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Double Cyclization of Bis(α‐hetarylmethyl)amino Esters to Optically Active Bridged N‐Heterocycles of HIV‐Inhibiting Activity
Author(s) -
Faltz Heike,
Bender Christoph,
Wöhrl Birgitta M.,
VogelBachmayr Karin,
Hübscher Ullrich,
Ramadan Kristijan,
Liebscher Jürgen
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400136
Subject(s) - chemistry , reverse transcriptase , alkylation , stereochemistry , optically active , dna , lithium (medication) , human immunodeficiency virus (hiv) , polymerase , amino acid , dna polymerase , biochemistry , organic chemistry , rna , gene , catalysis , medicine , family medicine , endocrinology
Anellated 1‐azabicyclo[3.3.1]nonanes 6 were synthesized by several routes starting from natural α‐amino esters 2 and o ‐haloaryl‐ 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 & Co. KGaA, 69451 Weinheim, Germany, 2004)