5-氰基-L-色氨酸甲酯 | 139393-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-氰基-L-色氨酸甲酯
• 英文名称: 5-Cyano-L-tryptophan methyl ester
• 英文别名: methyl (2S)-2-amino-3-(5-cyano-1H-indol-3-yl)propanoate
• CAS: 139393-04-7
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: DPHXTICOGXJMBV-NSHDSACASA-N

物化性质

• 沸点：
  461.8±40.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  91.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-氰基-L-色氨酸甲酯 在 tri-n-butyltin azide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 (2S)-2-[[1-cyclohexyl-2-(3-furyl)benzimidazole-5-carbonyl]amino]-3-[5-(1H-tetrazol-5-yl)-1H-indol-3-yl]propanoic acid
  参考文献：
  名称：

  Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase: discovery of benzimidazole 5-carboxylic amide derivatives with low-nanomolar potency

  摘要：

  Optimization of benzimidazole 5-carboxamide derivatives previously identified as specific inhibitors of the NS5B polymerase of the hepatitis C virus (HCV) has led to the discovery of potent analogues that inhibit the enzyme at low-nanomolar concentrations. Greater than 800-fold improvement in potency from the original lead structure was achieved through the combined effects of conformational rigidification, molecular size extension and the identification of previously unexploited interactions. Furthermore, these inhibitors retain specificity for HCV polymerase relative to other viral and mammalian RNA polymerases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.032
• 作为产物：
  描述：

  甲醇 、 氰化亚铜 、 8-Acetyl-5-bromo-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester 生成 5-氰基-L-色氨酸甲酯
  参考文献：
  名称：

  Synthesis of 5-cyano-l-tryptophan

  摘要：

  The 5-bromo derivative 2 of the cyclic tautomer of N(b)-methoxycarbonyl-L-tryptophan methyl ester 1 undergoes reaction with CuCN in refluxing N-methylpyrrolidone (NMP) to give 5-cyano derivative 3a with some ring opened 5-cyano product 3b. Both 3a and 3b can be converted, in high yield, into free 5-cyano-L-tryptophan 4 with BBr3 under mild conditions.

  DOI：

  10.1016/s0040-4039(00)77665-9