methyl-N'-[m-(2-propenyloxycarbonyl)phenyl]ureidoacetate | 171725-31-8

• 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: methyl-N'-[m-(2-propenyloxycarbonyl)phenyl]ureidoacetate
• 英文别名: Allyl 3-(methoxycarbonylmethylureido)benzoate；prop-2-enyl 3-[(2-methoxy-2-oxoethyl)carbamoylamino]benzoate
• CAS: 171725-31-8
• 化学式: C₁₄H₁₆N₂O₅
• 分子量: 292.291
• InChiKey: PDMOIJNRESDATJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl-N'-[m-(2-propenyloxycarbonyl)phenyl]ureidoacetate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2-[4-(N-Cbz-piperidino)carbonyl]-N-{N'[m-(2-propenyloxycarbonyl)phenyl]uridomethylcarbamoyl}aniline
  参考文献：
  名称：

  Synthesis and pharmacological properties of ureidomethylcarbamoylphenylketone derivatives. A new potent and subtype-selective nonpeptide CCK-B/gastrin receptor antagonist, S-0509

  摘要：

  A novel series of CCK-B/gastrin receptor antagonists-ureidomethylcarbamoylphenylketone derivatives were designed, synthesized, and evaluated for activity. Structure-activity relationship studies revealed the importance of a carboxylic acid at substituent R-2 and a tert-butoxycarbonyl group at R-1 in structure A. Compound 7a (S-0509) showed remarkable affinity for the CCK-B/gastrin receptor and a subtype selectivity profile in vitro. Administration (id) of 7a led to excellent inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats with an ED50 value of 0.014 mg/kg. Furthermore, 7a proved to have poor blood-brain permeability by its small effect on enhancement of morphine analgesia. Thus, S-0509 has an increase in selectivity for the peripheral effects of gastrin antagonism from the central effects of CCK-B antagonism. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00104-1
• 作为产物：
  描述：

  三光气 、 甘氨酸甲酯盐酸盐 、 allyl m-aminobenzoate hydrochloride 在 三乙胺 作用下， 生成 methyl-N'-[m-(2-propenyloxycarbonyl)phenyl]ureidoacetate
  参考文献：
  名称：

  Synthesis and pharmacological properties of ureidomethylcarbamoylphenylketone derivatives. A new potent and subtype-selective nonpeptide CCK-B/gastrin receptor antagonist, S-0509

  摘要：

  A novel series of CCK-B/gastrin receptor antagonists-ureidomethylcarbamoylphenylketone derivatives were designed, synthesized, and evaluated for activity. Structure-activity relationship studies revealed the importance of a carboxylic acid at substituent R-2 and a tert-butoxycarbonyl group at R-1 in structure A. Compound 7a (S-0509) showed remarkable affinity for the CCK-B/gastrin receptor and a subtype selectivity profile in vitro. Administration (id) of 7a led to excellent inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats with an ED50 value of 0.014 mg/kg. Furthermore, 7a proved to have poor blood-brain permeability by its small effect on enhancement of morphine analgesia. Thus, S-0509 has an increase in selectivity for the peripheral effects of gastrin antagonism from the central effects of CCK-B antagonism. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00104-1

文献信息

• Carbamoylmethylurea derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US05739162A1

  公开（公告）日：1998-04-14

  A compound of the formula (I): ##STR1## wherein R.sub.1 is a hydrogen atom or lower alkyl; R.sub.2 is a lower alkoxy, lower alkylamino, lower cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclic group; R.sub.3 is an optionally substituted phenyl; R.sub.4 is an optionally substituted phenyl, optionally substituted cycloalkyl, optionally substituted alkyl or optionally substituted heterocyclic group, or a pharmaceutically acceptable salt thereof, which has a high affinity for gastrin receptors and/or CCK-B receptors but not for CCK-A receptors, and is useful for treating diseases associated with gastrin receptors and/or CCK-B receptors without inducing the side effects associated with CCK-A receptors.

  化合物的公式（I）：##STR1##其中R.sub.1是氢原子或较低的烷基；R.sub.2是较低的烷氧基，较低的烷基氨基，较低的环烷基，可选择取代的苯基或可选择取代的杂环基；R.sub.3是可选择取代的苯基；R.sub.4是可选择取代的苯基，可选择取代的环烷基，可选择取代的烷基或可选择取代的杂环基，或其药学上可接受的盐，具有高亲和力，用于治疗与胃泌素受体和/或CCK-B受体相关的疾病，而不会引起与CCK-A受体相关的副作用。
• CARBAMOYLMETHYLUREA DERIVATIVE
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0739903B1

  公开（公告）日：2002-01-23
• US5739162A
  申请人：——

  公开号：US5739162A

  公开（公告）日：1998-04-14