Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-(3-methoxy-phenyl)-1-methylsulfanylcarbonyl-propyl ester | 672965-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-(3-methoxy-phenyl)-1-methylsulfanylcarbonyl-propyl ester
• CAS: 672965-06-9
• 化学式: C₁₉H₂₇NO₆S
• 分子量: 397.492
• InChiKey: HXOGVLYFGOZQEW-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-(3-methoxy-phenyl)-1-methylsulfanylcarbonyl-propyl ester 在 盐酸 、 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 生成 (R)-N-(2,6-dimethylbenzyl)-3-[(2S,3S)-3-amino-2-hydroxy-4-(3-methoxyphenyl)butanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide
  参考文献：
  名称：

  Structure–activity and structure–metabolism relationships of HIV protease inhibitors containing the 3-hydroxy-2-methylbenzoyl-allophenylnorstatine structure

  摘要：

  A series of peptidomimetic human immunodeficiency virus (HIV) protease inhibitors containing substituted allophenyinorstatine [Apns: (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid] were designed and synthesized. From the structure-metabolism relationship of this type of HIV protease inhibitors, the compounds having para substitution of the phenyl ring of Apris and/or 2,6-disubstitution of the P2' benzylamine were found to be able to avoid the P2 phenol glucuronidation that occurs with SM-319777 (formerly named JE-2147, KNI-764); one of the main metabolic pathways of SM-319777. These new analogues, such as SM-322377, had more desirable pharmacokinetic profiles and more potent antiviral activity against not only wild type HIV-1 but also the multi-drug-resistant HIV-1 than SM-319777. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.037
• 作为产物：
  描述：

  BOC-3-甲氧基-L-苯丙氨酸 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 、 sodium amide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-(3-methoxy-phenyl)-1-methylsulfanylcarbonyl-propyl ester
  参考文献：
  名称：

  Structure–activity and structure–metabolism relationships of HIV protease inhibitors containing the 3-hydroxy-2-methylbenzoyl-allophenylnorstatine structure

  摘要：

  A series of peptidomimetic human immunodeficiency virus (HIV) protease inhibitors containing substituted allophenyinorstatine [Apns: (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid] were designed and synthesized. From the structure-metabolism relationship of this type of HIV protease inhibitors, the compounds having para substitution of the phenyl ring of Apris and/or 2,6-disubstitution of the P2' benzylamine were found to be able to avoid the P2 phenol glucuronidation that occurs with SM-319777 (formerly named JE-2147, KNI-764); one of the main metabolic pathways of SM-319777. These new analogues, such as SM-322377, had more desirable pharmacokinetic profiles and more potent antiviral activity against not only wild type HIV-1 but also the multi-drug-resistant HIV-1 than SM-319777. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.037