Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines

Author(s)

Eric F. S. dos Santos ; Nathália M. Cury ; Tainara A. do Nascimento ; Cristiano Raminelli ; Gleison A. Casagrande ; Claudio M. P. Pereira ; Euclésio Simionatto ; José A. Yunes ; Lucas Pizzuti

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 28, n. 2, p. 217-224, Fev. 2017.

Abstract

3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides were efficiently prepared through a cyclocondensation of thiophenylchalcones with aminoguanidine hydrochloride under ultrasonic conditions in the presence of KOH and ethanol as a green solvent in short reaction times (15-35 min) and good yields (62-95%). All compounds produced were evaluated against the human Jurkat and RS4;11 acute lymphoblastic leukemia cell lines of T- and B-cell origin, respectively, and the K562 myelogenous leukemia cell line. Six compounds presented half maximal inhibitory concentration (IC50) values around 15 µmol L-1 and five compounds presented IC50 values around 40 µmol L-1 for at least one of the three cell lines analyzed. One compound was not significantly cytotoxic, presenting IC50 value > 100 µmol L-1. (AU)

• FAPESP's process: 12/12802-1 - Cooperating mutations, functional studies and antibodies against the mutant IL7R in acute lymphoblastic leukemia
• Grantee: José Andrés Yunes
• Support type: Regular Research Grants