Design and synthesis of 1-aroyl-2-ylidene hydrazines under conventional and microwave irradiation conditions and their cytotoxic activities

Abstract

Reportamos o planejamento e síntese de 1-aroil-2-(alquenil/aril)ideno hidrazinas como moléculas hibridas derivadas do ácido mafenamico e hidrazonas substituídas. Diferentes compostos baseados nesse novo plano foram preparados com bons rendimentos. O intermediário chave, N-acilidrazina, preparado a partir do ácido mafenamico, reagiu com uma variedade de aldeídos, sob condições experimentais convencionais ou com irradiação de microondas. Nesta última, que requer pequenos tempos reacionais, pode-se eliminar o uso de solvente e não é necessário catalisador ácido ou suporte sólido. Alguns compostos sintetisados mostraram atividades citotóxicas in vitro.We report the design and synthesis of 1-aroyl-2-(alkenyl/aryl)idene hydrazines as hybrid molecules derived from mefenamic acid and substituted hydrazones. A number of compounds based on this new scaffold were prepared in good yields. The key intermediate N-acylhydrazine, prepared from mefenamic acid, was coupled with a variety of aldehydes under conventional as well as microwave irradiation conditions. The second approach, that requires short reaction time, can be carried out under a solvent free condition and does not require the use of an acid catalyst or solid support. Some of the compounds synthesized showed cytotoxic activities in vitro.

A "green" synthesis of N-(quinoline-3-ylmethylene)benzohydrazide derivatives and their cytotoxicity activities

“…Some of the compounds synthesized showed significant cytotoxicity when tested against human lung adenocarcinoma cell line (A549) in vitro. Since quinoline 24 and benzohydrazide derivatives 25,26 have medicinal value, hence we believe that the present class of hydrazide derivatives represents an interesting profile for further experimental investigations especially in the area of anticancer research.…”

2-(2,3-Dimethylanilino)benzohydrazide

“…Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009). (Boschelli et al, 1990;Reddy et al, 2010;Aboul-Fadl et al, 2011). In view of the importance of the hydrazide of fenamic acid as an active synthon in the synthesis of compounds with biological interests (Reddy et al, 2010;Bhat et al, 2012), we report herein the crystal structure of the title compound.…”

“…For the biological activity of fenamates, see: Boschelli et al (1990); Reddy et al (2010); Aboul-Fadl et al (2011). For the synthesis, see: Reddy et al (2010); Aboul-Fadl et al (2011). For a related structure, see: Bhat et al (2012).…”

2-(4-Bromophenyl)-N-(5-methylpyridin-2-yl)acetamide

“…They are non-steroidal anti-inflammatory drugs (NSAIDs) used as potent analgesic and anti-inflammatory agents in the treatment of osteoarthritis and rheumatoid arthritis (Boschelli et al, 1990;Reddy et al, 2010;Aboul-Fadl et al, 2011). In view of the importance of the hydrazide of fenamic acid as an active synthon in the synthesis of compounds with biological interests (Reddy et al, 2010;Bhat et al, 2012), we report herein the crystal structure of the title compound.…”