1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylic acid | 1246972-58-6

• 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-(2,2-dimethoxyethyl)-β-carboline-3-carboxylic acid
• 英文别名: 1-(2,2-dimethoxyethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid
• CAS: 1246972-58-6
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: GBSAXTGXSBGWDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylic acid 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (S)-N-(1-(benzylamino)-5-(2-chloroacetimidamido)-1-oxopentan-2-yl)-1-(2,2-dimethoxyethyl)-9H-pyrido[3,4-b]indole-3-carboxamide
  参考文献：
  名称：

  A β-Carboline Derivate PAD4 Inhibitor Reshapes Neutrophil Phenotype and Improves the Tumor Immune Microenvironment against Triple-Negative Breast Cancer

  摘要：

  DOI：

  10.1021/acs.jmedchem.4c00030
• 作为产物：
  描述：

  methyl (1RS,3S)-1-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydrocarboline-3-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  A β-Carboline Derivate PAD4 Inhibitor Reshapes Neutrophil Phenotype and Improves the Tumor Immune Microenvironment against Triple-Negative Breast Cancer

  摘要：

  DOI：

  10.1021/acs.jmedchem.4c00030

文献信息

• A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis
  作者：Jianhui Wu、Chunyu Li、Ming Zhao、Wenjing Wang、Yuji Wang、Shiqi Peng

  DOI：10.1016/j.bmc.2010.07.043

  日期：2010.9

  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.