Yong-Sheng Xie

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.

Synthesis, single-crystal characterization and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives.

A series of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives was synthesized and characterized by 1H NMR, 13C NMR, IR, HRMS and X-ray diffraction analysis. Preliminary evaluation of biological applications showed that the compounds 6c and 6f inhibit the growth of A549 cells in dosage-dependent manners through cell cycle arrest.

5-Alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives inhibit growth of lung cancer A549 cell by inducing apoptosis

we found that 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives 8d, 8e and 8f could effectively induce apoptosis in A549 lung cancer cells and elevate the levels of integrin beta4 and ROS. The data suggested that these compounds might be promising agents for the cancer therapy, and these compounds would be useful tools for further investigate the functions of integrin beta4 in regulation of the cancer cell apoptosis.

The synthesis, X-ray crystal structure and optical properties of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives.

A series of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives was synthesized by the reaction of 3-substituted-1H-1,2,4-triazole-5-thiol and chloroacetyl ferrocene in the presence of sodium hydride and potassium iodide at reflux. The structures of the new compounds were determined by IR and (1)H NMR spectroscopy and HRMS. The structure of compound 5c was established by X-ray crystallography. UV-vis absorption and fluorescence spectra were recorded in ethanol and dichloromethane. The results showed that compounds 5a-g display similar absorptions ranging from 300 to 500nm and maximal emission bands are about 566nm. The intensity of fluorescence and maximal emission bands are dependent on the groups bonded to triazole rings.

4-(o-Tolyl­amino)­benzaldehyde

In the title compound, C14H13NO, the dihedral angle between the aromatic rings is 66.08 (9)°. Chains are formed along the b axis through intermolecular N—H⋯O hydrogen bonds. The crystal structure is further stabilized by C—H⋯π interactions.

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.

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.

Synthesis, X-Ray Crystal Structures and Optical Properties of Novel Substituted Pyrazoly 1,3,4-Oxadiazole Derivatives

Novel pyrazoly 1,3,4-oxadiazole derivatives were synthesized and characterized by 1H NMR, IR, HRMS and X-ray diffraction analysis. UV–vis absorption and fluorescence properties of these compounds in different solutions showed that the maximum absorption wavelength was not significantly changed in different solvents; however, maximal emission wavelength was red-shifted with the increase of solvent polarity. Absorption λmax and emission λmax was less correlated with substituent groups on aryl rings.

(E)-2,4-Dichloro-6-{1-[(2-chloro-eth-yl)imino]-eth-yl}phenol.

The title Schiff base compound, C10H10Cl3NO, was prepared by the condensation of 1-(3,5-dichloro-2-hydroxyphenyl)ethanone with chloroethylamine. The imine adopts an E configuration with respect to the C=N bond. The H atom of the phenolic OH group is disordered over two positions with site occupation factors of 0.52 (7) and 0.48 (7), respectively, and the major occupancy component is involved in an intramolecular N—H⋯O hydrogen bond. The compound therefore exists in an iminium–phenolate as well as in the imino–phenol form. In the crystal, molecules are connected by C—H⋯O and C—H⋯Cl hydrogen bonds and Cl⋯Cl interactions [3.7864 (9) Å] into a three-dimensional network. In addition, intermolecular π–π stacking interactions [centroid–centroid distance = 4.4312 (9) Å] are observed.

2-[5-(1,3-Benzodioxol-5-yl)-3-ferrocenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia-zole.

In the title compound, [Fe(C5H5)(C24H18N3O2S)], the pyrazoline ring adopts a twist conformation. The thiazole ring forms dihedral angles of 83.7 (2) and 34.4 (2)° with the benzene ring of the benzodioxole ring and the fused phenyl ring, respectively. The molecular conformation is stabilized by an intramolecular C—H⋯π interaction. The crystal packing features intermolecular C—H⋯N, C—H⋯O hydrogen bonds and weak C—H⋯π interactions.