Influence of susceptibility to hydrolysis and hydrophobicity of arylsemicarbazones on their anti-nociceptive and anti-inflammatory activities.

Abstract	Benzaldehyde semicarbazone (BS) inhibited zymosan writhing response, carrageenan paw edema and both phases of formaldehyde nociceptive response. 2-hydroxybenzaldehyde semicarbazone (2-OHBS) and semicarbazide inhibited carrageenan paw edema and the second phase of formaldehyde nociceptive response. 2-OHBS inhibited zymosan writhing response. 3- and 4-OHBS did not show such activities. 2-OHBS showed the lowest LUMO energy, the highest contribution of the iminic carbon to LUMO energy, the highest positive charge on the iminic carbon, the highest negative charge on the iminic nitrogen and the highest susceptibility to hydrolysis. Hence semicarbazide may play important roles in 2-OHBS's activities. Inhibition of the first phase of formaldehyde response by BS could be attributed to its higher hydrophobicity and lower susceptibility to hydrolysis in comparison to 2-OHBS.
Authors	Rafael P Vieira, Josane A Lessa, Wallace C Ferreira, Fernanda B Costa, Leandro F S Bastos, Willian R Rocha, Márcio M Coelho, Heloisa Beraldo
Journal	European journal of medicinal chemistry (Eur J Med Chem) Vol. 50 Pg. 140-8 (Apr 2012) ISSN: 1768-3254 [Electronic] France
PMID	22357114 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Copyright	Copyright Â© 2012 Elsevier Masson SAS. All rights reserved.
Chemical References	2-hydroxybenzaldehyde semicarbazone Analgesics Anti-Inflammatory Agents Semicarbazones benzaldehyde semicarbazone Formaldehyde Carrageenan
Topics	Analgesics (chemistry, pharmacology) Animals Anti-Inflammatory Agents (chemistry, pharmacology) Carrageenan (toxicity) Edema (chemically induced, drug therapy) Formaldehyde (toxicity) Hydrolysis (drug effects) Hydrophobic and Hydrophilic Interactions (drug effects) Male Mice Molecular Structure Motor Activity (drug effects) Pain (chemically induced, drug therapy) Pain Measurement Rats Rats, Wistar Semicarbazones (chemical synthesis, chemistry, pharmacology)

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