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Synthesis and Antimicrobial Evaluation of Fire Ant Venom Alkaloid Based 2-Methyl-6-alkyl-Δ1,6-piperideines.
Yan, Yujie; An, Yu; Wang, Xiaozhong; Chen, Yingqi; Jacob, Melissa R; Tekwani, Babu L; Dai, Liyan; Li, Xing-Cong.
Afiliación
  • Yan Y; Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University , Hangzhou 310027, People's Republic of China.
  • An Y; Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University , Hangzhou 310027, People's Republic of China.
  • Wang X; Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University , Hangzhou 310027, People's Republic of China.
  • Chen Y; Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University , Hangzhou 310027, People's Republic of China.
  • Jacob MR; National Centers for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi , University, Mississippi 38677, United States.
  • Tekwani BL; National Centers for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi , University, Mississippi 38677, United States.
  • Dai L; Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University , Hangzhou 310027, People's Republic of China.
  • Li XC; National Centers for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi , University, Mississippi 38677, United States.
J Nat Prod ; 80(10): 2795-2798, 2017 10 27.
Article en En | MEDLINE | ID: mdl-29023124
ABSTRACT
The first synthesis of 2-methyl-6-pentadecyl-Δ1,6-piperideine (1), a major alkaloid of the piperideine chemotype in fire ant venoms, and its analogues, 2-methyl-6-tetradecyl-Δ1,6-piperideine (2) and 2-methyl-6-hexadecyl-Δ1,6-piperideine (3), was achieved by a facile synthetic method starting with glutaric acid (4) and urea (5). Compound 1 showed in vitro antifungal activity against Cryptococcus neoformans and Candida albicans with IC50 values of 6.6 and 12.4 µg/mL, respectively, and antibacterial activity against vancomycin-resistant Enterococcus faecium with an IC50 value of 19.4 µg/mL, while compounds 2 and 3 were less active against these pathogens. All three compounds strongly inhibited the parasites Leishmania donovani promastigotes and Trypanosoma brucei with IC50 values in the range of 5.0-6.7 and 2.7-4.0 µg/mL, respectively.
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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Piperidinas / Alcaloides / Venenos de Hormiga / Antiinfecciosos Límite: Animals Idioma: En Revista: J Nat Prod Año: 2017 Tipo del documento: Article
Texto completo
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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Piperidinas / Alcaloides / Venenos de Hormiga / Antiinfecciosos Límite: Animals Idioma: En Revista: J Nat Prod Año: 2017 Tipo del documento: Article