(2RS,3R,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-3-<(2-methoxyethoxy)methoxy>-1,2-epoxypentane | 120476-92-8

• 分子结构分类: 有机化合物
• 英文名称: (2RS,3R,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-3-<(2-methoxyethoxy)methoxy>-1,2-epoxypentane
• 英文别名: (2RS,3R,4S)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-[(2-methoxyethoxy)methoxy]-1,2-epoxypentane；tert-butyl N-[(1R,2S)-3-cyclohexyl-1-(2-methoxyethoxymethoxy)-1-(oxiran-2-yl)propan-2-yl]carbamate
• CAS: 120476-92-8；120574-36-9；124150-91-0
• 化学式: C₂₀H₃₇NO₆
• 分子量: 387.517
• InChiKey: PMFRSFDCGMPYGK-PXKIYYGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  27.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  78.55
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2RS,3R,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-3-<(2-methoxyethoxy)methoxy>-1,2-epoxypentane 在 镍 氨 、 水 、 氢气 作用下， 以 甲醇 为溶剂， 反应 50.0h， 生成 (3R,4R,5S)-1-amino-5-<<(tertbutyloxy)carbonyl>amino>-6-cyclohexyl-3-hydroxy-4-<(methoxyethoxy)methoxy>hexane
  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：

  (4S,5S)-4-(cyclohexylmethyl)-5-vinyloxazolidin-2-one 在 barium dihydroxide 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 71.25h， 生成 (2RS,3R,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-3-<(2-methoxyethoxy)methoxy>-1,2-epoxypentane
  参考文献：
  名称：

  Azido glycols: potent, low molecular weight renin inhibitors containing an unusual post scissile site residue

  摘要：

  Azidomethyl-substituted 1,2- and 1,3-diols were prepared from Boc-cyclohexylalanal and evaluated as transition state analogue renin inhibitors, leading to the development of a small (MW less than 600), nanomolar inhibitor. Remarkable aqueous solubility enhancement followed the incorporation of an N-terminal urea functionality. Evaluation of selected compounds both in vivo and in vitro demonstrated that while transport across the intestine occurred upon id administration, extensive liver extraction resulted in low systemic levels.

  DOI：

  10.1021/jm00126a038

文献信息

• ROSENBERG, SAUL H.;WOODS, KEITH W.;KLEINERT, HOLLIS D.;STEIN, HERMAN;NELL+, J. MED. CHEM., 32,(1989) N, C. 1371-1378
  作者：ROSENBERG, SAUL H.、WOODS, KEITH W.、KLEINERT, HOLLIS D.、STEIN, HERMAN、NELL+

  DOI：——

  日期：——
• 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：——