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Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step Vorbrüggen glycosylation

I. A. Khalymbadzha, S. L. Deev, T. S. Shestakova, V. L. Rusinov, O. N. Chupakhin

Abstract


New analogues of acyclovir have been prepared by reacting 1,2,4-triazolo[1,5-a]pyrimidin-7-ones 1а-i and (2-acetoxyethoxy)methyl acetate 2 in the presence of trimethylsilyl trifluoromethanesulfonate as a catalyst. Thei nteraction between the compounds 1а-е and 2 has led to a mixture of N3 and N4 isomers. In contrast, the reaction of compounds 1g-i and 2 proceeded selectively to form N3 isomers. In the case of compounds 1a-c the predominant product is the one with the acyclic moiety in azine ring (N4 isomer). Interaction between 1d-f and 2 has led to mixtures comprising mainly N3 isomer. It has been found that the ratio of glycosylation products 1 and 2 are thermodynamically controlled. The structure of the obtained compounds has been proved by 1Н, 13С, two-dimensional 1Н-13С NMR spectroscopy and X-ray analysis.

Keywords


analogues of acyclovir

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References


Ai Y, Chen Y, Tang C, Yang GZ, Liang YJ, Fu LW, Liu JC, He HW. Synthesis and in vitro antiproliferative evaluation of pyrimido[5,4-c]quinoline-4-(3H)-one derivatives. Eur J Med Chem. 2012. 47; 206–2013. doi:10.1016/j.ejmech.2011.10.044

Boechat N, Pinheiro LCS, Silva TS, Carvalho AS, Bastos MM, Costa CC, Mendonca JS, Dutra KD, Santos-Filho OA, Pinto AC, Aguiar AC, Ceravolo IP, Krettli AU, Pinheiro S, Valverde AL. New trifluoromethyl triazolopyrimidines as Anti-Plasmodium falciparum agents. Molecules. 2012. 17:7;8285–8302. doi:10.3390/molecules17078285

Sanchez RM, Erhard K, Lin H, Moore ML, Yu H, Luengo JI, Tedesco R, Rivero RA, Hardwicke MA, Plant R, Rominger CM, McSurdy-Freed J, Spengler MD, Raha K, Schaber MD. Synthesis and structure-activity relationships of 1,2,4-triazolo[1,5-a] pyrimidin-7(3H)-ones as novel series of potent β isoform selective phosphatidylinositol 3-kinase inhibitors. Bioorg Med Chem Lett. 2012;22(9):3198–202. doi:10.1016/j.bmcl.2012.03.039

Deev SL, Chupakhin ON, Shestakova TS, Ulomskii EN, Rusinov VL, Yasko MV, Karpenko IL, Korovina AN, Khandazhinskaya AL, Kukhanova MK, Andronova VL, Galegov GA. 1,2,4-Triazoloazine derivatives as a new type of herpes simplex virus inhibitors. Bioorg Chem. 2010. 38:64; 265–270. doi:10.1016/j.bioorg.2010.09.002




DOI: https://doi.org/10.15826/chimtech.2015.2.2.017

Copyright (c) 2015 I. A. Khalymbadzha, S. L. Deev, T. S. Shestakova, V. L. Rusinov, O. N. Chupakhin

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Chimica Techno Acta, 2014-2022
ISSN 2411-1414 (Online)