Synthesis and biological evaluation of N-antipyrine-4-substituted amino-3-chloromaleimide derivatives.
This paper describes the synthesis of new cyclic imides obtained by reaction with N-antipyrine-3,4-dichloromaleimides and different aromatic amines. The analgesic activity of the synthesized compounds was initially investigated against the writhing test in mice, followed by analysis of the most promising compounds in this model and in the formalin-induced model. The results indicate that the compounds containing the electron-withdrawing substituents in the para position of the substitute ring exerted more potent analgesic activity in mice, being much more potent than the prototype N-antipyrine-3,4-dichloromaleimide and some reference drugs. Some compounds exhibited activity against human opportunistic and pathogenic fungi, with MIC values of between 40 and 100 μg/mL (91.74 and 236.96 μM), and it was verified that only a few compounds presented potential for cytotoxic activity.
Mahle
Fernanda
F
Núcleo de Investigações Químico-Farmacêuticas/CCS, Universidade do Vale do Itajaí, Caixa Postal 360, CEP 88302-202, Itajaí, Santa Catarina, Brazil.
Guimarães
Tatiana da Rosa
Tda R
Meira
Aleandra Vergilina
AV
Corrêa
Rogério
R
Bella Cruz
Rosana Cé
RC
Bella Cruz
Alexandre
A
Nunes
Ricardo José
RJ
Cechinel-Filho
Valdir
V
de Campos-Buzzi
Fátima
F
D000700:Analgesics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000983:Antipyrine / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D008301:Maleimides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D013329:Structure-Activity Relationship
D000700:Analgesics; D008301:Maleimides; D000983:Antipyrine