N-(N'-Cbz-glycyl)-2-(hept-4-ylcarbonyl)aniline | 171725-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(N'-Cbz-glycyl)-2-(hept-4-ylcarbonyl)aniline
• 英文别名: benzyl N-[2-oxo-2-[2-(2-propylpentanoyl)anilino]ethyl]carbamate
• CAS: 171725-13-6
• 化学式: C₂₄H₃₀N₂O₄
• 分子量: 410.513
• InChiKey: IMXFLWKBPIHFOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(N'-Cbz-glycyl)-2-(hept-4-ylcarbonyl)aniline 在 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 反应 1.0h， 生成 2-(hept-4-ylcarbonyl)-N-{N'-[m-(2-propenyloxycarbonyl)phenyl]ureidomethylcarbonyl}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：

  2,2-二-正丙基乙酰基氯 、 N-(N'-Cbz-glycyl)-2-(tri-n-butylstannyl)aniline 在 双(乙腈)氯化钯(II) 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以55%的产率得到N-(N'-Cbz-glycyl)-2-(hept-4-ylcarbonyl)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

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.