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Exploring the role ...
Exploring the role of 2-chloro-6-fluoro substitution in 2-alkylthio-6-benzyl-5-alkylpyrimidin-4(3H)-ones : effects in HIV-1-infected cells and in HIV-1 reverse transcriptase enzymes.
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- Rotili, Dante (författare)
- Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy
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- Tarantino, Domenico (författare)
- Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy
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- Nawrozkij, Maxim B (författare)
- Volgograd State Technical University, pr. Lenina, 28, 400131 Volgograd, Russia
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- Babushkin, Alexandre S (författare)
- Volgograd State Technical University, pr. Lenina, 28, 400131 Volgograd, Russia
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- Botta, Giorgia (författare)
- Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy
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- Marrocco, Biagina (författare)
- Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy
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- Cirilli, Roberto (författare)
- Dipartimento del Farmaco, Istituto Superiore di Sanita ̀ ,, Viale Regina Elena 299, 00161 Rome, Italy
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- Menta, Sergio (författare)
- Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy
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- Badia, Roger (författare)
- IrsiCaixa, Hospital Universitari Germans Trias i Pujol, Universitat Auto ̀ noma de Barcelona, 08916 Badalona, Spain
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- Crespan, Emmanuele (författare)
- Istituto di Genetica Molecolare IGM-CNR, via Abbiategrasso 207, 27100 Pavia, Italy
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- Ballante, Flavio (författare)
- Rome Center for Molecular Design, Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy; Department of Biochemistry and Molecular Biophysics, Washington University in St. Louis, School of Medicine, 700 South Euclid Avenue, St. Louis, Missouri 00185, United States
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- Ragno, Rino (författare)
- Rome Center for Molecular Design, Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy
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- Esté, José A (författare)
- IrsiCaixa, Hospital Universitari Germans Trias i Pujol, Universitat Auto ̀ noma de Barcelona, 08916 Badalona, Spain
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- Maga, Giovanni (författare)
- Istituto di Genetica Molecolare IGM-CNR, via Abbiategrasso 207, 27100 Pavia, Italy
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- Mai, Antonello (författare)
- Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy; Istituto Pasteur Fondazione Cenci Bolognetti, Universita ̀ degli Studi di Roma “ La Sapienza ” , P.le A. Moro 5, 00185 Roma, Italy
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Dipartimento di Chimica e Tecnologie del Farmaco, Universita ̀ degli Studi di Roma “ La Sapienza ” , Ple A. Moro 5, 00185 Roma, Italy Volgograd State Technical University, pr. Lenina, 28, 400131 Volgograd, Russia (creator_code:org_t)
- 2014-06-16
- 2014
- Engelska.
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Ingår i: Journal of Medicinal Chemistry. - : American Chemical Society (ACS). - 0022-2623 .- 1520-4804. ; 57:12, s. 5212-25
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- A comparison of the effects of the 6-(2-chloro-6-fluorobenzyl)-2-(alkylthio)pyrimidin-4(3H)-ones (2-Cl-6-F-S-DABOs) 7-12 and the related 6-(2,6-difluorobenzyl) counterparts 13-15 in HIV-1 infected cells and in the HIV-1 reverse transcriptase (RT) assays is here described. The new 2-Cl-6-F-S-DABOs showed up to picomolar activity against wt HIV-1. Against clinically relevant HIV-1 mutants and in enzyme assays, the simultaneous C5(methyl)/C6(methyl/ethyl) substitution in the 2-Cl-6-F- and 2,6-F2-benzyl series furnished compounds with the highest, wide-spectrum inhibitory activity against HIV-1. Three representative 2-Cl-6-F-S-DABOs carrying two (9c, 10c) or one (10a) stereogenic centers were resolved into their individual stereoisomers and showed a significant diastereo- and enantioselectivity in HIV-1 inhibition, the highest antiviral activity well correlating with the R absolute configuration to the stereogenic center of the C6-benzylic position in both cellular and enzymatic tests. Application of previously reported COMBINEr protocol on 9c and 10c confirmed the influence of the stereogenic centers on their binding modes in the HIV-1 RT.
Ämnesord
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Läkemedelskemi (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Medicinal Chemistry (hsv//eng)
- NATURVETENSKAP -- Biologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences (hsv//eng)
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
- NATURVETENSKAP -- Data- och informationsvetenskap (hsv//swe)
- NATURAL SCIENCES -- Computer and Information Sciences (hsv//eng)
Nyckelord
- HIV-1; DABO; COMBINEr; 3D QSAR; Structure Based Drug Design; in vitro Assays
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Rotili, Dante
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Tarantino, Domen ...
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Nawrozkij, Maxim ...
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Babushkin, Alexa ...
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Botta, Giorgia
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Marrocco, Biagin ...
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Cirilli, Roberto
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Menta, Sergio
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Badia, Roger
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Crespan, Emmanue ...
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Ballante, Flavio
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Ragno, Rino
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Esté, José A
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Maga, Giovanni
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Mai, Antonello
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NATURVETENSKAP
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