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Synthesis and Antimicrobial Activities of Hybrid Heterocyclic Molecules Based on 1-(4-Fluorophenyl)piperazine Skeleton

[ Vol. 14 , Issue. 9 ]

Author(s):

Serap Basoglu Ozdemir, Neslihan Demirbas, Yıldız Uygun Cebeci, Hacer Bayrak, Arif Mermer, Sule Ceylan and Ahmet Demirbas   Pages 1014 - 1034 ( 21 )

Abstract:


Background: The amine (2) was prepared starting from 1-(4-fluorophenyl) piperazine via two steps, and then converted to the corresponding hydrazide (4). The reaction of hydrazide (4) with carbon disulfide generated the corresponding 1,3,4-oxadiazole (5), while the treatment of hydrazide with ethyl bromoacetate produced 4-oxo-2-thioxo-1,3-thiazolidine compound (6). The fourcomponent condensation of 4 with several aldehydes gave the corresponding 4-oxo-2-thioxo-1,3- thiazolidinglycinamides (7a-f).

Methods: The synthesis of 4-oxo-1,3-oxazolidines (9a,b), 1,3-oxazoles (10a,b) and 1,3,4-triazoles (11a,b) was carried out starting from compounds 8a,b. Mannich bases (12a-d and 13a-f) were prepared using three component condensation of compounds 5 and 12a,b and corresponding amines. The synthesis of 16a-c, which were considered as the new analogues of azole class antifungals, was performed starting from the compound 14a via three steps.

Results and Conclusion: All the reactions were examined under traditional and microwave irradiation conditions, and optimum conditions were defined. The antimicrobial activities of the newly synthesized compounds were screened and some of the tested compounds were displayed good-moderate antibacterial activity.

Keywords:

Fluorophenyl piperazine, hybrid compound, multicomponent, microwave, antimicrobial activity, acids.

Affiliation:

Department of Chemistry, Karadeniz Technical University, Trabzon, Department of Chemistry, Karadeniz Technical University, Trabzon, Department of Chemistry, Karadeniz Technical University, Trabzon, Department of Chemistry and Chemical Processing Technology, Karadeniz Technical University, Trabzon, Department of Chemistry, Karadeniz Technical University, Trabzon, Department of Occupational Health and Safety, Artvin Coruh University, Artvin, Department of Chemistry, Karadeniz Technical University, Trabzon

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