{(S)-1-[(S)-1-{(S)-2-Benzothiazol-2-yl-1-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-pyrrolidin-3-ylmethyl]-2-hydroxy-ethylcarbamoyl}-2-(4-fluoro-phenyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester | 261615-12-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {(S)-1-[(S)-1-{(S)-2-Benzothiazol-2-yl-1-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-pyrrolidin-3-ylmethyl]-2-hydroxy-ethylcarbamoyl}-2-(4-fluoro-phenyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-3-[(3S)-1-[(2,4-dimethoxyphenyl)methyl]-2-oxopyrrolidin-3-yl]-1-hydroxypropan-2-yl]amino]-3-(4-fluorophenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 261615-12-7
• 化学式: C₄₂H₅₂FN₅O₈S
• 分子量: 805.968
• InChiKey: UUNVNHCVRCUQEQ-BXNXEVKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  57
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  197
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(S)-1-{(S)-2-Benzothiazol-2-yl-1-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-pyrrolidin-3-ylmethyl]-2-hydroxy-ethylcarbamoyl}-2-(4-fluoro-phenyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester 在 2,4,6-三甲基吡啶 、 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 5-Methyl-isoxazole-3-carboxylic acid {(S)-1-[(S)-1-{(S)-2-benzothiazol-2-yl-1-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-pyrrolidin-3-ylmethyl]-2-hydroxy-ethylcarbamoyl}-2-(4-fluoro-phenyl)-ethylcarbamoyl]-2-methyl-propyl}-amide
  参考文献：
  名称：

  Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitors

  摘要：

  Tripeptide-derived molecules incorporating C-terminal ketone electrophiles were evaluated as reversible inhibitors of the cysteine-containing human rhinovirus 3C protease (3CP). An optimized example of such compounds displayed potent 3CP inhibition activity (K-i = 0.0045 mu M) and in vitro antiviral properties (EC50 = 0.34 mu M) when tested against HRV serotype-14. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00587-9
• 作为产物：
  描述：

  tert-butyl N-[(2S)-1-(1,3-benzothiazol-2-yl)-3-[(3S)-1-[(2,4-dimethoxyphenyl)methyl]-2-oxopyrrolidin-3-yl]-1-oxopropan-2-yl]carbamate 在 N-甲基吗啉 、 盐酸 、 sodium tetrahydroborate 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 3.75h， 生成 {(S)-1-[(S)-1-{(S)-2-Benzothiazol-2-yl-1-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-pyrrolidin-3-ylmethyl]-2-hydroxy-ethylcarbamoyl}-2-(4-fluoro-phenyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitors

  摘要：

  Tripeptide-derived molecules incorporating C-terminal ketone electrophiles were evaluated as reversible inhibitors of the cysteine-containing human rhinovirus 3C protease (3CP). An optimized example of such compounds displayed potent 3CP inhibition activity (K-i = 0.0045 mu M) and in vitro antiviral properties (EC50 = 0.34 mu M) when tested against HRV serotype-14. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00587-9