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


OZDEMIR S. B. , DEMİRBAŞ N. , CEBECI Y. U. , BAYRAK H. , MERMER A., Ceylan S., ...Daha Fazla

LETTERS IN DRUG DESIGN & DISCOVERY, cilt.14, ss.1014-1034, 2017 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 14 Konu: 9
  • Basım Tarihi: 2017
  • Doi Numarası: 10.2174/1570180814666170113145023
  • Dergi Adı: LETTERS IN DRUG DESIGN & DISCOVERY
  • Sayfa Sayıları: ss.1014-1034

Özet

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 four-component condensation of 4 with several aldehydes gave the corresponding 4-oxo-2-thioxo-1,3-thiazolidinglycinamides (7a-f).

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 four-component 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.