N-(tert-butoxycarbonyl)histidine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane | 104882-15-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)histidine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane
• 英文别名: tert-butyl N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]carbamate
• CAS: 104882-15-7
• 化学式: C₂₅H₄₄N₄O₅
• 分子量: 480.648
• InChiKey: QVXJNJONSFBURH-MYGLTJDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)histidine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane 生成 N-[(2S)-3-cyclohexyl-1-[[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-methylheptan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]-3,3-dimethylbutanamide
  参考文献：
  名称：

  LULY, JAY R.;PLATTNER, JACOB J.;DALE, J. KEMPF

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-氨基-1-环己基-(R)-3,(S)-4-二羟基-6-甲基庚烷盐酸盐 、 N-Boc-L-组氨酸 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 N-(tert-butoxycarbonyl)histidine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane
  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

• LULY, JAY R.;PLATTNER, JACOB J.;DALE, J. KEMPF
  作者：LULY, JAY R.、PLATTNER, JACOB J.、DALE, J. KEMPF

  DOI：——

  日期：——
• LULY, JAY R.;PLATTNER, JACO J.;FUNG, ANTHONY K.
  作者：LULY, JAY R.、PLATTNER, JACO J.、FUNG, ANTHONY K.

  DOI：——

  日期：——
• Studies directed toward the design of orally active renin inhibitors. 1. Some factors influencing the absorption of small peptides
  作者：Saul H. Rosenberg、Kenneth P. Spina、Keith W. Woods、Jim Polakowski、Donald L. Martin、Zhengli Yao、Herman H. Stein、Jerome Cohen、Jennifer L. Barlow

  DOI：10.1021/jm00056a005

  日期：1993.2

  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.