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.
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]pyrimidines7a-o, 9-benzylideneamino-7-(4-halo-phenyl)-5-methoxy-8-imino-7H-benzo-[h]chromeno[2,3-d]pyrimidines8a-band 3-ethoxycarbonyl-14-(4-halophenyl)-12-methoxy-14H-benzo-[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-one derivatives12a-b. The structure of these novel compounds were confirmed using IR, ¹H- and13C-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.
Chemistry Department, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia. rawdao@yahoo.com.
Rawda M
RM
Okasha
Chemistry Department, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia. ffs_chem334@hotmail.com.
Fawzia F
FF
Albalawi
Chemistry Department, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia. afifith@yahoo.com.
Tarek H
TH
Afifi
Chemistry Department, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia. amfouda@hotmail.com.
Ahmed M
AM
Fouda
Chemistry Department, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia. nood-mansyaa@hotmail.com.
Al-Anood M
AM
Al-Dies
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, Egypt. elagrody_am@yahoo.com.
Ahmed M
AM
El-Agrody
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001578:Benzopyrans / Q000737:chemistry* / Q000494:pharmacology*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011743:Pyrimidines / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001578:Benzopyrans; D011743:Pyrimidines
14H-benzochromenotriazolo-pyrimidine; 4H-benzochromene; 7H-benzochromenopyrimidine; SAR; antimicrobial activities