Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1.
3,4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs) have emerged as non-nucleoside inhibitors of human immunodeficiency virus type 1 [Artico et al. (1993), Antiviral Chem Chemother 4: 361-368]. With a view to increasing their potency, a new series of DABO derivatives, differently substituted at p...
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ftopenaccessrep:oai:zenodo.org:107893 2023-10-25T01:36:25+02:00 Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1. Enzo Tramontano Gianluca Sbardella Marco Artico Antonello Mai P. Scano Silvio Massa Anna Giulia Loi P. La Colla 1995-02-01 https://www.openaccessrepository.it/record/107893 https://doi.org/10.1177/095632029500600101 eng eng url:https://www.openaccessrepository.it/communities/itmirror https://www.openaccessrepository.it/record/107893 doi:10.1177/095632029500600101 info:eu-repo/semantics/openAccess Psychiatry and Mental health Neuropsychology and Physiological Psychology info:eu-repo/semantics/article publication-article 1995 ftopenaccessrep https://doi.org/10.1177/095632029500600101 2023-09-26T22:19:47Z 3,4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs) have emerged as non-nucleoside inhibitors of human immunodeficiency virus type 1 [Artico et al. (1993), Antiviral Chem Chemother 4: 361-368]. With a view to increasing their potency, a new series of DABO derivatives, differently substituted at positions C-2 and/or C-5 of the pyrimidine ring and 3′ or 3′,5′ of the benzyl moiety, have been synthesized. DABOs were prepared by reacting O-methylisourea with the appropriate methyl 2-alkyl-4-phenylacetylacetate, with formation of 3,4-dihydro-2-methoxy-6-arylmethyl-4-oxopyrimidines. Subsequent displacement of the methoxy group linked at the 2-position of the pyrimidine ring by treatment with alkoxy and cycloalkoxy potassium salts led to the required derivatives. In vitro, the most potent compounds were 12e and 12p, which had an EC50 of 0.8 μM and a selective index of 400. Article in Journal/Newspaper artico Istituto Nazionale di Fisica Nucleare (INFN): Open Access Repository Antiviral Chemistry and Chemotherapy 6 1 1 8 |
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Istituto Nazionale di Fisica Nucleare (INFN): Open Access Repository |
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English |
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Psychiatry and Mental health Neuropsychology and Physiological Psychology |
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Psychiatry and Mental health Neuropsychology and Physiological Psychology Enzo Tramontano Gianluca Sbardella Marco Artico Antonello Mai P. Scano Silvio Massa Anna Giulia Loi P. La Colla Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1. |
topic_facet |
Psychiatry and Mental health Neuropsychology and Physiological Psychology |
description |
3,4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs) have emerged as non-nucleoside inhibitors of human immunodeficiency virus type 1 [Artico et al. (1993), Antiviral Chem Chemother 4: 361-368]. With a view to increasing their potency, a new series of DABO derivatives, differently substituted at positions C-2 and/or C-5 of the pyrimidine ring and 3′ or 3′,5′ of the benzyl moiety, have been synthesized. DABOs were prepared by reacting O-methylisourea with the appropriate methyl 2-alkyl-4-phenylacetylacetate, with formation of 3,4-dihydro-2-methoxy-6-arylmethyl-4-oxopyrimidines. Subsequent displacement of the methoxy group linked at the 2-position of the pyrimidine ring by treatment with alkoxy and cycloalkoxy potassium salts led to the required derivatives. In vitro, the most potent compounds were 12e and 12p, which had an EC50 of 0.8 μM and a selective index of 400. |
format |
Article in Journal/Newspaper |
author |
Enzo Tramontano Gianluca Sbardella Marco Artico Antonello Mai P. Scano Silvio Massa Anna Giulia Loi P. La Colla |
author_facet |
Enzo Tramontano Gianluca Sbardella Marco Artico Antonello Mai P. Scano Silvio Massa Anna Giulia Loi P. La Colla |
author_sort |
Enzo Tramontano |
title |
Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1. |
title_short |
Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1. |
title_full |
Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1. |
title_fullStr |
Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1. |
title_full_unstemmed |
Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1. |
title_sort |
synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (dabos), specific inhibitors of human immunodeficiency virus type 1. |
publishDate |
1995 |
url |
https://www.openaccessrepository.it/record/107893 https://doi.org/10.1177/095632029500600101 |
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artico |
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artico |
op_relation |
url:https://www.openaccessrepository.it/communities/itmirror https://www.openaccessrepository.it/record/107893 doi:10.1177/095632029500600101 |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1177/095632029500600101 |
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Antiviral Chemistry and Chemotherapy |
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6 |
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1 |
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1 |
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8 |
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1780731407037890560 |