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Molecules 2015, 20(11), 20434-20447; doi:10.3390/molecules201119701

Synthesis and Antimicrobial Evaluation of a New Series of Heterocyclic Systems Bearing a Benzosuberone Scaffold

1
Applied Organic Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt
2
Chemistry Department, Al-Azhar University, Nasr City, Cairo 1435, Egypt
3
Department of Pharmaceutical Chemistry, Drug Exploration & Development Chair, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
4
Chemistry of Natural and Microbial Products Department, Pharmaceutical Industries Division, National Research Centre, 33 El Buhouth St. (Former El Tahrir St.), Dokki, Giza 12622, Egypt
5
Deanship of Preparatory Year, Al jouf University, AL Jouf, Skaka 2014, Saudi Arabia
*
Author to whom correspondence should be addressed.
Academic Editor: Wim Dehaen
Received: 11 September 2015 / Revised: 30 October 2015 / Accepted: 4 November 2015 / Published: 16 November 2015
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [1396 KB, uploaded 19 November 2015]   |  

Abstract

A series of novel benzosuberone derivatives were synthesized and evaluated as antimicrobial agents by using substituted benzosuberone derivatives 1a,b as starting materials. Treatment of 1a,b with phenyl isothiocyanate in dimethylformamide was followed by treatment with cold HCl solution to afford the thioamides 4a,b, which was reacted with methyl iodide to obtain methylated products 5a,b. Cyclocondensation of 4a,b with chloroacetone 6 and phenacyl chloride 7 gave the corresponding thiophene derivatives 9ac. Reaction of 4a,b with C-acetyl-N- arylhydrazonoyl chlorides 14a and 14b in boiling EtOH in the presence of triethylamine, afforded the corresponding 1,3,4-thiadiazoline derivatives 16ad. The thioamides 4a,b were reacted with C-ethoxycarbonyl-N-arylhydrazonoyl chlorides 18a,b which afforded 1,3,4-thiadiazoline derivatives 19ad. The benzosuberones 1a,b were treated with 3-mercaptopropanoic acid to give compounds 21a,b, which were cyclized to tricyclic thiopyran-4(5H)-one derivatives 22a,b. The latter compounds 22a,b were reacted with 3-mercaptopropanoic acid to give compounds 23a,b, which were cyclized tetracyclic ring systems 24a,b. Finally, compounds 24a,b were oxidized using hydrogen peroxide under reflux conditions to afford the oxidized form of the novel tetracyclic heterogeneous ring systems 25a,b. The newly synthesized compounds were screened for antimicrobial activities. The structures of new compounds were characterized by 1H-NMR, 13C-NMR, IR, and EI-MS. View Full-Text
Keywords: benzosuberone; nitro-benzosuberone; thioamide; thiophene; thiadiazole; antimicrobial activity benzosuberone; nitro-benzosuberone; thioamide; thiophene; thiadiazole; antimicrobial activity
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MDPI and ACS Style

El-Salam, O.I.A.; Alsayed, A.S.; Ali, K.A.; Elwahab, A.A.A.; Amr, A.E.-G.; Awad, H.M. Synthesis and Antimicrobial Evaluation of a New Series of Heterocyclic Systems Bearing a Benzosuberone Scaffold. Molecules 2015, 20, 20434-20447.

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