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■ Synthesis, Characterization, and Computational Studies of Some Perfluorinated Cyclopentapyridazines for Biological Applications

Nathan C. Tice,* Steven Wild, Hannah Dendinger, Bangbo Yan, and Pauline Norris

*Department of Physical Sciences, The University of Findlay, 1000 North Main Street, Findlay, OH 45840, U.S.A.

Abstract

Fluorinated heterocycles are a major component of the field of modern medicinal chemistry due to the widespread presence of heterocyclic ring structures in naturally occurring biological molecules. The effect of the presence of fluorinated heterocyclic moieties on chemical properties such as intermolecular interactions and solubility can be used to impart synthetic molecules with useful, drug-like characteristics. Pyridazines, which are aromatic six-membered rings with a chemical formula (CH)4N2 and adjacent nitrogens, afford important biological activities to drug molecules by increasing their solubility and ability to complex with target molecules. Our method of synthesizing fluorinated pyridazines incorporates an SNAr reaction on 5,6-fused ring pyridazines with a variety of aryl substituents at the 1- and 4-positions with pentafluoropyridine. The target products were identified by spectroscopic characterization and confirmed via X-ray crystallography. Computational studies were also performed on the phenyl-substituted case, including the calculation of an optimized structure using PBE with a cc-pVTZ basis. This analysis found the addition of perfluorinated pyridine significantly altered the esp mapping, HOMO-LUMO, and NBOs of the modified pyridazine compared to other 5,6-fused ring heterocycles.