Synthesis, X-ray Diffraction and Computational Druglikeness Evaluation of New Pyrrolo[1,2-a][1,10]Phenanthrolines Bearing a 9-Cyano Group

Abstract

New 9-cyano-pyrrolo[1,2-a][1,10]phenanthrolines 5a–d, obtained by a 1,3-dipolar cycloaddition reaction between the corresponding N-ylides of 1,10-phenanthrolinium bromides 2a–d, generated in situ and acrylonitrile as a dipolarophile, were investigated by single-crystal X-ray diffraction and computational studies to assess their druglikeness and evaluate their structure-activity properties. The non-covalent interactions present within the supramolecular landscape of the new 9-cyano-pyrrolo[1,2-a][1,10]phenanthrolines were correlated with the SAR investigations with the aim of estimating the propensity for bioactivity in these compounds.

Keywords

• pyrrolo[1,2-a][1,10]phenanthroline
• 1,3-dipolar cycloaddition
• crystal structure
• helical chirality
• DFT
• druglikeness