(1'R,2'S,5S)-5-(2'-amino-3'-cyclohexyl-1'-hydroxypropyl)-3-ethyloxazolidin-2-one | 122225-24-5

• 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: (1'R,2'S,5S)-5-(2'-amino-3'-cyclohexyl-1'-hydroxypropyl)-3-ethyloxazolidin-2-one
• 英文别名: (5S)-5-[(1R,2S)-2-amino-3-cyclohexyl-1-hydroxypropyl]-3-ethyl-1,3-oxazolidin-2-one
• CAS: 122225-24-5
• 化学式: C₁₄H₂₆N₂O₃
• 分子量: 270.372
• InChiKey: GGRFWDVXYAJKPK-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'R,2'S,5S)-5-(2'-amino-3'-cyclohexyl-1'-hydroxypropyl)-3-ethyloxazolidin-2-one 在 N-甲基吗啉 、 盐酸 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Studies directed toward the design of orally active renin inhibitors. 1. Some factors influencing the absorption of small peptides

  摘要：

  A systematic evaluation of structure-absorption relationships using a high throughput intraduodenal rat screening model has led to the delineation of a set of structural parameters that appear to govern bioavailability in a series of peptide-based renin inhibitors. Optimum structures, exemplified by 25 and 41, incorporated a single, solubilizing substituent at the C- or N-terminus combined with a lipophilic P2-site residue. Both inhibitors gave unprecedented plasma drug levels upon intraduodenal administration to monkeys, and the calculated bioavailability for 41 (14 +/- 4%) is the highest reported for any peptidic renin inhibitor.

  DOI：

  10.1021/jm00056a005
• 作为产物：
  描述：

  (1'R,2'S,5S)-5-<2'-<(tert-butyloxycarbonyl)amino>-3'-cyclohexyl-1'-(methoxymethoxy)propyl>-3-ethyloxazolidin-2-one 在 盐酸 作用下， 反应 1.0h， 以95%的产率得到(1'R,2'S,5S)-5-(2'-amino-3'-cyclohexyl-1'-hydroxypropyl)-3-ethyloxazolidin-2-one
  参考文献：
  名称：

  Studies directed toward the design of orally active renin inhibitors. 1. Some factors influencing the absorption of small peptides

  摘要：

  A systematic evaluation of structure-absorption relationships using a high throughput intraduodenal rat screening model has led to the delineation of a set of structural parameters that appear to govern bioavailability in a series of peptide-based renin inhibitors. Optimum structures, exemplified by 25 and 41, incorporated a single, solubilizing substituent at the C- or N-terminus combined with a lipophilic P2-site residue. Both inhibitors gave unprecedented plasma drug levels upon intraduodenal administration to monkeys, and the calculated bioavailability for 41 (14 +/- 4%) is the highest reported for any peptidic renin inhibitor.

  DOI：

  10.1021/jm00056a005

文献信息

• Retroviral protease inhibitors
  申请人：ABBOTT LABORATORIES

  公开号：EP0342541A2

  公开（公告）日：1989-11-23

  A retroviral protease inhibiting compound of the formula: or a pharmaceutically acceptable salt, prodrug or ester thereof.

  一种抑制逆转录病毒蛋白酶的式化合物： 或其药学上可接受的盐、原药或酯。
• Non-peptide renin inhibitors
  申请人：ABBOTT LABORATORIES

  公开号：EP0364804A1

  公开（公告）日：1990-04-25

  A renin inhibiting compound of the formula: wherein A is a substituent; R1 is hydrogen, loweralkyl, substituted loweralkyl or loweralkenyl; X is CH2, CHOH, C(O), O, S, S(O), S02, NH, N(O) or -P(O)O-; R3 is loweralkyl, loweralkenyl or substituted loweralkyl; and T is mimic of the Leu-Val cleavage site of angiotensinogen; or a pharmaceutically acceptable salt, ester or prodrug thereof.

  式中的肾素抑制化合物： 其中 A 是取代基；R1 是氢、低级烷基、取代的低级烷基或低级烯基；X 是 CH2、CHOH、C(O)、O、S、S(O)、S02、NH、N(O)或-P(O)O-；R3 是低级烷基、低级烯基或取代的低级烷基；T 是血管紧张素原的 Leu-Val 裂解位点的模拟物；或其药学上可接受的盐、酯或原药。
• Derivatives of amino acids as inhibitors of renin, methods for their preparation, medicaments containing them and their use
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0483403A1

  公开（公告）日：1992-05-06

  Renin inhibitory compounds of formula I in which the residues have the following meaning: R'1 a residue of formula II or III in which the residues are as defined in the specification, methods for their preparation, medicaments containing them and their use.

  式 I 的肾素抑制化合物 其中残基的含义如下： R'1 式 II 或 III 的残基 其中残基的定义见说明书、其制备方法、含有这些残基的药物及其用途。
• US4994477A
  申请人：——

  公开号：US4994477A

  公开（公告）日：1991-02-19