Synthesis, Characterization, DFT, and In Silico Investigation of Two Newly Synthesized β-Diketone Derivatives as Potent COX-2 Inhibitors.

Despite extensive genetic and biochemical characterization, the molecular genetic basis underlying the biosynthesis of β-diketones remains largely unexplored. β-Diketones and their complexes find broad applications as biologically active compounds. In this study, in silico molecular docking results revealed that two β-diketone derivatives, namely 2-(2-(4-fluorophenyl)hydrazono)-5,5-dimethylcyclohexane-1,3-dione and 5,5-dimethyl-2-(2-(2-(trifluoromethyl)phenyl)hydrazono)cyclohexane-1,3-dione, exhibit anti-COX-2 activities.

Crystal structure, Hirshfeld surface analysis and DFT study of (5,5',6,6')-6,6'-[ethane-1,2-diyl-bis(aza-nylyl-idene)]bis-{5-[2-(4-fluoro-phen-yl)hydra-zono]-3,3-di-methyl-cyclo-hexa-none} 2.5-hydrate.

The title compound, CHFNO·2.5HO, was obtained by condensation of 2-[2-(4-fluoro-phen-yl)hydrazono]-5,5-di-methyl-cyclo-hexan-1,3-dione with ethyl-enedi-amine in ethanol and crystallized as a 1:2.5 hydrate in space group 2/.

Ethyl 4-(5-bromo-2-hy-droxy-phen-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

In the title compound, C21H24BrNO4, the dihedral angle between the heterocyclic ring and the pendant aromatic ring is 80.20 (13)°. The hexahydroquinone [i.

Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

In the title compound, C(21)H(25)NO(3), the hydro-pyridine ring that constitutes a part of the hexa-hydro-quinoline fused-ring system adopts a sofa conformation; the methine C atom deviates from the least-squares plane defined by the remaining five non-H atoms (r.m.s.

9-(2-Hy-droxy-4,4-dimethyl-6-oxocyclo-hex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetra-hydro-1H-xanthen-1-one.

The cyclo-hexene ring that constitutes a part of the tetra-hydroxanthene fused-ring system of the title compound, C(23)H(26)O(4), adopts a flattened half-chair conformation that approximates an envelope conformation (in which the methyl-ene C atom bearing the two methyl substituents represents the flap) as five of the six atoms lie approximately on a plane (r.m.s.

1-(9-Methyl-11-sulfanyl-idene-8-oxa-10,12-diaza-tricyclo-[7.3.1.0]trideca-2,4,6-trien-13-yl)ethanone.

The six-membered oxacyclo-hexene ring of the title compound, C(13)H(14)N(2)O(2)S, is fused with the benzene ring and the quarternary C atom lies above the plane of the benzene ring by 0.229 (8) Å, whereas the methine C atom (which bears the acetyl substituent) lies below this plane by 0.595 (8) Å.

1-(2-Oxo-3,4-dihydro-2H-1,3-benzoxazin-4-yl)urea monohydrate.

The organic molecule in the title hydrate, C(9)H(9)N(3)O(3)·H(2)O, was obtained by the condenstation of salicylic aldehyde with urea in acetonitrile. The oxazine ring adopts a slightly distorted sofa conformation, with the N atom deviating from the plane passing through the other atoms of the ring by 0.267 (2) Å.