Name
Title | ||
|---|---|---|
Computational analysis of aza analogues of [2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranose]-3'-spiro-5"-(4"-amino-1",2"-oxathiole-2",2"-dioxide) (TSAO) as HIV-1 reverse transcriptase inhibitors: relevance of conformational properties on the inhibitory activity. |
Abstract | ||
|---|---|---|
We have carried out a theoretical analysis of aza analogues of [2', 5'-bis-O-(tert-butyldimethylsilyl)-beta- D-ribofuranosyl]-3' -spiro-5"-(4"-amino-1", 2"-oxathiole-2", 2"-dioxide) by a variety of computational tools, aimed to account for the effect of the endocyclic amino moiety N-2" on the inhibitory activity against HIV-1. Docking studies suggest that compounds substituted at the N-3 and N-2" positions present the same binding mode to the [2', 5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5"-(4"-amino-1", 2"-oxathiole-2", 2"-dioxide) thymine prototype, where the endocyclic amino group remains mostly exposed to the solvent. A careful conformational analysis performed through different theoretical levels, from molecular mechanics to high-level quantum mechanical calculations, provides a rationalization based on conformational preferences, which appears as strongly determined by the substitution at N-2", and on electrostatic effects from the bulk water. |
Year | DOI | Venue |
|---|---|---|
2006 | 10.1021/ci0600410 | JOURNAL OF CHEMICAL INFORMATION AND MODELING |
Field | DocType | Volume |
Reverse transcriptase,Chemistry,Stereochemistry,Computational analysis | Journal | 46 |
Issue | ISSN | Citations |
4 | 1549-9596 | 1 |
PageRank | References | Authors |
2.25 | 1 | 5 |
Name | Order | Citations | PageRank |
|---|---|---|---|
| Elena Soriano | 1 | 1 | 2.25 |
| José Marco-Contelles | 2 | 1 | 2.25 |
| Cyrille Tomassi | 3 | 1 | 2.25 |
| Albert Nguyen Van Nhien | 4 | 1 | 2.25 |
| Denis Postel | 5 | 1 | 2.25 |