1-Substituted derivatives of 2-phenylpyrrolidine-2-carboxamide

Abstract

The structures of two potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitors (NNRTI), namely 1-(2-chlorobenzoyl)-2-phenylpyrrolidine-2-carboxamide, C(18)H(17)ClN(2)O(2), and 1-(2-furoyl)-2-phenylpyrrolidine-2-carboxamide, C(16)H(16)N(2)O(3), have been investigated by X-ray diffraction and the butterfly-like conformation established in each case. The pyrrolidine ring has the same half-chair conformation in both structures.

1-(4-Bromobenzoyl)-2-phenylpyrrolidine-2-carboxamide

“…In (I) ( Fig. 1), all bond lengths and angles are in good agreement with those observed in the related compounds (Karapetyan et al, 2002;Tamazyan et al, 2002Tamazyan et al, , 2007. Both H atoms of amide group, H7b and H7a, respectively, are involved in intra-and intermolecular N-H•••O hydrogen bonds ( Table 1).…”

“…For related crystal structures, see: Karapetyan et al (2002); Tamazyan et al (2002Tamazyan et al ( , 2007. For details of the synthesis, see: Martirosyan et al (2000Martirosyan et al ( , 2004.…”

1-Benzyl-2-(1H-indol-3-yl)-5-oxopyrrolidine-2-carbonitrile

“…For details of the pharmacological properties of compounds of this family, see: De Clercq (1996). For the crystal structures of some analogs of the title compound, see: Karapetyan et al (2002); Tamazyan et al (2002).…”

1-(4-Methylphenyl)-5-oxo-2-phenylpyrrolidine-2-carboxamide–methanol (1/1)

“…For details of the pharmacological properties of compounds of this family, see: De Clercq (1996). For the crystal structures of some analogs of the title compound, see: Karapetyan et al (2002) and Tamazyan et al (2002). Table 1 Hydrogen-bond geometry (Å , ).…”

“…These compounds belong to a family of non-nucleoside reverse transcriptase inhibitors (NNRTIs). Related structures have been published by Karapetyan et al, 2002 andTamazyan, et al, 2002. A view of the molecule with our numbering scheme is depicted in Fig. 1.…”