methyl 1-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline-2-carboxylate | 1186490-56-1

• 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-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline-2-carboxylate
• 英文别名: methyl (1R)-1-pent-4-enyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
• CAS: 1186490-56-1
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: VXXVKWQYDNYNNP-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-pentenyl)-2,3,4,9-tetrahydro-1H-β-carboline-2-carboxylate 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到methyl 1-(4,5-dihydroxypentyl)-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)-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

文献信息

• 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.