Four pyrrole derivatives used as building blocks in the synthesis of minor-groove binders.

ABSTRACT: The title nitro-pyrrole-based compounds, C₇H₈N₂O₄, (I) (ethyl 4-nitro-1H-pyrrole-2-carboxyl-ate), its derivative C₁₂H₁₄N₂O₄, (II) [ethyl 4-nitro-1-(4-pent-yn-yl)-1H-pyrrole-2-carboxyl-ate], C₁₅H₂₆N₄O₃, (III) {N-[3-(di-methyamino)prop-yl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide}, and C₂₀H₂₇N₉O₅, (IV) {1-(3-azido-prop-yl)-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-N-[2-(morpholin-4-yl)eth-yl]-1H-pyrrole-2-carboxamide}, are inter-mediates used in the synthesis of modified DNA minor-groove binders. In all four compounds, the nitro groups lie in the plane of the pyrrole ring. In compounds (I) and (II), the ester groups also lie in the plane of the pyrrole ring. In compound (III), both of the other substituents lie out of the plane of the pyrrole ring. In the case of compound (IV), the coplanarity extends to the second pyrrole ring and through both amide groups. In the crystals of all four compounds, layer-like structures are formed, via a combination of N-H⋯O and C-H⋯O hydrogen bonds for (I), (III) and (IV), but by only C-H⋯O hydrogen bonds for (II).

SUBMITTER: Kennedy AR 

PROVIDER: S-EPMC5290577 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature