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Molecules 2016, 21(7), 959; doi:10.3390/molecules21070959

New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity

1
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland
2
Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 16 June 2016 / Revised: 14 July 2016 / Accepted: 19 July 2016 / Published: 22 July 2016
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [1059 KB, uploaded 22 July 2016]   |  

Abstract

A novel series of (3-diethoxyphosphoryl)isoxazolidines substituted at C5 with various quinazolinones have been synthesized by the 1,3-dipolar cycloaddition of N-methyl-C-(diethoxyphosphoryl)nitrone with N3-substitued 2-vinyl-3H-quinazolin-4-ones. All isoxazolidines were assessed for antiviral activity against a broad range of DNA and RNA viruses. Isoxazolidines trans-11f/cis-11f (90:10), trans-11h and trans-11i/cis-11i (97:3) showed weak activity (EC50 = 6.84, 15.29 and 9.44 μM) toward VZV (TK+ strain) which was only one order of magnitude lower than that of acyclovir used as a reference drug. Phosphonates trans-11b/cis-11b (90:10), trans-11c, trans-11e/cis-11e (90:10) and trans-11g appeared slightly active toward cytomegalovirus (EC50 = 27–45 μM). Compounds containing benzyl substituents at N3 in the quinazolinone skeleton exhibited slight antiproliferative activity towards the tested immortalized cells with IC50 in the 21–102 μM range. View Full-Text
Keywords: phosphonate; isoxazolidine; quinazolinones; antiviral; cytostatic phosphonate; isoxazolidine; quinazolinones; antiviral; cytostatic
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Piotrowska, D.G.; Andrei, G.; Schols, D.; Snoeck, R.; Grabkowska-Drużyc, M. New Isoxazolidine-Conjugates of Quinazolinones—Synthesis, Antiviral and Cytostatic Activity. Molecules 2016, 21, 959.

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