Novel pyrazolo[3,4-d]pyrimidine derivatives as potential antitumor agents: Exploratory synthesis, preliminary structure-activity relationships, and in vitro biological evaluation

Molecules

Volumn 16, Issue 12, 2011, Pages 10685-10694

  He, Hai Yun ^a   Zhao, Jin Ni ^a   Jia, Ruo ^b   Zhao, Ying Lan ^a   Yang, Sheng Yong ^a   Yu, Luo Ting ^a   Yang, Li ^a  

^a SICHUAN UNIVERSITY   (China)

^b CHONGQING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Anticancer activity; Apoptosis; Exploratory synthesis; Pyrazolo 3,4 d pyrimidine

Indexed keywords

ANTINEOPLASTIC AGENT; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE;

APOPTOSIS; ARTICLE; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; PYRAZOLES; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84555189764     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules161210685     Document Type: Article

References (29)

1. Jemal, A.; Siegel, R.; Xu, J.; Ward, E. Cancer Statistics 2010. CA Cancer J. Clin. 2010, 60, 277-300.
2. Simonetti, R.G.; Liberati, A.; Angiolini, C.; Pagliaro, L. Treatment of hepatocellular carcinoma: A systematic review of randomized controlled trials. Ann. Oncol. 1997, 8, 117-136. (Pubitemid 27112878)
3. Zheng, Y.Z.; Zhao, Y.L.; Deng, X.Q.; Yang, S.Y.; Mao, Y.Q.; Li, Z.G.; Jiang, P.D.; Zhao, X.; Wei, Y.Q. Chloroquine inhibits colon cancer cell growth in vitro and tumor growth in vivo via induction of apoptosis. Cancer Invest. 2009, 27, 286-292.
4. Xie, H.Z.; Li, L.L.; Ren, J.X.; Zou, J.; Yang, L.; Wei, Y.Q.; Yang, S.Y. Pharmacophore modeling study based on known spleen tyrosine kinase inhibitors together with virtual screening for identifying novel inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 1944-1949.
5. Wang, H.Y.; Cao, Z.X.; Li, L.L.; Jiang, P.D.; Zhao, Y.L.; Luo, S.D.; Yang, L.; Wei, Y.Q.; Yang, S.Y. Pharmacophore modeling and virtual screening for designing potential PLK1 inhibitors. Bioorg. Med. Chem. Lett. 2008, 18, 4972-4977.
6. Luo, Y.F.; Xu, Y.B.; Chen, L.J.; Hu, J.; Peng, C.; Xie, D.C.; Shi, J.Y.; Huang, W.C.; Xu, G.B.; Peng, M.; Han, J.; Li, R.; Yang, S.Y.; Wei, Y.Q. Semi-synthesis and anti-proliferative activity evaluation of novel analogues of Honokiol. Bioorg. Med. Chem. Lett. 2009, 19, 4702-4705.
7. Wei, Y.Q.; Wang, Q.R.; Zhao, X.; Yang, L.; Tian, L.; Lu, Y.; Kang, B.; Lu, C.J.; Huang, M.J.; Lou, Y.Y.; et al. Immunotherapy of tumors with xenogeneic endothelial cells as a vaccine. Nat. Med. 2000, 6, 1160-1166.
8. Yang, L.; Zhao, Y.L.; Yang, S.Y.; Yu, L.T.; Wei, Y.Q. CN Patent 200810304724.X, 28 September 2008.
9. Deng, X.Q.; Wang, H.Y.; Zhao, Y.L.; Xiang, M.L.; Jiang, P.D.; Cao, Z.X.; Zheng, Y.Z.; Luo, S.D.; Yu, L.T.; Wei, Y.Q.; et al. Pharmacophore modelling and virtual screening for identification of new Aurora-A kinase inhibitors. Chem. Biol. Drug Des. 2008, 71, 533-539.
10. Jiang, P.D.; Zhao, Y.L.; Shi, W.; Deng, X.Q.; Xie, G.; Mao, Y.Q.; Li, Z.G.; Zheng, Y.Z.; Yang, S.Y.; Wei, Y.Q. Cell growth inhibition, G2/M cell cycle arrest, and apoptosis induced by chloroquine in human breast cancer cell line Bcap-37. Cell. Physiol. Biochem. 2008, 22, 431-440.
11. Toque, H.A.F.; Priviero, F.B.M.; Texeira, C.E.; Perissutti, E.; Fiorino,F.; Severino, B.; Frecentese, F.; Lorenzetti, R.; Baracat, J.S.; Santagada, V.; et al. Synthesis and Pharmacological Evaluations of Sildenafil Analogues for Treatment of Erectile Dysfunction. J. Med. Chem. 2008, 51, 2807-2815. (Pubitemid 351620802)
12. Gillespie, R.J.; Cliffe, I.A.; Dawson, C.E.; Dourish, C.T.; Gaur, S.; Jordan, A.M.; Knight, A.R.; Lerpiniere, J.; Misra, A.; Pratt, R.M.; et al. Antagonists of the human adenosine A2A receptor. Part 3: Design and synthesis of pyrazolo[3,4-d]pyrimidines, pyrrolo[2,3-d]pyrimidines and 6-arylpurines. Bioorg. Med. Chem. Lett. 2008, 18, 2924-2929. (Pubitemid 351608872)
13. Amjad, A.; Gayle, E.T.; Ken, E.; Georgianna, H.; Ronald, P.; Lynn, L.S.; Katherine, Y. Novel Pyrazolo[3,4-d]pyrimidine-Based Inhibitors of Staphlococcus aureus DNA Polymerase III: Design, Synthesis, and Biological Evaluation. J. Med. Chem. 2003, 46, 1824-1830.
14. Wang, H.M.; Eiji, S.; Tang, Y.P.; Min, C.; Maureen, K.; Zuo, W.Q.; Daphne, A.R.; Peter, J.A.; Zhang, C.; Hiromi, M.; et al. Inducible protein knockout reveals temporal requirement of CaMKII reactivation for memory consolidation in the brain. Proc. Natl. Acad. Sci. USA 2003, 100, 4287-4292. (Pubitemid 36418195)
15. Kim, D.C.; Lee, Y.R.; Yang, B.S.; Shin, K.J.; Kim, D.J.; Chung, B.Y.; Yoo, K.H. Synthesis and biological evaluations of pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 inhibitors. Eur. J. Med. Chem. 2003, 38, 525-532. (Pubitemid 36588919)
16. Carraro, F.; Naldini, A.; Pucci, A.; Locatelli, G,A.; Maga, G.; Schenone, S.; Bruno, O.; Ranise, A.; Bondavalli, F.; Brullo, C.; et al. Pyrazolo[3,4-d]pyrimidines as Potent Antiproliferative and Proapoptotic Agents toward A431 and 8701-BC Cells in Culture via Inhibition of c-Src Phosphorylation. J. Med. Chem. 2006, 49, 1549-1561. (Pubitemid 43376502)
17. Schenone, S.; Bruno, O.; Bondavalli, F.; Ranise, A.; Mosti, L.; Menozzi, G.; Fossa, P.; Donnini, S.; Santoro, A.; et al. Antiproliferative activity of new 1-aryl-4-amino-1H-pyrazolo[3,4- d]pyrimidine derivatives toward the human epidermoid carcinoma A431 cell line. Eur. J. Med. Chem. 2004, 39, 939-946. (Pubitemid 39389104)
18. Bol'but, A.V.; Vovk, M.V. Condensed pyrimidine systems 5: 6-methyl-functionalized in pyrazolo[3,4-d]pyrimidin-4(5H)-ones. Zh. Org. Farm. Khim. 2006, 4, 57-61.
19. Harden, F.A.; Quinn, R.J.; Scammells, P.J. Synthesis and Adenosine Receptor Affinity of a Series of Pyrazolo[3,4-d]pyrimidine Analogues of 1-Methylisoguanosine. J. Med. Chem. 1991, 34, 2892-2898.
20. Bavetsias, V. A Facile Route to Quinazolin-4(3H)-ones Functionalised at the 2-Position. Syn. Commun. 1998, 28, 4547-4559. (Pubitemid 28541706)
21. Cheng, C.C.; Robins, R.K. Potential Purine Antagonists VII. Synthesis of 6-Alkylpyrazolo-[3,4-d] pyrimidine. J. Org. Chem. 1958, 23, 191-200.
22. Hermecz, I.; Kökösi, J.; Podányi, B.; Szász, G. Syntheses of indolyl-(3H)-quinazolinones. Heterocycles 1994, 37, 903-914.
23. Masayuki, I.; Yukuo, E. Syntheses of 2-hydroxymethyl-4(3H)-quinazolinone and its analogs. Heterocycles 1981, 16, 31-34.
24. Hu, T.S.; Yu, Q.; Wu, Y.L.; Wu, Y. Enantioselective syntheses of monotetrahydrofuran Annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates. J. Org. Chem. 2001, 66, 853-861. (Pubitemid 32163081)
25. Faul, M.M.; Winneroski, L.L.; Krumrich, C.A. Synthesis of Rebeccamycin and 11-Dechlororebeccamycin. J. Org. Chem. 1999, 64, 2465-2470. (Pubitemid 29180470)
26. Baker, B.R.; Almaula, P.I. Nonclassical Antimetabolites. X.1, 2 A Facile Synthesis of 4-Quinazolone-2-carboxylic Acid and the Structure of Bogert's Ammonium Salt. J. Org. Chem. 1962, 27, 4672-4764.
27. Brown, H.C.; Narasimhan, S.; Choi, Y.M. Selective Reductions. 30. Effect of Cation and Solvent on the Reactivity of Saline Borohydrides for Reduction of Carboxylic Esters. Improved Procedures for the Conversion of Esters to Alcohols by Metal Borohydrides. J. Org. Chem. 1982, 47, 4702-4708.
28. Peng, F.; Wei, Y.Q.; Tian, L.; Yang, L.; Zhao, X.; Lu, Y.; Mao, Y.Q.; Kan, B.; Lei, S.; Wang, G.S.; et al. Induction of apoptosis by norcantharidin in human colorectal carcinoma cell lines: Involvement of the CD95 receptor/ligand. J. Cancer Res. Clin. Oncol. 2002, 128, 223-230. (Pubitemid 34280381)
29. Wei, Y.Q.; Zhao, X.; Kariya, Y.; Fukata, H.; Teshigawara, K.; Uchida, A. Induction of apoptosis by quercetin: Involvement of heat shock protein. Cancer Res. 1994, 54, 4952-4957. (Pubitemid 24289427)