(S)-3-(1H-Indol-3-yl)-N,N-dipentyl-2-(3-m-tolyl-ureido)-propionamide | 127369-03-3

• 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: (S)-3-(1H-Indol-3-yl)-N,N-dipentyl-2-(3-m-tolyl-ureido)-propionamide
• 英文别名: (2S)-3-(1H-indol-3-yl)-2-[(3-methylphenyl)carbamoylamino]-N,N-dipentylpropanamide
• CAS: 127369-03-3
• 化学式: C₂₉H₄₀N₄O₂
• 分子量: 476.662
• InChiKey: MJFWJRHZFCTBNY-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二戊胺 在 盐酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-3-(1H-Indol-3-yl)-N,N-dipentyl-2-(3-m-tolyl-ureido)-propionamide
  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

• Derivatives of tryptophan as CCK antagonists
  申请人：ABBOTT LABORATORIES

  公开号：EP0336356A2

  公开（公告）日：1989-10-11

  A compound of the formula: wherein R₁ and R₂ are independently selected from hydrogen, loweralkyl, cycloalkyl, loweralkenyl, adamantyl, aryl, substituted aryl, heterocyclic group, substituted alkyl, substituted amide, functionalized carbonyl, and nitrogen containing ring wherein R₁, R₂ and the adjacent nitrogen atom form a ring; R₁₁ is hydrogen, loweralkyl, or loweralkenyl; R₂₀ is hydrogen, loweralkyl, or loweralkenyl; B is -(CH₂)m-, substituted alkenylene, -QCH₂- wherein Q is O, S, NH or substituted amino, -CH₂Q- wherein Q is as defined or B is NH; Z is C=O, S(O)₂, or C=S; Ar is a heterocyclic group, aryl or substituted aryl; D is unsubstituted or substituted indol-3-yl, indolin-3-yl or oxindol-3-yl; and m is 0 to 4; or a pharmaceutically acceptable salt thereof.

  式中的化合物 其中 R₁ 和 R₂ 独立选自氢、低级烷基、环烷基、低级烯基、金刚烷基、芳基、取代的芳基、杂环基团、取代的烷基、取代的酰胺、官能化羰基和含氮环，其中 R₁、R₂ 和相邻的氮原子形成一个环； R₁₁ 是氢、低级烷基或低级烯基； R₂₀ 是氢、低级烷基或低级烯基； B 是-(CH₂)m-、取代烯基、-QCH₂-（其中 Q 是 O、S、NH 或取代氨基）、-CH₂Q-（其中 Q 如所定义）或 B 是 NH； Z 是 C=O、S(O)₂ 或 C=S； Ar 是杂环基团、芳基或取代的芳基； D 是未取代或取代的吲哚-3-基、吲哚啉-3-基或氧杂吲哚-3-基；以及 m 是 0 至 4； 或其药学上可接受的盐。
• 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.