D,L-α-methyl-3-(2-quinolyl)alanine methyl ester | 143004-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: D,L-α-methyl-3-(2-quinolyl)alanine methyl ester
• 英文别名: 3-quinolinyl-2-methyl-alanine methyl ester；Methyl 2-amino-2-methyl-3-quinolin-2-ylpropanoate
• CAS: 143004-77-7
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: HZOZHTWOPWVZAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D,L-α-methyl-3-(2-quinolyl)alanine methyl ester 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 2-(2-Adamantyloxycarbonylamino)-2-methyl-3-quinolin-2-ylpropanoic acid
  参考文献：
  名称：

  Synthesis and receptor-binding affinity of dipeptoid cholecystokinin ligands

  摘要：

  This paper describes the synthesis of novel derivatives 4a-i, which are structurally related to PD134308 and in which the indole moiety is replaced by other aromatic groups. Cholecystokinin-A and -B (CCK-A and CCK-B) receptor binding affinities of these analogues are described and the contribution of the various rings is discussed. Several of the compounds prepared have CCK-B receptor binding values similar to that reported for PD134308 and are highly selective over the CCK-A receptor. They represent potential therapeutic agents for anxiety.

  DOI：

  10.1016/0223-5234(96)89137-9
• 作为产物：
  描述：

  2-Methyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-3-quinolin-2-yl-propionic acid methyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 D,L-α-methyl-3-(2-quinolyl)alanine methyl ester
  参考文献：
  名称：

  Synthesis and receptor-binding affinity of dipeptoid cholecystokinin ligands

  摘要：

  This paper describes the synthesis of novel derivatives 4a-i, which are structurally related to PD134308 and in which the indole moiety is replaced by other aromatic groups. Cholecystokinin-A and -B (CCK-A and CCK-B) receptor binding affinities of these analogues are described and the contribution of the various rings is discussed. Several of the compounds prepared have CCK-B receptor binding values similar to that reported for PD134308 and are highly selective over the CCK-A receptor. They represent potential therapeutic agents for anxiety.

  DOI：

  10.1016/0223-5234(96)89137-9

文献信息

• Schoellkopf, Ulrich; Hartwig, Wolfgang; Groth, Ulrich, Liebigs Annalen der Chemie, 1981, # 4, p. 696 - 708
  作者：Schoellkopf, Ulrich、Hartwig, Wolfgang、Groth, Ulrich、Westphalen, Karl-Otto

  DOI：——

  日期：——
• US5331006A
  申请人：——

  公开号：US5331006A

  公开（公告）日：1994-07-19
• [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.
• Synthesis and receptor-binding affinity of dipeptoid cholecystokinin ligands
  作者：G Araldi、D Donati、B Oliosi、A Pasquarello、S Polinelli、G Tarzia、A Ursini、FTM van Amsterdam

  DOI：10.1016/0223-5234(96)89137-9

  日期：1996.1

  This paper describes the synthesis of novel derivatives 4a-i, which are structurally related to PD134308 and in which the indole moiety is replaced by other aromatic groups. Cholecystokinin-A and -B (CCK-A and CCK-B) receptor binding affinities of these analogues are described and the contribution of the various rings is discussed. Several of the compounds prepared have CCK-B receptor binding values similar to that reported for PD134308 and are highly selective over the CCK-A receptor. They represent potential therapeutic agents for anxiety.