ABSTRACT
In the title compound, C(20)H(17)ClN(2)O(3), the dihedral angles between the pyrazole ring and the substituted and unsubstituted benzene rings are 3.64â (13) and 81.15â (17)°, respectively. Mol-ecules are connected via three pairs of weak hydrogen bonds into a centrosymmetric dimer. The crystal structure is stabilized by inter-molecular C-Hâ¯O and C-Hâ¯π inter-actions.
ABSTRACT
In the title compound, C(19)H(17)ClN(2)O(2), the pyrazole ring is almost planar with a maximum deviation of 0.009â (3)â Å and makes a dihedral angle of 8.96â (9)° with the oxazine ring. The dihedral angles between the pyrazole ring and the chlorine- and meth-oxy-substituted benzene rings are 50.95â (8) and 13.24â (9)°, respectively. An inter-molecular C-Hâ¯N hydrogen bond links the mol-ecules into infinite chains along the a axis. The crystal structure is further stabilized by C-Hâ¯π inter-actions.
ABSTRACT
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.
Subject(s)
Pyrazines/chemistry , Pyrazoles/chemistry , Pyridines/chemistry , Pyridines/chemical synthesis , Crystallography, X-Ray , Models, Biological , Models, Molecular , Molecular Dynamics Simulation , Molecular Structure , Pyrazines/chemical synthesis , Pyrazoles/chemical synthesis , Spectrometry, Fluorescence/methodsABSTRACT
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.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Pyrazines/chemical synthesis , Pyrazines/pharmacology , Animals , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Survival/drug effects , Crystallography, X-Ray , Humans , Inhibitory Concentration 50 , Lung Neoplasms/drug therapy , Magnetic Resonance Spectroscopy , Molecular Structure , Pyrazines/chemistryABSTRACT
A series of novel 5-aryl-3-ferrocenyl-1-pyridazinyl pyrazoline derivatives was synthesized by the reaction of ferrocenyl chalcone and 3-chloro-6-hydrazinylpyridazine in 10-65% yields. The compounds were characterized using IR, (1)H NMR, HRMS spectroscopic techniques and representative compounds 3c and 4c were assigned based on the X-ray crystallographic structure. The absorption and fluorescence characteristics of the compounds were investigated in chloroform, tetrahydrofuran and acetonitrile, respectively. The results showed that the absorption maxima of the compounds varied from 323 to 327 nm depending on the groups bonded to benzene and pyridazine ring. The maximum emission spectra of compounds in CHCl(3) were dependent on groups in pyridazine ring in which a strong donating-electron group such as propoxyl group on pyridazine ring in N-1 position of pyrazoline made the emission wavelength of 4a-4e small red shifte than that of compounds 3a-3e with chlorine group. The intensity of absorption and fluorescence was also correlated with substituent on aryl ring in C-5 position of pyrazoline. In addition, the absorption spectra of these compounds changed very little, but the fluorescence spectra had much change with increasing solvent polarity.
ABSTRACT
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.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Benzyl Alcohols/chemical synthesis , Benzyl Alcohols/pharmacology , Pyrazoles/chemical synthesis , Pyrazoles/pharmacology , Antineoplastic Agents/chemistry , Benzyl Alcohols/chemistry , Cell Cycle/drug effects , Cell Death/drug effects , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Crystallography, X-Ray , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Flow Cytometry , Humans , Models, Molecular , Molecular Structure , Pyrazoles/chemistry , Stereoisomerism , Structure-Activity RelationshipABSTRACT
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.
Subject(s)
Antineoplastic Agents/chemical synthesis , Apoptosis/drug effects , Autophagy/drug effects , Lung Neoplasms/drug therapy , Oximes/chemistry , Pyrazoles/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/therapeutic use , Cell Line, Tumor , Crystallography, X-Ray , Drug Evaluation, Preclinical , Humans , Lung Neoplasms/pathology , Molecular Conformation , Pyrazoles/chemical synthesis , Pyrazoles/therapeutic use , Structure-Activity RelationshipABSTRACT
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.
Subject(s)
Autophagy/drug effects , Glycosides/chemical synthesis , Glycosides/pharmacology , Lung Neoplasms/immunology , Cell Line, Tumor , Cell Proliferation/drug effects , Glycosides/chemistry , Humans , Lung Neoplasms/pathology , Structure-Activity RelationshipABSTRACT
A series of novel 3-aryl-1-(4-tert-butylbenzyl)-1H-pyrazole-5-carbohydrazide hydrazone derivatives were synthesized 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 (E)-1-(4-tert-butylbenzyl)-N'-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-3-(4-chlorophenyl)-1H-pyrazole-5-carbohydrazide (3e) possessed the highest growth inhibitory effect and induced apoptosis of A549 lung cancer cells.