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

• Published in: Bioorganic & medicinal chemistry letters Vol. 21; no. 13; pp. 3909 - 3913
• Main Authors: Zheng, Liang-Wen, Shao, Jin-Hui, Zhao, Bao-Xiang, Miao, Jun-Ying
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.07.2011; Elsevier
• Subjects: 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; 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
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2011.05.035

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.