Liang-Wen Zheng

Synthesis of novel oxime-containing pyrazole derivatives and discovery of regulators for apoptosis and autophagy in A549 lung cancer cells

A series of novel oxime-containing pyrazole derivatives were synthesized by the reaction of ethyl 3-phenyl-1H-pyrazole-5-carboxylate derivatives and 2-bromo-1-phenylethanone followed by the reaction with hydroxylamine hydrochloride. The structures were determined by IR, (1)H NMR, HRMS, and X-ray analysis. A dose- and time-dependent inhibition of proliferation was observed in A549 lung cancer cell after compound treatment. Inhibition of growth was mainly attributed to the autophagy induction.

Synthesis and discovery of pyrazole-5-carbohydrazide N-glycosides as inducer of autophagy in A549 lung cancer cells

A series of novel 3-aryl-1-arylmethyl-1H-pyrazole-5-carbohydrazide N-beta-glycoside derivatives was synthesized by the reaction of substituted 1H-pyrazole-5-carbohydrazide with d-sugar and the effects of all the compounds on A549 cell growth were investigated. The results showed that all compounds had inhibitory effects on the growth of A549 lung cancer cells and compound 3d possessed the highest growth inhibitory effect and induced autophagy of A549 lung cancer cells.

Synthesis of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives and their inhibition against growth of A549 and H322 lung cancer cells.

A series of substituted pyrazolo[1,5-a]pyrazin-4(5H)-one was synthesized by the reaction of ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate derivatives and 2-(2-aminoethoxy)ethanol or 2-morpholinoethanamine in the condition of microwave-assisted one-step and solvent-free in a good yield. The structures of the compounds were determined by IR, (1)H NMR and mass spectroscopy. In addition, a representative single-crystal structure was characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 and H322 cells in dosage-dependent manners.

Synthesis, crystal structure and biological evaluation of novel 2-(5-(hydroxymethyl)-3-phenyl-1H-pyrazol-1-yl)-1-phenylethanol derivatives.

A series of novel 2-(5-(hydroxymethyl)-3-phenyl-1H-pyrazol-1-yl)-1-phenylethanol derivatives (4) was synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate derivatives (3) and characterized by means of IR, 1H NMR, HRMS and X-ray crystal diffraction. Structures of 4a, 4d, 4e and 4f were also determined by 13C NMR. Isomeric intermediates, 3a and 5a, were unambiguously confirmed by X-ray crystal structure analysis and successfully differentiated with 1H NMR chemical shifts of methylene bonded to pyrazole ring. Preliminary biological evaluation showed that compounds 4d and 4e could suppress A549 lung cancer cell growth through cell cycle arrest and autophagy.

Synthesis, X-ray crystal structure and fluorescent spectra of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives

A series of fluorescent compounds, containing pyrazolo[1,5-a]pyrazin-4(5H)-one moiety, were designed and synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylates. The structures of the compounds have been confirmed by IR, (1)H NMR, HRMS and X-ray crystal diffraction. The optical properties of the compounds were investigated by UV-vis absorption and fluorescence spectroscopy. The effect of pH on the UV-vis absorption of compound 2a in methanol-H(2)O solutions was studied and interpreted by theory calculation. The pK(a) value of compound 2a was determined by the absorption spectra.

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°.

Synthesis, Structure Characterization, and X-ray Crystallography of Novel 1-Benzyl-3-phenyl-1H-pyrazole-5-carboxylate Derivatives with a Carbohydrate Moiety

A series of novel (2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-2H-pyran-2-yl 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylate derivatives (3) were synthesized by the reaction of 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide (2) and 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylic acid (1) in the presence of sodium bicarbonate and tetrabutylammonium bromide in dichloromethane at reflux temperature. The structures of new compounds were determined by IR and 1H NMR spectroscopy and HR mass spectrometry (HRMS), and the configuration of the newly generated chiral carbon (C-1) in the xylose ring was tentatively assigned based on the X-ray crystallographic structure of 3d and 3g.

Ethyl 3-(4-chloro-phen-yl)-1-(2-oxo-2-phenyl-eth-yl)-1H-pyrazole-5-carboxyl-ate.

In the title compound, C20H17ClN2O3, the dihedral angles between the pyrazole ring and the substituted and unsubstituted benzene rings are 3.64 (13) and 81.15 (17)°, respectively. Molecules are connected via three pairs of weak hydrogen bonds into a centrosymmetric dimer. The crystal structure is stabilized by intermolecular C—H⋯O and C—H⋯π interactions.

6-(4-Chloro-phen-yl)-2-(4-meth-oxy-phen-yl)-6,7-dihydro-4H-pyrazolo-[5,1-c][1,4]oxazine.

In the title compound, C19H17ClN2O2, the pyrazole ring is almost planar with a maximum deviation of 0.009 (3) Å and makes a dihedral angle of 8.96 (9)° with the oxazine ring. The dihedral angles between the pyrazole ring and the chlorine- and methoxy-substituted benzene rings are 50.95 (8) and 13.24 (9)°, respectively. An intermolecular C—H⋯N hydrogen bond links the molecules into infinite chains along the a axis. The crystal structure is further stabilized by C—H⋯π interactions.

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)°