4-[3-(4-Chloro-phenyl)-ureido]-4-dipentylcarbamoyl-butyric acid benzyl ester | 117997-61-2

• 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: 4-[3-(4-Chloro-phenyl)-ureido]-4-dipentylcarbamoyl-butyric acid benzyl ester
• 英文别名: benzyl 4-[(4-chlorophenyl)carbamoylamino]-5-(dipentylamino)-5-oxopentanoate
• CAS: 117997-61-2
• 化学式: C₂₉H₄₀ClN₃O₄
• 分子量: 530.107
• InChiKey: MZWIKTNSIAYTJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[3-(4-Chloro-phenyl)-ureido]-4-dipentylcarbamoyl-butyric acid benzyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(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
• 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 、 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 4-[3-(4-Chloro-phenyl)-ureido]-4-dipentylcarbamoyl-butyric acid benzyl ester
  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

• 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.