methyl 1-(1-acetyl-1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylate | 1242336-84-0

• 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-(1-acetyl-1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: methyl 1-(1-acetylindol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1242336-84-0
• 化学式: C₂₃H₁₇N₃O₃
• 分子量: 383.406
• InChiKey: VSJVVBZFLQAZHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(1-acetyl-1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylate 在 sodium tetrahydroborate 、 potassium carbonate 、 calcium chloride 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 3.5h， 生成 (9-benzyl-1-(1H-indol-3-yl)-9H-pyrido[3,4-b]indol-3-yl)methanol
  参考文献：
  名称：

  Computer-aided drug discovery: Novel 3,9-disubstituted eudistomin U derivatives as potent antibacterial agents

  摘要：

  Thirty-two new 3,9-disubstituted eudistomin U derivatives were designed and synthesized based on computer-aided drug discovery (CADD). Sixteen 3,9-disubstituted eudistomin U derivatives (6a-6p) have exhibited potent antibacterial activity. Specially, the most active compound 6p displayed better activity than commercial drugs fosfomycin sodium, ciprofloxacin and propineb, with a peak minimum inhibitory concentration (MIC) of 1.5625 mu mol/L. The antibacterial mechanism indicated that these compounds could exert bactericidal effect by damaging bacterial cell membrane and disrupting the function of DNA gyrase. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.001
• 作为产物：
  描述：

  N-乙酰基吲哚-3-甲醛 在 碘苯二乙酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 methyl 1-(1-acetyl-1H-indol-3-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  PhI(OAc)₂-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: synthesis of norharmane, harmane, eudistomin U and eudistomin I

  摘要：

  首次开发了一种在室温下通过一锅法氧化脱羧合成β-咔啉的新策略。

  DOI：

  10.1039/c5ob00871a

文献信息

• Room-Temperature Aromatization of Tetrahydro-β-carbolines by 2-Iodoxybenzoic Acid: Utility in a Total Synthesis of Eudistomin U
  作者：Joseph D. Panarese、Stephen P. Waters

  DOI：10.1021/ol101688x

  日期：2010.9.17

  2-Iodoxybenzoic acid is a convenient reagent for the dehydrogenation of tetrahydro-beta-carbolines to their aromatic forms under mild conditions. The utility of the method was demonstrated in a total synthesis of the marine indole alkaloid eudistomin U.
• 3-Amide-β-carbolines block the cell cycle by targeting CDK2 and DNA in tumor cells potentially as anti-mitotic agents
  作者：Dongming Zhi、Zhiyuan An、Lishan Li、Chaojia Zheng、Xiaorong Yuan、Yu Lan、Jinghan Zhang、Yujie Xu、Huiya Ma、Na Li、Junru Wang

  DOI：10.1016/j.bioorg.2024.107216

  日期：2024.4