ethyl 1-(3,4,5-trimethoxy)phenyl-9-(3-phenyl)propyl-β-carboline-3-carboxylate | 1015792-23-0

• 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: ethyl 1-(3,4,5-trimethoxy)phenyl-9-(3-phenyl)propyl-β-carboline-3-carboxylate
• 英文别名: Ethyl 9-(3-phenylpropyl)-1-(3,4,5-trimethoxyphenyl)pyrido[3,4-b]indole-3-carboxylate
• CAS: 1015792-23-0
• 化学式: C₃₂H₃₂N₂O₅
• 分子量: 524.616
• InChiKey: MPEXCFFLRMRNQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-(3,4,5-trimethoxy)phenyl-9-(3-phenyl)propyl-β-carboline-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以97%的产率得到1-(3,4,5-trimethoxyphenyl)-9-(3-phenylpropyl)-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  3位双β-咔啉碱类化合物、其制法和其药物组 合物与用途

  摘要：

  本发明公开了3位连接双β‑咔啉碱类化合物、其制法和其药物组合物与用途。具体而言，所述的双β‑咔啉碱类化合物及其可药用盐如通式I所述，这类双β‑咔啉碱类化合物的制备是通过β‑咔啉中间体和二卤代烷烃缩合。本发明还公开了一种药物组合物，包括有效剂量的式I所示双β‑咔啉碱类化合物和药效学上可接受的载体，以及这类双β‑咔啉碱类化合在制备抗肿瘤药物中的应用，包括黑色素瘤、胃癌、肺癌、乳腺癌、肾癌、肝癌、口腔表皮癌、宫颈癌、卵巢癌、胰腺癌、前列腺癌、结肠癌。

  公开号：

  CN102952151B
• 作为产物：
  描述：

  ethyl 1-(3,4,5-trimethoxy)phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 在 sodium hydride 、 sulfur 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 8.0h， 生成 ethyl 1-(3,4,5-trimethoxy)phenyl-9-(3-phenyl)propyl-β-carboline-3-carboxylate
  参考文献：
  名称：

  Synthesis and preliminary evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors

  摘要：

  一系列新颖的双价β-咔啉类化合物被合成并评估为有效的血管生成抑制剂。

  DOI：

  10.1039/c6md00360e

文献信息

• Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents
  作者：Rongqin Sun、Rui Liu、Chi Zhou、Zhenghua Ren、Liang Guo、Qin Ma、Wenxi Fan、Liqin Qiu、Huijuan Yu、Guang Shao、Rihui Cao

  DOI：10.1039/c5md00312a

  日期：——

  A series of bivalent β-carbolines with a piperazine group spacer between 3-methylene units were synthesized and their cytotoxic activities in vitro were evaluated. Compounds 7e and 7g exhibited potent cytotoxic activity.

  一系列具有3-亚甲基单元之间的哌嗪基间隔的二价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性。化合物7e和7g表现出强大的细胞毒活性。
• Synthesis and in vitro cytotoxic evaluation of novel 3,4,5-trimethoxyphenyl substituted β-carboline derivatives
  作者：Qifeng Wu、Rihui Cao、Manxiu Feng、Xiangdong Guan、Chunming Ma、Jinbing Liu、Huacan Song、Wenlie Peng

  DOI：10.1016/j.ejmech.2008.03.030

  日期：2009.2

  To elucidate further our SARs' study on the chemistry and cytotoxic activity and probe the structural requirement for the potent antitumor activity of beta-carbolines, a series of novel 1,9-disubstituted and 1,3,9-trisubstituted beta-carboline derivatives were designed and synthesized from the starting material L-tryptophan and 3,4,5-trimethoxybenezaldehyde. Cytotoxic activities of these compounds in vitro were investigated, and the SARs associated with position-1, 3 and 9 substituents in beta-carbolines have also been discussed. It has been observed that these compounds only displayed moderate to weak cytotoxic activities. Interestingly, most of the investigated compounds displayed selectively cytotoxic activities to human BCG-823 cell lines with IC50 value lower than 100 mu M. In addition, the short alkyl substituents in position-9 increased the cytotoxic activities with the tendency of n-butyl > ethyl > methyl. These data confirmed that (1) an alkyl substituent at position-9 of beta-carboline nucleus plays an important role in determining their antitumor activities; (2) different beta-carbolines bearing various substituents in beta-carboline nucleus interacted selectively with specific targets leading to the difference of biochemical and pharmacological effects. (C) 2008 Elsevier Masson SAS. All fights reserved.
• 3位双β-咔啉碱类化合物、其制法和其药物组 合物与用途
  申请人：新疆华世丹药物研究有限责任公司

  公开号：CN102952151B

  公开（公告）日：2017-07-28

  本发明公开了3位连接双β‑咔啉碱类化合物、其制法和其药物组合物与用途。具体而言，所述的双β‑咔啉碱类化合物及其可药用盐如通式I所述，这类双β‑咔啉碱类化合物的制备是通过β‑咔啉中间体和二卤代烷烃缩合。本发明还公开了一种药物组合物，包括有效剂量的式I所示双β‑咔啉碱类化合物和药效学上可接受的载体，以及这类双β‑咔啉碱类化合在制备抗肿瘤药物中的应用，包括黑色素瘤、胃癌、肺癌、乳腺癌、肾癌、肝癌、口腔表皮癌、宫颈癌、卵巢癌、胰腺癌、前列腺癌、结肠癌。
• Synthesis and preliminary evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors
  作者：Liang Guo、Wei Chen、Wenxi Fan、Qin Ma、Rongqin Sun、Guang Shao、Rihui Cao

  DOI：10.1039/c6md00360e

  日期：——

  A series of novel bivalent β-carbolines were synthesized and evaluated as potent angiogenesis inhibitors.

  一系列新颖的双价β-咔啉类化合物被合成并评估为有效的血管生成抑制剂。