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

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 13, 2011, Pages 3909-3913

  Zheng, Liang Wen ^a   Shao, Jin Hui ^a   Zhao, Bao Xiang ^a   Miao, Jun Ying ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

A549 cells; H322 cells; Microwave assisted; Pyrazinone; Synthesis; X ray

Indexed keywords

ANTINEOPLASTIC AGENT; PYRAZOLO(1,5 ALPHA)PYRAZIN 4 (5H) ONE DERIVATIVE; PYRAZOLONE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CANCER CELL CULTURE; CANCER GROWTH; CANCER INHIBITION; CATALYST; CELL PROLIFERATION; CHEMICAL REACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DOSE RESPONSE; DRUG CYTOTOXICITY; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; LUNG CANCER; MASS SPECTROMETRY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; X RAY DIFFRACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; HUMANS; INHIBITORY CONCENTRATION 50; LUNG NEOPLASMS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PYRAZINES;

EID: 79958753893     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.05.035     Document Type: Article

References (29)

1. Abdel-Aziz, H. A.; El-Zahabi, H. S. A.; Dawood, K. M. Eur. J. Med. Chem. 2010, 45, 2427.
2. Ma, H.-J.; Li, Y.-H.; Zhao, Q.-F.; Zhang, T.; Xie, R.-L.; Mei, X.-D.; Ning, J. J. Agric. Food. Chem. 2010, 58, 4356.
3. Ragavan, R. V.; Vijayakumar, V.; Kumari, N. S. Eur. J. Med. Chem. 2010, 45, 1173.
4. Mattson, M. N.; Neitzel, M. L.; Quincy, D. A.; Semko, C. M.; Garofalo, A. W.; Keim, P. S.; Konradi, A. W.; Pleiss, M. A.; Sham, H. L.; Brigham, E. F.; Goldbach, E. G.; Zhang, H. B.; Sauer, J. M.; Basi, G. S. Bioorg. Med. Chem. Lett. 2010, 20, 2148.
5. Riyadh, S. M.; Farghaly, T. A.; Abdallah, M. A.; Abdalla, M. M.; Abd El-Aziz, M. R. Eur. J. Med. Chem. 2010, 45, 1042.
6. Bakavoli, M.; Bagherzadeh, G.; Vaseghifar, M.; Shiri, A.; Pordel, M.; Mashreghi, M.; Pordeli, P.; Araghi, M. Eur. J. Med. Chem. 2010, 45, 647.
7. Ghorab, M. M.; Ragab, F. A.; Alqasoumi, S. I.; Alafeefy, A. M.; Aboulmagd, S. A. Eur. J. Med. Chem. 2010, 45, 171.
8. Gilbert, A. M.; Nowak, P.; Brooijmans, N.; Bursavich, M. G.; Dehnhardt, C.; Santos, E. D.; Feldberg, L. R.; Hollander, I.; Kim, S.; Lombardi, S.; Park, K. J.; Venkatesan, A. M.; Mallon, R. Bioorg. Med. Chem. Lett. 2010, 20, 636.
9. Kim, I.; Song, J.-H.; Park, C.-M.; Jeong, J.-W.; Kim, H.-R.; Ha, J.-R.; No, Z.; Hyun, Y.-L.; Cho, Y.-S.; Kang, N.-S.; Jeon, D.-J. Bioorg. Med. Chem. Lett. 2010, 20, 922.
10. Devegowda, V. N.; Kim, J.-H.; Han, K.-C.; Yang, E.-G.; Choo, H.; Pae, A.-N.; Nam, G.; Choi, K.-I. Bioorg. Med. Chem. Lett. 2010, 20, 1630.
11. Mousseau, J. J.; Fortier, A.; Charette, A. B. Org. Lett. 2010, 12, 516.
12. Nascimento-Júnior, N. M.; Mendes, T. C. F.; Leal, D. M.; Corrêa, C. M. N.; Sudo, R. T.; Zapata-Sudo, G.; Barreiro, E. J.; Fraga, C. A. M. Bioorg. Med. Chem. Lett. 2010, 20, 74.
13. Wei, F.; Zhao, B.-X.; Dong, W.-L.; Zuo, H.; Shin, D.-S.; Wang, D.-W.; Xia, Y.; Ge, Y.-Q. Synth. Commun. 2007, 37, 4415.
14. Xie, Y.-S.; Zhao, B.-X.; Lv, H.-S.; Li, J.-K.; Wang, B.-S.; Shin, D.-S. J. Mol. Struc. 2009, 930, 83.
15. Xie, Y.-S.; Zhao, H.-L.; Su, H.; Zhao, B.-X.; Liu, J.-T.; Li, J.-K.; Lv, H.-S.; Wang, B.-S.; Shin, D.-S.; Miao, J.-Y. Eur. J. Med. Chem. 2010, 45, 210.
16. Xie, Y.-S.; Pan, X.-H.; Zhao, B.-X.; Liu, J.-T.; Shin, D.-S.; Zhang, J.-H.; Zheng, L.-W.; Zhao, J.; Miao, J.-Y. J. Organomet. Chem. 2008, 693, 1367.
17. Zhang, J.-H.; Fan, C.-D.; Zhao, B.-X.; Shin, D.-S.; Dong, W.-L.; Xie, Y.-S.; Miao, J.-Y. Bioorg. Med. Chem. 2008, 16, 10165.
18. Zhang, J.-H.; Zuo, H.; Xie, Y.-S.; Zhao, B.-X. Acta Crystallogr. Sect. E: Struct. Rep. 2009, E65, o1457.
19. Pineiro, M.; Pinho e Melo, T. M. V. D. Eur. J. Org. Chem. 2009, 5287.
20. Roberts, B. A.; Strauss, C. R. Acc. Chem. Res. 2005, 38, 653.
21. Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629.
22. Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
23. Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Buriol, L.; Machado, P. Chem. Rev. 2009, 109, 4140.
24. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
25. + 376.1661; found 376.1659.
26. -3, CCDC 779358 contains the Supplementary crystallographic data for compound 3i.
27. Lian, S.; Su, H.; Zhao, B.-X.; Liu, W.-Y.; Zheng, L.-W.; Miao, J.-Y. Bioorg. Med. Chem. 2009, 17, 7085.
28. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107.
29. Rubinstein, L. V.; Shoemaker, R. H.; Paull, K. D.; Simon, R. M.; Tosini, S.; Skehan, P.; \Scudiero, D. A.; Monks, A.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1113.