methyl O,alpha-dimethyl-N-[(tricyclo[3.3.1.13,7]dec-2-yloxy)carbonyl]-DL-tyrosinate | 163798-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl O,alpha-dimethyl-N-[(tricyclo[3.3.1.13,7]dec-2-yloxy)carbonyl]-DL-tyrosinate
• 英文别名: methyl 2-(2-adamantyloxycarbonylamino)-3-(4-methoxyphenyl)-2-methylpropanoate
• CAS: 163798-86-5
• 化学式: C₂₃H₃₁NO₅
• 分子量: 401.503
• InChiKey: ACNGHPSXMSTTFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl O,alpha-dimethyl-N-[(tricyclo[3.3.1.13,7]dec-2-yloxy)carbonyl]-DL-tyrosinate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 O,alpha-dimethyl-N-[(tricyclo[3.3.1.13,7]dec-2-yloxy)carbonyl]-DL-tyrosine
  参考文献：
  名称：

  SAR study of the indole moiety of CI-988, a potent and selective CCK-B antagonist

  摘要：

  Due to the interesting pharmacological activity observed for CI-988, a potent and selective CCK-B receptor antagonist, we have continued to study the SAR of this antagonist. This particular study examines the importance of the indole moiety for binding affinity. The synthesis and receptor binding affinity for analogs containing functionalized indole derivatives and replacing the indole with various heterocycles are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00356-9
• 作为产物：
  描述：

  2-adamantyl chloroformate 在 potassium carbonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 methyl O,alpha-dimethyl-N-[(tricyclo[3.3.1.13,7]dec-2-yloxy)carbonyl]-DL-tyrosinate
  参考文献：
  名称：

  SAR study of the indole moiety of CI-988, a potent and selective CCK-B antagonist

  摘要：

  Due to the interesting pharmacological activity observed for CI-988, a potent and selective CCK-B receptor antagonist, we have continued to study the SAR of this antagonist. This particular study examines the importance of the indole moiety for binding affinity. The synthesis and receptor binding affinity for analogs containing functionalized indole derivatives and replacing the indole with various heterocycles are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00356-9

文献信息

• Amino acid analogs as CCK antagonists
  申请人：Warner-Lambert Company

  公开号：US05331006A1

  公开（公告）日：1994-07-19

  Novel unnatural dipeptoids useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, or as antipsychotics are disclosed. Further, the compounds are antianxiety agents and antiulcer agents. The compounds are agents useful for preventing the response to withdrawal from chronic treatment or use of nicotine, diazepam, alcohol, cocaine, caffeine, and opioids. The compounds are also useful in treating and/or preventing panic attacks. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare diagnostic compositions.

  本发明揭示了一种新型的不自然二肽衍生物，其可用作治疗肥胖、消化道胃酸过多、胃泌素依赖性肿瘤或作为抗精神病药物的药剂。此外，这些化合物还具有抗焦虑和抗溃疡的作用。这些化合物可用于预防尼古丁、地西泮、酒精、可卡因、咖啡因和阿片类药物的慢性治疗或使用引起的戒断反应。这些化合物还可用于治疗和/或预防惊恐发作。此外，本发明还揭示了使用这些二肽衍生物制备药物组合物和治疗方法，以及用于制备诊断组合物的新型中间体。
• [EN] AMINO ACID ANALOGS AS CCK ANTAGONISTS
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1992004025A1

  公开（公告）日：1992-03-19

  (EN) Novel unnatural dipeptoids useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, or as antipsychotics are disclosed. Further, the compounds are antianxiety agents and antiulcer agents. The compounds are agents useful for preventing the response to withdrawal from chronic treatment or use of nicotine, diazepam, alcohol, cocaine, caffeine, and opioids. The compounds are also useful in treating and/or preventing panic attacks. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare diagnostic compositions.(FR) L'invention se rapporte à de nouveaux dipeptoïdes non naturels, qui sont utiles comme agents de traitement de l'obésité, de l'hypersécrétion d'acide gastrique dans l'intestin, de tumeurs dépendantes de la gastrine ou comme neuroleptiques. Ces composés peuvent en outre servir d'anxiolytiques et d'agents anti-ulcéreux. Ils sont utiles pour empêcher la réaction à l'arrêt d'un traitement chronique à la nicotine, au diazépam, à l'alcool, à la cocaïne, à la caféine et aux opioïdes ou d'un usage chronique de ces substances. Ces composés sont également utiles dans le traitement et/ou la prévention des crises de panique. La présente invention décrit aussi des compositions pharmaceutiques et des procédés de traitement qui utilisent ces dipeptoïdes, ainsi que des processus de préparation de ces dipeptoïdes et de nouveaux intermédiaires utiles dans leur préparation. Une autre caractéristique de la présente invention est l'utilisation de ces composés dans la préparation de compositions diagnostiques.
• SAR study of the indole moiety of CI-988, a potent and selective CCK-B antagonist
  作者：Corinne E. Augelli-Szafran、Terri S. Purchase、Bruce D. Roth、Bradley Tait、Bharat K. Trivedi、Michael Wilson、Nirmala Suman-Chauhan、Louise Webdale

  DOI：10.1016/s0960-894x(97)00356-9

  日期：1997.8

  Due to the interesting pharmacological activity observed for CI-988, a potent and selective CCK-B receptor antagonist, we have continued to study the SAR of this antagonist. This particular study examines the importance of the indole moiety for binding affinity. The synthesis and receptor binding affinity for analogs containing functionalized indole derivatives and replacing the indole with various heterocycles are reported. (C) 1997 Elsevier Science Ltd.