2,9-diethyl-9H-β-carbolinium; iodide

• 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-diethyl-9H-β-carbolinium; iodide
• 英文别名: 2,9-Diaethyl-9H-β-carbolinium; Jodid；2,9-Diethylpyrido[3,4-b]indol-2-ium;iodide
• 化学式: C₁₅H₁₇N₂*I
• 分子量: 352.218
• InChiKey: BFLCFZLDQZWDHK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-乙基-1-苯肼 在 聚合甲醛 、 硫酸 、 钯 、 zinc(II) chloride 、 苯 作用下， 生成 2,9-diethyl-9H-β-carbolinium; iodide
  参考文献：
  名称：

  ALSTONIA ALKALOIDS. I. DEGRADATION OF ALSTONINE TO β-CARBOLINE BASES AND THE REDUCTION OF TETRAHYDROALSTONINE WITH SODIUM AND BUTYL ALCOHOL

  摘要：

  DOI：

  10.1021/jo01200a014

文献信息

• 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.
• ALSTONIA ALKALOIDS. I. DEGRADATION OF ALSTONINE TO β-CARBOLINE BASES AND THE REDUCTION OF TETRAHYDROALSTONINE WITH SODIUM AND BUTYL ALCOHOL
  作者：NELSON J. LEONARD、ROBERT C. ELDERFIELD

  DOI：10.1021/jo01200a014

  日期：1942.11