cis-4-(2-methoxyphenyl)-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: cis-4-(2-methoxyphenyl)-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid
• 英文别名: (3R,4R)-1-benzyl-4-(2-methoxyphenyl)pyrrolidin-1-ium-3-carboxylate
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: KHORCGWXPAYAIP-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-4-(2-methoxyphenyl)-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid 在 palladium on activated charcoal copper(l) iodide 、 叠氮磷酸二苯酯 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 26.42h， 生成 1,1-dimethylethyl cis-<4-(2-methoxyphenyl)-3-pyrrolidinyl>carbamate
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of a series of 7-[3-amino (or aminomethyl)-4-aryl (or cyclopropyl)-1-pyrrolidinyl]-4-quinolone and -1,8-naphthyridone-3-carboxylic acids

  摘要：

  A series of 6-fluoroquinolone- and 6-fluoro-1,8-naphthyridone-3-carboxylic acids possessing a [3-amino (or aminomethyl)-4-aryl (or cyclopropyl)-1-pyrrolidinyl] group at C-7 were synthesized and evaluated for their antimicrobial activity. The effect of the relative stereochemistry of the pyrrolidinyl substituents, as well as the presence of different functional groups on the 4-aryl (or cyclopropyl) moiety, was investigated in conjunction with their attachment to several quinolone or naphthyridone nuclei. In general, the incorporation of substituents on the aryl (or cyclopropyl) ring decreased in vitro and in vivo activity, regardless of the nature and relative position of the substituent. Bulky, lipophilic groups and substitution at the 2- and 3-position of the aromatic ring were particularly deleterious. Within a limited subset of derivatives, cis substitution of the pyrrolidine ring was less favorable than trans substitution. The majority of these effects were more apparent against the Enterobacteriaceae than against any other Gram-negative or Gram-positive organism and could be associated with negative interactions related to permeability or transport factors.

  DOI：

  10.1021/jm00078a002
• 作为产物：
  描述：

  顺-2-甲氧基肉桂酸 、 N-(甲氧甲基)-N-(三甲基硅甲基)苄胺 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以58%的产率得到cis-4-(2-methoxyphenyl)-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of a series of 7-[3-amino (or aminomethyl)-4-aryl (or cyclopropyl)-1-pyrrolidinyl]-4-quinolone and -1,8-naphthyridone-3-carboxylic acids

  摘要：

  A series of 6-fluoroquinolone- and 6-fluoro-1,8-naphthyridone-3-carboxylic acids possessing a [3-amino (or aminomethyl)-4-aryl (or cyclopropyl)-1-pyrrolidinyl] group at C-7 were synthesized and evaluated for their antimicrobial activity. The effect of the relative stereochemistry of the pyrrolidinyl substituents, as well as the presence of different functional groups on the 4-aryl (or cyclopropyl) moiety, was investigated in conjunction with their attachment to several quinolone or naphthyridone nuclei. In general, the incorporation of substituents on the aryl (or cyclopropyl) ring decreased in vitro and in vivo activity, regardless of the nature and relative position of the substituent. Bulky, lipophilic groups and substitution at the 2- and 3-position of the aromatic ring were particularly deleterious. Within a limited subset of derivatives, cis substitution of the pyrrolidine ring was less favorable than trans substitution. The majority of these effects were more apparent against the Enterobacteriaceae than against any other Gram-negative or Gram-positive organism and could be associated with negative interactions related to permeability or transport factors.

  DOI：

  10.1021/jm00078a002

文献信息

• Nouveaux dérivés de pyrrolidine portant en position 3 un groupe acide gras saturé ou non-saturé, procédé pour leur préparation et compositions pharmaceutiques ayant une activité d'inhibiteurs de thromboxane-A2 les contenant
  申请人：ADIR ET COMPAGNIE

  公开号：EP0556119A1

  公开（公告）日：1993-08-18

  Composés de formule (I) : dans laquelle : R₁ représente : un groupement alkyl éventuellement substitué, un groupement phényle éventuellement substitué, un groupement pyridyle, un groupement phénylsulfonyl éventuellement substitué, un groupement acyle, un groupement benzoyle ou pyridylcarbonyl éventuellement substitué, un groupement alkylaminocarbonyle ou phénylaminocarbonyle, un groupement acylamino ou benzoylamino, R₂ représente : un atome d'hydrogène, un groupement phényle éventuellement substitué, un groupement pyridin-3-yle ou pyridin-2-yle éventuellement substitué, R₃ représente l'un quelconque des groupements suivants :         -(CH₂)n-CO₂R dans lesquels       m est égal à 2, 3 ou 4,       n est égal à 4, 5, 6 ou 7,    et R représente un atome d'hydrogène ou un groupement alkyle. Médicaments.

  式(I)化合物： 其中 R₁ 代表： 一个任选取代的烷基 任选取代的苯基 一个吡啶基 任选取代的苯磺酰基 一个酰基 任选取代的苯甲酰基或吡啶羰基 烷基氨基羰基或苯基氨基羰基 酰氨基或苯甲酰氨基、 R₂ 代表： 氢原子 一个任选取代的苯基 任选取代的吡啶-3-基或吡啶-2-基、 R₃ 代表以下任何一个基团： -(CH₂)n-CO₂R 其中 m 等于 2、3 或 4、 n 为 4、5、6 或 7、 R 代表氢原子或烷基。 医药产品。
• Dérivés de pyrrolidine portant en position 3 un groupe acide gras saturé ou non-saturé, procédé pour leur préparation et compositions pharmaceutiques ayant une activité d'inhibiteurs de thromboxane-A2 les contenant
  申请人：ADIR ET COMPAGNIE

  公开号：EP0556119B1

  公开（公告）日：1997-05-14
• US5387591A
  申请人：——

  公开号：US5387591A

  公开（公告）日：1995-02-07
• Synthesis and antimicrobial evaluation of a series of 7-[3-amino (or aminomethyl)-4-aryl (or cyclopropyl)-1-pyrrolidinyl]-4-quinolone and -1,8-naphthyridone-3-carboxylic acids
  作者：Ruth A. Bucsh、John M. Domagala、Edgardo Laborde、Josephine C. Sesnie

  DOI：10.1021/jm00078a002

  日期：1993.12

  A series of 6-fluoroquinolone- and 6-fluoro-1,8-naphthyridone-3-carboxylic acids possessing a [3-amino (or aminomethyl)-4-aryl (or cyclopropyl)-1-pyrrolidinyl] group at C-7 were synthesized and evaluated for their antimicrobial activity. The effect of the relative stereochemistry of the pyrrolidinyl substituents, as well as the presence of different functional groups on the 4-aryl (or cyclopropyl) moiety, was investigated in conjunction with their attachment to several quinolone or naphthyridone nuclei. In general, the incorporation of substituents on the aryl (or cyclopropyl) ring decreased in vitro and in vivo activity, regardless of the nature and relative position of the substituent. Bulky, lipophilic groups and substitution at the 2- and 3-position of the aromatic ring were particularly deleterious. Within a limited subset of derivatives, cis substitution of the pyrrolidine ring was less favorable than trans substitution. The majority of these effects were more apparent against the Enterobacteriaceae than against any other Gram-negative or Gram-positive organism and could be associated with negative interactions related to permeability or transport factors.