(2'R)-2-<<<2'-Benzyl-2',4'-bis<(benzyloxycarbonyl)amino>-1'-oxobutyl>amino>methyl>-1,3-dithiane | 159801-79-3

• 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: (2'R)-2-<<<2'-Benzyl-2',4'-bis<(benzyloxycarbonyl)amino>-1'-oxobutyl>amino>methyl>-1,3-dithiane
• 英文别名: benzyl N-[(2R)-2-benzyl-1-(1,3-dithian-2-ylmethylamino)-1-oxo-4-(phenylmethoxycarbonylamino)butan-2-yl]carbamate
• CAS: 159801-79-3
• 化学式: C₃₂H₃₇N₃O₅S₂
• 分子量: 607.795
• InChiKey: XMHWKDIIPCQAFI-YTTGMZPUSA-N

物化性质

• 沸点：
  860.511±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.246±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'R)-2-<<<2'-Benzyl-2',4'-bis<(benzyloxycarbonyl)amino>-1'-oxobutyl>amino>methyl>-1,3-dithiane 在 碘代三甲硅烷 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.25h， 生成 (4R,2'S)-2-<2'-<<(Benzyloxycarbonyl)amino>ethyl>>-4-benzyl-4-<<<2-(1,3-dithianyl)methyl>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
• 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 128.0h， 生成 (2'R)-2-<<<2'-Benzyl-2',4'-bis<(benzyloxycarbonyl)amino>-1'-oxobutyl>amino>methyl>-1,3-dithiane
  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.