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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Online Access: | http://hdl.handle.net/11386/3006544 https://doi.org/10.1177/095632029500600101 http://journals.sagepub.com/doi/10.1177/095632029500600101 |
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ftunisalernoiris:oai:www.iris.unisa.it:11386/3006544 2024-02-11T10:01:54+01:00 Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus type 1. Silvio Massa Antonello Mai Marino Artico Enzo Tramontano Anna Giulia Loi Patrizia Scano Paolo La Colla SBARDELLA, Gianluca Silvio, Massa Antonello, Mai Marino, Artico Sbardella, Gianluca Enzo, Tramontano Anna Giulia, Loi Patrizia, Scano Paolo La, Colla 1995 http://hdl.handle.net/11386/3006544 https://doi.org/10.1177/095632029500600101 http://journals.sagepub.com/doi/10.1177/095632029500600101 eng eng info:eu-repo/semantics/altIdentifier/wos/WOS:A1995QA06000001 volume:6 firstpage:1 lastpage:8 numberofpages:8 journal:ANTIVIRAL CHEMISTRY & CHEMOTHERAPY http://hdl.handle.net/11386/3006544 doi:10.1177/095632029500600101 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-0028869436 http://journals.sagepub.com/doi/10.1177/095632029500600101 AIDS chemotherapy Anti-HIV agent Dihydroalkoxybenzyloxopyrimidine DABO Nonnucleoside reverse transcriptase inhibitors (NNRTI) info:eu-repo/semantics/article 1995 ftunisalernoiris https://doi.org/10.1177/095632029500600101 2024-01-24T17:37:13Z 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-oxoprimidines. 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 EC(50) of 0.8 mu M and a selective index of 400. Article in Journal/Newspaper artico EleA@Unisa (Università degli Studi di Salerno) Antiviral Chemistry and Chemotherapy 6 1 1 8 |
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EleA@Unisa (Università degli Studi di Salerno) |
op_collection_id |
ftunisalernoiris |
language |
English |
topic |
AIDS chemotherapy Anti-HIV agent Dihydroalkoxybenzyloxopyrimidine DABO Nonnucleoside reverse transcriptase inhibitors (NNRTI) |
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AIDS chemotherapy Anti-HIV agent Dihydroalkoxybenzyloxopyrimidine DABO Nonnucleoside reverse transcriptase inhibitors (NNRTI) Silvio Massa Antonello Mai Marino Artico Enzo Tramontano Anna Giulia Loi Patrizia Scano Paolo La Colla SBARDELLA, Gianluca 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 |
AIDS chemotherapy Anti-HIV agent Dihydroalkoxybenzyloxopyrimidine DABO Nonnucleoside reverse transcriptase inhibitors (NNRTI) |
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-oxoprimidines. 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 EC(50) of 0.8 mu M and a selective index of 400. |
author2 |
Silvio, Massa Antonello, Mai Marino, Artico Sbardella, Gianluca Enzo, Tramontano Anna Giulia, Loi Patrizia, Scano Paolo La, Colla |
format |
Article in Journal/Newspaper |
author |
Silvio Massa Antonello Mai Marino Artico Enzo Tramontano Anna Giulia Loi Patrizia Scano Paolo La Colla SBARDELLA, Gianluca |
author_facet |
Silvio Massa Antonello Mai Marino Artico Enzo Tramontano Anna Giulia Loi Patrizia Scano Paolo La Colla SBARDELLA, Gianluca |
author_sort |
Silvio Massa |
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 |
http://hdl.handle.net/11386/3006544 https://doi.org/10.1177/095632029500600101 http://journals.sagepub.com/doi/10.1177/095632029500600101 |
genre |
artico |
genre_facet |
artico |
op_relation |
info:eu-repo/semantics/altIdentifier/wos/WOS:A1995QA06000001 volume:6 firstpage:1 lastpage:8 numberofpages:8 journal:ANTIVIRAL CHEMISTRY & CHEMOTHERAPY http://hdl.handle.net/11386/3006544 doi:10.1177/095632029500600101 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-0028869436 http://journals.sagepub.com/doi/10.1177/095632029500600101 |
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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8 |
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