N-[(2R)-1-(dipentylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-6-hydroxynaphthalene-2-carboxamide | 127368-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(2R)-1-(dipentylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-6-hydroxynaphthalene-2-carboxamide
• CAS: 127368-91-6
• 化学式: C₃₂H₃₉N₃O₃
• 分子量: 513.68
• InChiKey: OCJWTEOWJCRLKQ-SSEXGKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  BOC-D-色氨酸 在 盐酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-[(2R)-1-(dipentylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-6-hydroxynaphthalene-2-carboxamide
  参考文献：
  名称：

  Cholecystokinin (CCK) antagonists: (R)-tryptophan-based hybrid antagonists of high affinity and selectivity for CCK-A receptors

  摘要：

  The intriguing structural similarities of glutamic acid based cholecystokinin (CCK) antagonists (A-64718 and A-65186) and the benzodiazepine CCK antagonist MK-329 (L-364,718) have been reported. Efforts to include the weak CCK antagonist benzotript into this construct utilizing a similar approach have resulted in a novel series of benzotript-based hybrid antagonists N-alpha-(3'-quinolylcarbonyl)-(R)-tryptophan di-n-pentylamide (9, A-67396), N-alpha-(4',8'-dihydroxy-2'-quinolylcarbonyl)-(R)-tryptophan di-n-pentylamide (23, A-70276), and N-alpha-(3'-quinolylcarbonyl)-(R)-5'-hydroxytryptophan di-n-pentylamide (36, A-71134) which possess respectively binding affinities of 23, 21, and 11 nM for the pancreatic CCK-A receptor and which inhibit CCK8-induced amylase secretion. Compound 9 possesses a selectivity of > 500-fold for the pancreatic CCK-A receptor over the CCK-B receptor 1.

  DOI：

  10.1021/jm00116a002

文献信息

• Cholecystokinin (CCK) antagonists: (R)-tryptophan-based hybrid antagonists of high affinity and selectivity for CCK-A receptors
  作者：James F. Kerwin、Frank Wagenaar、Hana Kopecka、Chun Wel Lin、Thomas Miller、David Witte、Michael Stashko、Alex M. Nadzan

  DOI：10.1021/jm00116a002

  日期：1991.12

  The intriguing structural similarities of glutamic acid based cholecystokinin (CCK) antagonists (A-64718 and A-65186) and the benzodiazepine CCK antagonist MK-329 (L-364,718) have been reported. Efforts to include the weak CCK antagonist benzotript into this construct utilizing a similar approach have resulted in a novel series of benzotript-based hybrid antagonists N-alpha-(3'-quinolylcarbonyl)-(R)-tryptophan di-n-pentylamide (9, A-67396), N-alpha-(4',8'-dihydroxy-2'-quinolylcarbonyl)-(R)-tryptophan di-n-pentylamide (23, A-70276), and N-alpha-(3'-quinolylcarbonyl)-(R)-5'-hydroxytryptophan di-n-pentylamide (36, A-71134) which possess respectively binding affinities of 23, 21, and 11 nM for the pancreatic CCK-A receptor and which inhibit CCK8-induced amylase secretion. Compound 9 possesses a selectivity of > 500-fold for the pancreatic CCK-A receptor over the CCK-B receptor 1.