[2-(N-(tert-butoxycarbonylmethyl)-N-{N'-[m-(2-propenyloxycarbonyl)ureidomethylcarbonyl]amino}phenyl)thienyl-2-yl]ketone | 171724-68-8

• 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: [2-(N-(tert-butoxycarbonylmethyl)-N-{N'-[m-(2-propenyloxycarbonyl)ureidomethylcarbonyl]amino}phenyl)thienyl-2-yl]ketone
• CAS: 171724-68-8
• 化学式: C₃₀H₃₁N₃O₇S
• 分子量: 577.658
• InChiKey: SFVBBUJJLYWVPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  131.11
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [2-(N-(tert-butoxycarbonylmethyl)-N-{N'-[m-(2-propenyloxycarbonyl)ureidomethylcarbonyl]amino}phenyl)thienyl-2-yl]ketone 在 四氢吡咯 、 四(三苯基膦)钯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (2-{N-(tert-butoxycarbonylmethyl)-N-[N'-(m-carboxyphenyl)ureidomethylcarbonyl]amino}phenyl)thienyl-2-ylketone
  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：

  (2-aminophenyl)(thiophen-2-yl)methanone 在 六甲基磷酰三胺 、 氯化亚砜 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成 [2-(N-(tert-butoxycarbonylmethyl)-N-{N'-[m-(2-propenyloxycarbonyl)ureidomethylcarbonyl]amino}phenyl)thienyl-2-yl]ketone
  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