2-(4-(4-Chlorophenyl)-2-(4-phenylpiperidin-4-yl)thiazol-5-yl)acetic acid | 870966-30-6

• 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: 2-(4-(4-Chlorophenyl)-2-(4-phenylpiperidin-4-yl)thiazol-5-yl)acetic acid
• 英文别名: 2-[4-(4-chlorophenyl)-2-(4-phenylpiperidin-4-yl)-1,3-thiazol-5-yl]acetic acid
• CAS: 870966-30-6
• 化学式: C₂₂H₂₁ClN₂O₂S
• 分子量: 412.94
• InChiKey: SVOLDBJYHRIHMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-phenylpiperidine-4-carbothioamide 、 3-溴-4-(4-氯苯基)-4-氧丁酸 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-(4-Chlorophenyl)-2-(4-phenylpiperidin-4-yl)thiazol-5-yl)acetic acid
  参考文献：
  名称：

  Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 2

  摘要：

  Structure-activity relationships have been established by exploring the eastern and western side of 5-thiazolyleacetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Benzhydryl motifs in the 2-position of the thiazole was found to be most advantageous. The 4-thiazole position should either carry 3- or 4-fluorophenyl rings or a 4-pyridyl suitably substituted in the flanking 2-position. Several compounds with single digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained. The compound series display a good PK profile and selectivity over a large number of other targets. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.015

文献信息

• [EN] SUBSTITUTED THIAZOLEACETIC AS CRTH2 LIGANDS<br/>[FR] ACIDES THIAZOLEACETIQUES SUBSTITUES EN TANT QUE LIGANDS CRTH2
  申请人：7TM PHARMA AS

  公开号：WO2005116001A1

  公开（公告）日：2005-12-08

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis; wherein X1 is -S-, -O-, -N=N-. -NR7-, -CR7=CR8-, -CR7=N-, wherein R7 and R8 are independently hydrogen or C1-C3 alkyl; A is a carboxyl group -COOH, or a carboxyl bioisostere; rings Ar2 and Ar3 each independently represent a phenyl or 5- or 6­-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; ring B is as defined for Ar2 and Ar3, or an optionally substituted N-­pyrrolidinyl, N-piperidinyl or N-azepinyl ring; s is 0 or 1; L1, L2 and L4 are linker radicals as defined in the description; Q1 and Q2 represent substituents as defined in the description.

  式(I)的化合物对于治疗对CRTH2受体活性调节敏感的疾病有用，如哮喘、鼻炎、过敏性气道综合征和过敏性鼻支气管炎；其中X1为-S-，-O-，-N=N-，-NR7-，-CR7=CR8-，-CR7=N-，其中R7和R8独立地为氢或C1-C3烷基；A为羧基-COOH，或羧基生物异构体；环Ar2和环Ar3各自独立地表示苯基或5-或6-成员的单环杂芳基环，或由5-或6-成员的碳环或杂环环组成的双环系统，该环或环系可以选择性地被取代；环B的定义与环Ar2和环Ar3相同，或者是一个可选择性取代的N-吡咯烷基，N-哌啶基或N-氮杂七元环；s为0或1；L1、L2和L4为描述中定义的连接基；Q1和Q2表示描述中定义的取代基。
• Substituted Thiazoleacetic Acid as Crth2 Ligands
  申请人：Ulven Trond

  公开号：US20080119456A1

  公开（公告）日：2008-05-22

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis; wherein X 1 is —S—, —O—, —N═N—. —NR 7 —, —CR 7 ═CR 8 —, —CR 7 ═N—, wherein R 7 and R 8 are independently hydrogen or C 1 -C 3 alkyl; A is a carboxyl group —COOH, or a carboxyl bioisostere; rings Ar 2 and Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; ring B is as defined for Ar 2 and Ar 3 , or an optionally substituted N-pyrrolidinyl, N-piperidinyl or N-azepinyl ring; s is 0 or 1; L1, L2 and L4 are linker radicals as defined in the description; Q 1 and Q 2 represent substituents as defined in the description.

  式(I)的化合物对于治疗对CRTH2受体活性调节敏感的疾病，如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎是有用的；其中X1为—S—、—O—、—N═N—、—NR7—、—CR7═CR8—、—CR7═N—，其中R7和R8独立地为氢或C1-C3烷基；A为羧基—COOH，或羧基生物同位素；环Ar2和Ar3各自表示苯基或5-或6-成员单环杂芳基环，或由5-或6-成员碳环或杂环环组成的双环系统，该环或环系统可以选择性地被取代；环B与Ar2和Ar3的定义相同，或是一个可以选择性地被取代的N-吡咯烷基、N-哌啶基或N-氮杂环己基环；s为0或1；L1、L2和L4为描述中定义的连接基团；Q1和Q2表示描述中定义的取代基。
• SUBSTITUTED THIAZOLEACETIC ACIDS AS CRTH2 LIGANDS
  申请人：7TM Pharma A/S

  公开号：EP1758874A1

  公开（公告）日：2007-03-07