β-(2'-chloro-4-biphenylyl)propionyl chloride | 39802-81-8

• 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: β-(2'-chloro-4-biphenylyl)propionyl chloride
• 英文别名: beta-(2'-Chloro-4-biphenylyl)propionyl chloride；3-[4-(2-chlorophenyl)phenyl]propanoyl chloride
• CAS: 39802-81-8
• 化学式: C₁₅H₁₂Cl₂O
• 分子量: 279.166
• InChiKey: XBNXCXDSXAAOMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  β-(2'-chloro-4-biphenylyl)propionyl chloride 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 2-(3-(2'-chloro-[1,1'-biphenyl]-4-yl)propanamido)cyclohex-1-ene-1-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of ( E )-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists

  摘要：

  Novel series of compounds consisting of 2-amidocyclohex-1-ene carboxylate and phenyl parts which are connected by enyne (compounds 2a-f), but-1-yne (compounds 4a-j), and phenylethylene (compounds 5a-f) linkers as HCA2 full agonists were designed and their functional activity using cAMP assay and binding affinity using radioligand (H-3-niacin) binding assay were evaluated. In general, compounds of all three series exhibit similar HCA2 binding and activation profile. However, the activity is strongly dependent on the substituent at the aromatic part of the structure. Among the structures evaluated, the highest affinity and potency in all series were exhibited by compounds containing 4-hydroxy and/or 2-chloro or 2-fluoro substituents. The most active compounds in the enyne and but-1-yne series in the cAMP assay are 2-fluoro, 4-hydroxy and 2-chloro, 4-hydroxy phenyl derivatives 2f, 4f, and 4g showing potency similar to the previously described 4-hydroxy-biphenyl analogue 5c. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.06.028
• 作为产物：
  描述：

  4-(2-羧基乙基)苯硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 草酰氯 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 β-(2'-chloro-4-biphenylyl)propionyl chloride
  参考文献：
  名称：

  Synthesis and evaluation of ( E )-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists

  摘要：

  Novel series of compounds consisting of 2-amidocyclohex-1-ene carboxylate and phenyl parts which are connected by enyne (compounds 2a-f), but-1-yne (compounds 4a-j), and phenylethylene (compounds 5a-f) linkers as HCA2 full agonists were designed and their functional activity using cAMP assay and binding affinity using radioligand (H-3-niacin) binding assay were evaluated. In general, compounds of all three series exhibit similar HCA2 binding and activation profile. However, the activity is strongly dependent on the substituent at the aromatic part of the structure. Among the structures evaluated, the highest affinity and potency in all series were exhibited by compounds containing 4-hydroxy and/or 2-chloro or 2-fluoro substituents. The most active compounds in the enyne and but-1-yne series in the cAMP assay are 2-fluoro, 4-hydroxy and 2-chloro, 4-hydroxy phenyl derivatives 2f, 4f, and 4g showing potency similar to the previously described 4-hydroxy-biphenyl analogue 5c. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.06.028

文献信息

• Phenyl butyric acids and derivatives thereof
  申请人：William H. Rorer, Inc.

  公开号：US03966801A1

  公开（公告）日：1976-06-29

  Novel substituted phenyl butyric acids and their derivatives are described. Therapeutic compositions and method of treatment of inflammation is also disclosed.

  本文描述了一种新型的取代苯丁酸及其衍生物。还公开了治疗炎症的治疗组合物和方法。
• US3966801A
  申请人：——

  公开号：US3966801A

  公开（公告）日：1976-06-29
• Synthesis and evaluation of ( E )-2-(5-phenylpent-2-en-4-ynamido)cyclohex-1-ene-1-carboxylate derivatives as HCA2 receptor agonists
  作者：Olga Bobileva、Martins Ikaunieks、Gunars Duburs、Ilona Mandrika、Ramona Petrovska、Janis Klovins、Einars Loza

  DOI：10.1016/j.bmc.2017.06.028

  日期：2017.8

  Novel series of compounds consisting of 2-amidocyclohex-1-ene carboxylate and phenyl parts which are connected by enyne (compounds 2a-f), but-1-yne (compounds 4a-j), and phenylethylene (compounds 5a-f) linkers as HCA2 full agonists were designed and their functional activity using cAMP assay and binding affinity using radioligand (H-3-niacin) binding assay were evaluated. In general, compounds of all three series exhibit similar HCA2 binding and activation profile. However, the activity is strongly dependent on the substituent at the aromatic part of the structure. Among the structures evaluated, the highest affinity and potency in all series were exhibited by compounds containing 4-hydroxy and/or 2-chloro or 2-fluoro substituents. The most active compounds in the enyne and but-1-yne series in the cAMP assay are 2-fluoro, 4-hydroxy and 2-chloro, 4-hydroxy phenyl derivatives 2f, 4f, and 4g showing potency similar to the previously described 4-hydroxy-biphenyl analogue 5c. (C) 2017 Elsevier Ltd. All rights reserved.