REN Xiao-hui, CHEN Xin, LIU Jia, ZHENG Can-hui, REN Xue-qin, WU Bing, WANG Ru-feng, ZHOU You-jun. Synthesis,crystal structures and antifungal activity of novel triazole compounds containing 1,3-dioxolane[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(5): 344-347. doi: 10.3969/j.issn.1006-0111.2012.05.007
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REN Xiao-hui, CHEN Xin, LIU Jia, ZHENG Can-hui, REN Xue-qin, WU Bing, WANG Ru-feng, ZHOU You-jun. Synthesis,crystal structures and antifungal activity of novel triazole compounds containing 1,3-dioxolane[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(5): 344-347. doi: 10.3969/j.issn.1006-0111.2012.05.007
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Synthesis,crystal structures and antifungal activity of novel triazole compounds containing 1,3-dioxolane
- 1.
School of Biology and Pharmaceutical Engineering, Wuhan Polytechnic University, Wuhan 430023, China;Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
- 2.
School of Biology and Pharmaceutical Engineering, Wuhan Polytechnic University, Wuhan 430023, China
- 3.
Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
- Received Date: 2012-02-20
- Rev Recd Date:
2012-03-21
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Abstract
Objective To synthesize the geometric isomer of (E)-1-((4-(2,4-difluorophenyl)-2-(4-fluorostyryl)-1,3-dioxolan-4-yl)methyl)-1H-1,2,4-triazole, determine their structures by XRD and evaluate their antifungal activities in vitro. Methods The target compounds were prepared from 1H-1, 2, 4-triazole and 2-chloro-2',4'-difluoroacetophenone, the key oxirane intermediate was obtained by Corey-Chaykov-asky epoxidation. The key oxirane intermediate was hydrolyzed in the presence of 9% sulphuric acid,then the product was reacted with 4-Fluorocinnamaldehyde by condensation reaction to afford 6Ka and 6Kb. Their structures were charact-erized by 1H NMR,MS and XRD. Results Compound 6Ka belonged to monoclinic crystal system, space group P2(1)/c and had a cis configuration. While Compound 6Kb belonged to monoclinic crystal system, space group P2(1)/n and had a trans configuration.Both compounds which showed strong antifungal activities in vitro against five fungis. The antifungal activities of compound 6Kb was better than that of 6Ka. Conclusion The trans configuration of this kind had a predominant in vitro antifungal activities than the corresponding cis configuration.
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