7-n-butyl-oxy-9-phenylpropyl-1-methyl-β-carboline | 1015792-04-7

• 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: 7-n-butyl-oxy-9-phenylpropyl-1-methyl-β-carboline
• 英文别名: 7-Butoxy-1-methyl-9-(3-phenylpropyl)pyrido[3,4-b]indole；7-butoxy-1-methyl-9-(3-phenylpropyl)pyrido[3,4-b]indole
• CAS: 1015792-04-7
• 化学式: C₂₅H₂₈N₂O
• 分子量: 372.51
• InChiKey: XPBXSBBDXOITGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-n-butyl-oxy-9-phenylpropyl-1-methyl-β-carboline 、 对硝基苯甲醛 在 乙酸酐 作用下， 生成 7-Butoxy-1-[2-(4-nitrophenyl)ethenyl]-9-(3-phenylpropyl)pyrido[3,4-b]indole
  参考文献：
  名称：

  Synthesis and cytotoxic activities of 1-benzylidine substituted β-carboline derivatives

  摘要：

  A series of new beta-carboline derivatives, bearing a benzylidine substituent at position-1, has been prepared and evaluated in vitro against a panel of human cell lines. The N-2-benzylated beta-carbolinium bromates represented the most interesting cytotoxic activities. In particular, compounds 19 were found to be the most potent compounds with IC50 values lower than 5 mu M against 10 strains human tumor cell lines. These results confirmed that the N-2-benzyl substituent on the beta-carboline ring played an important role in the modulation of the cytotoxic activities and suggested that further development of such compounds may be interest. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.043
• 作为产物：
  描述：

  肉叶云香碱 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-n-butyl-oxy-9-phenylpropyl-1-methyl-β-carboline
  参考文献：
  名称：

  Synthesis and structure–activity relationships of harmine derivatives as potential antitumor agents

  摘要：

  Harmine, a naturally occurring beta-carboline alkaloid, showed good antitumor activities together with remarkable neurotoxic effects in animal models. In order to search for novel leading compounds endowed with better antitumor activities and less neurotoxicities, a series of harmine derivatives were designed and synthesized by modification of position-2, 7 and 9 of beta-carboline nucleus, and their cytotoxic activities against human tumor cell lines were investigated. Acute toxicities and antitumor activities of the selected compounds in mice were also evaluated. Structure activity relationships studies confirmed that (1) the 7-methoxy structural moiety was the pharmacophore responsible for the neurotoxic effects of this class of compounds; (2) the substituents in position-2 and 9 played a vital role in modulation of their antitumor activities. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.045

文献信息

• Synthesis and structure–activity relationships of N2-alkylated quaternary β-carbolines as novel antitumor agents
  作者：Guoxian Zhang、Rihui Cao、Liang Guo、Qin Ma、Wenxi Fan、Xuemei Chen、Jianru Li、Guang Shao、Liqin Qiu、Zhenghua Ren

  DOI：10.1016/j.ejmech.2013.04.031

  日期：2013.7

  A series of novel N-2-alkylated quaternary beta-carbolines was synthesized by modification of position-1, 2,7 and 9 of beta-carboline nucleus with various alkyl and arylated alkyl substituents, and their cytotoxic activities in vitro and antitumor potencies in mice were evaluated. Compound 3m was found to be the most potent antitumor agent. SARs analysis revealed that (1) the substituents in position-2 and 9 of beta-carboline nucleus played a vital role in modulation of antitumor activity; (2) the benzyl and 3-phenylpropyl substituents in position-2 and 9 of beta-carboline ring were the optimal substituents giving rise to significant antitumor agent. These compounds might be a novel promising class of antitumor agents with clinical development potential. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis and structure–activity relationships of harmine derivatives as potential antitumor agents
  作者：Rihui Cao、Wenxi Fan、Liang Guo、Qin Ma、Guoxian Zhang、Jianru Li、Xuemei Chen、Zhenghua Ren、Liqin Qiu

  DOI：10.1016/j.ejmech.2012.11.045

  日期：2013.2

  Harmine, a naturally occurring beta-carboline alkaloid, showed good antitumor activities together with remarkable neurotoxic effects in animal models. In order to search for novel leading compounds endowed with better antitumor activities and less neurotoxicities, a series of harmine derivatives were designed and synthesized by modification of position-2, 7 and 9 of beta-carboline nucleus, and their cytotoxic activities against human tumor cell lines were investigated. Acute toxicities and antitumor activities of the selected compounds in mice were also evaluated. Structure activity relationships studies confirmed that (1) the 7-methoxy structural moiety was the pharmacophore responsible for the neurotoxic effects of this class of compounds; (2) the substituents in position-2 and 9 played a vital role in modulation of their antitumor activities. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and cytotoxic activities of 1-benzylidine substituted β-carboline derivatives
  作者：Rihui Cao、Wei Yi、Qifeng Wu、Xiangdong Guan、Manxiu Feng、Chunming Ma、Zhiyong Chen、Huacan Song、Wenlie Peng

  DOI：10.1016/j.bmcl.2008.10.043

  日期：2008.12

  A series of new beta-carboline derivatives, bearing a benzylidine substituent at position-1, has been prepared and evaluated in vitro against a panel of human cell lines. The N-2-benzylated beta-carbolinium bromates represented the most interesting cytotoxic activities. In particular, compounds 19 were found to be the most potent compounds with IC50 values lower than 5 mu M against 10 strains human tumor cell lines. These results confirmed that the N-2-benzyl substituent on the beta-carboline ring played an important role in the modulation of the cytotoxic activities and suggested that further development of such compounds may be interest. (C) 2008 Elsevier Ltd. All rights reserved.