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Convergent synthesis and cytotoxicity of novel trifluoromethyl-substituted (1H-pyrazol-1-yl)(quinolin-4-yl) methanones.
- Source :
-
Journal of Fluorine Chemistry . Oct2016, Vol. 190, p31-40. 10p. - Publication Year :
- 2016
-
Abstract
- A convergent synthesis of a series of 16 new polysubstituted (5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1 H -pyrazol-1-yl)(quinolin-4-yl)methanones, starting from isatin and alky(aryl/heteroaryl) ketones, is described. The diheteroaryl methanones were achieved at yields of up to 95% by a [3 + 2] cyclocondensation reaction involving 4-alkyl(aryl/heteroaryl)-4-methoxy-1,1,1-trifluorobut-3-en-2-ones (by two-step reaction) and 2-alkyl(aryl/heteroaryl)-4-carbohydrazides (by three-step reaction). Subsequently, representative dehydrated heterocyclic derivatives were obtained from the respective 5-hydroxy-2-pyrazoline moieties by classical dehydration reactions, which resulted in the corresponding (5-(trifluoromethyl)-1 H -pyrazol-1-yl)(quinolin-4-yl)methanones (three examples) at yields of 69–82%. The subsequent cytotoxicity evaluation showed that compounds with aromatic groups at the 2-position of the quinoline and a methyl moiety at the 3-position of the pyrazole have significant cytotoxicity in human leukocytes at high concentrations (200 μM). [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00221139
- Volume :
- 190
- Database :
- Academic Search Index
- Journal :
- Journal of Fluorine Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 118311669
- Full Text :
- https://doi.org/10.1016/j.jfluchem.2016.08.012