Phenyl(2-thienyl)glycolic acid | 28560-51-2

• 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: Phenyl(2-thienyl)glycolic acid
• 英文别名: 2-hydroxy-2-phenyl-2-(2-thienyl) acetic acid；2-Phenyl-2-(2-thienyl)glykolsaeure；2-hydroxy-2-phenyl-2-(thiophen-2-yl)acetic acid；hydroxy-phenyl-thiophen-2-yl-acetic acid；(+)-2-Hydroxy-2-phenyl-2-thien-2-ylacetic acid；Hydroxy-phenyl-[2]thienyl-essigsaeure；hydroxy-phenyl-[2]thienyl-acetic acid；Hydroxy(phenyl)2-thienylacetic acid；2-hydroxy-2-phenyl-2-thiophen-2-ylacetic acid
• CAS: 28560-51-2
• 化学式: C₁₂H₁₀O₃S
• 分子量: 234.276
• InChiKey: BIHFCPRVAAVAPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Phenyl(2-thienyl)glycolic acid 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 2-苯甲酰噻吩
  参考文献：
  名称：

  Ott, Organic syntheses with isotopes (Arthur Murray and D. Lloyd Williams), 1958, p. 152,153

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻酚乙酯乙酸乙酯 在 乙醚 作用下， 生成 Phenyl(2-thienyl)glycolic acid
  参考文献：
  名称：

  Antispasmodics. VII¹

  摘要：

  DOI：

  10.1021/ja01238a011

文献信息

• Identification of Novel Fragments Binding to the PDZ1‐2 Domain of PSD‐95
  作者：Jie Zang、Fei Ye、Sara M. Ø. Solbak、Lars J. Høj、Mingjie Zhang、Anders Bach

  DOI：10.1002/cmdc.202000865

  日期：2021.3.18

  promising strategy for the treatment of ischemic stroke, as shown with peptide‐based compounds that target the PDZ domains of PSD‐95. In contrast, developing potent and drug‐like small molecules against the PSD‐95 PDZ domains has so far been unsuccessful. Here, we explore the druggability of the PSD‐95 PDZ1‐2 domain and use fragment screening to investigate if this protein is prone to binding small molecules

  抑制 PSD-95 已成为治疗缺血性中风的一种有前景的策略，如靶向 PSD-95 PDZ 结构域的基于肽的化合物所示。相比之下，开发针对 PSD-95 PDZ 结构域的强效药物样小分子迄今尚未成功。在这里，我们探索了 PSD-95 PDZ1-2 结构域的成药性，并使用片段筛选来研究该蛋白质是否易于结合小分子。我们通过荧光偏振 (FP) 筛选了 2500 个片段，并通过表面等离子共振 (SPR) 验证了命中，包括抑制反测，并发现了四个有希望的片段。1 H、15 N HSQC NMR显示三个配体有效片段结合在小的疏水性 P 0PDZ1-2 的口袋，其中一个进行了构效关系（SAR）研究。总体而言，我们证明了片段筛选可以成功应用于 PSD-95 的 PDZ1-2，并公开了可作为优化小分子 PDZ 域抑制剂的起点的新片段。
• [EN] COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY<br/>[FR] COMPOSÉS AYANT UNE ACTIVITÉ ANTAGONISTE DES RÉCEPTEURS MUSCARINIQUES ET UNE ACTIVITÉ AGONISTE DES RÉCEPTEURS ADRÉNERGIQUE BÊTA-2
  申请人：CHIESI FARMA SPA

  公开号：WO2012168349A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds of general formula (I), acting both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists, to processes for their preparation, to compositions comprising them, to therapeutic uses and combinations with other pharmaceutical active ingredients.

  这项发明涉及一般式(I)的化合物，它们既作为肌肉收缩受体拮抗剂，又作为β2肾上腺素受体激动剂，涉及它们的制备方法，包含它们的组合物，治疗用途以及与其他药用活性成分的组合。
• NOVEL QUINUCLIDINE DERIVATIVES AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
  申请人：ALMIRALL, S.A.

  公开号：US20150246026A1

  公开（公告）日：2015-09-03

  A compound according to formula (I) wherein z© is a phenyl ring, a C 4 to C 9 heteroaromatic compound containing one or more heteroatoms, or a naphthalenyl, 5,6,7,8-tetrahydronaphthalenyl or biphenyl group; R 1 , R 2 and R 3 each independently represent a hydrogen or halogen atom, or a hydroxy group, or a phenyl, —OR 4 , —SR 4 , —NR 4 R 5 , —NHCOR 4 , —CONR 4 R 5 , —CN, —NO 2 , —COOR 4 or —CF 3 group, or a straight or branched lower alkyl group which may optionally be substituted, for example, with a hydroxy or alcoxy group, wherein R 4 and R 5 each independently represent a hydrogen atom, straight or branched lower alkyl group, or together form an alicyclic ring; or R 1 and R 2 together form an aromatic, alicyclic or heterocyclic ring; n is an integer from 0 to 4; A represents a —CH 2 —, —CH═CR 6 , —CR 6 ═CH—, —CR 6 12 2 —, —CO—, —O—, —S—, —S(O)—, SO 2 or NR 6 — group, wherein R 6 and R 2 each independently represent a hydrogen atom, straight or branched lower alkyl group, or R 6 and 12 2 together form an alicyclic ring; m is an integer from 0 to 8; provided that when m=0, A is not —CH 2 —; p is an integer from 1 to 2 and the substitution in the azoniabicyclic ring may be in the 2,3 or 4 position including all possible configurations of the asymmetric carbons; B represents a group of formula (i) or (ii), wherein R 10 represents a hydrogen atom, a hydroxy or methyl group; and R 8 and R 9 each independently represents formulae (a), (b), (c), (d) and wherein R 11 represents a hydrogen or halogen atom, or a straight or branched lower alkyl group and Q represents a single bond, —CH 2 —, —CH 2 —CH 2 , —O—, —O—CH 2 —, —S—, —S—CH 2 — or —CH═CH—, and when (i) or (ii) contain a chiral centre they may represent either configuration; X represents a pharmaceutically acceptable anion of a mono or polyvalent acid, which shows high affinity for muscarinic M 3 receptors (Hm3).

  根据式(I)的化合物，其中z©是苯环，含有一个或多个杂原子的C4至C9杂芳环化合物，或者是萘基、5,6,7,8-四氢萘基或联苯基；R1、R2和R3分别独立表示氢原子或卤素原子，或羟基，或苯基，—OR4，—SR4，—NR4R5，—NHCOR4，—CONR4R5，—CN，—NO2，—COOR4或—CF3基团，或直链或支链低碳烷基基团，该基团可能被羟基或烷氧基取代，其中R4和R5分别独立表示氢原子，直链或支链低碳烷基基团，或者共同形成脂环；或者R1和R2共同形成芳香环、脂环或杂环；n是从0到4的整数；A表示—CH2—，—CH═CR6，—CR6═CH—，—CR6122—，—CO—，—O—，—S—，—S(O)—，SO2或NR6—基团，其中R6和R2分别独立表示氢原子，直链或支链低碳烷基基团，或者R6和122共同形成脂环；m是从0到8的整数；但当m=0时，A不是— —；p是从1到2的整数，而在azoniabicyclic环中的取代基可以在2,3或4位置，包括对不对称碳的所有可能构型；B表示式(i)或(ii)的基团，其中R10表示氢原子，羟基或甲基基团；而R8和R9分别表示式(a)，(b)，(c)，(d)，其中R11表示氢原子或卤素原子，或者直链或支链低碳烷基基团，Q表示单键，— —，— — ，—O—，—O— —，—S—，—S— —或—CH═CH—，当(i)或(ii)含有手性中心时，它们可以表示任一构型；X表示单价或多价酸的药用可接受阴离子，对M3胆碱能受体（Hm3）具有高亲和力。
• Quinuclidine derivatives and their use as muscarinic M3 receptor ligands
  申请人：——

  公开号：US20030055080A1

  公开（公告）日：2003-03-20

  A compound according to formula (I) 1 wherein: is a phenyl ring, a C 4 to C 9 heteroaromatic compound containing one or more heteroatoms, or a naphthalenyl, 5,6,7,8-tetrahydronaphthalenyl or biphenyl group; R 1 , R 2 and R 3 each independently represent a hydrogen or halogen atom, or a hydroxy group, or a phenyl, —OR 4 , —SR 4 , —NR 4 R 5 , —NHCOR 4 , —CONR 4 R 5 , —CN, —NO 2 , —COOR 4 or —CF 3 group, or a straight or branched lower alkyl group which may optionally be substituted, for example, with a hydroxy or alcoxy group, wherein R 4 and R 5 each independently represent a hydrogen atom, straight or branched lower alkyl group, or together form an alicyclic ring; or R 1 and R 2 together form an aromatic, alicyclic or heterocyclic ring; n is an integer from 0 to 4; A represents a —CH 2 —, —CH═CR 6 , —CR 6 =CH—, —CR 6 R 7 —, —CO—, —O—, —S—, —S(O)—, SO 2 or —NR 6 — group, wherein R 6 and R 7 each independently represent a hydrogen atom, straight or branched lower alkyl group, or R 6 and R 7 together form an alicyclic ring; m is an integer from 0 to 8; provided that when m= 0 , A is not —CH 2 —; p is an integer from 1 to 2 and the substitution in the azoniabicyclic ring may be in the 2, 3 or 4 position including all possible configurations of the asymmetric carbons; B represents a group of formula i) or ii): 2 wherein R 10 represents a hydrogen atom, a hydroxy or methyl group; and R 8 and R 9 each independently represents 3 wherein R 11 represents a hydrogen or halogen atom, or a straight or branched lower alkyl group and Q represents a single bond, —CH 2 —, —CH 2 —CH 2 —, —O—, —O—CH 2 —, —S—, —S—CH 2 — or —CH═CH—, and when i) or ii) contain a chiral centre they may represent either configuration; X represents a pharmaceutically acceptable anion of a mono or polyvalent acid, which shows high affinity for muscarinic M 3 receptors (Hm3).

  根据公式（I）1，其中：是苯环，含有一个或多个杂原子的C4至C9杂芳族化合物，或者是萘基、5,6,7,8-四氢萘基或联苯基；R1、R2和R3分别独立表示氢或卤素原子，或羟基，或苯基，—OR4，—SR4，—NR4R5，—NHCOR4，—CONR4R5，—CN，—NO2，—COOR4或—CF3基团，或直链或支链的较低烷基基团，该基团可以选择性地被取代，例如，取代物可以是羟基或醇基，其中R4和R5分别独立表示氢原子，直链或支链较低烷基基团，或者共同形成脂环；或R1和R2共同形成芳香族、脂环或杂环；n是从0到4的整数；A表示—CH2—，—CH═CR6，—CR6=CH—，—CR6R7—，—CO—，—O—，—S—，—S(O)—，SO2或—NR6—基团，其中R6和R7分别独立表示氢原子，直链或支链较低烷基基团，或R6和R7共同形成脂环；m是从0到8的整数；但是当m=0时，A不是— —；p是从1到2的整数，而在azoniabicyclic环中的取代物可以在2、3或4位置，包括所有可能的手性碳的构型；B表示i)或ii)式的基团，其中R10表示氢原子，羟基或甲基基团；而R8和R9分别表示，其中R11表示氢或卤素原子，或直链或支链较低烷基基团，Q表示单键，— —，— — —，—O—，—O— —，—S—，—S— —或—CH═CH—，当i)或ii)含有手性中心时，它们可以代表任何构型；X表示单价或多价酸的药学上可接受的阴离子，该阴离子对Hm3亲和力高的胆碱能M3受体具有高亲和力。
• [EN] NEW QUATERNIZED QUINUCLIDINE ESTERS<br/>[FR] NOUVEAUX ESTERS DE QUINUCLIDINE QUATERNISES
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2005090342A1

  公开（公告）日：2005-09-29

  Compounds of formula (1) wherein the different substituents and/or radicals have the values defined in the claims. The invention also relates to a process for the preparation of said compounds, to pharmaceutical compositions comprising them, as well as to combinations of said compounds with other compounds which are active in the treatment of respiratory, urological or gastrointestinal disorders or diseases. Finally the invention also relates to the use of the compounds of formula (I) for the treatment of respiratory, urological or gastrointestinal disorders or diseases.

  公式（1）中的化合物，其中不同的取代基和/或基团具有权利要求中定义的值。本发明还涉及一种制备所述化合物的方法，包括含有它们的药物组合物，以及含有其他对治疗呼吸道、泌尿系统或消化系统疾病有活性的化合物与所述化合物的组合物。最后，本发明还涉及利用公式（I）的化合物治疗呼吸道、泌尿系统或消化系统疾病的用途。