4-carboxy-4-phenylpiperidin-2-one | 167398-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-carboxy-4-phenylpiperidin-2-one
• 英文别名: 2-Oxo-4-phenylpiperidine-4-carboxylic acid
• CAS: 167398-75-6
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: FLBZEGKUSFNMLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-carboxy-4-phenylpiperidin-2-one 、 8-methyl-8-azabicyclo[3.2.1]octan-3-olate sodium 在 N,N'-羰基二咪唑 作用下， 生成 (8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) 2-oxo-4-phenylpiperidine-4-carboxylate
  参考文献：
  名称：

  New pyrrolidin-, piperidin- and azepin-2-oxocarboxylic acid esters are preferential M1, M3 muscarinic antagonists. Synthesis and bronchospasmolytic activity

  摘要：

  A series of new 3-tropanol and 3-quinuclidinol esters of phenyl-substituted pyrrolidin-, piperidin- and azepin-2-oxocarboxylic acid were synthesized and tested for antimuscarinic activity. The compounds showed a preferential in vitro activity at M(1) and M(3) receptor subtypes and an interesting activity profile in vivo. A potential use as selective bronchospasmolytic agents has been suggested for selected compounds.

  DOI：

  10.1016/0223-5234(94)90068-x
• 作为产物：
  描述：

  去甲哌替啶 在 盐酸 、 ruthenium(IV) oxide 、 氢氧化钾 、 sodium periodate 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 194.0h， 生成 4-carboxy-4-phenylpiperidin-2-one
  参考文献：
  名称：

  New pyrrolidin-, piperidin- and azepin-2-oxocarboxylic acid esters are preferential M1, M3 muscarinic antagonists. Synthesis and bronchospasmolytic activity

  摘要：

  A series of new 3-tropanol and 3-quinuclidinol esters of phenyl-substituted pyrrolidin-, piperidin- and azepin-2-oxocarboxylic acid were synthesized and tested for antimuscarinic activity. The compounds showed a preferential in vitro activity at M(1) and M(3) receptor subtypes and an interesting activity profile in vivo. A potential use as selective bronchospasmolytic agents has been suggested for selected compounds.

  DOI：

  10.1016/0223-5234(94)90068-x

文献信息

• New R(-) 3-quinuclidinol derivatives
  申请人：BOEHRINGER INGELHEIM ITALIA S.p.A.

  公开号：EP0404737A2

  公开（公告）日：1990-12-27

  Pharmacologically active R(-) 3-quinuclidinol derivatives are described which are muscarinic receptor blocking agents useful for the treatment of gastrointestinal and respiratory tract disorders of the following formula (I) wherein R represents a linear or branched lower alkyl group, a cycloalkyl-C₁₋₂alkyl or an aralkyl group, or it is absent; X represents the anion of an organic or inorganic acid, or it is absent, when R is absent; R₁ represents H, a linear or branched lower alkyl group or an acyl group of the type R₂-CO, in which R₂ is H or a linear or branched lower alkyl group; A represents a cycloalkyl, an aromatic ring or a 5- or 6-membered heterocyclic ring; Y and Z may be simultaneously or alternatively present or absent; when they are simultaneously present, they represent oxygen; when only one of them is present, it is oxygen or sulphur; n is 1, 2 or 3; A and the 3-quinuclidinyl ester groups are inserted simultaneously on the same carbon atom of the ring to give rise to a geminal substitution. The process of the preparation of the compounds of formula (I) as well as pharmaceutical compositions containing them are also described.

  描述了具有药理活性的 R(-) 3-quinuclidinol 衍生物，它们是有助于治疗胃肠道和呼吸道疾病的毒蕈碱受体阻断剂，如下式 (I) 所示 其中 R 代表直链或支链低级烷基、环烷基-C₁₋₂烷基或芳烷基，或不含； 当 R 不存在时，X 代表有机酸或无机酸的阴离子； R₁ 代表 H、直链或支链低级烷基或 R₂-CO 类型的酰基，其中 R₂ 是 H 或直链或支链低级烷基； A 代表环烷基、芳香环或 5 或 6 元杂环； Y 和 Z 可同时或交替存在或不存在；当它们同时存在时，它们代表氧；当它们中只有一个存在时，它是氧或硫； n 为 1、2 或 3； A 和 3-quinuclidinyl 酯基同时插入环的同一碳原子上，以产生宝石取代。 此外，还描述了式（I）化合物的制备过程以及含有这些化合物的药物组合物。
• US5164386A
  申请人：——

  公开号：US5164386A

  公开（公告）日：1992-11-17
• New pyrrolidin-, piperidin- and azepin-2-oxocarboxylic acid esters are preferential M1, M3 muscarinic antagonists. Synthesis and bronchospasmolytic activity
  作者：E Cereda、A Ezhaya、E Bellora、GB Schiavi、A Sagrada、HN Doods、A Donetti

  DOI：10.1016/0223-5234(94)90068-x

  日期：1994.1

  A series of new 3-tropanol and 3-quinuclidinol esters of phenyl-substituted pyrrolidin-, piperidin- and azepin-2-oxocarboxylic acid were synthesized and tested for antimuscarinic activity. The compounds showed a preferential in vitro activity at M(1) and M(3) receptor subtypes and an interesting activity profile in vivo. A potential use as selective bronchospasmolytic agents has been suggested for selected compounds.