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 y...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 21; no. 13; pp. 3909 - 3913 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Amsterdam
Elsevier Ltd
01.07.2011
Elsevier |
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| Abstract | 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, ¹H 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. |
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| AbstractList | 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. 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, ¹H 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. 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, [super]1H 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. |
| Author | Zheng, Liang-Wen Miao, Jun-Ying Shao, Jin-Hui Zhao, Bao-Xiang |
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| Keywords | Antineoplastic agent Human A549 cells H322 cells Lung Pyrazinone Microwave-assisted Microwave heating In vitro Biological activity Operating conditions Cell line Synthesis Solvent free X-ray Chemical synthesis Tumor cell |
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| Snippet | 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... 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... |
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| SubjectTerms | Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Cell Survival - drug effects chemistry Crystallography, X-Ray ethanol General aspects Humans Inhibitory Concentration 50 lung neoplasms Lung Neoplasms - drug therapy Magnetic Resonance Spectroscopy mass spectrometry Medical sciences microwave treatment Molecular Structure nuclear magnetic resonance spectroscopy Pharmacology. Drug treatments Pyrazines - chemical synthesis Pyrazines - chemistry Pyrazines - pharmacology X-ray diffraction |
| Title | Synthesis of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives and their inhibition against growth of A549 and H322 lung cancer cells |
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