Highly Efficient Synthesis of New 3,5 Substituted (Isoxazolines) and 2,3,5-Trisubstituted (Pyrazolines) Mediated by Choramin-T and their Evaluation of Antioxidant and Antibacterial Activities

Ebraheem Abdu Musad^{a, 1}, Abdullah Mohammed AL Dawsari^a, Zaki Eldin Ali Abdalla^a, Kakul Husain^a, Razaz Saeed Saeed AL Sharabi^b, K. M. Lokanatha Rai^c

¹Phone: + (009) 665 09-30-25-82; , P.O. Box 56; e-mail: alhashmi.ibrahim@yahoo.com

ªDepartment of Chemistry, Prince Sattam Bin Abdulaziz University,College of Arts and Science, Wadi Al-Dawasir 11991, Saudi Arabia;
^bDepartment of Mathematics, Prince Sattam Bin Abdulaziz University, College of Sciences and Humanities – Slayel;
^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India

Received 22.12.2019; revised 05.03.2020; accepted 08.03.2020

DOI: 10.1134/S1068162020050180

Abstract –– Two short series of five membered heterocyclic 3,5-disubstituted–isoxazolines derivatives (Va-f) and 2,3,5-trisubstituted-pyrazolines derivatives (VIIa-f) were synthesized via 1,3-dipolar cycloaddition reaction of 2-(allyloxy)-4,6-dimethoxypyrimidine (III) with aromatic aldoximes (IV) which undergo oxidative–dehydrogenation with chloramine–T to give 3,5-disubstituted–isoxazolines derivatives (Va-f) and oxidative cyclization of diphenyl hydrazones (VI) using chloramine-T to give 2,3,5-trisubstituted-pyrazoline derivatives (VIIa-f) in good yield. The newly synthesized compounds were screened for anti-oxidant and anti-microbial activities. 2,3,5-trisubstituted-pyrazolines derivatives (VIIb-e) revealed higher antioxidant activity at 10μg/ml while 3,5-disubstituted–isoxazolines derivatives (Va-c) and 2,3,5-trisubstituted-pyrazolines derivatives (VIIa-c) showed better anti-microbial activity at 100μg/ml compared with standard vitamin C and ciprofloxacin, respectively. Structures of newly synthesized compounds were established on the basis of their elemental analysis and spectral IR, ¹H-NMR and ¹³C-NMR.

Keywords: isoxazolines, pyrazolines, chloramine–T, antioxidant, antibacterial
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Полный текст статьи печатается в переводной версии журнала Russian Journal of Bioorganic Chemistry, V.46, Issue 5, P. 814–821 (Springer).