(RS)-4-[(4-chlorophenylaminocarbonyl)amino]-5-(dipentylamino)-5-oxo-pentanoic acid | 117997-60-1

• 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: (RS)-4-[(4-chlorophenylaminocarbonyl)amino]-5-(dipentylamino)-5-oxo-pentanoic acid
• 英文别名: 4-[3-(4-Chloro-phenyl)-ureido]-4-dipentylcarbamoyl-butyric acid: (0.85 methanol)；4-[(4-chlorophenyl)carbamoylamino]-5-(dipentylamino)-5-oxopentanoic acid
• CAS: 117997-60-1
• 化学式: C₂₂H₃₄ClN₃O₄
• 分子量: 439.983
• InChiKey: GFMBISIECXFEJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  98.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 (RS)-4-[(4-chlorophenylaminocarbonyl)amino]-5-(dipentylamino)-5-oxo-pentanoic acid 在 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， 反应 48.0h， 以37%的产率得到2-[(4-chlorophenyl)carbamoylamino]-5-oxo-N,N-dipentyl-5-pyrrolidin-1-ylpentanamide
  参考文献：
  名称：

  Novel glutamic acid-derived cholecystokinin receptor ligands

  摘要：

  Novel aryl amide analogues of glutamic acid dialkylamide have been synthesized to test for a possible structural analogy between glutamic acid and benzodiazepine CCK antagonists such as compounds 2 and 24 (lorglumide and MK-329, respectively). In support of the structural model, certain of these hybrid compounds are more potent in pancreas CCK radioligand binding assays than corresponding lorglumide-type reference compounds. Modifications previously found in the benzodiazepine antagonists to result in brain CCK/gastrin receptor selectivity were also incorporated to produce an aryl urea series of glutamic acid analogues. None of these compounds were brain CCK/gastrin selective; however, one was potent and selective in the pancreas binding assay. The model appears to be most useful in the design of selective ligands for the pancreas type CCK receptor.

  DOI：

  10.1021/jm00164a020
• 作为产物：
  描述：

  5-(苄氧基)-2-({[(2-甲基-2-丙基)氧基]羰基}氨基)-5-氧代戊酸 在 盐酸 、 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.33h， 生成 (RS)-4-[(4-chlorophenylaminocarbonyl)amino]-5-(dipentylamino)-5-oxo-pentanoic acid
  参考文献：
  名称：

  Novel glutamic acid-derived cholecystokinin receptor ligands

  摘要：

  Novel aryl amide analogues of glutamic acid dialkylamide have been synthesized to test for a possible structural analogy between glutamic acid and benzodiazepine CCK antagonists such as compounds 2 and 24 (lorglumide and MK-329, respectively). In support of the structural model, certain of these hybrid compounds are more potent in pancreas CCK radioligand binding assays than corresponding lorglumide-type reference compounds. Modifications previously found in the benzodiazepine antagonists to result in brain CCK/gastrin receptor selectivity were also incorporated to produce an aryl urea series of glutamic acid analogues. None of these compounds were brain CCK/gastrin selective; however, one was potent and selective in the pancreas binding assay. The model appears to be most useful in the design of selective ligands for the pancreas type CCK receptor.

  DOI：

  10.1021/jm00164a020

文献信息

• Amino acid analogs as CCK-antagonists
  申请人：Merck & Co., Inc.

  公开号：EP0250148A2

  公开（公告）日：1987-12-23

  Analogs of glutamic acid and related amino acids and pharmaceutically-acceptable salts thereof which antagonize the function of cholecystokinins and gastrin disease states in animals and compositions for and methods of preventing or treating disorders of the gastrointestinal, central nervous and appetite regulatory systems of mammals, especially of humans.

  谷氨酸和相关氨基酸的类似物及其药学上可接受的盐，可拮抗动物体内胆囊收缩素的功能和胃泌素疾病状态，以及用于预防或治疗哺乳动物，尤其是人类的胃肠道、中枢神经和食欲调节系统疾病的组合物和方法。
• US4880938A
  申请人：——

  公开号：US4880938A

  公开（公告）日：1989-11-14
• US5089638A
  申请人：——

  公开号：US5089638A

  公开（公告）日：1992-02-18
• Novel glutamic acid-derived cholecystokinin receptor ligands
  作者：R. M. Freidinger、W. L. Whitter、N. P. Gould、M. K. Holloway、R. S. L. Chang、V. J. Lotti

  DOI：10.1021/jm00164a020

  日期：1990.2

  Novel aryl amide analogues of glutamic acid dialkylamide have been synthesized to test for a possible structural analogy between glutamic acid and benzodiazepine CCK antagonists such as compounds 2 and 24 (lorglumide and MK-329, respectively). In support of the structural model, certain of these hybrid compounds are more potent in pancreas CCK radioligand binding assays than corresponding lorglumide-type reference compounds. Modifications previously found in the benzodiazepine antagonists to result in brain CCK/gastrin receptor selectivity were also incorporated to produce an aryl urea series of glutamic acid analogues. None of these compounds were brain CCK/gastrin selective; however, one was potent and selective in the pancreas binding assay. The model appears to be most useful in the design of selective ligands for the pancreas type CCK receptor.