Synthesis and study of cholosubstituted 4-aroyl pyrazolines and isoxazolines and their effects on inorganic ions in blood serum in albino rats

AMOL D. BHOYAR, GANESH N. VANKHADE, PRITHVISIGH R. RAJPUT

Abstract. Bhoyar AD, Vankhade GN, Rajput PR. 2011. Synthesis and study of cholosubstituted 4-aroyl pyrazolines and isoxazolines and their effects on inorganic ions in blood serum in albino rats. Nusantara Bioscience 3: 118-123. Condensation of 2-substitutied 3,5-dichloroacetophenones (2a-b) obtained from the condensation of 2-hydroxy 3,5-dichloro-acetophenone (1) and benzoyl chloride were dissolved in NaOH, on treatment under Baker-Venkatraman transformation in presence of KOH with pyridine gives 1-(2-hydroxy-3,5-dichlorophenyl)-3-substituted-1,3-propanediones (3a-b). Then converted into 3-aroyl-6,8-dichloroflavanones (4a-d) by using different aromatic aldehyde in ethanol containing little piperidine. The condensation of (4a-d) and phenylhydrazinehydrochloride, piperidine in DMF gives 3-(2-hydroxy3,5-dichlorophenyl)-4-substitution-1-phenyl-D2pyrazolines (5a-d) and condensation of (4a-d) and hydroxylamine-hydrochloride gives 3-(2-hydroxy-3,5-dichlorophenyl)-4-aroyl-5-substituted isoxazolines (6a-d). The above compounds are screened for their activities and have been found to exhibit significant effects on inorganic ions in blood serum in albino rats.

Key words: flavanone, isoxazoline, pyrazoline.

Abstrak. Bhoyar AD, Vankhade GN, Rajput PR. 2011. Sintesis dan studi cholo-tersubtitusi 4-aroil pirazolina dan isoxazolina serta efeknya pada ion anorganik dalam serum darah tikus albino. Nusantara Bioscience 3: 118-123. Kondensasi 2-tersubtitusi 3,5-dikloroasetofenon (2a-b) yang diperoleh dari kondensasi 2-hidroksi 3,5-dikloro-asetofenon (1) dan benzoil klorida yang dilarutkan dalam NaOH, pada perlakuan berdasarkan transformasi Baker-Venkatraman dengan keberadaan KOH dengan piridin menghasilkan 1-(2-hidroksi-3,5-diklorofenil)-3-tersubstitusi-1,3-propanedion (3a-b). Kemudian diubah menjadi 3-aroil-6,8-dikloroflavanone (4a-d) dengan aldehida aromatik yang berbeda dalam etanol yang mengandung sedikit piperidina. Kondensasi (4a-d) dan fenilhidrazina-hidroklorida, piperidina dalam DMF menghasilkan 3-(2-hidroksi 3,5-diklorofenil)-4-substitusi-1-fenil-D2pirazolina (5a-d) dan kondensasi (4a-d) dan hidroksilamin-hidroklorida menghasilkan 3-(2-hidroksi-3,5-diklorofenil)-4-aroil-5-tersubstitusi isoxazoline (6a-d). Senyawa-senyawa di atas diuji untuk mengetahui aktivitasnya dan diketahui menunjukkan efek yang signifikan pada ion anorganik dalam serum darah pada tikus albino.

Kata kunci: flavanone, isoxazoline, pirazolina.

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