Topological Analysis of the Electronic Charge Density in Nucleoside Analogues derivatives of the AZT. Effects of X-H..O and X-H..F Intramolecular H-Bonds.

FIDANZA, N. G.; SOSA, G. L.; LOBAYAN, R.; NELIDA MARIA PERUCHENA

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Lugar: Elsevier Science B.V.; Año: 2005 vol. 727 p. 57 - 68

0166-1280

In this work, the topology of the electronic charge density is applied to study the hydrogen bonds for all compounds analogues of the nucleosides derivatives of the AZT (denoted 1) with XZCH3, and its derivatives substituted in C5 with XZ–H (2), –F (3), –Br (4), –OH (5), –OCH3 (6), –NH2 (7), –CF3 (8), –SCN (9), –CHO (10) and –COOH (11) in the anti conformation. These calculations were carried out, using the Theory of Atoms in Molecules (AIM). Finally calculations in other derivatives of AZT such as 30-N3-FMAU (12) and its isostere 30-N3- C-FMAU compound (13) in syn and anti conformations at RHF/6-311CCG**//3-21G were included. Comparing the results obtained in all the nucleosides derivatives studied here with the ones results in both conformations of 30-N3-CFMAU, 13, biologically inactive compound, allows us to know the characteristic of the intramolecular hydrogen bonds in nucleoside analogues derivatives of AZT in greater detail and relate them to the conformational and stereo-electronics requirements necessary to produce the biological activity.