[2-(N-Cbz-glycylamino)phenyl]thienyl-2-ylketone | 171725-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(N-Cbz-glycylamino)phenyl]thienyl-2-ylketone
• 英文别名: benzyl N-[2-oxo-2-[2-(thiophene-2-carbonyl)anilino]ethyl]carbamate
• CAS: 171725-23-8
• 化学式: C₂₁H₁₈N₂O₄S
• 分子量: 394.451
• InChiKey: WMVGHLMEXCNSEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(N-Cbz-glycylamino)phenyl]thienyl-2-ylketone 在 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 thienyl-{2-[N'-(m-tolyl)ureidomethylcarbamoyl]phenyl}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
• 作为产物：
  描述：

  (2-aminophenyl)(thiophen-2-yl)methanone 、 N-苄氧羰基甘氨酸 在 六甲基磷酰三胺 、 氯化亚砜 作用下， 生成 [2-(N-Cbz-glycylamino)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

文献信息

• 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
• Synthesis and pharmacological properties of ureidomethylcarbamoylphenylketone derivatives. A new potent and subtype-selective nonpeptide CCK-B/gastrin receptor antagonist, S-0509
  作者：Sanji Hagishita、Yasushi Murakami、Kaoru Seno、Susumu Kamata、Nobuhiro Haga、Toshiro Konoike、Yasuhiko Kanda、Ryuichi Kiyama、Takeshi Shiota、Yasunobu Ishihara、Michio Ishikawa、Mayumi Shimamura、Koji Abe、Koji Yoshimura

  DOI：10.1016/s0968-0896(97)00104-1

  日期：1997.8

  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.