{Benzyl-[(R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-amino}-acetic acid ethyl ester | 127369-22-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: {Benzyl-[(R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-amino}-acetic acid ethyl ester
• 英文别名: Boc-D-Trp-N(Bn)Gly-OEt；ethyl 2-[benzyl-[(2R)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetate
• CAS: 127369-22-6
• 化学式: C₂₇H₃₃N₃O₅
• 分子量: 479.576
• InChiKey: GKLFZTRZNRESJG-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {Benzyl-[(R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-amino}-acetic acid ethyl ester 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (Benzyl-{(R)-3-(1H-indol-3-yl)-2-[(quinoline-3-carbonyl)-amino]-propionyl}-amino)-acetic acid ethyl ester
  参考文献：
  名称：

  Cholecystokinin (CCK) antagonists: (R)-tryptophan-based hybrid antagonists of high affinity and selectivity for CCK-A receptors

  摘要：

  The intriguing structural similarities of glutamic acid based cholecystokinin (CCK) antagonists (A-64718 and A-65186) and the benzodiazepine CCK antagonist MK-329 (L-364,718) have been reported. Efforts to include the weak CCK antagonist benzotript into this construct utilizing a similar approach have resulted in a novel series of benzotript-based hybrid antagonists N-alpha-(3'-quinolylcarbonyl)-(R)-tryptophan di-n-pentylamide (9, A-67396), N-alpha-(4',8'-dihydroxy-2'-quinolylcarbonyl)-(R)-tryptophan di-n-pentylamide (23, A-70276), and N-alpha-(3'-quinolylcarbonyl)-(R)-5'-hydroxytryptophan di-n-pentylamide (36, A-71134) which possess respectively binding affinities of 23, 21, and 11 nM for the pancreatic CCK-A receptor and which inhibit CCK8-induced amylase secretion. Compound 9 possesses a selectivity of > 500-fold for the pancreatic CCK-A receptor over the CCK-B receptor 1.

  DOI：

  10.1021/jm00116a002
• 作为产物：
  描述：

  N-苄基甘氨酸乙酯 、 BOC-D-色氨酸 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 {Benzyl-[(R)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-amino}-acetic acid ethyl ester
  参考文献：
  名称：

  Cholecystokinin (CCK) antagonists: (R)-tryptophan-based hybrid antagonists of high affinity and selectivity for CCK-A receptors

  摘要：

  The intriguing structural similarities of glutamic acid based cholecystokinin (CCK) antagonists (A-64718 and A-65186) and the benzodiazepine CCK antagonist MK-329 (L-364,718) have been reported. Efforts to include the weak CCK antagonist benzotript into this construct utilizing a similar approach have resulted in a novel series of benzotript-based hybrid antagonists N-alpha-(3'-quinolylcarbonyl)-(R)-tryptophan di-n-pentylamide (9, A-67396), N-alpha-(4',8'-dihydroxy-2'-quinolylcarbonyl)-(R)-tryptophan di-n-pentylamide (23, A-70276), and N-alpha-(3'-quinolylcarbonyl)-(R)-5'-hydroxytryptophan di-n-pentylamide (36, A-71134) which possess respectively binding affinities of 23, 21, and 11 nM for the pancreatic CCK-A receptor and which inhibit CCK8-induced amylase secretion. Compound 9 possesses a selectivity of > 500-fold for the pancreatic CCK-A receptor over the CCK-B receptor 1.

  DOI：

  10.1021/jm00116a002

文献信息

• Substituted imidazole compound and use thereof
  申请人：Kuroita Takanobu

  公开号：US20090227560A1

  公开（公告）日：2009-09-10

  The present invention relates to a compound represented by the formula: wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof. The compound of the present invention has a superior renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension, and the like.

  本发明涉及一种由以下式表示的化合物：其中每个符号如描述中所定义，或其盐或前药。本发明的化合物具有优越的肾素抑制活性，因此可用作预防或治疗高血压、由高血压引起的各种器官损伤等的药物。
• [EN] SUBSTITUTED IMIDAZOLE COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ D'IMIDAZOLE SUBSTITUÉ ET SON UTILISATION
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2008139941A1

  公开（公告）日：2008-11-20

  [EN] The present invention relates to a compound represented by the formula: wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof. The compound of the present invention has a superior renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension, and the like.
  [FR] La présente invention concerne un composé représenté par la formule : dans laquelle chaque symbole est tel que défini dans la description, ou l'un de ses sels ou précurseurs. Le composé de la présente invention possède une activité supérieure d'inhibition de la rénine et est ainsi utile en tant qu'agent destiné à la prophylaxie ou au traitement de l'hypertension, de diverses lésions d'organes attribuables à l'hypertension et analogues.