(2S,3S)-2-amino-5-azido-1-cyclohexylpentan-3-ol | 122079-09-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2S,3S)-2-amino-5-azido-1-cyclohexylpentan-3-ol
• CAS: 122079-09-8
• 化学式: C₁₁H₂₂N₄O
• 分子量: 226.322
• InChiKey: OAMUMFYXKLLDQF-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-amino-5-azido-1-cyclohexylpentan-3-ol 、 Boc-Phe-His-OH 在 N-甲基吗啉 、 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 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl N-[(2S)-1-[[(2S)-1-[[(2S,3S)-5-azido-1-cyclohexyl-3-hydroxypentan-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：

  (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-1,3-dihydroxypentane 在 盐酸 、 sodium azide 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.25h， 生成 (2S,3S)-2-amino-5-azido-1-cyclohexylpentan-3-ol
  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

• PEPTIDE ANALOGS
  申请人：DELLARIA, Joseph

  公开号：EP0258289A1

  公开（公告）日：1988-03-09
• EP0258289A4
  申请人：——

  公开号：EP0258289A4

  公开（公告）日：1991-01-02
• US4857507A
  申请人：——

  公开号：US4857507A

  公开（公告）日：1989-08-15
• [EN] PEPTIDE ANALOGS
  申请人：DELLARIA, Joseph

  公开号：WO1987004349A1

  公开（公告）日：1987-07-30

  (EN) A genus of novel peptide analogs which have potent renin-inhibiting activity, methods of treating renin-based hypertension using these compounds, and pharmaceutical compositions containing these compounds as active ingredients.(FR) Est décrit un genre de nouveaux analogues de peptides qui possèdent une puissante activité d'inhibition de la rénine, des procédés de traitement de l'hypertension causée par la rénine au moyen de ces composés, et des compositions pharmaceutiques renfermant ces composés comme principes actifs.
• Azido glycols: potent, low molecular weight renin inhibitors containing an unusual post scissile site residue
  作者：Saul H. Rosenberg、Keith W. Woods、Hollis D. Kleinert、Herman Stein、Hugh N. Nellans、Daniel J. Hoffman、Stephen G. Spanton、Richard A. Pyter、Jerome Cohen

  DOI：10.1021/jm00126a038

  日期：1989.6

  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.