| Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond(s) in the polyene spacer. | |
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MedLine Citation:
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PMID: 19939514 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Dimitra Hadjipavlou-Litina; George E Magoulas; Marios Krokidis; Dionissios Papaioannou |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2009-10-14 |
Journal Detail:
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Title: European journal of medicinal chemistry Volume: 45 ISSN: 1768-3254 ISO Abbreviation: Eur J Med Chem Publication Date: 2010 Jan |
Date Detail:
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Created Date: 2010-02-01 Completed Date: 2010-04-29 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0420510 Medline TA: Eur J Med Chem Country: France |
Other Details:
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Languages: eng Pagination: 298-310 Citation Subset: IM |
Copyright Information:
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Copyright 2009 Elsevier Masson SAS. All rights reserved. |
Affiliation:
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Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece. hadjipav@pharm.auth.gr |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acitretin
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analogs & derivatives,
chemical synthesis*,
pharmacology*,
therapeutic use Amides / chemistry* Animals Antioxidants / chemical synthesis*, chemistry, pharmacology*, therapeutic use Edema / drug therapy Electrons Esters / chemistry Female Heterocyclic Compounds / chemistry Hydrophobicity Inflammation / drug therapy Lipid Peroxidation / drug effects Lipoxygenase / metabolism Lipoxygenase Inhibitors / chemical synthesis, chemistry, pharmacology, therapeutic use Male Polyenes / chemistry* Rats Soybeans / enzymology |
| Chemical | |
Reg. No./Substance:
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0/Amides; 0/Antioxidants; 0/Esters; 0/Heterocyclic Compounds; 0/Lipoxygenase Inhibitors; 0/Polyenes; 55079-83-9/Acitretin; EC 1.13.11.12/Lipoxygenase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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