(4S,5R,1'S,3'S)-3-<(tert-butyloxy)carbonyl>-4-(cyclohexylmethyl)-5-(1'4'-dihydroxy-3'-methylbutyl)-2',2'-dimethyloxazolidine | 122226-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R,1'S,3'S)-3-<(tert-butyloxy)carbonyl>-4-(cyclohexylmethyl)-5-(1'4'-dihydroxy-3'-methylbutyl)-2',2'-dimethyloxazolidine
• 英文别名: (4S,5R,1'S,3'S)-3-[(tert-butyloxy)carbonyl]-4-(cyclohexylmethyl)-5-(1'4'-dihydroxy-3'-methylbutyl)-2',2'-dimethyloxazolidine；tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(1S,3S)-1,4-dihydroxy-3-methylbutyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 122226-04-4
• 化学式: C₂₂H₄₁NO₅
• 分子量: 399.571
• InChiKey: HFUOFPPDQYKXPL-DSLXNQLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R,1'S,3'S)-3-<(tert-butyloxy)carbonyl>-4-(cyclohexylmethyl)-5-(1'4'-dihydroxy-3'-methylbutyl)-2',2'-dimethyloxazolidine 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4S,5R,2'S,4'S)-3-<(tert-butyloxy)carbonyl>-4-(cyclohexylmethyl)-2,2-dimethyl-5-(4'-methyltetrahydrofuran-2'-yl)oxazolidine
  参考文献：
  名称：

  Potent, low molecular weight renin inhibitors containing a C-terminal heterocycle: hydrogen bonding at the active site

  摘要：

  A series of low-nanomolar renin inhibitors containing novel C-terminal heterocycles has been designed by formally cyclizing the C-terminus of a glycol-based inhibitor to the second hydroxyl. Molecular modeling suggests that the heterocyclic oxygen hydrogen bonds as an acceptor to the flap region of renin and that the second hydroxyl in the glycol-based inhibitors behaves similarly.

  DOI：

  10.1021/jm00168a009
• 作为产物：
  描述：

  (3RS,4S)-4-<(tert-butyloxy)carbonyl>-5-(cyclohexylmethyl)-3-hydroxy-1-pentene 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 4-甲基苯磺酸吡啶 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 25.0~50.0 ℃ 、405.3 kPa 条件下， 反应 50.0h， 生成 (4S,5R,1'S,3'S)-3-<(tert-butyloxy)carbonyl>-4-(cyclohexylmethyl)-5-(1'4'-dihydroxy-3'-methylbutyl)-2',2'-dimethyloxazolidine
  参考文献：
  名称：

  Potent, low molecular weight renin inhibitors containing a C-terminal heterocycle: hydrogen bonding at the active site

  摘要：

  A series of low-nanomolar renin inhibitors containing novel C-terminal heterocycles has been designed by formally cyclizing the C-terminus of a glycol-based inhibitor to the second hydroxyl. Molecular modeling suggests that the heterocyclic oxygen hydrogen bonds as an acceptor to the flap region of renin and that the second hydroxyl in the glycol-based inhibitors behaves similarly.

  DOI：

  10.1021/jm00168a009

文献信息

• ROSENBERG, SAUL H.;DELLARIA, JOSEPH F.;KEMPF, DALE J.;HUTCHINS, CHARLES W+, J. MED. CHEM., 33,(1990) N, C. 1582-1590
  作者：ROSENBERG, SAUL H.、DELLARIA, JOSEPH F.、KEMPF, DALE J.、HUTCHINS, CHARLES W+

  DOI：——

  日期：——
• Potent, low molecular weight renin inhibitors containing a C-terminal heterocycle: hydrogen bonding at the active site
  作者：Saul H. Rosenberg、Joseph F. Dellaria、Dale J. Kempf、Charles W. Hutchins、Keith W. Woods、Robert G. Maki、Ed De Lara、Kenneth P. Spina、Herman H. Stein

  DOI：10.1021/jm00168a009

  日期：1990.6

  A series of low-nanomolar renin inhibitors containing novel C-terminal heterocycles has been designed by formally cyclizing the C-terminus of a glycol-based inhibitor to the second hydroxyl. Molecular modeling suggests that the heterocyclic oxygen hydrogen bonds as an acceptor to the flap region of renin and that the second hydroxyl in the glycol-based inhibitors behaves similarly.