3-Amino-1-(4-fluorophenyl)-7-methoxy-1H-benzo[f]chromene-2-carbonitrile

Abstract

In the title compound, C21H15FN2O2, the furan ring has a flattened half-chair conformation [the methine C atom lies 0.136 (2) Å above the C5 plane which has an r.m.s. deviation of 0.0229 Å]. Overall, the 1H-benzo[f]chromene fused-ring system approximates a plane (r.m.s. deviation of the 14 non-H atoms = 0.049 Å). The fluoro­benzene ring is almost perpendicular to this plane [dihedral angle = 89.58 (8)°]. Zigzag supra­molecular tapes along the b axis are the most notable feature of the crystal packing. This arises through an alternating sequence of 12-membered {⋯HNC3N}2 and eight-membered {⋯HNCO}2 synthons. These are connected into a three-dimensional architecture by π–π [inter­centroid distance for centrosymmetrically related fluoro­benzene rings = 3.5181 (10) Å] and C—H⋯π inter­actions.

Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3

“…Literature reveals that chromenes and benzochromenes are an important chemical synthon, associated with a broad range of pharmacological activities such as antimicrobial [2][3][4][5], anticancer agent [6] hypolipidemic [7], antioxidant [8,9], analgesic [10], antileishmanial [11,12], vascular-disrupting activity [13], estrogenic anticoagulant and antispasmolytic [14], blood platelet antiaggregating [15] effects and activities. As part of our programmed aim to develop new methodologies for the preparation of 1H-benzo[f ]chromene derivatives [16][17][18], we have synthesized the title compound under microwave irradiation conditions. In the title compound, the asymmetric unit of the title compound contains one independent molecule.…”

The Crystal Structure of 3-Amino-1-(4-Chlorophenyl)-9-Methoxy-1H-Benzo[f]Chromene-2-Carbonitrile: Antimicrobial Activity and Docking Studies

“…The route adopted for the preparation of compound 4 is depicted in Scheme 1. The synthesis was initiated by reacting 7-methoxynaphthalen-2-ol (1) with 4-chlorobenzal-dehyde (2) and malononitrile (3) in an ethanolic-piperidine solution under microwave irradiation conditions to furnish 3-amino-1-(4-chlorophenyl)-9-methoxy-1H-benzo[f ]-chromene-2carbonitrile (4). By repeating the reaction at various watt powers (200, 300, 400 W) and time intervals (1, 1.5, 2 min.…”

“…The crystalline configurations of drug candidates have amassed substantial appreciation as a critical criterion for rational drug design with the manipulation of their functional moieties impacting the drug's structure-activity relationship. Generally, the attained crystallographic data offer explicit/precise structural identification and absolute configuration [1][2][3][4][5][6], which accordingly elucidates the performance of the novel drugs without triggering the adverse response of the biological system stimuli. Of the drug candidates with an elevated disposition to forge crystallographic structures, chromene compounds are among the most notorious and prosperous [7][8][9].…”