Abstract：
:Synthesis and antiviral activity of the title fluoromethylenecyclopropane analogues 15a, 15b, 16a, and 16b is described. Methylenecyclopropane carboxylate was first transformed to 2,2-bis-hydroxymethylmethylenecyclopropane. Selective monoacetylation followed by introduction of fluorine gave 2-acetoxymethyl-2-fluoromethylmethylenecyclopropane as the key intermediate. The synthesis of analogues 15a, 15b, 16a, and 16b then followed alkylation-elimination procedure as described previously for other methylenecyclopropane analogues [corrected] Compounds 15a, 15b, 16a and 16b were not active against Epstein-Barr virus (EBV) [corrected] Analogue 15a inhibited hepatitis C virus by virtue of its cytotoxicity and it moderately inhibited replication of the Towne strain of human cytomegalovirus (HCMV). The E-isomer 16a was a substrate for adenosine deaminase, whereas the Z-isomer 15a was not deaminated.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Li C,Prichard MN,Korba BE,Drach JC,Zemlicka Jdoi
10.1016/j.bmc.2007.11.082subject
Has Abstractpub_date
2008-03-01 00:00:00pages
2148-55issue
5eissn
0968-0896issn
1464-3391pii
S0968-0896(07)01050-4journal_volume
16pub_type
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