Synthesis, in vitro antimicrobial and in vivo antitumor evaluation of novel pyrimidoquinolines and its nucleoside derivatives

European Journal of Medicinal Chemistry

Volumn 46, Issue 1, 2011, Pages 21-30

  Abbas, Hebat Allah S ^a   Hafez, Hend N ^a   El Gazzar, Abdel Rahman B A ^b  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b AL IMAM MOHAMMAD IBN SAUD ISLAMIC UNIVERSITY IMSIU   (Saudi Arabia)

Author keywords

Antimicrobial and antitumor activities; Pyrimidoquinoline; Tetrazolo ; Triazolopyrimidoquinoline and its N nucleoside

Indexed keywords

1 AMINO 2 PHENYL 5 (4 NITROPHENYL) 8 DIMETHYL 5,6,7,8,9,10 HEXAHYDRO[1,3]IMIDAZOLO[3',2':1,2]PYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 1 AMINO 2,8,8 TRIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROIMIDAZOLO[3',2':1,2]PYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 2 [N' (4 CHLOROPHENYLMETHYLEN)HYDRAZONE] 8,8 DIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 2 [N' (4 METHOXYPHENYLMETHYLEN)HYDRAZONE] 8,8 DIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 2 [N' (PHENYLMETHYLEN)HYDRAZONE] 8,8 DIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 2 AMINO 8,8 DIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 2 HYDRAZINO 8,8 DIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TERAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 2 HYDRAZINO 8,8 DIMETHYL 5 PHENYL 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 2,6 BIS[8,8 DIMETHYL 5 (4 NITROPHENYL) 3,4,5,6,7,8,9,10 OCTAHYDROPYRIMIDO[4,5 B]QUINOLINE 2 YL AMINO 4,6 DIONE]PYRROLO[3,4 F]ISOINDOLE 1,3,5,7 TETRAONE; 3 (4 CHLOROPHENYL) 8,8 DIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDRO[1,2,3]TRIAZOLO[4',3':1,2]PYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 3,8,8 TRIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 3,8,8 TRIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDRO[1,2,4]TRIAZOLO[4',3':1,2] PYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 5 (4 CHLOROPHENYL) 2 HYDRAZINO 8,8 DIMETHYL 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 6 CHLORO 3,8,8 TRIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 6 CHLORO 8,8 DIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 8,8 DIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 10 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 8,8 DIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 10 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 8,8 DIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 10 (2',3',5' TRI O ACETYL BETA DEXTRO ARABINOFURANOSYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 8,8 DIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 10 (BETA DEXTRO ARABINOPYRANOSYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 8,8 DIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 10 (BETA DEXTRO GALACTOPYRANOSYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 8,8 DIMETHYL 2 METHYLTHIO 5 (4 NITROPHENYL) 10 (BETA DEXTRO GLUCOPYRANOSYL) 5,8,9,10 TETRAHYDROPYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 8,8 DIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDRO[1,2,4]TRIAZOLO[4',3':1,2]PYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; 8,8 DIMETHYL 5 (4 NITROPHENYL) 5,8,9,10 TETRAHYDROTETRAZOLO[4',3':1,2]PYRIMIDO[4,5 B]QUINOLINE 4,6 DIONE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; CISPLATIN; NALIDIXIC ACID; NUCLEOSIDE DERIVATIVE; NYSTATIN; PYRIMIDOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACUTE TOXICITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANCER INHIBITION; CANDIDA ALBICANS; CANDIDA GLABRATA; CONTROLLED STUDY; DRUG ACETYLATION; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LACTOCOCCUS LACTIS; MALE; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PSEUDOMONAS AERUGINOSA;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; BACTERIA; DRUG EVALUATION, PRECLINICAL; FUNGI; HELA CELLS; HEP G2 CELLS; HUMANS; MALE; MICE; MICROBIAL SENSITIVITY TESTS; NUCLEOSIDES; QUINOLINES;

EID: 78650510351     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.09.071     Document Type: Article

References (47)

1. M. Balasubramanian, and J.G. Keay A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II vol. 5 1996 Pergamon: Oxford 245 300 (Chapter 5.06)
2. K. Mogilaiah, D.S. Chowdary, and R.B. Rao Indian J. Chem. 40B 2001 43
3. Y.-L. Chen, K.-C. Fang, J.-Y. Sheu, S.-L. Hsu, and C.-C. Tzeng J. Med. Chem. 44 2001 2374 2377
4. R.D. Larsen, E.G. Corley, A.O. King, J.D. Carrol, P. Davis, T.R. Verhoeven, P.J. Reider, M. Labelle, J.Y. Gauthier, Y.B. Xiang, and R.J. Zamboni J. Org. Chem. 61 1996 3398 3405
5. P.L. Ferrarini, C. Mori, M. Badawneh, V. Calderone, R. Greco, C. Manera, A. Martinelli, P. Nieri, and G. Saccomanni Eur. J. Med. Chem. 35 2000 815 826
6. G. Roma, M.D. Braccio, G. Grossi, F. Mattioli, and M. Ghia Eur. J. Med. Chem. 35 2000 1021 1035
7. G.Y. Lesher, E.J. Froelich, M.D. Gruett, J.H. Bailey, and R.P. Brundage J. Med. Pharm. Chem. 5 1962 1063 1065
8. A. Kleeman, and J. Engel Pharmaceutical Substances fourth ed. 2001 Thieme New York, NY pp. 1466-1467
9. H. Koga, A. Itoh, S. Murayama, S. Suzue, and T. Irikura J. Med. Chem. 23 1980 1358 1363
10. A. Kleeman, and J. Engel Pharmaceutical Substances fourth ed. 2001 Thieme New York, NY pp. 482-483
11. K. Grohe, and H. Heitzer Liebigs Ann. Chem. 1987 29 37
12. A. Kleeman, and J. Engel Pharmaceutical Substances fourth ed. 2001 Thieme New York, NY pp. 1479-1480
13. O.A. El-Sayed, B.A. Al-Bassam, and M.E. Hussein Arch. Pharm. 335 2002 403
14. U.S. Pathak, S. Singh, and J. Padh Indian J. Chem. Sect. B 30 1991 618
15. C.J. Shishoo, M.B. Devani, V.S. Bhadti, K.S. Jain, I.S. Rathod, R.K. Goyal, T.P. Gandti, R.B. Patel, and S.R. Naik Arzneim. Forsch. 40 1990 567
16. M. Sugiyama, T. Sakamoto, K. Tabata, K. Endo, M. Ito, M. Kobayashi, and H. Fukumi Chem. Pharm. Bull. 37 1989 2122
17. U. Jordis, F. Sauter, and S.M. Siddiqi Vest. Slov. Kem. Drus 33 1986 217
18. V. Darias, S.S. Abdallah, M.L. Tello, L.D. Delgado, and S. Vega Arch. Pharm. 327 1994 779
19. L. Cordeu, E. Cubedo, E. Bandres, A. Rebollo, X. Saenz, H. Chozes, M. Victoria Dominquez, M. Echeverria, B. Mendivil, C. Sanmartin, J.A. Palop, M. Font, and J. Garcia-Foncillas Bioorg. Med. Chem. 15 2007 1659
20. D. Carclunescu, A.D. Lopez, E.G. Iriarte, G. Tina, G. Gomez, R. Tana, and C. Ghirvu Ann. Real Acad. Farm. 51 1985 241
21. Newberry, R.A.; Bushell, B.J. US 3,979,402 (Cl.269-302R; Co7 D227122), 07 September 1976, Br. Appl. 748, 870, 27 February 1974.
22. Chem. Abstr. 86 1977 29795z
23. M.Yu. Gavrilov, I.G. Mardanova, V.E. Kolla, and M.E. Konshin Pharmceut. Chem. J. 22 1988 554
24. P. BraJeswar, and K. Walter Carbohydr. Res. 126 1984 27
25. C.S. Kuhn, J. Lehmann, and J. Steck Tetrahedron 46 1990 3129
26. M. Blanc-Muesser, L. Vigne, H. Driguez, J. Lehmann, J. Steck, and K. Urbahns Carbohydr. Res. 224 1992 59
27. C. Appuru, H. Driguer, G. Williamson, and B. Svensson Carbohydr. Res. 227 1995 313
28. J. Defaye, J.M. Guillot, P. Biely, and M. Vrsanska Carbohydr. Res. 228 1992 47
29. K.L. Matta, R.N. Girotra, and J.J. Barlow Carbohydr. Res. 43 1975 101
30. R.L. Schnaar, and Y.C. Lee Biochemistry 14 1975 1535
31. C. Orgeret, E. Scillier, C. Gautier, J. Defaye, and H. Driguez Carbohydr. Res. 224 1992 29
32. E.S.H. El-Ashry, L.F. Awad, and A.I. Atta Tetrahedron 62 2006 2943
33. S. Scala, N. Akhmed, U.S. Rao, K. Paull, L. Lan, B. Dickslein, J. Lee, G.E.H. Elgemeie, W.D. Stein, and S.E. Bates Mol. Pharmacol. 51 1997 1024
34. A.B.A. El-Gazzar, M.A. El-Enany, and M.N. Youssif J. Bioorg. Med. Chem. 16 2008 3261
35. A.B.A. El-Gazzar, H.N. Hafez, and H.S. Abbas Eur. J. Med. Chem. 44 2009 4249
36. A.B.A. El-Gazzar, H.N. Hafez, and G.A. Nawwar Eur. J. Med. Chem. 44 2009 1427
37. A.B.A. El-Gazzar, and H.N. Hafez Bioog. Med. Chem. Lett. 19 2009 4143
38. J. Quiroga, A. Hormaza, and B. Insuasty J. Heterocycl. Chem. 35 1998 231
39. C.J. Shishoo, and K.S. Jain J. Heterocycl. Chem. 29 1992 883
40. S.M. Hussain, A.M. El-Reedy, A.M.H. Rezk, and K.H.A. Sife El-Dien J. Heterocycl. Chem. 24 1987 1605
41. A.B.A. El-Gazzar, A.E.M. Gaafar, H.N. Hafez, and A.S. Aly Phosphorous, Sulfur, Silicon, Relat. Elem. 181 2006 1859
42. Weinstein, M.J.; Nagman, G.H.; in: Antibiotics, Elsevier Scientific Publishing Company, Amsterdam, pp. 464.
43. A.L. Barry, and C. Thornsbery J.P. Lennette, Manual of Clinical Microbiology 1981 American Society for Microbiology Washington, DC 561
44. G.S. Ahluwalia, H.N. Jayaram, J.P. Plowhan, D.A. Cooney, and D.G. Johns Biochem. Pharmacol. 33 1984 1195
45. K.L. Joy, N.V. RaJeshkumar, G. Kuttan, and R. Kuttan J. Ethnopharmacol 71 2000 261
46. D.J. Prieur, D.M. Young, R.D. Davis, D.A. Cooney, E.R. Homan, R.L. Dixon, and A.M. Guarino Cancer Chemother. Rep. 4 1973 1
47. M.N. Ghosh Toxicity Studies M.N. Ghosh, Fundamentals of Experimental Pharmacology 1984 Scientific Book Agency Calcutta, India 153