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

Heike Faltz; Christoph Bender; Birgitta M. Wöhrl; Karin Vogel-Bachmayr; Ullrich Hübscher; Kristijan Ramadan; Jürgen Liebscher

doi:10.1002/ejoc.200400136

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

Heike Faltz, Christoph Bender, Birgitta M. Wöhrl^*, Karin Vogel-Bachmayr, Ullrich Hübscher, Kristijan Ramadan, Jürgen Liebscher

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3484-3496
Number of pages	13
Journal	European Journal of Organic Chemistry
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.200400136
Publication status	Published - Aug 13 2004
Externally published	Yes

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry

Keywords

Antiviral agents
Cyclization
Inhibitors
Lithiation
Nitrogen heterocycles

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/ejoc.200400136

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title = "Double cyclization of bis(α-hetarylmethyl)amino esters to optically active bridged N-heterocycles of HIV-inhibiting activity",

abstract = "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.",

keywords = "Antiviral agents, Cyclization, Inhibitors, Lithiation, Nitrogen heterocycles",

author = "Heike Faltz and Christoph Bender and W{\"o}hrl, {Birgitta M.} and Karin Vogel-Bachmayr and Ullrich H{\"u}bscher and Kristijan Ramadan and J{\"u}rgen Liebscher",

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doi = "10.1002/ejoc.200400136",

language = "English",

pages = "3484--3496",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

number = "16",

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T1 - Double cyclization of bis(α-hetarylmethyl)amino esters to optically active bridged N-heterocycles of HIV-inhibiting activity

AU - Faltz, Heike

AU - Bender, Christoph

AU - Wöhrl, Birgitta M.

AU - Vogel-Bachmayr, Karin

AU - Hübscher, Ullrich

AU - Ramadan, Kristijan

AU - Liebscher, Jürgen

PY - 2004/8/13

Y1 - 2004/8/13

N2 - 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.

AB - 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.

KW - Antiviral agents

KW - Cyclization

KW - Inhibitors

KW - Lithiation

KW - Nitrogen heterocycles

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DO - 10.1002/ejoc.200400136

M3 - Article

AN - SCOPUS:4544242709

SN - 1434-193X

SP - 3484

EP - 3496

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 16

ER -

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

Abstract

ASJC Scopus Subject Areas

Keywords

UN SDGs

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