Synthesis, characterization and physiological activity of some novel isoxazoles

VINAYSINGH J. HUSHARE, PRITHVIRAJSINGH R. RAJPUT, MANOJKUMAR O. MALPANI, NITIN G. GHODILE

Abstract. Hushare VJ, Rajput PR, Malpani MO, Ghodile NG. 2012. Synthesis, characterization and physiological activity of some novel isoxazoles. Nusantara Bioscience 4: 81-85. A series of chlorosubstituted 4-aroylisoxazoles have been synthesized by refluxing chlorosubstituted-3-aroylflavones and 3-alkoylchromone with hydroxylamine hydrochloride in dioxane medium containing 0.5 mL piperidine. Chlorosubstituted-3-aroylflavones and chlorosubstituted-3-alkoylchromone were prepared by refluxing them separately with iodine crystal in ethanol. Initially chlorosubstituted-3-aroylflavanones and 3-alkoylchromanone were prepared by the interaction of different aromatic and aliphatic aldehydes with 1-(2’-hydroxy-3’,5’-dichlorophenyl)-3-phenyl-1,3-propanedione. Constitutions of synthesized compounds were confirmed on the basis of elemental analysis, molecular weight determination, UV-Visible, I.R. and 1H-NMR spectral data. The titled compounds were evaluated for their growth promoting activity on some flowering plants viz. Papaver rhoeas, Calendula officinalise, Gladiola tristis, Gaillardia aristata,  Dianthus chinensis, and Iberis sp. (candytuft). The results indicate that applicated plants had higher shoots and more number of leaves.

 

Key words: chlorosubstituted 3-aroylflavanones, 3-alkoylchromanone, 3-aroylflavones, 3-alkoylchromone, isoxazoles.

 

Abstrak. Hushare VJ, Rajput PR, Malpani MO, Ghodile NG. 2012. Sintesis, karakterisasi dan aktivitas fisiologis beberapa isoxazoles baru. Nusantara Bioscience 4: 81-85. Serangkaian chlorosubstituted-4-aroylisoxazoles telah disintesis dengan mencampur chlorosubstituted-3-aroylflavones dan 3-alkoylchromone dengan hidroksilamin hidroklorida dalam medium dioksan yang mengandung 0.5 mL piperidine. Chlorosubstituted-3-aroylflavones dan chlorosubstituted-3-alkoylchromone dibuat dengan cara mencampur keduanya secara terpisah dengan yodium kristal dalam etanol. Awalnya, chlorosubstituted-3-aroylflavanones dan 3-alkoylchromanone dibuat melalui interaksi antara aldehida aromatik dan alifatik yang berbeda dengan 1-(2′-hidroksi-3′,5′-Dikhlorofenil)-3-fenil-1,3-propanedione. Senyawa yang terbentuk diuji berdasarkan analisis unsur, berat molekul, serta data spektrum UV-Vis, IR dan 1H-NMR. Senyawa tersebut dievaluasi aktivitas fisiologisnya dalam mendorong pertumbuhan beberapa tanaman berbunga, yaitu: Papaver rhoeas, Calendula officinalise, Gladiola tristis, Gaillardia aristata,  Dianthus chinensis, dan Iberis sp. (candytuft). Hasilnya, tanaman yang diaplikasi dengan senyawa tersebut lebih tinggi dan jumlah daunnya lebih banyak.

 

Kata kunci: chlorosubstituted 3-aroylflavanones, 3-alkoylchromanone, 3-aroylflavones, 3-alkoylchromone, isoxazoles.

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