suprofen | 52779-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: suprofen
• 英文别名: alpha-Methyl-3-(2-thienylcarbonyl)benzeneacetic acid；2-[3-(thiophene-2-carbonyl)phenyl]propanoic acid
• CAS: 52779-89-2
• 化学式: C₁₄H₁₂O₃S
• 分子量: 260.313
• InChiKey: OKKUZOASBYWBPX-UHFFFAOYSA-N

物化性质

• 沸点：
  445.3±30.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-酪氨酸甲酯 、 suprofen 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以27%的产率得到methyl 3-(4-hydroxyphenyl)-2-(1-<4-(2-thienylcarbonyl)phenyl>-ethylcarboxamido)propanoate
  参考文献：
  名称：

  Photobinding of Tiaprofenic Acid and Suprofen to Proteins and Cells: A Combined Study Using Radiolabeling, Antibodies and Laser Flash Photolysis of Model Bichromophores

  摘要：

  AbstractDrug photoallergy is a matter of current concern. It involves the formation of drug‐protein photoadducts (pho‐toantigens) that may ultimately trigger an immunological response. Tyrosine residues appear to be key binding sites in proteins. The present work has investigated the photobinding of tiaprofenic and (TPA) and the closely related isomer suprofen (SUP) to proteins and cells by means of radioactive labeling and drug‐directed antibodies. To ascertain whether preassociation with the protein may play a role in photoreactivity, two model bichro‐mophoric compounds (TPA‐Tyr and SUP‐Tyr) have been prepared and studied by laser flash photolysis. The results of this work show that (a) TPA and SUP photo‐bind to proteins with similar efficiencies, (b) both drugs form photoadducts that share a basic common structure, as they are recognized by the same antibody and (c) drug‐protein preassociation must play a key role in photoreactivity, as indicated by the dramatic decrease in the triplet state lifetimes of the model bichromophores compared to the parent drugs.

  DOI：

  10.1111/j.1751-1097.1998.tb02526.x
• 作为产物：
  描述：

  3-(1-氰基乙基)苯甲酰氯 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 suprofen
  参考文献：
  名称：

  设计对CXCR1和CXCR2起作用的非竞争性白介素8抑制剂。

  摘要：

  趋化因子CXCL8和CXCL1在炎症部位中性粒细胞募集中起关键作用。CXCL8结合两个膜受体CXCR1和CXCR2，而CXCL1是CXCR2的选择性激动剂。在过去的十年中，已经研究了CXCL8和CXCL1的生理病理学作用。已鉴定出一类新型的小分子量变构CXCR1抑制剂，第一个候选药物reparixin目前正在临床研究中，以预防器官移植中的缺血/再灌注损伤。研究了Reparixin与CXCR1的结合模式，并将其用于双变构CXCR1和CXCR2抑制剂的计算机辅助设计程序。本文讨论了由模型驱动的SAR研究用于鉴定有效双重抑制剂的结果，并提出了三种新化合物（56、67，

  DOI：

  10.1021/jm061469t

文献信息

• Aroyl-substituted phenylacetic acid derivatives
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04035376A1

  公开（公告）日：1977-07-12

  Compounds of the class of aroyl-substituted phenylacetic acids and corresponding esters, amides and hydroxamic acids, useful as anti-inflammatory agents and certain novel precursors therefor.

  芳酰基取代苯乙酸及其相应的酯、酰胺和羟肟酸类化合物，可用作抗炎药物和某些新颖前体。
• [EN] 2-ARYL-PROPIONAMIDE DERIVATIVES USEFUL AS BRADYKININ RECEPTOR ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DÉRIVÉS DE 1-ARYL-PROPIONAMIDE UTILES COMME ANTAGONISTES DES RÉCEPTEURS DE LA BRADYKININE ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：DOMPE SPA

  公开号：WO2011051375A1

  公开（公告）日：2011-05-05

  (R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B1 pathway.

  (R,S) 2-芳基丙酰胺衍生物，或其单对映体(R)和(S)，被披露用于治疗或预防与布雷金肽B1途径相关的症状和疾病，如疼痛和炎症。
• 2-aryl-propionamide derivatives useful as bradykinin receptor antagonists and pharmaceutical compositions containing them
  申请人：Dompe S.p.A.

  公开号：EP2316820A1

  公开（公告）日：2011-05-04

  (R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B1 pathway.

  (R,S) 2-芳基丙酰胺衍生物，或其单对映体(R)和(S)，被披露为在治疗或预防与布雷金肽B1通路相关的疼痛和炎症症状和疾病中有用。
• ISOTOPE LABELED 2-ARYLPROPIONIC ACID COMPOUNDS AND PROCESS FOR PRODUCTION OF SAME, AND MOLECULAR PROBE FOR POSITRON EMISSION TOMOGRAPHY AND METHOD FOR IMAGING OF CYCLOOXYGENASE AND THE LIKE USING SAME
  申请人：Takashima Misato

  公开号：US20120128588A1

  公开（公告）日：2012-05-24

  Disclosed are: labeled NSAIDs compounds which can be produced within a short time, can be used suitably for a PET method, and enable the imaging of cyclooxygenase-2; and a process for producing the labeled NSAIDs compounds. Specifically disclosed are isotope-labeled 2-arylpropionic acid compounds, each of which is a compound represented by general formula (1) (wherein Ar represents an aryl group which may have a substituent; R 1 represents anyone selected from 11 CH 3 , CH 2 18 F and CF 2 18 F; and R 2 represents a hydrogen atom, or an alkyl group which may have a branch, wherein a compound wherein Ar is a benzene ring, R 1 is 11 CH 3 , and R 2 is a hydrogen atom is excluded), or a pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof.

  披露了：标记的NSAIDs化合物可以在短时间内生产，适用于PET方法，并能够成像环氧合酶-2；以及制备标记的NSAIDs化合物的方法。具体披露的是同位素标记的2-芳基丙酸化合物，每个化合物都是由通式（1）表示的化合物（其中Ar代表可能具有取代基的芳基；R1代表从11CH3、CH218F和CF218F中选择的任一种；R2代表氢原子，或可能具有支链的烷基，其中Ar为苯环，R1为11CH3，R2为氢原子的化合物被排除），或其药用可接受的盐、水合物、溶剂合物或前药。
• 2-ARYL-PROPIONAMIDE DERIVATIVES USEFUL AS BRADYKININ RECEPTOR ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Beccari Andrea

  公开号：US20120316169A1

  公开（公告）日：2012-12-13

  (R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B1 pathway.

  本文披露了(R,S) 2-芳基丙酰胺衍生物，或其单一对映体(R)和(S)，适用于治疗或预防与布雷金肽B1途径相关的疼痛和炎症等症状和疾病。