N-(1-methyl-9-butyl-beta-carboline-3-carbonyl)-L-methionine ethyl ester | 1223075-64-6

• 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: N-(1-methyl-9-butyl-beta-carboline-3-carbonyl)-L-methionine ethyl ester
• 英文别名: ethyl (2S)-2-[(9-butyl-1-methylpyrido[3,4-b]indole-3-carbonyl)amino]-4-methylsulfanylbutanoate
• CAS: 1223075-64-6
• 化学式: C₂₄H₃₁N₃O₃S
• 分子量: 441.594
• InChiKey: HYKKTFBEIJFUKZ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-n-butyl-1-methyl-β-carboline-3-carboxylic acid 、 四氯邻苯二甲酸二丁酯 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到N-(1-methyl-9-butyl-beta-carboline-3-carbonyl)-L-methionine ethyl ester
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of N2-benzylated quaternary β-carboline amino acid ester conjugates

  摘要：

  The beta-carboline alkaloids have been characterized as a class of potential antitumor agents. To further enhance the cytotoxic potency and improve water solubility of beta-carboline, a series of new beta-carboline amino acid ester, beta-carboline amino acid and N-2-benzylated quaternary beta-carboline amino acid ester conjugates were designed and synthesized, and the cytotoxic activities of these compounds were evaluated using a panel of human tumor cell lines. The N-2-benzylated quaternary beta-carboline amino acid ester conjugates represented the most interesting cytotoxic activities. Particularly, compounds 8b and 8g were found to be the most potent compounds with IC50 values lower than 20 mu M against all human tumor cell lines investigated. These results confirmed that the N-2-benzyl substituent on the beta-carboline ring played an important role in the modulation of the cytotoxic potencies. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.060

文献信息

• Synthesis and cytotoxic evaluation of N2-benzylated quaternary β-carboline amino acid ester conjugates
  作者：Chunming Ma、Rihui Cao、Buxi Shi、Shaoxue Li、Zhiyong Chen、Wei Yi、Wenlie Peng、Zhenhua Ren、Huacan Song

  DOI：10.1016/j.ejmech.2009.12.060

  日期：2010.4

  The beta-carboline alkaloids have been characterized as a class of potential antitumor agents. To further enhance the cytotoxic potency and improve water solubility of beta-carboline, a series of new beta-carboline amino acid ester, beta-carboline amino acid and N-2-benzylated quaternary beta-carboline amino acid ester conjugates were designed and synthesized, and the cytotoxic activities of these compounds were evaluated using a panel of human tumor cell lines. The N-2-benzylated quaternary beta-carboline amino acid ester conjugates represented the most interesting cytotoxic activities. Particularly, compounds 8b and 8g were found to be the most potent compounds with IC50 values lower than 20 mu M against all human tumor cell lines investigated. These results confirmed that the N-2-benzyl substituent on the beta-carboline ring played an important role in the modulation of the cytotoxic potencies. (C) 2010 Elsevier Masson SAS. All rights reserved.