Document Detail

Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond(s) in the polyene spacer.
MedLine Citation:
PMID:  19939514     Owner:  NLM     Status:  MEDLINE    
Ester analogs of the antipsoriatic drug acitretin were synthesized by coupling either anilines with N-protected indole-3-carboxylic acid, followed by deprotection and coupling with O-monoprotected dicarboxylic acids or Wittig reaction of indole-3-carboxaldehyde, 3-acetyl-1-tosylpyrrole and 4-amino-9-fluorenone with Ph3P=CHCO2tBu, followed by N-deprotection, where necessary, and finally coupling with cinnamoyl fluorides. Corresponding free acids were obtained through TFA-mediated carboxyl group deprotection. Although these analogs and acitretin showed very low reducing abilities, analogs 5, 6, 8 and 12 strongly inhibited LOX with IC50 values ranging from 35-65 microM. Acitretin and its analogs 5-7, 10, 11 and 15 inhibited lipid peroxidation more strongly than trolox whereas acitretin and analog 4 were in vivo more potent anti-inflammatory agents on rat paw oedema induced by Carrageenan than indomethacin.
Dimitra Hadjipavlou-Litina; George E Magoulas; Marios Krokidis; Dionissios Papaioannou
Related Documents :
12951114 - Arachidonylsulfonyl derivatives as cannabinoid cb1 receptor and fatty acid amide hydrol...
8411214 - Imidazole-substituted analogues of trh limit behavioral deficits after experimental bra...
21259444 - 1-(3-biaryloxy-2-oxopropyl)indole-5-carboxylic acids and related compounds as dual inhi...
2611944 - Syntheses and antitumor activities of n6,n6-dimethyladenosine carboxylate analogues.
5665894 - The bacterial transformation of abietic acid.
19323744 - Comparisons of chemical and physical properties of catfish oils prepared from different...
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-10-14
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  45     ISSN:  1768-3254     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2010-02-01     Completed Date:  2010-04-29     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  298-310     Citation Subset:  IM    
Copyright Information:
Copyright 2009 Elsevier Masson SAS. All rights reserved.
Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Acitretin / analogs & derivatives,  chemical synthesis*,  pharmacology*,  therapeutic use
Amides / chemistry*
Antioxidants / chemical synthesis*,  chemistry,  pharmacology*,  therapeutic use
Edema / drug therapy
Esters / chemistry
Heterocyclic Compounds / chemistry
Inflammation / drug therapy
Lipid Peroxidation / drug effects
Lipoxygenase / metabolism
Lipoxygenase Inhibitors / chemical synthesis,  chemistry,  pharmacology,  therapeutic use
Polyenes / chemistry*
Soybeans / enzymology
Reg. No./Substance:
0/Amides; 0/Antioxidants; 0/Esters; 0/Heterocyclic Compounds; 0/Lipoxygenase Inhibitors; 0/Polyenes; 55079-83-9/Acitretin; EC

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  8-Sulfonyl-substituted tetrahydro-1H-pyrido[4,3-b]indoles as 5-HT(6) receptor antagonists.
Next Document:  Asymmetrically substituted cationic indole- and fluorene porphyrins inhibit tumor proliferation in s...