(1S,3R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid | 1046143-19-4

• 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: (1S,3R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• CAS: 1046143-19-4
• 化学式: C₂₇H₂₆N₂O₅
• 分子量: 458.514
• InChiKey: SWLCCZLWLRMCGE-QPPBQGQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.81
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,3R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 在 4-二甲氨基吡啶 、 二甲羟胺盐酸盐 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以78%的产率得到(6S,14S,15aR,7aR)-6,14-bis[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-6,8,14,16,14a,15a,6a,7a-octahydro-β-carbolino[2',3'-2,1]piperazino[4,5-b]-β-carboline-7,15-dione
  参考文献：
  名称：

  Synthesis of diketopiperazine-based carboline homodimers and in vitro growth inhibition of human carcinomas

  摘要：

  Starting from D-or L-tryptophan, we have synthesized and characterized six compounds 2.29-2.31a and b that belong to a class of nitrogen heterocycles: the carboline-based homodimers. Each individual homodimer features a 1,3-trans relationship on each side of the central diketopiperazine core, but differs in absolute stereochemistry and also in substitution on the 40 and 400 oxygens (-Bn, -CH(3), or -H). The in vitro cytotoxicity of the six compounds was evaluated by measuring the growth inhibition in NCI-H520 and PC-3 human carcinoma cells. Phenol 2.30a inhibited cancer cell growth approximately three times better than its enantiomer 2.30b and possessed a GI(50) comparable to the clinically used agent etoposide in both cell lines. We have concluded that both the stereochemistry imparted by L-tryptophan and the presence of hydroxy substituents at the 40 and 400 positions are necessary to generate cytotoxic properties in the homodimer class. We are now employing 2.30a as a new lead compound in our efforts to discover improved indole-based cancer chemotherapeutics. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.022
• 作为产物：
  描述：

  methyl (3R,1S)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到(1S,3R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of diketopiperazine-based carboline homodimers and in vitro growth inhibition of human carcinomas

  摘要：

  Starting from D-or L-tryptophan, we have synthesized and characterized six compounds 2.29-2.31a and b that belong to a class of nitrogen heterocycles: the carboline-based homodimers. Each individual homodimer features a 1,3-trans relationship on each side of the central diketopiperazine core, but differs in absolute stereochemistry and also in substitution on the 40 and 400 oxygens (-Bn, -CH(3), or -H). The in vitro cytotoxicity of the six compounds was evaluated by measuring the growth inhibition in NCI-H520 and PC-3 human carcinoma cells. Phenol 2.30a inhibited cancer cell growth approximately three times better than its enantiomer 2.30b and possessed a GI(50) comparable to the clinically used agent etoposide in both cell lines. We have concluded that both the stereochemistry imparted by L-tryptophan and the presence of hydroxy substituents at the 40 and 400 positions are necessary to generate cytotoxic properties in the homodimer class. We are now employing 2.30a as a new lead compound in our efforts to discover improved indole-based cancer chemotherapeutics. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.022