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Citation: HU Guo-Qiang, HOU Li-Li, XIE Song-Qiang, DU Gang-Jun, HUANG Wen-Long, ZHANG Hui-Bin. Synthesis and Bioactivity of Asymmetrical Bis-heterocyclic Substituted s-Triazolothiadiazole Piperazine Derivatives[J]. Chinese Journal of Applied Chemistry, ;2009, 26(1): 63-66. shu

Synthesis and Bioactivity of Asymmetrical Bis-heterocyclic Substituted s-Triazolothiadiazole Piperazine Derivatives

1.
a Institute of Pharmacy, Henan University, Kaifeng 475001;
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b Center of Drug Discovery, China Pharmaceutical University, Nanjing

Corresponding author: HU Guo-Qiang,
Received Date: 30 December 2007
Available Online: 9 April 2008
Fund Project: 国家自然科学基金(20872028) (20872028)河南大学重点科研基金(04ZDZR009)资助项目 (04ZDZR009)

To improve the water solubility of fused heterocyclis so as to find a novel structural lead compound from them for the development of potential antibacterial agents,the intermediates of 6-(5-chloro-3-methyl-1-substituted phenyl-1H-pyrazol-4-yl)-3-pyrid-3-yl-s-triazolothiadia-zoles(3a~3c) were synthesized via cyclocondensation of 4-amino-3-pyrid-3-yl-5-mercapto-s-triazole(2) with chloro-pyrazole carboxylic acids(1a~1c) catalyzed with a phase transfer catalyst TBAB and an acylating catalyst DMAP in the presence of POCl₃ in high yields,respectively.The compounds 3a~3c were subjected to nucleophilic substitution of the chlorine at the pyrazole ring with substituted piperazine under the catalysis of PEG-600 to give the corresponding free bases 4a~4o successfully,which were subsequently treated with hydrochloride to afford corresponding chlorides of 4a~4o.The structures of the title compounds were characterized by elemental analysis and spectral data,and the in vitro inhibitory activities of the title compounds against three microorgranisms,S.aureus,E.coli,and P.aeruginosa,were evaluated via the respective MICs values by means of 2-fold agar dilution assay.The results showed that the introduction of a polar piperazine group around the fused heterocyclic core of s-tria-zolothiadiazole could result in a significant enhancement of bioactivity of the corresponding parent compounds.
- striazole,
- pyrazole,
- striazolothiadiazole,
- piperazine,
- antibacterial activity
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