(4S,5S)-4-(cyclohexylmethyl)-5-<3'-(mesyloxy)-2'-propenyl>oxazolidin-2-one | 120477-18-1

• 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,5S)-4-(cyclohexylmethyl)-5-<3'-(mesyloxy)-2'-propenyl>oxazolidin-2-one
• 英文别名: (4S,5S)-4-(cyclohexylmethyl)-5-[3'-(mesyloxy)-2'-propenyl]oxazolidin-2-one；2-[(4S,5S)-4-(cyclohexylmethyl)-2-oxo-1,3-oxazolidin-5-yl]prop-2-enyl methanesulfonate
• CAS: 120477-18-1
• 化学式: C₁₄H₂₃NO₅S
• 分子量: 317.406
• InChiKey: CLMLUXUYAADSCF-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-(cyclohexylmethyl)-5-<3'-(mesyloxy)-2'-propenyl>oxazolidin-2-one 在 N-甲基吗啉 、 barium dihydroxide 、 sodium azide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 tert-butyl N-[(2S)-1-[[(2S)-1-[[(2S,3S)-4-(azidomethyl)-1-cyclohexyl-3-hydroxypent-4-en-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
  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
• 作为产物：
  描述：

  2-((4S,5S)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-propenal 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (4S,5S)-4-(cyclohexylmethyl)-5-<3'-(mesyloxy)-2'-propenyl>oxazolidin-2-one
  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：——