Synthesis of Fluorescent 1-(3-Amino-4-(4-(tert-butyl)phenyl)−6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one: Crystal Structure, Fluorescence Behavior, Antimicrobial and Antioxidant Studies

Abstract

Furopyridine III, namely 1-(3-amino-4-(4-(tert-butyl)phenyl)-6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one, synthesized from 4-(4-(tert-butyl)phenyl)-2-oxo-6-(p-tolyl)-1,2-dihydropyridine-3-carbonitrile I in two steps. The title compound is characterized by NMR, MS and its X-ray structure. The molecular structure consists of planar furopyridine ring with both phenyl rings being inclined from the furopyridine scaffold to a significant different extent. There are three intramolecular hydrogen bonds within the structure. The lattice is stabilized by N-H…O, HC-H …π and π…π intermolecular interactions leading to three-dimensional network. Compound III exhibits fluorescent properties, which are investigated. Antimicrobial potential and antioxidant activity screening studies for the title compound III and the heterocyclic derivatives, I and II, show no activity towards neither bacterial nor fungal strains, while they exhibited weak to moderate antioxidant activity compared to reference.

Investigation of Solvent Effect and H-Bonding on Spectroscopic Properties of 1-(3-Amino-6-(2,5-dichlorothiophen-3-yl)-4-phenylfuro[2,3-b]Pyridin-2-yl) Ethenone: Experimental and Computational Study

“…The characteristic absorption bands in the region 250 to 390 nm, are attributed to 𝜋 → 𝜋 * and 𝑛 → 𝜋 * transitions within the furo-pyridine portion, which are in a good agreement with the reported literature on similar fragments (Fig. 2) [9,[14][15]. The position of the absorption bands does not show any clear relation to solvent polarity, except with water, where dramatic changes are observed.…”

Synthesis of 1-Amino-3-oxo-2,7-naphthyridines via Smiles Rearrangement: A New Approach in the Field of Chemistry of Heterocyclic Compounds

“…Furthermore, it is well known that fused derivatives of furo[2,3- b ]pyridine show high biological activity [ 18 , 19 , 20 , 21 , 22 , 23 , 24 ]. Along this line we have previously synthesized several condensed furo[2,3- b ]pyridines based on the cyclopenta[ c ]pyridines, 5,6,7,8-tetrahydroisoquinolines and pyrano[3,4- c ]pyridines, obtaining compounds with neurotropic [ 25 , 26 ], antimicrobial [ 27 ], antitumor [ 28 ] and potent antiviral [ 29 ] activities.…”

The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure–Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles

“…Furthermore, they are important precursors for synthetic manipulations and have been commonly used as precursors and key intermediates in organic synthesis [12,13]. In recent years, we reported the synthesis of different pyridine derivatives bearing carbonitrile and 2,5-dichlorothiophene substituents [14,15,16,17,18,19]. In continuation of our ongoing work, herein, we present the synthesis and characterization of new pyridine-3-carbonitrile derivatives (Scheme 1).…”