benzyl 1-(carbonylmethyl)-β-carboline-3-carboxylate | 1246972-60-0

• 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: benzyl 1-(carbonylmethyl)-β-carboline-3-carboxylate
• 英文别名: benzyl 1-(2-oxoethyl)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1246972-60-0
• 化学式: C₂₁H₁₆N₂O₃
• 分子量: 344.37
• InChiKey: TXLFRYOSAVLZSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 1-(carbonylmethyl)-β-carboline-3-carboxylate 、 L-aspartic acid dibenzyl ester hydrochloride 在 sodium hydroxide 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 2.17h， 以50%的产率得到N-(3-benzyloxycarbonyl-β-carbolin-1-yl)ethyl-L-aspartic acid dibenzyl ester
  参考文献：
  名称：

  A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis

  摘要：

  Based on DOCK scores 18 N-(3-benzyloxycarbonylcarboline-1-yl) ethylamino acid benzylesters (6a-r) were synthesized as anti-tumor agents. Their IC50 values against five human carcinoma cell lines ranged from 11.1 mu M to more than 100 mu M. The in vivo assay identified five derivatives of them had no antitumor action, the anti-tumor activity of nine derivatives of them equaled that of cytarabine, and the anti-tumor activity of three derivatives of them was higher than that of cytarabine. The UV and fluorescence spectra, as well as the relative viscosity and melting temperature measurements of calf thymus DNA (CT DNA) with and without the representative compound suggested that DNA intercalation could be their action mechanism. The 3D QSAR analysis of N-(3-benzyloxycarbonylcarboline-1-yl) ethylamino acid benzylesters (6a-r) revealed that their in vivo anti-tumor activity significantly depends on the molecular electrostatic and steric fields of the side chain of the amino acid residue. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.043
• 作为产物：
  描述：

  benzyl 1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylate 在 盐酸 、 水 、 溶剂黄146 作用下， 反应 4.5h， 以66.7%的产率得到benzyl 1-(carbonylmethyl)-β-carboline-3-carboxylate
  参考文献：
  名称：

  A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis

  摘要：

  Based on DOCK scores 18 N-(3-benzyloxycarbonylcarboline-1-yl) ethylamino acid benzylesters (6a-r) were synthesized as anti-tumor agents. Their IC50 values against five human carcinoma cell lines ranged from 11.1 mu M to more than 100 mu M. The in vivo assay identified five derivatives of them had no antitumor action, the anti-tumor activity of nine derivatives of them equaled that of cytarabine, and the anti-tumor activity of three derivatives of them was higher than that of cytarabine. The UV and fluorescence spectra, as well as the relative viscosity and melting temperature measurements of calf thymus DNA (CT DNA) with and without the representative compound suggested that DNA intercalation could be their action mechanism. The 3D QSAR analysis of N-(3-benzyloxycarbonylcarboline-1-yl) ethylamino acid benzylesters (6a-r) revealed that their in vivo anti-tumor activity significantly depends on the molecular electrostatic and steric fields of the side chain of the amino acid residue. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.043