A GENERAL PROCEDURE FOR ISOTOPIC (DEUTERIUM) LABELING OF NONSTEROIDAL ANTIINFLAMMATORY 2-ARYLPROPIONIC ACIDS

被引:19
|
作者
CASTELL, JV
MARTINEZ, LA
MIRANDA, MA
TARREGA, P
机构
[1] HOSP UNIV LA FE,CTR INVEST,AVE CAMPANAR 21,E-46009 VALENCIA,SPAIN
[2] UNIV POLITECN VALENCIA,CSIC,INST TECNOL QUIM,DEPT QUIM,E-46071 VALENCIA,SPAIN
关键词
2-ARYLPROPIONIC ACIDS; DEUTERIUM LABELING; PHOTOALLERGY; PHOTOCHEMISTRY;
D O I
10.1002/jlcr.2580340113
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Alkaline treatment of nonsteroidal antiinflammatory 2-arylpropionic acids in deuterium oxide led in all cases to isotopic exchange of the proton located at the alpha-position of the side chain. Monodeuteration was observed in the case of carprofen, ibuprofen, ketoprofen, fenoprofen, flurbiprofen and naproxen. Additional exchange of one or two protons of the heterocyclic ring occurred in indoprofen, suprofen and tiaprofenic acid. The isotopic labelling survived under the conditions required to perform in vitro photoallergic studies (photolysis in non-deuterated aqueous media).
引用
收藏
页码:93 / 100
页数:8
相关论文
共 50 条
  • [41] LIGHT-MEDIATED DIRECT TRANSFORMATION OF 2-CHLORO-PROPIOPHENONES INTO 2-ARYLPROPIONIC ACIDS
    SONAWANE, HR
    KULKARNI, DG
    AYYANGAR, NR
    TETRAHEDRON LETTERS, 1990, 31 (51) : 7495 - 7496
  • [42] On the stereochemically peculiar two-dimensional separation of 2-arylpropionic acids by chiral TLC
    Sajewicz, Mieczyslaw
    Pietka, Robert
    Drabik, Gabriela
    Namyslo, Ewa
    Kowalska, Teresa
    JPC-JOURNAL OF PLANAR CHROMATOGRAPHY-MODERN TLC, 2006, 19 (110) : 273 - 277
  • [43] ONE-POT REDUCTIVE DICHLOROCARBENE ADDITION TO ARYL KETONES - A NEW GENERAL-METHOD FOR THE SYNTHESIS OF 2-ARYLPROPIONIC ACIDS
    LLAMA, EF
    DELCAMPO, C
    SINISTERRA, JV
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1992, 24 (02) : 165 - 167
  • [44] Oscillatory transenantiomerization of the selected 2-arylpropionic acids (2-APAs) in vitro as a spontaneous phenomenon
    Sajewicz, Mieczyslaw
    Kowalska, Teresa
    PAKISTAN JOURNAL OF ANALYTICAL & ENVIRONMENTAL CHEMISTRY, 2006, 7 (01) : 17 - 30
  • [45] On the Stereochemically Peculiar Two-Dimensional Separation of 2-Arylpropionic Acids by Chiral TLC
    Mieczysław Sajewicz
    Robert Piętka
    Gabriela Drabik
    Ewa Namysło
    Teresa Kowalska
    JPC – Journal of Planar Chromatography – Modern TLC, 2006, 19 : 273 - 277
  • [46] Highly active supported palladium catalyst for the regioselective synthesis of 2-arylpropionic acids by carbonylation
    Jayasree, S
    Seayad, A
    Chaudhari, RV
    CHEMICAL COMMUNICATIONS, 1999, (12) : 1067 - 1068
  • [47] Microbial metabolism of 2-arylpropionic acids: Effect of environment on the metabolism of ibuprofen by Verticillium lecanii
    Hanlon, G.W.
    Kooloobandi, A.
    Hutt, A.J.
    Journal of Applied Bacteriology, 1994, 76 (05): : 442 - 447
  • [48] Electrosynthesis of 2-arylpropionic acids from α-methylbenzyl chlorides and carbon dioxide by [Co(salen)]
    Damodar, J
    Mohan, SK
    Lateef, SKK
    Reddy, SJ
    SYNTHETIC COMMUNICATIONS, 2005, 35 (09) : 1143 - 1150
  • [49] PURE ENANTIOMERS OF 2-ARYLPROPIONIC ACIDS - TOOLS IN PAIN RESEARCH AND IMPROVED DRUGS IN RHEUMATOLOGY
    BRUNE, K
    GEISSLINGER, G
    MENZELSOGLOWEK, S
    JOURNAL OF CLINICAL PHARMACOLOGY, 1992, 32 (10): : 944 - 952
  • [50] ALPHA-HYDROXY ESTERS AS CHIRAL REAGENTS - ASYMMETRIC-SYNTHESIS OF 2-ARYLPROPIONIC ACIDS
    LARSEN, RD
    CORLEY, EG
    DAVIS, P
    REIDER, PJ
    GRABOWSKI, EJJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) : 7650 - 7651