1-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline | 1186490-54-9

• 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-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: (S)-1-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline；(S)-1-(4-pentenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole；(1S)-1-pent-4-enyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 1186490-54-9
• 化学式: C₁₆H₂₀N₂
• 分子量: 240.348
• InChiKey: XXKWGRARCMCTDL-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline 、 氯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到methyl 1-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline-2-carboxylate
  参考文献：
  名称：

  Antiproliferative activity of arborescidine alkaloids and derivatives

  摘要：

  Current issues in cancer research involve searching for novel anticancer compounds that can be used to regulate the cell cycle and lead to more effective treatments of tumors. In this study, it was hypothesized that possessing a cyclic alkaloid similar to harmine, arborescidines can disrupt the proliferative state of cancer cells and block the activity of topoisomerases. The antiproliferative activity of arborescidines A-C and their derivatives was evaluated in vitro against four human tumor cell lines: gastric adenocarcinoma, lung cancer, bladder carcinoma and leukemia. Assuming the mechanism of action by topoisomerase II binding model, the compounds possessing the greatest activity had nonpolar side-chain into hydrophobic binding region on the DNA/topo II complex. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.005
• 作为产物：
  描述：

  1-(4-pentenyl)-4,9-dihydro-3H-β-carboline 在 甲酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以95%的产率得到1-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Antiproliferative activity of arborescidine alkaloids and derivatives

  摘要：

  Current issues in cancer research involve searching for novel anticancer compounds that can be used to regulate the cell cycle and lead to more effective treatments of tumors. In this study, it was hypothesized that possessing a cyclic alkaloid similar to harmine, arborescidines can disrupt the proliferative state of cancer cells and block the activity of topoisomerases. The antiproliferative activity of arborescidines A-C and their derivatives was evaluated in vitro against four human tumor cell lines: gastric adenocarcinoma, lung cancer, bladder carcinoma and leukemia. Assuming the mechanism of action by topoisomerase II binding model, the compounds possessing the greatest activity had nonpolar side-chain into hydrophobic binding region on the DNA/topo II complex. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.005

文献信息

• Novel Supramolecular Palladium Catalyst for the Asymmetric Reduction of Imines in Aqueous Media
  作者：Wender A. da Silva、Manoel T. Rodrigues、N. Shankaraiah、Renan B. Ferreira、Carlos Kleber Z. Andrade、Ronaldo A. Pilli、Leonardo S. Santos

  DOI：10.1021/ol9011772

  日期：2009.8.6

  A novel approach to the asymmetric reduction of dihydro-β-carboline derivatives to the corresponding tetrahydro-β-carbolines is described based on the supramolecular lyophilized complex formed from β-cyclodextrin/imines as an enzyme mimetic and palladium hydride as the reducing agent. The methodology allowed us to develop a short and efficient preparation of (R)-harmicine and (R)-deplancheine alkaloids

  基于由β-环糊精/亚胺作为酶模拟物和氢化钯作为还原剂形成的超分子冻干复合物，描述了一种将二氢-β-咔啉衍生物不对称还原为相应的四氢-β-咔啉的新方法。该方法使我们能够开发出一种短而有效的（R）-甜菜碱和（R）-十倍体碱生物碱的制备方法，分别具有89％和90％的高总收率和ee。
• Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus
  作者：Marlene Espinoza-Moraga、Tania Petta、Marco Vasquez-Vasquez、V. Felipe Laurie、Luis A.B. Moraes、Leonardo Silva Santos

  DOI：10.1016/j.tetasy.2010.06.036

  日期：2010.8

  beta-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compounds presenting C-1-C-11 aliphatic substituent groups afforded amines with an (S)-configuration, whereas C-15 and higher aliphatic, and aromatic substituted B-carboline imines achieved inversion of the configuration in the final (R)-2 amine products. Based on this data, a model for the Saccharomyces reduction is proposed. (C) 2010 Elsevier Ltd. All rights reserved.
• Antiproliferative activity of arborescidine alkaloids and derivatives
  作者：Leonardo S. Santos、Cristina Theoduloz、Ronaldo A. Pilli、Jaime Rodriguez

  DOI：10.1016/j.ejmech.2009.04.005

  日期：2009.9

  Current issues in cancer research involve searching for novel anticancer compounds that can be used to regulate the cell cycle and lead to more effective treatments of tumors. In this study, it was hypothesized that possessing a cyclic alkaloid similar to harmine, arborescidines can disrupt the proliferative state of cancer cells and block the activity of topoisomerases. The antiproliferative activity of arborescidines A-C and their derivatives was evaluated in vitro against four human tumor cell lines: gastric adenocarcinoma, lung cancer, bladder carcinoma and leukemia. Assuming the mechanism of action by topoisomerase II binding model, the compounds possessing the greatest activity had nonpolar side-chain into hydrophobic binding region on the DNA/topo II complex. (C) 2009 Elsevier Masson SAS. All rights reserved.