Double cyclization of bis(alpha-hetarylmethyl)amino esters to optically active bridged N-heterocycles of HIV-inhibiting activity

Journal article

Anellated 1-azabicyclo[3.3.1]nonanes 6 were synthesized by several routes starting from natural α-amino esters 2 and ohaloaryl- or o-bromohetarylmethyl bromides 1. N-Alkylation of the starting amino esters to 5 and 3 was followed by halogen/lithium exchange and double cyclization. The cyclization products 6 exhibit interesting inhibition of RNase H and DNA-polymerase activity of reverse transcriptase (RT) of HIV-1 at concentrations where human cellular DNA polymerases are not affected. © Wiley-VCH Verlag GmbH and Co. KGaA, 69451 Weinheim, Germany, 2004.

Authors: Faltz, H; Bender, C; Wohrl, B; Vogel-Bachmayr, K; Hubscher, U

• Publication status: Published
• Journal: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
• Volume: 2004
• Issue: 16
• Pages: 3484-3496
• Publication date: 2004-08-13
• DOI: 10.1002/ejoc.200400136
• EISSN: 1099-0690
• ISSN: 1434-193X
• Language: English
• Keywords: cyclization; nitrogen heterocycles; lithiation; inhibitors; antiviral agents