substituent into position-1 of beta-carboline facilitated antitumor potencies. (C) 2012 Elsevier Masson SAS. All rights reserved.