2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies

Dante Rotili; Alberta Samuele; Domenico Tarantino; Rino Ragno; Ira Musmuca; Flavio Ballante; Giorgia Botta; Ludovica Morera; Marco Pierini; Roberto Cirilli; Maxim B. Nawrozkij; Emmanuel Gonzalez; Bonaventura Clotet; Marino Artico; José A. Esté; Giovanni Maga; Antonello Mai

doi:10.1021/jm201308v

2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies

Dante Rotili, Alberta Samuele, Domenico Tarantino, Rino Ragno, Ira Musmuca, Flavio Ballante, Giorgia Botta, Ludovica Morera, Marco Pierini, Roberto Cirilli, Maxim B. Nawrozkij, Emmanuel Gonzalez, Bonaventura Clotet, Marino Artico, José A. Esté, Giovanni Maga, Antonello Mai

Department of Medicine

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

28 Citations (Scopus)

Abstract

The single enantiomers of two pyrimidine-based HIV-1 non-nucleoside reverse transcriptase inhibitors, 1 (MC1501) and 2 (MC2082), were tested in both cellular and enzyme assays. In general, the R forms were more potent than their S counterparts and racemates and (R)-2 was more efficient than (R)-1 and the reference compounds, with some exceptions. Interestingly, (R)-2 displayed a faster binding to K103N RT with respect to WT RT, while (R)-1 showed the opposite behavior. © 2012 American Chemical Society.

Original language	English
Pages (from-to)	3558-3562
Journal	Journal of Medicinal Chemistry
Volume	55
Issue number	7
DOIs	https://doi.org/10.1021/jm201308v
Publication status	Published - 12 Apr 2012

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Rotili, D., Samuele, A., Tarantino, D., Ragno, R., Musmuca, I., Ballante, F., Botta, G., Morera, L., Pierini, M., Cirilli, R., Nawrozkij, M. B., Gonzalez, E., Clotet, B., Artico, M., Esté, J. A., Maga, G., & Mai, A. (2012). 2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies. Journal of Medicinal Chemistry, 55(7), 3558-3562. https://doi.org/10.1021/jm201308v

Rotili, Dante ; Samuele, Alberta ; Tarantino, Domenico ; Ragno, Rino ; Musmuca, Ira ; Ballante, Flavio ; Botta, Giorgia ; Morera, Ludovica ; Pierini, Marco ; Cirilli, Roberto ; Nawrozkij, Maxim B. ; Gonzalez, Emmanuel ; Clotet, Bonaventura ; Artico, Marino ; Esté, José A. ; Maga, Giovanni ; Mai, Antonello. / 2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies. In: Journal of Medicinal Chemistry. 2012 ; Vol. 55, No. 7. pp. 3558-3562.

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title = "2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies",

abstract = "The single enantiomers of two pyrimidine-based HIV-1 non-nucleoside reverse transcriptase inhibitors, 1 (MC1501) and 2 (MC2082), were tested in both cellular and enzyme assays. In general, the R forms were more potent than their S counterparts and racemates and (R)-2 was more efficient than (R)-1 and the reference compounds, with some exceptions. Interestingly, (R)-2 displayed a faster binding to K103N RT with respect to WT RT, while (R)-1 showed the opposite behavior. {\textcopyright} 2012 American Chemical Society.",

author = "Dante Rotili and Alberta Samuele and Domenico Tarantino and Rino Ragno and Ira Musmuca and Flavio Ballante and Giorgia Botta and Ludovica Morera and Marco Pierini and Roberto Cirilli and Nawrozkij, {Maxim B.} and Emmanuel Gonzalez and Bonaventura Clotet and Marino Artico and Est{\'e}, {Jos{\'e} A.} and Giovanni Maga and Antonello Mai",

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doi = "10.1021/jm201308v",

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Rotili, D, Samuele, A, Tarantino, D, Ragno, R, Musmuca, I, Ballante, F, Botta, G, Morera, L, Pierini, M, Cirilli, R, Nawrozkij, MB, Gonzalez, E, Clotet, B, Artico, M, Esté, JA, Maga, G & Mai, A 2012, '2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies', Journal of Medicinal Chemistry, vol. 55, no. 7, pp. 3558-3562. https://doi.org/10.1021/jm201308v

2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies. / Rotili, Dante; Samuele, Alberta; Tarantino, Domenico; Ragno, Rino; Musmuca, Ira; Ballante, Flavio; Botta, Giorgia; Morera, Ludovica; Pierini, Marco; Cirilli, Roberto; Nawrozkij, Maxim B.; Gonzalez, Emmanuel; Clotet, Bonaventura; Artico, Marino; Esté, José A.; Maga, Giovanni; Mai, Antonello.

In: Journal of Medicinal Chemistry, Vol. 55, No. 7, 12.04.2012, p. 3558-3562.

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

TY - JOUR

T1 - 2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies

AU - Rotili, Dante

AU - Samuele, Alberta

AU - Tarantino, Domenico

AU - Ragno, Rino

AU - Musmuca, Ira

AU - Ballante, Flavio

AU - Botta, Giorgia

AU - Morera, Ludovica

AU - Pierini, Marco

AU - Cirilli, Roberto

AU - Nawrozkij, Maxim B.

AU - Gonzalez, Emmanuel

AU - Clotet, Bonaventura

AU - Artico, Marino

AU - Esté, José A.

AU - Maga, Giovanni

AU - Mai, Antonello

PY - 2012/4/12

Y1 - 2012/4/12

N2 - The single enantiomers of two pyrimidine-based HIV-1 non-nucleoside reverse transcriptase inhibitors, 1 (MC1501) and 2 (MC2082), were tested in both cellular and enzyme assays. In general, the R forms were more potent than their S counterparts and racemates and (R)-2 was more efficient than (R)-1 and the reference compounds, with some exceptions. Interestingly, (R)-2 displayed a faster binding to K103N RT with respect to WT RT, while (R)-1 showed the opposite behavior. © 2012 American Chemical Society.

AB - The single enantiomers of two pyrimidine-based HIV-1 non-nucleoside reverse transcriptase inhibitors, 1 (MC1501) and 2 (MC2082), were tested in both cellular and enzyme assays. In general, the R forms were more potent than their S counterparts and racemates and (R)-2 was more efficient than (R)-1 and the reference compounds, with some exceptions. Interestingly, (R)-2 displayed a faster binding to K103N RT with respect to WT RT, while (R)-1 showed the opposite behavior. © 2012 American Chemical Society.

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DO - 10.1021/jm201308v

M3 - Article

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ER -

2-(Alkyl/Aryl)amino-6-benzylpyrimidin-4(3 H)-ones as inhibitors of wild-type and mutant HIV-1: Enantioselectivity studies

Abstract

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