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

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

doi:10.5935/0103-5053.20160166

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Journal of the Brazilian Chemical Society

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Articles • J. Braz. Chem. Soc. 28 (2) • Feb 2017 • https://doi.org/10.5935/0103-5053.20160166 copy

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

Authorship SCIMAGO INSTITUTIONS RANKINGS

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.

Keywords:
amidinopyrazole; pyrazoline; cytotoxic activity; leukemia; ultrasonic irradiation


entry	Product	R¹	R²	R³	R⁴	time^a a Sonication time; / min	Yield^b b yields of the isolated compounds. / %
1	2a	H	H	H	H	20	88
2	2b	OMe	H	H	H	25	80
3	2c	Br	H	H	H	30	70
4	2d	H	NO₂	H	H	15	65
5	2e	H	H	Me	H	35	80
6	2f	H	H	CF₃	H	15	62
7	2g	H	H	OMe	H	25	86
8	2h	H	H	F	H	30	73
9	2i	H	H	Cl	H	30	71
10	2j	H	H	Br	H	30	75
11	2k	Cl	H	Cl	H	30	66
12	2l	H	OMe	OMe	H	25	83

entry	Compound	IC₅₀ ^a a The drug concentration resulting in a 50% of maximal inhibition of cell proliferation (as measured by MTT staining). / (µmol L^-1)
entry	Compound	Jurkat	RS4;11	K562
1	2a	29.5	70.5	21.26
2	2b	10.2	29.4	5.9
3	2c	21.5	20.5	14.7
4	2d	29.5	46.4	33.4
5	2e	34.2	28.7	24.8
6	2f	24.7	17.3	17.4
7	2g	28.6	47.1	40.0
8	2h	42.4	51.5	36.2
9	2i	37.9	16.7	30.4
10	2j	22.0	14.4	23.7
11	2k	21.3	16.2	5.7
12	2l	> 100	> 100	> 100

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[1] *e-mail: lucas.pizzuti@gmail.com