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Molecules 2016, 21(11), 1450; doi:10.3390/molecules21111450

Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives

1
Chemistry Department, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia
2
Chemistry Department, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia
3
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: Philippe Belmont
Received: 30 September 2016 / Revised: 22 October 2016 / Accepted: 28 October 2016 / Published: 1 November 2016
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

Three new series of chromene molecules have been synthesized in order to explore their antimicrobial activity. The series encompass 2-substituted 14-(4-halophenyl)-12-methoxy-14H-benzo[h]chromeno[3,2-e][1,2,4]-triazolo[1,5-c]pyrimidines 7ao, 9-benzylideneamino-7-(4-halo-phenyl)-5-methoxy-8-imino-7H-benzo-[h]chromeno[2,3-d]pyrimidines 8ab and 3-ethoxycarbonyl-14-(4-halophenyl)-12-methoxy-14H-benzo-[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-one derivatives 12ab. The structure of these novel compounds were confirmed using IR, 1H- and 13C-NMR as well as MS spectroscopy. The new compounds were evaluated in vitro for their antimicrobial activity and it was demonstrated that 7H-benzochromenopyrimidine and derivatives of 14H-benzochromenotriazolopyrimidine exhibited the most promising antibacterial activities compared to the reference antimicrobial agents. The structure activity relationship (SAR) studies of the target compounds agreed with the in vitro essays and confirmed higher potent antimicrobial activity against some of the tested microorganisms. View Full-Text
Keywords: 4H-benzochromene; 7H-benzochromenopyrimidine; 14H-benzochromenotriazolo-pyrimidine; antimicrobial activities; SAR 4H-benzochromene; 7H-benzochromenopyrimidine; 14H-benzochromenotriazolo-pyrimidine; antimicrobial activities; SAR
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Okasha, R.M.; Albalawi, F.F.; Afifi, T.H.; Fouda, A.M.; Al-Dies, A.-A.M.; El-Agrody, A.M. Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives. Molecules 2016, 21, 1450.

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