3-(2-bromomethyl-5-chlorophenyl)acrylic acid ethyl ester | 244103-42-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2-bromomethyl-5-chlorophenyl)acrylic acid ethyl ester
• 英文别名: Ethyl (E)-3-[2-(bromomethyl)-5-chlorophenyl]-2-propenoate；Ethyl(E)-3-[2-(bromomethyl)-5-chlorophenyl]-2-propenoate；ethyl (E)-3-[2-(bromomethyl)-5-chlorophenyl]prop-2-enoate
• CAS: 244103-42-2
• 化学式: C₁₂H₁₂BrClO₂
• 分子量: 303.583
• InChiKey: ZXNPPYXRDHODFH-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-bromomethyl-5-chlorophenyl)acrylic acid ethyl ester 在 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5-bromo-N-{3-[5-chloro-2-(6-chloronaphthalen-2-ylmethyl)phenyl]acryloyl}-2-methoxybenzenesulfonamide
  参考文献：
  名称：

  Structure–activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor

  摘要：

  Potent and selective antagonists of the human EP3 receptor have been identified. The structure-activity relationship of the chemical series was conducted and we found several analogues displaying sub-nanomolar K-i values at the EP3 receptor and micromolar activities at the EP1, EP2 and EP4 receptors. The effect of added human serum albumin (HSA) on the binding affinity at the EP3 receptor was also investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00110-9
• 作为产物：
  描述：

  (E)-ethyl 3-(2-methyl-5-chlorophenyl)acrylate 生成 3-(2-bromomethyl-5-chlorophenyl)acrylic acid ethyl ester
  参考文献：
  名称：

  Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment

  摘要：

  公式I的化合物，以及其药学上可接受的盐、水合物和酯被揭示出来。这些化合物可用于治疗或预防前列腺素介导的疾病。还包括含有这些化合物的药物组合物和治疗方法。

  公开号：

  US06242493B1

文献信息

• CARBOXYLIC ACIDS AND ACYLSULFONAMIDES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT
  申请人：Merck Frosst Canada & Co.

  公开号：EP1071648A2

  公开（公告）日：2001-01-31
• US6242493B1
  申请人：——

  公开号：US6242493B1

  公开（公告）日：2001-06-05
• [EN] CARBOXYLIC ACIDS AND ACYLSULFONAMIDES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT<br/>[FR] ACIDES CARBOXYLIQUES ET ACYLSULFONAMIDES, COMPOSITIONS CONTENANT CES COMPOSES ET METHODES DE TRAITEMENT
  申请人：——

  公开号：WO1999047497A2

  公开（公告）日：1999-09-23

  [EN] Compounds of formula (I), as well as pharmaceutically acceptable salts, hydrates and esters thereof, are disclosed. The compounds are useful for treating or preventing prostaglandin mediated diseases. Pharmaceutical compositions containing such compounds and methods of treatment are also included.
  [FR] L'invention concerne des composés représentés par la formule (I), ainsi que des sels, des hydrates et des esters de ceux-ci qui sont acceptables d'un point de vue pharmaceutique. Les composés sont utiles pour traiter ou prévenir des maladies dans lesquelles intervient la prostaglandine. L'invention concerne également des compositions pharmaceutiques contenant ces composés et des méthodes de traitement.
• Structure–activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor
  作者：Hélène Juteau、Yves Gareau、Marc Labelle、Claudio F Sturino、Nicole Sawyer、Nathalie Tremblay、Sonia Lamontagne、Marie-Claude Carrière、Danielle Denis、Kathleen M Metters

  DOI：10.1016/s0968-0896(01)00110-9

  日期：2001.8

  Potent and selective antagonists of the human EP3 receptor have been identified. The structure-activity relationship of the chemical series was conducted and we found several analogues displaying sub-nanomolar K-i values at the EP3 receptor and micromolar activities at the EP1, EP2 and EP4 receptors. The effect of added human serum albumin (HSA) on the binding affinity at the EP3 receptor was also investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment
  申请人：Merck Frosst Canada & Co.

  公开号：US06242493B1

  公开（公告）日：2001-06-05

  Compounds of formula I: as well as pharmaceutically acceptable salts, hydrates and esters thereof, are disclosed. The compounds are useful for treating or preventing prostaglandin mediated diseases. Pharmaceutical compositions containing such compounds and methods of treatment are also included.

  公式I的化合物，以及其药学上可接受的盐、水合物和酯被揭示出来。这些化合物可用于治疗或预防前列腺素介导的疾病。还包括含有这些化合物的药物组合物和治疗方法。