Novel pyrimidinone derivatives: Synthesis, antitumor and antimicrobial evaluation

Chemical and Pharmaceutical Bulletin

Volumn 60, Issue 4, 2012, Pages 521-530

  Taher, Azza ^a   Helwa, Amira Atef ^b  

^a CAIRO UNIVERSITY   (Egypt)

^b Misr University for Science and Technology   (Egypt)

Author keywords

Antimicrobial activity; Antitumor activity; Pyrimidinone; Synthesis

Indexed keywords

2 (ETHYLTHIO) 4 (4 FLUOROPHENYL) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (3 BROMOPHENYL) 1 METHYL 2 (METHYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (3 BROMOPHENYL) 2 (ISOPROPYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (3 BROMOPHENYL) 2 (METHYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (4 BROMOPHENYL) 1 ETHYL 2 (ETHYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (4 BROMOPHENYL) 2 (ETHYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (4 BROMOPHENYL) 2 (ISOPROPYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (4 BROMOPHENYL) 2 (METHYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (4 CHLOROPHENYL) 2 (ISOPROPYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 4 (4 FLUOROPHENYL) 2 (ISOPROPYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 5 (4 BROMOPHENYL) 7 OXO 1,7 DIHYDRO[1,2,4]TRIAZOLO[4,3 A]PYRIMIDINE 6 CARBONITRILE; 5 (4 CHLOROPHENYL) 7 OXO 1,7 DIHYDRO[1,2,4]TRIAZOLO[4,3 A]PYRIMIDINE 6 CARBONITRILE; 5 (4 FLUOROPHENYL) 7 OXO 1,7 DIHYDRO[1,2,4]TRIAZOLO[4,3 A]PYRIMIDINE 6 CARBONITRILE; 6 (4 BROMOPHENYL) 3,8 DIOXO 1,3,4,8 TETRAHYDRO 2H PYRIMIDO[2,1 C][1,2,4]TRIAZINE 7 CARBONITRILE; 6 (4 CHLOROPHENYL) 3,8 DIOXO 1,3,4,8 TETRAHYDRO 2H PYRIMIDO[2,1 C][1,2,4]TRIAZINE 7 CARBONITRILE; 6 (4 FLUOROPHENYL) 2 HYDRAZINYL 4 OXO 1,4 DIHYDROPYRIMIDINE 5 CARBONITRILE; 6 (4 FLUOROPHENYL) 3,8 DIOXO 1,3,4,8 TETRAHYDRO 2H PYRIMIDO[2,1 C][1,2,4]TRIAZINE 7 CARBONITRILE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; FLUCONAZOLE; FORMIC ACID; PYRIMIDINONE DERIVATIVE; TOBRAMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANDIDA ALBICANS; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYCLIZATION; DRUG SCREENING; DRUG SYNTHESIS; ENTEROBACTER AEROGENES; FEMALE; HUMAN; HUMAN CELL; HYDRAZINOLYSIS; KLEBSIELLA; MALE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SALMONELLA; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; CANDIDA ALBICANS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICROBIAL SENSITIVITY TESTS; PYRIMIDINONES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84859463510     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.60.521     Document Type: Article

References (35)

1. Rashad A. E., Mahmoud A. E., Ali M. M., Eur. J. Med. Chem., 46, 1019-1026 (2011).
2. Hafez H. N., El-Gazzar A. R., Bioorg. Med. Chem. Lett., 19, 4143-4147 (2009).
3. Large J. M., Torr J. E., Raynaud F. I., Clarke P. A., Hayes A., Stefano F., Urban F., Shuttleworth S. J., Saghir N., Sheldrake P., Workman P., McDonald E., Bioorg. Med. Chem., 19, 836-851 (2011).
4. Tangeda S. J., Garlapati A., Eur. J. Med. Chem., 45, 1453-1458 (2010).
5. Kraljević T. G., Krištafor S., Šuman L., Kralj M., Ametamey S. M., Cetina M., Raić-Malić S., Bioorg. Med. Chem., 18, 2704-2712 (2010).
6. Callery P., Gannett P., "Foye's Principles of Medicinal Chemistry,"5th ed. Lippincott Williams & Wilkins, Philadelphia, 2002, pp. 934-935.
7. Jain K. S., Chitre T. S., Miniyar P. B., Kathiravan M. K., Bendre V. S., Veer V. S., Shahane S. R., Shishoo C. J., Current Sci., 90(6), 793-803 (2006).
8. Sawyer R. C., Stolfi R. L., Martin D. S., Balis M. E., Biochem. Pharmacol., 38, 2305-2311 (1989).
9. Ghoshal K., Jacob S. T., Biochem. Pharmacol., 53, 1569-1575 (1997).
10. Abdel-Mohsen H. T., Ragab F. A., Ramla M. M., El Diwani H. I., Eur. J. Med. Chem., 45, 2336-2344 (2010).
11. El-Nassan H. B., Eur. J. Med. Chem., 46, 2031-2036 (2011).
12. Prachayasittikul S., Worachartcheewan A., Nantasenamat C., Chinworrungsee M., Sornsongkhram N., Ruchirawat S., Prachayasittikul V., Eur. J. Med. Chem., 46, 738-742 (2011).
13. Amr A. E., World J. Chem, 4(2), 201-206 (2009).
14. Habib N. S., Soliman R., El-Tombary A. A., El-Hawash S. A., Shaaban O. G., Arch. Pharm. Res., 30, 1511-1520 (2007).
15. Said M., Abouzid K. H., Mouneer A., Ahmedy A., Osman A. M., Arch. Pharm. Res., 27, 471-477 (2004).
16. Rose Y., Ciblat S., Reddy R., Belley A. C., Dietrich E., Lehoux D., McKay G. A., Poirier H., Far A. R., Delorme D., Bioorg. Med. Chem. Lett., 16, 891-896 (2006).
17. Kambe S., Saito K., Kishi H., Synthesis, 1979, 287-289 (1979).
18. Ram V. J., Goel A., Nath M., Srivastava P., Bioorg. Med. Chem. Lett., 4, 2653-2656 (1994).
19. Ram V. J., J. Prakt. Chem., 331, 893-905 (1989).
20. Ram V. J., Vanden Berghe D. A., Vlietinck A. J., Liebigs Ann. Chem., 1987, 797-801 (1987).
21. Ram V. J., Vanden Berghe D. A., Vlietinck A. J., J. Heterocyclic Chem., 21, 1307-1312 (1984).
22. Attaby F. A., Eldin S. M., Naturforsch, 54b, 788-798 (1999).
23. Attaby F. A., Eldin S. M., Hanafi E. A., Arch. Pharm. Res., 20, 620-628 (1997).
24. Taher A., Raafat M., Bull. Fac. Pharm. Cairo Univ., 43, 43-55 (2005).
25. Grever M. R., Schepartz S. A., Chabner B. A., Semin. Oncol., 19, 622-638 (1992).
26. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A., Gray-Goodrich M., Campbell H., Mayo J., Boyd M., J. Natl. Cancer Inst., 83, 757-766 (1991).
27. Boyd M. R., Paull K. D., Drug Der. Res., 34, 91-109 (1995).
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., 82, 1107-1112 (1990).
29. Wiart C., Evid. Based Complement. Alternat. Med., 4, 299 (2007).
30. Andrews J., J. Antimicrob. Chemother., 48 (Suppl. S1), 5-16 (2001).
31. Williams D. A., Lemke T. L., "Foye's Principles of Medicinal Chemistry," 5th ed., Lippincott Williams & Wilkins, 2002, p. 48.
32. Bello C., Dal Bello G., Cea M., Nahimana A., Aubry D., Garuti A., Motta G., Moran E., Fruscione F., Pronzato P., Grossi F., Patrone F., Ballestrero A., Dupuis M., Sordat B., Zimmermann K., Loretan J., Wartmann M., Duchosal M. A., Nencioni A., Vogel P., Bioorg. Med. Chem., 19, 7720-7727 (2011).
33. Balzarini J., Orzeszko B., Maurin J. K., Orzeszko A., Eur. J. Med. Chem., 42, 993-1003 (2007).
34. Yeh V. S., Kurukulasuriya R., Madar D., Patel J. R., Fung S., Monzon K., Chiou W., Wang J., Jacobson P., Sham H. L., Link J. T., Bioorg. Med. Chem. Lett., 16, 5408-5413 (2006).
35. Rho H. S., Baek H. S., Ahn S. M., Yoo J. W., Kim D. H., Kim H. G., Bioorg. Med. Chem. Lett., 19, 1532-1533 (2009).