methyl 1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylate | 1037673-51-0

• 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: methyl 1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylate
• 英文别名: methyl 1-(2,2-dimethoxyethyl)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1037673-51-0
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: XKGMKIPODBBGSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylate 在 水 、 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 生成 1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylic acid
  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：

  methyl (1RS,3S)-1-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydrocarboline-3-carboxylate 在 potassium permanganate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以80.3%的产率得到methyl 1-(2,2-dimethoxyethyl)-β-carboline-3-carboxylate
  参考文献：
  名称：

  新型N-（3-羧基-9-苄基-β-咔啉-1-基）乙基氨基酸：合成，抗肿瘤评估，插层测定，3D QSAR分析和对接研究

  摘要：

  合成了16种新型N-（3-羧基-9-苄基-β-咔啉-1-基）乙基氨基酸（6a - p）作为嵌入的先导化合物。在体外细胞毒性试验中，它们对五种人类癌细胞系的IC 50值范围为10.95μM至约400μM。在S180小鼠模型上，其中8个具有抗肿瘤作用，其中4个具有与阿糖胞苷相同的抗肿瘤能力。初步毒性评估表明，LD 50值为6a – p应超过500 mg / kg。以CT DNA为模型系统，探索了一种嵌入机制。使用3D QSAR分析定量描述了体内抗肿瘤活性与结构的关系。通过将6a – p与d（CGATCG）2寡核苷酸对接，证明了嵌入。

  DOI：

  10.1016/j.ejmech.2009.05.006

文献信息

• Novel N-(3-carboxyl-9-benzyl-β-carboline-1-yl)ethylamino acids: Synthesis, anti-tumor evaluation, intercalating determination, 3D QSAR analysis and docking investigation
  作者：Jianhui Wu、Ming Zhao、Keduo Qian、Kuo-Hsiung Lee、Susan Morris-Natschke、Shiqi Peng

  DOI：10.1016/j.ejmech.2009.05.006

  日期：2009.10

  anti-tumor action, four of them showed the same anti-tumor potency as that of cytarabine. The preliminary toxicity evaluation revealed that the LD50 values of 6a–p should be more than 500 mg/kg. With CT DNA as model system an intercalating mechanism was explored. Using 3D QSAR analysis the relationship of the in vivo anti-tumor activity and the structure was quantitatively described. By docking 6a–p

  合成了16种新型N-（3-羧基-9-苄基-β-咔啉-1-基）乙基氨基酸（6a - p）作为嵌入的先导化合物。在体外细胞毒性试验中，它们对五种人类癌细胞系的IC 50值范围为10.95μM至约400μM。在S180小鼠模型上，其中8个具有抗肿瘤作用，其中4个具有与阿糖胞苷相同的抗肿瘤能力。初步毒性评估表明，LD 50值为6a – p应超过500 mg / kg。以CT DNA为模型系统，探索了一种嵌入机制。使用3D QSAR分析定量描述了体内抗肿瘤活性与结构的关系。通过将6a – p与d（CGATCG）2寡核苷酸对接，证明了嵌入。
• 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.
• 10.1021/acs.jmedchem.4c00030
  作者：Zhu, Di、Lu, Yu、Yan, Zhanchao、Deng, Qian、Hu, Bo、Wang, Yinsong、Wang, Wenjing、Wang, Yanming、Wang, Yuji

  DOI：10.1021/acs.jmedchem.4c00030

  日期：——