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  • Synthesis and evaluation of the anti-nociceptive and anti-inflammatory activity of 4-aminoquinoline derivatives.

Synthesis and evaluation of the anti-nociceptive and anti-inflammatory activity of 4-aminoquinoline derivatives.

Bioorganic & medicinal chemistry (2015-06-28)
Raquel de Meneses Santos, Pooline Rocha Barros, Janaína Heberle Bortoluzzi, Mario Roberto Meneghetti, Yolanda Karla Cupertino da Silva, Amanda Evelyn da Silva, Mariana da Silva Santos, Magna Suzana Alexandre-Moreira
ABSTRACT

In this paper, we describe the synthesis and pharmacological evaluation of a series of 4-aminoquinolines. The compounds were characterised and tested in models of pain and inflammation, using the writhing test with acetic acid, formalin test, peritonitis test by zymosan and arthritis test with Freund's adjuvant complete assay. The results revealed that all of the 4-aminoquinolines that were prepared promoted anti-nociceptive activity as well as acute and chronic anti-inflammatory effects, with marked activity in the derivates labelled with BAQ and 7-CF3-MAQ. After 7 days of treatment, 7-CF3-MAQ did not induce significant hepatotoxicity, gastrotoxicity or nephrotoxicity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tetramethylsilane, ≥99.0% (GC)
Sigma-Aldrich
Acetic acid, for luminescence, BioUltra, ≥99.5% (GC)
Sigma-Aldrich
Acetic acid, ≥99.5%, FCC, FG
Sigma-Aldrich
Acetic acid, natural, ≥99.5%, FG
Sigma-Aldrich
Acetic acid-12C2, 99.9 atom % 12C
Sigma-Aldrich
Tetramethylsilane, electronic grade, ≥99.99% trace metals basis
Sigma-Aldrich
5α-Androstan-17β-ol-3-one, purum, ≥99.0% (TLC)
Sigma-Aldrich
5α-Androstan-17β-ol-3-one, ≥97.5%