Design, Molecular Modeling and Synthesis of Some New Purine-diones and Pyridopyrimidine-diones with Anticancer Activity
DOI:
https://doi.org/10.24297/jac.v13i12.6043Keywords:
olomoucine, cyclin-depenent kinase, synthesis, anticancerAbstract
An olomoucine analogues of 2-[(1-substituted)-2,6-dioxo-2,3,6,7–tetrahydro-1H-purin-8-ylsulfanyl]-N-substituted acetamide 6a-g and 7a-g, 1-substituted-8-[2-(4-substituted phenyl)-2-oxoethylsulphanyl]-3,7-dihydro-1H-purine-2,6-diones 9a-g and 10a-g, 3-(2-substituted benzyl)-6-(4-substituted phenyl)-1H-thiazolo[2,3-f]purine-2,4-dione 11a-g and 12a-g and their isosteres 3-substituted benzyl-5-methyl-7-substituted-1H-pyrido[2,3-d]pyrimidine-2,4-dione 13a-c and 14a-c were designed and synthesized. The target compounds 11a-g and 12a-g were prepared by cyclodehydration of 9a-g and 10a-g in PPA, while 13a-c and 14a-c were synthesized by condensation of 6-amino-3-(2-substituted benzyl)-1H-pyrimidine-2,4-dione 1a or 1b and the appropriate acylacetone in glacial acetic acid. Structures of the new compounds were verified on the basis of their IR, 1H NMR, MS, HRMS and elemental analyses. The newly synthesized compounds were tested for their anticancer activity and most of the tested compounds showed good to excellent inhibition activity against the tested human breast cancer cell line MCF-7 in comparison to doxorubicin as a reference drug.
KEYWORDS: olomoucine; cyclin-depenent kinase; synthesis; anticancer
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References
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4. Haesslein, J.; Jullian, N., Recent advances in cyclin-dependent kinase inhibition. Purine-based derivatives as anti-cancer agents. Roles and perspectives for the future. Curr. Top. Med. Chem. 2002, 2 (9), 1037-1050.
5. Legraverend, M.; Tunnah, P.; Noble, M.; Ducrot, P.; Ludwig, O.; Grierson, D. S.; Leost, M.; Meijer, L.; Endicott, J., Cyclin-dependent kinase inhibition by new C-2 alkynylated purine derivatives and molecular structure of a CDK2-inhibitor complex. J. Med. Chem. 2000, 43 (7), 1282-1292.
6. Azevedo, W. F.; Leclerc, S.; Meijer, L.; Havlicek, L.; Strnad, M.; Kim, S. H., Inhibition of Cyclinâ€Dependent Kinases by Purine Analogues. Eur. J. Biochem. 1997, 243 (1â€2), 518-526.
7. KryÅ¡tof, V. r.; Lenobel, R.; HavlıÌÄek, L.; Kuzma, M.; Strnad, M., Synthesis and biological activity of olomoucine II. Bioorg. Med. Chem. Lett. 2002, 12 (22), 3283-3286.
8. Weyler, S.; Hayallah, A. M.; Müller, C. E., Versatile, convenient synthesis of pyrimido[1,2,3-cd]purinediones. Tetrahedron 2003, 59 (1), 47-54.
9. Sadzuka, Y.; Sugiyama, T.; Suzuki, H.; Sawanishi, H.; Miyamoto, K.-i., Increased effects of MPDAX, a novel xanthine derivative, on antitumor activity of doxorubicin. Toxicol. Lett. 2004, 150 (3), 341-349.
10. Hayallah, A. M.; Momekov, G.; Famulok, M., Antitumor activity of some new 1,3,8-trisubstituted purine-2,6-diones and 1,3,6-trisubstituted thiazolo[2,3-f]purine-2,4-diones. Bull. Pharm. Sci., Assiut University 2008, 31, 391-399.
11. Kode, N. R.; Phadtare, S., Synthesis and cytotoxic activity of some new 2,6-substituted purines. Molecules 2011, 16 (7), 5840-5860.
12. Ashour, F. A.; Rida, S. M.; El-Hawash, S. A.; ElSemary, M. M.; Badr, M. H., Synthesis, anticancer, anti-HIV-1, and antimicrobial activity of some tricyclic triazino and triazolo[4,3-e]purine derivatives. Med. Chem. Res. 2012, 21 (7), 1107-1119.
13. Ibrahim, D. A.; Ismail, N. S., Design, synthesis and biological study of novel pyrido[2,3-d]pyrimidine as anti-proliferative CDK2 inhibitors. Eur. J. Med. Chem. 2011, 46 (12), 5825-5832.
14. Shanmugasundaram, P.; Harikrishnan, N.; Vijey Aanandini, M.; Sathish Kumar, M.; Sateesh, J., Synthesis and biological evaluation of pyrido[2,3-d]pyrimidine-carboxylate derivatives. Indian J. Chem. 2011, 50 (3), 284.
15. Gineinah, M. M.; Nasr, M. N.; Badr, S. M.; El-Husseiny, W. M., Synthesis and antitumor activity of new pyrido[2,3-d]pyrimidine derivatives. Med. Chem. Res. 2013, 22 (8), 3943-3952.
16. Hayallah, A. M., Design and synthesis of new 1,8-disubstituted purine-2,6-diones and 3,6-disubstituted thiazolo[2,3-f]purine-2,4-diones as potential antinociceptive and anti-inflammatory agents. pharmacia 2007, 54, 3-13.
17. Bilkei-Gorzo, A.; Abo-Salem, O. M.; Hayallah, A. M.; Michel, K.; Müller, C. E.; Zimmer, A., Adenosine receptor subtype-selective antagonists in inflammation and hyperalgesia. Naunyn-Schmiedeberg's Arch. Pharmacol. 2008, 377 (1), 65-76.
18. Hayallah, A. M.; Isper, S. A.; Al-Okosh, a. A. S., Design and synthesis of some new theophylline linked amides and schiff’s bases as bronchodilatros and anti-inflammatory agents. Int. Res. J. Pharm. Pharmacol. 2012, 2 (13), 323-336.
19. Hafez, H. N.; Abbas, H.-A. S.; El-Gazzar, A.-R. B., Synthesis and evaluation of analgesic, anti-inflammatory and ulcerogenic activities of some triazolo-and 2-pyrazolyl-pyrido[2,3-d]pyrimidines. Acta Pharm. 2008, 58 (4), 359-378.
20. Said, S.; Abdulla, M., Synthesis and Antiflammatory Activities of Some New Pyridopyridine, Pyridipyrimidine and Pyridopyrimidotriazine Derivatives. World Appl. Sci. J. 2010, 9, 589-599.
21. Fhid, O.; Pawlowski, M.; Filipek, B.; Horodyñska, R.; Maciag, D., Central nervous system activity of new pyrimidine-8-on[2,1-f]theophylline-9-alkylcarboxylic acids derivatives. Pol. J. Pharmacol. 2002, 54 (3), 245-254.
22. Drabczyńska, A.; Müller, C. E.; Schumacher, B.; Hinz, S.; Karolak-Wojciechowska, J.; Michalak, B.; Pękala, E.; Kieć-Kononowicz, K., Tricyclic oxazolo[2,3-f]purinediones: potency as adenosine receptor ligands and anticonvulsants. Bioorg. Med. Chem. 2004, 12 (18), 4895-4908.
23. Kolaczkowski, M.; Zajdel, P.; Fhid, O.; Duszyñska, B.; Tatarczyñska, E.; Pawlowski, M., Synthesis and 5-HT1A/5-HT2A activity of some butyl analogues in the group of phenylpiperazine alkyl pyrimido[2,1-f]theophyllines. Pharmacological reports 2005, 57 (229), 229-235.
24. Hayallah, A. M.; Elgaher, W. A.; Salem, O. I.; Alim, A. A. M. A., Design and synthesis of some new theophylline derivatives with bronchodilator and antibacterial activities. Arch. Pharm. Res. 2011, 34 (1), 3-21.
25. Hayallah, A. K.; Talhouni, A. A.; Alim, A. A. M. A., Design and synthesis of new 8-anilide theophylline derivatives as bronchodilators and antibacterial agents. Arch. Pharm. Res. 2012, 35 (8), 1355-1368.
26. Abdel-Aziem, A.; El-Gendy, M. S.; Abdelhamid, A. O., Synthesis and antimicrobial activities of pyrido[2,3-d]pyrimidine, pyridotriazolopyrimidine, triazolopyrimidine, and pyrido[2,3-d:6,5-d']dipyrimidine derivatives. Eur. J. Chem. 2012, 3 (4), 455â€460.
27. Foley, L. H.; Wang, P.; Dunten, P.; Ramsey, G.; Gubler, M.-L.; Wertheimer, S. J., X-ray Structures of two xanthine inhibitors bound to PEPCK and N-3 modifications of substituted 1,8-Dibenzylxanthines. Bioorg. Med. Chem. Lett. 2003, 13 (21), 3871-3874.
28. Foley, L. H.; Wang, P.; Dunten, P.; Ramsey, G.; Gubler, M.-L.; Wertheimer, S. J., Modified 3-alkyl-1,8-dibenzylxanthines as GTP-competitive inhibitors of phosphoenolpyruvate carboxykinase. Bioorg. Med. Chem. Lett. 2003, 13 (20), 3607-3610.
29. Abou-Ghadir, O. F.; Hayallah, A. M.; Abdel-Moty, S. G.; Hussein, M. A., Design and synthesis of some new purine-dione derivatives of potential anti-inflammatory activity. Der Pharma Chemica 2014, 6 (2), 199-211.
30. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82 (13), 1107-1112.
31. Smellie, A.; Teig, S. L.; Towbin, P., Poling: promoting conformational variation. J. Comput. Chem. 1995, 16 (2), 171-187.
32. Hayallah, A. M.; Famulok, M., Synthesis of new 1,3,8-trisubstitutedpurine-2,6-diones and 1,3,6-trisubstituted thiazolo[2,3-f]purine-2,4-diones. Heterocycles 2007, 74, 369-382.
33. Hayallah, A. M.; Abdel-Hamid, M. K., Design, convenient synthesis and molecular modeling of new pyrido[2,3-d]pyrimidine-1,4-dione derivatives as potential anti-inflammatory agents. . Der Pharma Chemica 2014, 6 (5), 45-57.
34. Catalyst, 4.11 User Guide, Accelrys Inc., San Diego, CA 92121 , USA. 2005.
35. Kurogi, Y.; Guner, O. F., Pharmacophore modeling and three-dimensional database searching for drug design using catalyst. Curr. Med. Chem. 2001, 8 (9), 1035-1055.
36. Li, H.; Sutter, J.; Hoffmann, R., HypoGen: an automated system for generating 3D predictive pharmacophore models. Pharmacophore Perception, Development, and Use in Drug Design 2000, 2, 171.
37. Fischer, P. M.; Lane, D. P., Inhibitors of cyclin-dependent kinases as anti-cancer therapeutics. Curr. Med. Chem. 2000, 7 (12), 1213-1245.
38. Drees, M.; Dengler, W. A.; Roth, T.; Labonte, H.; Mayo, J.; Malspeis, L.; Grever, M.; Sausville, E. A.; Fiebig, H. H., Flavopiridol (L86-8275): selective antitumor activity in vitro and activity in vivo for prostate carcinoma cells. Clin. Cancer Res. 1997, 3 (2), 273-279.
39. Goodnow Jr, R. A.; Gillespie, P., 1 Hit and Lead Identification: Efficient Practices for Drug Discovery. Prog. Med. Chem. 2007, 45, 1-62.
40. Zaharevitz, D. W.; Gussio, R.; Leost, M.; Senderowicz, A. M.; Lahusen, T.; Kunick, C.; Meijer, L.; Sausville, E. A., Discovery and initial characterization of the paullones, a novel class of small-molecule inhibitors of cyclin-dependent kinases. Cancer Res. 1999, 59 (11), 2566-2569.
41. Schultz, C.; Link, A.; Leost, M.; Zaharevitz, D. W.; Gussio, R.; Sausville, E. A.; Meijer, L.; Kunick, C., Paullones, a series of cyclin-dependent kinase inhibitors: synthesis, evaluation of CDK1/cyclin B inhibition, and in vitro antitumor activity. J. Med. Chem. 1999, 42 (15), 2909-2919.
42. Meijer, L.; Raymond, E., Roscovitine and other purines as kinase inhibitors. From starfish oocytes to clinical trials. Acc. Chem. Res. 2003, 36 (6), 417-425.
43. Chang, Y.-T.; Gray, N. S.; Rosania, G. R.; Sutherlin, D. P.; Kwon, S.; Norman, T. C.; Sarohia, R.; Leost, M.; Meijer, L.; Schultz, P. G., Synthesis and application of functionally diverse 2, 6, 9-trisubstituted purine libraries as CDK inhibitors. Chem. Biol. 1999, 6 (6), 361-375.
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2017-07-10
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Hayallah, A. M. (2017). Design, Molecular Modeling and Synthesis of Some New Purine-diones and Pyridopyrimidine-diones with Anticancer Activity. JOURNAL OF ADVANCES IN CHEMISTRY, 13(2), 5959–5976. https://doi.org/10.24297/jac.v13i12.6043
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