(4R,1'S)-2-<1'-<(benzyloxycarbonyl)-amino>ethyl>-4-benzyl-4-<<(2,2-dimethoxyethyl)amino>carbonyl>-3,4,5,6-tetrahydropyrimidine | 159801-74-8

• 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: (4R,1'S)-2-<1'-<(benzyloxycarbonyl)-amino>ethyl>-4-benzyl-4-<<(2,2-dimethoxyethyl)amino>carbonyl>-3,4,5,6-tetrahydropyrimidine
• 英文别名: benzyl N-[(1S)-1-[(6R)-6-benzyl-6-(2,2-dimethoxyethylcarbamoyl)-4,5-dihydro-1H-pyrimidin-2-yl]ethyl]carbamate
• CAS: 159801-74-8
• 化学式: C₂₆H₃₄N₄O₅
• 分子量: 482.58
• InChiKey: UXFKQZVFXXUZTH-SIBVEZHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,1'S)-2-<1'-<(benzyloxycarbonyl)-amino>ethyl>-4-benzyl-4-<<(2,2-dimethoxyethyl)amino>carbonyl>-3,4,5,6-tetrahydropyrimidine 、 三氟乙酸 反应 0.75h， 以99%的产率得到(4R,1'S)-2-<1'-<(Benzyloxycarbonyl)-amino>ethyl>-4-benzyl-4-<<(2-oxoethyl)amino>carbonyl>-3,4,5,6-tetrahydropyrimidine trifluoroacetate
  参考文献：
  名称：

  Design and Synthesis of a Conformationally Restricted Cysteine Protease Inhibitor

  摘要：

  Using the X-ray analyses of papain and papain-chloromethyl ketone inhibitor complexes as representative cysteine protease structures, molecular graphics analyses were applied to design (4R,1'S)-2-[1'-[(benzyloxycarbon)amino]ethyl]4-benzyl-4-[[(2-oxoethyl)amino]carbonyl]-3,4,5,6-tetrahydropyrimidine (1) as a conformationally restricted, competitive inhibitor of cysteine proteases. Two routes to this target inhibitor, which was found to be a good competitive inhibitor of papain with a K-I of 790 nM, are described.

  DOI：

  10.1021/jo00104a022
• 作为产物：
  描述：

  (2S,4R)-2-Phenyl-3-(carbobenzyloxy)-4-benzyl-4-(2-hydroxyethyl)oxazolidinone 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium hydroxide 、 sodium azide 、 二苯基磷酸 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 55.0 ℃ 、379.21 kPa 条件下， 反应 131.0h， 生成 (4R,1'S)-2-<1'-<(benzyloxycarbonyl)-amino>ethyl>-4-benzyl-4-<<(2,2-dimethoxyethyl)amino>carbonyl>-3,4,5,6-tetrahydropyrimidine
  参考文献：
  名称：

  Design and Synthesis of a Conformationally Restricted Cysteine Protease Inhibitor

  摘要：

  Using the X-ray analyses of papain and papain-chloromethyl ketone inhibitor complexes as representative cysteine protease structures, molecular graphics analyses were applied to design (4R,1'S)-2-[1'-[(benzyloxycarbon)amino]ethyl]4-benzyl-4-[[(2-oxoethyl)amino]carbonyl]-3,4,5,6-tetrahydropyrimidine (1) as a conformationally restricted, competitive inhibitor of cysteine proteases. Two routes to this target inhibitor, which was found to be a good competitive inhibitor of papain with a K-I of 790 nM, are described.

  DOI：

  10.1021/jo00104a022

文献信息

• Design and Synthesis of a Conformationally Restricted Cysteine Protease Inhibitor
  作者：Hengmiao Cheng、Paul Keitz、J. Bryan Jones

  DOI：10.1021/jo00104a022

  日期：1994.12

  Using the X-ray analyses of papain and papain-chloromethyl ketone inhibitor complexes as representative cysteine protease structures, molecular graphics analyses were applied to design (4R,1'S)-2-[1'-[(benzyloxycarbon)amino]ethyl]4-benzyl-4-[[(2-oxoethyl)amino]carbonyl]-3,4,5,6-tetrahydropyrimidine (1) as a conformationally restricted, competitive inhibitor of cysteine proteases. Two routes to this target inhibitor, which was found to be a good competitive inhibitor of papain with a K-I of 790 nM, are described.