Effect of C–H ⋯ S and C–H ⋯ Cl interactions on the conformational preference of inhibitors of TIBO family

• Published in: Chemical physics letters Vol. 423; no. 1; pp. 131 - 137
• Main Authors: Freitas, Renato F., Galembeck, Sérgio E.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 20.05.2006
• ISSN: 0009-2614; 1873-4448
• DOI: 10.1016/j.cplett.2006.03.041

The non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs) are an important class of drugs employed in antiviral therapy. The coordinates of three inhibitors, derived from TIBO, tetrahydroimidazo-(4,5,1-1- jk)(1,4)-benzodi-azepin-2(1 H)-one (which belongs to the NNRTIs class), were taken from PDB database and the electronic structure were investigated by using the B3LYP/6-31+G(d,p) model. Results obtained by means of the natural bond orbital (NBO) and atoms in molecules (AIM) methods indicated the presence of weak hydrogen bonds of the C–H ⋯ S and C–H ⋯ Cl type, which are partially responsible for the conformational differences observed between the inhibitors 8 Cl-TIBO and 9 Cl-TIBO.