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• W2029043829 abstract "All stereoisomers of adenine and guanine methylene-3-fluoromethylenecyclopropane analogues of nucleosides 9a, 9b, 10a, 10b, 11a, 11b, 12a, and 12b were synthesized and their antiviral activities were evaluated. A highly convergent approach permitted the synthesis of all these analogues using a single intermediate 15. Reaction of aldehyde 13 with fluorotrichloromethane and tri-n-butylphosphine gave fluoroalkenes 14a + 14b (83:17). Addition of carbene derived from ethyl diazoacetate gave cyclopropane 15 as the major product. Reduction (19), bromination (20), and phenylselenenylation (21), followed by Se oxidation and β-elimination gave cis-methylenecyclopropane 22. Addition of bromine provided the reagent 23 for alkylation−elimination. Reaction of 23 with adenine led to an isomeric mixture 25a + 26a that after deprotection afforded analogues 9a and 10a. The 2-amino-6-chloropurine furnished 25e + 26e and after deblocking (9e and 10e) and hydrolysis gave targets 9b and 10b. Intermediate 15 provided, after debenzylation (27), 2-nitrophenylselenenylation (28), reduction (29), benzylation (30), and oxidation−elimination trans-methylenecyclopropane 31. Addition of bromine gave reagent 32. Further transformations followed the sequence outlined for analogues 9a, 9b, 10a, and 10b. Analogue 9b was effective against human cytomegalovirus (HCMV; Towne) with EC50 2.9 μM. The trans-isomer 10b inhibited AD169 strain of HCMV (EC50 15 μM) and the murine virus MCMV (EC50 2.5 μM). Compound 12a was effective against Epstein−Barr virus (EC50 < 0.03 μM). Analogue 9a inhibited varicella zoster virus (EC50 5.9 μM) and human immunodeficiency virus type 1 (EC50 5.2 μM). Analogues 9a, 10a, and 11a are moderate substrates for adenosine deaminase. The structure−activity relationships will be discussed in context with other methylenecyclopropane analogues." @default.
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• W2029043829 date "2006-09-09" @default.
• W2029043829 modified "2023-10-03" @default.
• W2029043829 title "9-{[3-Fluoro-2-(hydroxymethyl)cyclopropylidene]methyl}adenines and -guanines. Synthesis and Antiviral Activity of All Stereoisomers" @default.
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• W2029043829 doi "https://doi.org/10.1021/jm0607404" @default.
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