Double Cyclization of Bis(α‐hetarylmethyl)amino Esters to Optically Active Bridged N‐Heterocycles of HIV‐Inhibiting Activity | Zendy

Faltz Heike | Zendy; Bender Christoph | Zendy; Wöhrl Birgitta M. | Zendy; VogelBachmayr Karin | Zendy; Hübscher Ullrich | Zendy; Ramadan Kristijan | Zendy; Liebscher Jürgen | Zendy

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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)

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