Synthesis and cytotoxic activity of some new 2,6-substituted purines

Molecules

Volumn 16, Issue 7, 2011, Pages 5840-5860

  Kode, Nageswara Rao ^a   Phadtare, Shashikant ^a  

^a XAVIER UNIVERSITY OF LOUISIANA   (United States)

Author keywords

2,6 substituted purines; Cytotoxic activity; Pyridiniumtribromide bromination; Suzuki Miyaura cross coupling reaction

Indexed keywords

PURINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PURINES;

EID: 79960764010     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16075840     Document Type: Article

References (21)

1. Chan, M. World health organization's fight against cancer: strategies that prevent cure and care. Accessed online: http://www.who.int/cancer/publicat/ WHOCancerBrochure2007.FINALweb.pdf. (accessed on 7 July 2011)
2. Bischoff, P.L.; Holl, V.; Coelho, D.; Dufour, P.; Weltin, D.; Luu, B. Apoptosis at the interface of immunosuppressive and anticancer activities: The examples of two classes of chemical inducers, oxysterols and alkylating agents. Curr. Med. Chem. 2000, 7, 693-713. (Pubitemid 30366637)
3. Kidwai, M.; Venkataramanan, R.; Mohan, R.; Sapra, P. Cancer chemotherapy and heterocyclic compounds. Curr. Med. Chem. 2002, 9, 1209-1228. (Pubitemid 34568194)
4. De Clercq, E. Novel compounds in preclinical/early clinical development for the treatment of HIV infections. Rev. Med. Virol. 2000, 10, 255-277. (Pubitemid 30465989)
5. Kode, N.; Chen, L.; Murthy, D.; Adewumi, D.; Phadtare, S. New bis-N9-(methylphenylmethyl)- purine derivatives. Eur. J. Med. Chem. 2007, 42, 327-333.
6. Brakta, M.; Murthy, D.; Ellis, L.; Phadtare, S. 9-[(Hydroxymethyl)phenyl] adenines: New aryl adenine substrates of adenosine deaminase. Bioorg. Med. Chem. Lett. 2002, 12, 1489-1492. (Pubitemid 34521919)
7. Murthy, D.; Brakta, M.; Ellis, L.; Abanah O.; Phadtare, S. 9-[(hydroxymethylphenyl)methyl]-purine nucleoside analogues: Synthesis, antiviral and cytotoxic properties against cancer cells. Med. Chem. Res. 2003, 12, 13-25. (Pubitemid 37393012)
8. Averett, D.R.; Koszalka, G.W.; Fyfe, J.D.; Roberts, G.B. 6-Methoxypurine arabinoside as a selective and potent inhibitor of varicella-zoster virus. Antimicrob. Agents Chemother. 1991, 35, 851-857.
9. Robak, T.; Korycka, A.; Lech-Maranda, E.; Robak, P. Current status of older and new purine nucleoside analogues in the treatment of lymphoproliferative diseases. Molecules 2009, 14, 1183-1226.
10. Hocek, M.; Holy, A.; Votruba, I.; Dvorakova, H. Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides: application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids. J. Med. Chem. 2000, 43, 1817-1825. (Pubitemid 30305014)
11. Pilli, R.A.; Robello, L.G. Palladium-catalyzed double cross-coupling of E-vinylic dibromides with PhZnCl and the synthesis of tamoxifen. J. Braz. Chem. Soc. 2004, 15, 1-11.
12. Phadtare, S.; Kessel, D.; Corbett, T.H.; Renis, H.E.; Court, B.A.; Zemlicka, J. Unsaturated and Carbocyclic Nucleoside Analogues: Synthesis, Antitumor, and Antiviral Activity. J. Med. Chem. 1991, 34, 421-429.
13. Hua, M.; Korkowski, P.M.; Vince, R. Synthesis and biological evaluation of acyclic neplanocin analogs. J. Med. Chem. 1987, 30,198-200. (Pubitemid 17221639)
14. Miyaura, N.; Suzuki, A. Palladium catalyzed cross-coupling reactions of organo-boron compounds. Chem. Rev. 1995, 95, 2457-2483.
15. Yeom, C.-E.; Shin, Y.J.; Kim, B.M. Acetyl Chloride-Mediated Mild and Chemoselective Attachment and Removal of Tetrahydropyranyl (THP) Group. Bull. Kor. Chem. Soc. 2007, 28, 103-107. (Pubitemid 46168783)
16. Grever, M.R.; Schepartz, S.A.; Chabner, B.A. The National Cancer. Institute: Cancer Drug Discovery and. Development Program. Semin. Oncol. 1992, 19, 622-638. (Pubitemid 23004840)
17. Boyd, M.R.; Shomaker, R.H.; McLemore, T.L. New Drug Development In Thoracic Oncology; Ruckdeschel, J.C., Weisenburger, T.H., Eds.; Saunders: Philadelphia, PA, USA, 1989; pp. 711-721.
18. Boyd, M.R.; Paul, K.D. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug. Dev. Res.1995, 34, 91-109.
19. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolf, A.; et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Nat. Cancer Inst. 1991, 83, 757-766.
20. Skehan, P.; Storing, R.; Scudiero, D. New coloriroetric cytotoxicity assay for anticancer-drug screening. J. Nat. Cancer Inst. 1990, 82, 1107-1112. (Pubitemid 20213250)
21. Gray, G.D.; Wickstorm, E. Evaluation of anchorage-independent proliferation in tumorigenic cellsusing the redox dye alamar blue. Biotechniques 1996, 21, 780-782. (Pubitemid 26380338)