N1-[2-(1H-indol-3-yl)ethyl]-5-hexenamide | 1229623-09-9

• 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: N1-[2-(1H-indol-3-yl)ethyl]-5-hexenamide
• 英文别名: N-[2-(1H-3-indolyl)ethyl]-5-hexenamide；N-[2-(1H-indol-3-yl)ethyl]hex-5-enamide
• CAS: 1229623-09-9
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: CXMMEQMSKSYTIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N1-[2-(1H-indol-3-yl)ethyl]-5-hexenamide 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以86%的产率得到1-(4-pentenyl)-4,9-dihydro-3H-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
• 作为产物：
  描述：

  色胺 、 5-己烯酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到N1-[2-(1H-indol-3-yl)ethyl]-5-hexenamide
  参考文献：
  名称：

  铱催化的烯烃异构化对映选择性加氢炔化

  摘要：

  开发了铱催化的亚甲基 CH键 γ 与酰胺基团的对映选择性炔基化。该反应通过烯烃异构化和区域选择性加氢炔化进行。该方法可以快速获得各种立体定义的炔基化化合物，收率高，对映选择性好。

  DOI：

  10.1016/j.tetlet.2021.153108

文献信息

• 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.
• Iridium-catalyzed enantioselective hydroalkynylation via alkene isomerization
  作者：Wen-Wen Zhang、Bi-Jie Li

  DOI：10.1016/j.tetlet.2021.153108

  日期：2021.6

  An iridium-catalyzed enantioselective alkynylation of methylene CH bonds γ to the amide group is developed. The reaction proceeds through alkene isomerization followed by regioselective hydroalkynylation. This method provides rapid access to a wide range of stereodefined alkynylated compounds in good yields and good enantioselectivities.

  开发了铱催化的亚甲基 CH键 γ 与酰胺基团的对映选择性炔基化。该反应通过烯烃异构化和区域选择性加氢炔化进行。该方法可以快速获得各种立体定义的炔基化化合物，收率高，对映选择性好。
• 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.