A Novel Synthetic Compound (E)-5-((4-oxo-4H-chromen-3-yl)methyleneamino)-1-phenyl-1H-pyrazole-4-carbonitrile Inhibits TNF alpha-Induced MMP9 Expression via EGR-1 Downregulation in MDA-MB-231 Human Breast Cancer Cells

Breast cancer is a common malignancy among women worldwide. Gelatinases such as matrix metallopeptidase 2 (MMP2) and MMP9 play crucial roles in cancer cell migration, invasion, and metastasis. To develop a novel platform compound, we synthesized a flavonoid derivative, (E)-5-((4-oxo-4H-chromen-3-yl)methyleneamino)-1-phenyl-1H-pyrazole-4-carbonitrile (named DK4023) and characterized its inhibitory effects on the motility andMMP2andMMP9expression of highly metastatic MDA-MB-231 breast cancer cells. We found that DK4023 inhibited tumor necrosis factor alpha (TNF alpha)-induced motility and F-actin formation of MDA-MB-231 cells. DK4023 also suppressed the TNF alpha-induced mRNA expression ofMMP9through the downregulation of the TNF alpha-extracellular signal-regulated kinase (ERK)/early growth response 1 (EGR-1) signaling axis. These results suggest that DK4023 could serve as a potential platform compound for the development of novel chemopreventive/chemotherapeutic agents against invasive breast cancer

3-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-4H-chromen-4-one

In the title molecule, C16H9N3O3, the plane of oxadiazole ring is almost coplanar with attached pyridine ring and chromenyl ring system, forming dihedral angles of 2.37 (3) and 6.71 (2)°, respectively. In the crystal, a pair of C—H...O and C—H...N hydrogen-bond interactions lead to the formation of dimers, which are linked together into [100] chains

(E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-(thiazol-2-yl)prop-2-en-1-one

In the title molecule, C21H15N3OS, the C5=C6 double bond in the central enone group adopts a trans configuration. The dihedral angle between planes of the thiazole and pyrazole rings is 6.6 (2)°. In the crystal, pairs of C—H...O hydrogen bonds generate inversion dimers and another pair of C—H...N hydrogen bonds link the dimers into chains propagating along a-axis direction

2-(2-Fluorophenyl)-3-hydroxy-4H-chromen-4-one

The asymmetric unit of the title compound, C15H9FO3, contains two independent molecules in which the fluorine-substituted benzene ring is twisted by 47.64 (3) and 56.02 (4)° relative to the 4H-chromenon skeleton. The hydroxyl group in each molecule is tilted from 4H-chromenon skeleton by 24.5 (1) and 16.1 (1)°, respectively. In the crystal, pairs of O—H...O hydrogen bonds form inversion dimers with an R22(10) graph-set motif

(E)-3-(2,3-Dimethoxyphenyl)-1-(2-hydroxy-5-methoxyphenyl)prop-2-en-1-one

In the title chalcone derivative, C18H18O5, the dihedral angle formed by the planes of the benzene rings is 29.6 (2)° and an intramolecular O—H...O hydrogen bond closes an S(6) ring. In the crystal, weak C—H...O hydrogen bonds link molecules into chains propagating along [001]

Crystal structure of 1-(8-methoxy-2H-chromen-3-yl)ethanone

In the structure of the title compound, C12H12O3, the dihydropyran ring is fused with the benzene ring. The dihydropyran ring is in a half-chair conformation, with the ring O and methylene C atoms positioned 1.367 (3) and 1.504 (4) Å, respectively, on either side of the mean plane formed by the other four atoms. The methoxy group is coplanar with the benzene ring to which it is connected [Cb—Cb—Om—Cm torsion angle = −0.2 (4)°; b = benzene and m = methoxy], and similarly the aldehyde is coplanar with respect to the double bond of the dihydropyran ring [Cdh—Cdh—Ca—Oa = −178.1 (3)°; dh = dihydropyran and a = aldehyde]. In the crystal, molecules are linked by weak methyl–methoxy C—H...O hydrogen bonds into supramolecular chains along the a-axis direction

8-Methoxy-2H-chromene-3-carbaldehyde

In the title molecule, C11H10O3, the fused dihydropyran ring is in a half-chair conformation with the O atom and the methylene C atom positioned 0.1318 (13) and 0.143 (2) Å, respectively, on either side of the mean plane formed by the other four atoms. In the crystal, weak C—H...O hydrogen bonds link molecules along [001]

Crystal structure of 3,5-dimethoxy-2-[5-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-3-yl]phenol

In the title compound, C21H20N2O3, the planes of the benzene ring and the naphthalene ring system are inclined to one another by 70.95°, and by 4.99 (6) and 75.93 (5)°, respectively, to the mean plane of the pyrazoline ring. The latter has an envelope conformation with the methine (CH) C atom as the flap. There is an intramolecular O—H...N hydrogen bond that forms an S(6) ring motif. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming chains along [100]. The chains are linked via C—H...N hydrogen bonds, forming sheets parallel to the ab plane. The sheets are linked by a series of N—H...π and C—H...π interactions forming a three-dimensional structure