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

Molecules

Osama I. Abd El-Salam³  Ali S. Alsayed²  Korany A. Ali³  Ahmed A. Abd Elwahab³  Abd El-Galil E. Amr⁴  Hassan M. Awad¹ 

[1]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

[2]Chemistry Department, Al-Azhar University, Nasr City, Cairo 1435, Egypt

[3]Applied Organic Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt

[4]

[5]Department of Pharmaceutical Chemistry, Drug Exploration & Development Chair, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia

关键词: benzosuberone;    nitro-benzosuberone;    thioamide;    thiophene;    thiadiazole;    antimicrobial activity;   

DOI  :  10.3390/molecules201119701

来源: mdpi

【 摘 要 】

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 9a–c. 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 16a–d. The thioamides 4a,b were reacted with C-ethoxycarbonyl-N-arylhydrazonoyl chlorides 18a,b which afforded 1,3,4-thiadiazoline derivatives 19a–d. 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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.