A semiempirical AM1 conformational study of 3'-substituted deoxythymidines
Identifieur interne : 001023 ( Istex/Corpus ); précédent : 001022; suivant : 001024A semiempirical AM1 conformational study of 3'-substituted deoxythymidines
Auteurs : Carlos M. Estévez ; Ana M. Gra A ; Miguel A. RíosSource :
- Journal of Molecular Structure: THEOCHEM [ 0166-1280 ] ; 1993.
English descriptors
- Teeft :
- Agents chemother, Chem, Conformation, Conformer, Conformers, Derivative, Exocyclic sugar moiety, Hydrogen bond lengths, Intramolecular hydrogen, Kcal, Kilocalorie, Other molecules, Parametersb, Parametersb conformer, Relative energies, Sabio, Stable conformer, Stationary points, Struct, Sugar ring, Theochem, Thymidine, Topiol, Torsion.
Abstract
Abstract: Semiempirical AM1 calculations of the conformations of thymidine and certain of its 3'-derivatives were performed with a view to identifying structural trends that might correlate with the anti-HIV activity of these compounds. The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. The orientation of the exocyclic sugar moiety and stabilization by intramolecular hydrogen bonds are also discussed.
Url:
DOI: 10.1016/0166-1280(93)87051-E
Links to Exploration step
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<front><div type="abstract" xml:lang="en">Abstract: Semiempirical AM1 calculations of the conformations of thymidine and certain of its 3'-derivatives were performed with a view to identifying structural trends that might correlate with the anti-HIV activity of these compounds. The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. The orientation of the exocyclic sugar moiety and stabilization by intramolecular hydrogen bonds are also discussed.</div>
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<abstract>Abstract: Semiempirical AM1 calculations of the conformations of thymidine and certain of its 3'-derivatives were performed with a view to identifying structural trends that might correlate with the anti-HIV activity of these compounds. The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. The orientation of the exocyclic sugar moiety and stabilization by intramolecular hydrogen bonds are also discussed.</abstract>
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<abstract lang="en">Abstract: Semiempirical AM1 calculations of the conformations of thymidine and certain of its 3'-derivatives were performed with a view to identifying structural trends that might correlate with the anti-HIV activity of these compounds. The series examined included high-activity derivatives with N3 or F as the 3'-substituent, low-activity derivatives with CN or NH2, and the moderately active 3'-H and 2',3'-unsaturated compounds. Only small energy differences were found among the different conformers, and all the molecules examined had similar conformations, except the 2',3'-unsaturated compound, whose five-membered ring was less flexible than those of the others and adopted different conformations. Most conformers were anti or syn/anti around the glycoside bond and had N or N/S sugar ring puckering angles. The orientation of the exocyclic sugar moiety and stabilization by intramolecular hydrogen bonds are also discussed.</abstract>
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