7-ethoxy-9-ethyl-1-methyl-β-carboline | 1229021-17-3

• 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: 7-ethoxy-9-ethyl-1-methyl-β-carboline
• 英文别名: Harmol, bis(ethyl)-；7-ethoxy-9-ethyl-1-methylpyrido[3,4-b]indole
• CAS: 1229021-17-3
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: KECXMPMSGNHSLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-ethoxy-9-ethyl-1-methyl-β-carboline 、 溴甲苯 以 乙酸乙酯 为溶剂， 以85%的产率得到7-ethoxy-2-benzyl-9-ethyl-1-methyl-β-carbolinium bromide
  参考文献：
  名称：

  Design, synthesis and 3D-QSAR of β-carboline derivatives as potent antitumor agents

  摘要：

  In a continuing effort to develop novel beta-carbolines endowed with better pharmacological profiles, a series of beta-carboline derivatives were designed and synthesized based on the previously developed SARs. Cytotoxicities in vitro of these compounds against a panel of human tumor cell lines were also investigated. The results demonstrated that the N(2)-benzylated beta-carbolinium bromides 56-60 represented the most potent compounds with IC(50) values lower than 10 mu M. The application of 3D-QSAR to these compounds explored the structural basis for their biological activities. CoMFA (q(2) = 0.513, r(2) = 0.862) and CoMSIA (q(2) = 0.503, r(2) = 0.831) models were developed for a set of 47 beta-carbolines. The results indicated that the antitumor pharmacophore of these molecules were marked at position-1, -2, -3, -7 and -9 of beta-carboline ring.

  DOI：

  10.1016/j.ejmech.2010.02.036
• 作为产物：
  描述：

  肉叶云香碱 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-ethoxy-9-ethyl-1-methyl-β-carboline
  参考文献：
  名称：

  Synthesis and structure–activity relationships of harmine derivatives as potential antitumor agents

  摘要：

  Harmine, a naturally occurring beta-carboline alkaloid, showed good antitumor activities together with remarkable neurotoxic effects in animal models. In order to search for novel leading compounds endowed with better antitumor activities and less neurotoxicities, a series of harmine derivatives were designed and synthesized by modification of position-2, 7 and 9 of beta-carboline nucleus, and their cytotoxic activities against human tumor cell lines were investigated. Acute toxicities and antitumor activities of the selected compounds in mice were also evaluated. Structure activity relationships studies confirmed that (1) the 7-methoxy structural moiety was the pharmacophore responsible for the neurotoxic effects of this class of compounds; (2) the substituents in position-2 and 9 played a vital role in modulation of their antitumor activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.045