2,9-dibenzyl-β-carbolinium bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,9-dibenzyl-β-carbolinium bromide
• 英文别名: 2,9-Dibenzylpyrido[3,4-b]indol-2-ium;bromide
• 化学式: Br*C₂₅H₂₁N₂
• 分子量: 429.359
• InChiKey: AJTUSARUEKTBIZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 在 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 2,9-dibenzyl-β-carbolinium bromide
  参考文献：
  名称：

  N 2 ,N 9 -Bis (Substituted benzyl)- β- Carbolineum Bromides 作为潜在的抗癌疗法：设计、合成、细胞毒性、药物-DNA 嵌入和硅片结合特性

  摘要：

  本研究报告了一系列由 L-色氨酸分三步合成的新型N 2 , N 9 -双（取代苄基）-β-溴化碳（4a-f），产率极好（>80%）。合成化合物4a-f的结构经1 H-和13 C-NMR、FT-IR、LC-MS (ESI-MS)光谱和元素分析证实。同时，化合物4f的晶体结构通过X射线单晶衍射确定。该晶体属于P12 1 /c 1空间群中的单斜空间群，a  = 13.253(6) Å, b = 20.809(10) Å, c  = 9.116(6) Å, β  = 107.215(13)°, V = 2401.4(19) Å 3和 Z = 4, F(000) = 1048, D c  = 1.403 Mg/m 3和 µ = 1.743 mm -1。评估了化合物4a-f对选定的人类癌细胞系的体外抗癌活性，例如 HT-29（结肠直肠腺癌）、HeLa（宫颈癌）、HepG2（肝细胞癌）和 K562（慢性粒细胞白血病，CML）

  DOI：

  10.1016/j.molstruc.2021.130771

文献信息

• HARMINE DERIVATIVES, INTERMEDIATES USED IN THEIR PREPARATION, PREPARATION PROCESSES AND USE THEREOF
  申请人：Xinjiang Huashidan Pharmaceutical Research Co., Ltd.

  公开号：EP1634881B1

  公开（公告）日：2011-07-27
• Design, synthesis and in vitro and in vivo antitumor activities of novel β-carboline derivatives
  作者：R. Cao、H. Chen、W. Peng、Y. Ma、X. Hou、H. Guan、X. Liu、A. Xu

  DOI：10.1016/j.ejmech.2005.04.008

  日期：2005.10

  To further our SAR study on the chemistry and antitumor activity/neurotoxicity of beta-carboline alkaloids. several series of beta-carboline derivatives with various substituents were designed and synthesized from the starting material L-tryptophan on the basis of harmine chemical structure. Cytotoxic activities of these compounds were investigated in vitro. The results showed that some beta-carboline derivatives had significant cytotoxic activities against human tumor cell lines. Among all the synthesized beta-carboline derivatives, the compounds 27, 28 and 32, having a benzyl substituent at both position-2 and 9, respectively, were found to be the most potent compounds with IC50 value lower than 50 mu M against all human tumor cell lines examined. Acute toxicities and antitumor activities of the selected beta-carboline derivatives in mice were also evaluated. The results demonstrated that a benzyl substituent at position-2 increased the antitumor activity as well as acute toxicity significantly. However an (ethoxycarbonyl)amino substituent at position-3 reduced the acute toxicity as well as antitumor activity remarkedly. These data suggested that (1) the antitumor potencies of beta-carboline derivatives were enhanced by the introduction of benzyl substituent into the position-2; (2) the acute toxicity of beta-carboline derivatives reduced dramatically by the introduction of an appropriate substituent into the position-3 and 9; (3) the beta-carboline structure might be an important basis for the design and synthesis of new antitumor drugs with significant antitumor activity and low toxicity. (c) 2005 Elsevier SAS. All rights reserved.
• Synthesis and structure–activity relationships of N2-alkylated quaternary β-carbolines as novel antitumor agents
  作者：Guoxian Zhang、Rihui Cao、Liang Guo、Qin Ma、Wenxi Fan、Xuemei Chen、Jianru Li、Guang Shao、Liqin Qiu、Zhenghua Ren

  DOI：10.1016/j.ejmech.2013.04.031

  日期：2013.7

  A series of novel N-2-alkylated quaternary beta-carbolines was synthesized by modification of position-1, 2,7 and 9 of beta-carboline nucleus with various alkyl and arylated alkyl substituents, and their cytotoxic activities in vitro and antitumor potencies in mice were evaluated. Compound 3m was found to be the most potent antitumor agent. SARs analysis revealed that (1) the substituents in position-2 and 9 of beta-carboline nucleus played a vital role in modulation of antitumor activity; (2) the benzyl and 3-phenylpropyl substituents in position-2 and 9 of beta-carboline ring were the optimal substituents giving rise to significant antitumor agent. These compounds might be a novel promising class of antitumor agents with clinical development potential. (C) 2013 Elsevier Masson SAS. All rights reserved.
• N,N-Bis(Substituted benzyl)-β-Carbolineum Bromides as Potential Anticancer Therapeutics: Design, Synthesis, Cytotoxicity, Drug-DNA Intercalation and In-Silico Binding Properties
  作者：Mazlin Mohideen、Nur Azzalia Kamaruzaman、Muhamad Azwan Hamali、Mohd Nizam Mordi、Sharif Mahsufi Mansor、A. F. M. Motiur Rahman

  DOI：10.1016/j.molstruc.2021.130771

  日期：2021.11

  a = 13.253(6) Å, b = 20.809(10) Å, c = 9.116(6) Å, β = 107.215(13)°, V = 2401.4(19) Å3 and Z = 4, F(000) = 1048, Dc = 1.403 Mg/m3 and µ = 1.743 mm−1. Compounds 4a-f were evaluated for their in-vitro anticancer activity against selected human cancer cell lines, such as HT-29 (colorectal adenocarcinoma), HeLa (cervical carcinoma), HepG2 (hepatocellular carcinoma) and K562 (chronic myelogenous leukaemia,

  本研究报告了一系列由 L-色氨酸分三步合成的新型N 2 , N 9 -双（取代苄基）-β-溴化碳（4a-f），产率极好（>80%）。合成化合物4a-f的结构经1 H-和13 C-NMR、FT-IR、LC-MS (ESI-MS)光谱和元素分析证实。同时，化合物4f的晶体结构通过X射线单晶衍射确定。该晶体属于P12 1 /c 1空间群中的单斜空间群，a  = 13.253(6) Å, b = 20.809(10) Å, c  = 9.116(6) Å, β  = 107.215(13)°, V = 2401.4(19) Å 3和 Z = 4, F(000) = 1048, D c  = 1.403 Mg/m 3和 µ = 1.743 mm -1。评估了化合物4a-f对选定的人类癌细胞系的体外抗癌活性，例如 HT-29（结肠直肠腺癌）、HeLa（宫颈癌）、HepG2（肝细胞癌）和 K562（慢性粒细胞白血病，CML）