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 Musada, 1, Abdullah Mohammed AL Dawsaria, Zaki Eldin Ali Abdallaa, Kakul Husaina, Razaz Saeed Saeed AL Sharabib, K. M. Lokanatha Raic

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-disubstitutedisoxazolines 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 oxidativedehydrogenation with chloramineT to give 3,5-disubstitutedisoxazolines 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-disubstitutedisoxazolines 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, chloramineT, antioxidant, antibacterial
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Russian Journal of Bioorganic Chemistry, V.46, Issue 5, P. 814821 (Springer).