4.0 Article

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

Journal

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
Volume 28, Issue 2, Pages 217-+

Publisher

SOC BRASILEIRA QUIMICA
DOI: 10.5935/0103-5053.20160166

Keywords

amidinopyrazole; pyrazoline; cytotoxic activity; leukemia; ultrasonic irradiation

Funding

  1. Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) [483021/2013-0]
  2. Fundacao de Apoio ao Desenvolvimento do Ensino, Ciencia e Tecnologia do Estado de Mato Grosso do Sul (FUNDECT) [0180/12]
  3. Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [12/12802-1]
  4. Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES)
  5. FAPESP
  6. CNPq
  7. Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [12/12802-1] Funding Source: FAPESP

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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 mu mol L-1 and five compounds presented IC50 values around 40 mu mol L-1 for at least one of the three cell lines analyzed. One compound was not significantly cytotoxic, presenting IC50 value > 100 mu mol L- 1.

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