Conformational studies of novel antiretroviral analogs of zidovudine
Conformational properties of three novel zidovudine analogs, namely 3′-azido-3′-deoxy-5′-O-isonicotinoylthymidine (AZT-Iso, 2), (-)-trans-(5S,6S)-5-bromo-6, 5′-epoxy-5,6-dihydro-3′-azido-3′-deoxythymidine (3) and (+)-trans-(5R,6R)-5-bromo-6,5′-epoxy-5,6-dihydro-3′- azido-3′-deoxythymidine (4), have...
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2003
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| LEADER | 13669caa a22012017a 4500 | ||
|---|---|---|---|
| 001 | PAPER-5003 | ||
| 003 | AR-BaUEN | ||
| 005 | 20250204092301.0 | ||
| 008 | 190411s2003 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0037238689 | |
| 024 | 7 | |2 cas |a zidovudine, 30516-87-1; 3'-azido-3'-deoxy-5'-O-isonicotinoylthymidine; Anti-Retroviral Agents; trans-(5S,6S)-5-bromo-6, 5'-epoxy-5,6-dihydro-3'-azido-3'-deoxythymidine; Zidovudine, 30516-87-1 | |
| 030 | |a NNNAF | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Baumgartner, M.T. | |
| 245 | 1 | 0 | |a Conformational studies of novel antiretroviral analogs of zidovudine |
| 260 | |c 2003 | ||
| 270 | 1 | 0 | |m Briñón, M.C.; Departamento de Farmacia, Ciudad Universitaria, Universidad Nacional de Cordoba, 5000 Córdoba, Argentina; email: macribri@dqo.fcq.unc.edu.ar |
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| 504 | |a Teijeiro, S.A., Moroni, G.N., Motura, M.I., Briñón, M.C., Lipophilic character of pyrimidinic nucleoside derivatives. Correlation between shake flask, chromatographic (RP-TLC and RP-HPLC) and theoretical methods (2000) J. Liq. Chrom. & Rel. Technol., 23 (6), pp. 855-872 | ||
| 504 | |a Motura, M.I., Moroni, G.N., Teijeiro, S.A., Salomón, H., Briñón, M.C., 3′-Azido-3′-deoxy-5′-O-isonicotinoylthymidine, a new prodrug of zidovudine., synthesis, solid state characterization and anti HIV-1 activity (2002) Nucleos. Nucleot. & Nucleic Acids, 21 (3), pp. 231-241 | ||
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| 504 | |a Swapna, G.V.T., Jagannadh, B., Gurjar, M.K., Kunwar, A.C., NMR Investigation on the structure and conformation of 3′-azido-2′,3′-dideoxyribosylthymine (AZT), an inhibitor of the HIV (AIDS Virus) (1989) Biochem. Biophys. Res. Commun., 164 (3), pp. 1086-1092 | ||
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| 504 | |a Kumar, R., Wang, L., Wiebe, L.I., Knaus, E.E., Synthesis, antiviral (HIV-1, HBV) activities of 5-halo-6-methoxy (or azido)-5,6-dihydro-3′-fluoro-3′-deoxythymidine diastereomers. Potential prodrugs to 3′-fluoro-3′-deoxythymidine (1994) J. Med. Chem., 37, pp. 3554-3560 | ||
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| 504 | |a De Leeuw, F.A.A.M., Altona, C., Conformational analysis of β-D-Ribo-, β-D-Deoxyribo, β-D-arabino-, β-D-xylo-, and β-D-lyxo-nucleosides from proton-proton coupling constants (1982) J. Chem. Soc. Perkin II, pp. 375-384 | ||
| 504 | |a note | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a Conformational properties of three novel zidovudine analogs, namely 3′-azido-3′-deoxy-5′-O-isonicotinoylthymidine (AZT-Iso, 2), (-)-trans-(5S,6S)-5-bromo-6, 5′-epoxy-5,6-dihydro-3′-azido-3′-deoxythymidine (3) and (+)-trans-(5R,6R)-5-bromo-6,5′-epoxy-5,6-dihydro-3′- azido-3′-deoxythymidine (4), have been investigated by AM1 calculations and NMR studies, and compared with those of the parent nucleoside (AZT, 1). Based on the results obtained the following correlation may be established, a) AZT and AZT-Iso exhibit a conformational behavior analog to other pyrimidinic nucleosides, displaying a dynamic equilibrium in solution where the two conformers (North and South) undergo a constant transformation. b) Compounds 3 and 4 show a different conformational profile. The estimate of the pseudorotation phase angle reveals the rigid structures of the latter compounds, which do not evidence conformational equilibrium in solution; the azide group being the only group free to rotate. c) Diastereoisomers 3 and 4 exhibit an extra conformational parameter compared with other pyrimidinic nucleosides: the chair or boat conformation in the third ring formed between the sugar and the base. In all cases, a reasonable correlation was obtained between theoretical and NMR spectroscopic data. |l eng | |
| 536 | |a Detalles de la financiación: Agencia Córdoba Ciencia | ||
| 536 | |a Detalles de la financiación: Secretaria de Ciencia y Tecnología - Universidad Nacional de Córdoba | ||
| 536 | |a Detalles de la financiación: Fundación Antorchas | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Fondo para la Investigación Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: The authors thank the Agencia Córdoba Ciencia, the Agencia Nacional de Pro-moción Científica y Tecnológica (FONCyT), the Secretaria de Ciencia y Técnica de la Universidad Nacional de Córdoba (SECyT-UNC), the Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Argentina, and Fundación Antorchas for financial support. The authors also wish to express their sincere thanks to Dra. L. Alassia (FILAXIS Laboratories, Buenos Aires, Argentina) for supplying zidovudine, Dr. C. Altona (State University Leiden, Gorlaeus Laboratories, The Netherlands) for PSEUROT calculations, and Dr. V. J. Kowalesky for recording NMR spectra in a 500 MHz apparatus (LANAIS RMN500). | ||
| 593 | |a Depto. de Quimica Organica-INFIQC, Ciudad Universitaria, Universidad Nacional de Cordoba, Córdoba, Argentina | ||
| 593 | |a Departamento de Farmacia, Ciudad Universitaria, Universidad Nacional de Cordoba, 5000 Córdoba, Argentina | ||
| 593 | |a Departamento de Física, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a AM1 CALCULATIONS |
| 690 | 1 | 0 | |a ANTIRETROVIRAL ANALOGS |
| 690 | 1 | 0 | |a CONFORMATIONAL ANALYSIS |
| 690 | 1 | 0 | |a NMR STUDIES |
| 690 | 1 | 0 | |a NOVEL AZT DERIVATIVES |
| 690 | 1 | 0 | |a 3' AZIDO 3' DEOXY 5' O ISONICOTINOYLTHYMIDINE |
| 690 | 1 | 0 | |a 5 BROMO 6,5' EPOXY 5,6 DIHYDRO 3' AZIDO 3' DEOXYTHYMIDINE |
| 690 | 1 | 0 | |a NUCLEOSIDE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ZIDOVUDINE |
| 690 | 1 | 0 | |a ZIDOVUDINE DERIVATIVE |
| 690 | 1 | 0 | |a ANALYTIC METHOD |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CALCULATION |
| 690 | 1 | 0 | |a CORRELATION ANALYSIS |
| 690 | 1 | 0 | |a DIASTEREOISOMER |
| 690 | 1 | 0 | |a DRUG CONFORMATION |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a ROTATION |
| 690 | 1 | 0 | |a STRUCTURE ANALYSIS |
| 690 | 1 | 0 | |a ANTI-RETROVIRAL AGENTS |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MOLECULAR CONFORMATION |
| 690 | 1 | 0 | |a ZIDOVUDINE |
| 700 | 1 | |a Motura, M.I. | |
| 700 | 1 | |a Contreras, Rubén Horacio | |
| 700 | 1 | |a Pierini, A.B. | |
| 700 | 1 | |a Briñón, M.C. | |
| 773 | 0 | |d 2003 |g v. 22 |h pp. 45-62 |k n. 1 |p Nucleosides Nucleotides Nucleic Acids |x 15257770 |w (AR-BaUEN)CENRE-6328 |t Nucleosides, Nucleotides and Nucleic Acids | |
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