Jin-Hua Zhang

Synthesis and preliminary biological evaluation of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as potential agents against A549 lung cancer cells.

A series of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives were synthesized by the reaction of ethyl 3-aryl-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate and amine in the general heating condition and microwave-assisted condition. The structures of the compounds were determined by IR, (1)H NMR and mass spectroscopy, in addition, representative single-crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 cells in dosage- and time-dependent manners. The study on structure-activity relationships showed that compounds with 4-chlorophenyl group at pyrazole moiety, such as 5-benzyl-2-(4-chlorophenyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (3o) had much more inhibitory effects. Compound 3o was the most effective small molecule in inhibiting A549 cell growth and might perform its action through modulating autophagy.

Microwave-assisted synthesis, crystal structure of pyrazolo[1,5-a]pyrazin-4(5H)-ones and their selective effects on lung cancer cells.

A series of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives with hydrophilic group was synthesized under general heating condition and microwave-assisted condition. The structures of compounds were determined by IR, 1H NMR and HRMS, moreover, representative crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that some compounds could inhibit the growth of A549, H322 and H1299 cells in dosage dependent manners. The compounds could inhibit growth of A549, H322 and H1299 cells in different mechanism. Compounds 3e-h inhibited growth of A549 cells by inducing a strong G1-phase arrest. Whereas these compounds inhibited growth of H1299 and H322 cells by inducing apoptosis.

2-(4-Chloro­phen­yl)-5-(3,4-dimethoxy­pheneth­yl)-6,7-dihydro­pyrazolo[1,5-a]pyrazin-4(5H)-one

In the title compound, C(22)H(22)ClN(3)O(3), the dihedral angles between the planes of the benzene rings and the pyrazole ring are 16.05 (10) and 84.84 (10)°. The conformation of the six-membered heterocyclic ring is close to a screw-boat. The crystal packing is stabilized by weak inter-molecular C-H⋯O inter-actions and is also consolidated by C-H⋯π inter-actions.

1-(2-Hydr­oxy-5-methoxy­phen­yl)ethan-1-one N-[(E)-1-(2-hydr­oxy-5-methoxy­phen­yl)ethyl­idene]hydrazone

In the title molecule, C18H20N2O4, which resides on a crystallographic centre of inversion (at the centre of the N—N bond), all non-H atoms apart from the methoxy substituent are approximately coplanar. The structure displays intramolecular O—H⋯N hydrogen bonding.

Synthesis and X-ray crystal structure of novel (3 E ,4 E )-1-aryl-3,4-bis[(benzo[ d ][1,3]dioxol-5-yl)methylidene]pyrrolidene-2,5-dione

A series of novel (3E,4E)-1-aryl-3,4-bis[(benzo[d][1,3]dioxol-5-yl)methylidene]pyrrolidene-2,5-dione derivatives was synthesised and characterised by IR, 1H NMR and HRMS. Moreover, the molecular structure of (3E,4E)-3,4-bis [(benzo[d][1,3]dioxol-5-yl)methylene]-1-(4-ethoxyphenyl)pyrrolidine-2,5-dione was confirmed by the X-ray crystal structure determination.

Ethyl 1-(2-bromo­ethyl)-3-ferrocenyl-1H-pyrazole-5-carboxyl­ate

In the structure of the title compound, [Fe(C5H5)(C13H14BrN2O2)], the two cyclopentadienyl (Cp) rings are in an eclipsed conformation and are parallel. The dihedral angle between the substituted Cp ring and the heterocyclic ring is 8.20°.

3-[(1,3-Benzodioxol-6-yl)methylene]-4-(pentan-3-ylidene)tetrahydrofuran-2,5-dione

In the structure of the title compound, C17H16O5, the dihydrofuran ring adopts an envelope conformation while the methylenedioxyphenyl ring system is essentially planar. The vinyl group is inclined to the dihydrofuran ring by 30.22 (12)°. The dihedral angle between the atoms defining the planar part of the dihydrofuran ring and the aryl ring is 19.12 (8)°