Microwave-assisted synthesis of antimicrobial dihydropyridines and tetrahydropyrimidin-2-ones: Novel compounds against aspergillosis

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 4, 2006, Pages 973-981

  Chhillar, Anil K ^a   Arya, Pragya ^b   Mukherjee, Chandrani ^b   Kumar, Pankaj ^b,c   Yadav, Yogesh ^b,c   Sharma, Ajendra K ^b,d   Yadav, Vibha ^a   Gupta, Jyotsana ^a   Dabur, Rajesh ^a   Jha, Hirday N ^c   Watterson, Arthur C ^d   Parmar, Virinder S ^b,d   Prasad, Ashok K ^b   Sharma, Gainda L ^a  

^a CSIR INSTITUTE OF GENOMICS AND INTEGRATIVE BIOLOGY   (India)

^b UNIVERSITY OF DELHI   (India)

^c MMH College   (India)

^d University of Massachusetts Lowell   (United States)

Author keywords

4 Aryl 1,2,3,4 tetrahydropyrimidinone; 4 Aryl 1,4 dihydropyridine; Antifungal agent; Aspergillosis; Microwave assisted reaction

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENT; DIETHYL 4 ( 2 BROMOPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIETHYL 4 (3 CHLOROPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIETHYL 4 (3 HYDROXY 4 METHOXYPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIETHYL 4 (3 HYDROXYPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIETHYL 4 (4 BROMOPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIETHYL 4 (4 HYDROXY 3 METHOXYPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIETHYL 4 (4 METHOXYPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIETHYL 4 [3 (3 CHLORO 2 HYDROXYPROPOXY)PHENYL] 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIMETHYL 4 (3 HYDROXYPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; DIMETHYL 4 (4 METHOXYPHENYL) 2,6 DIMETHYL 1,4 DIHYDROPYRIDIN 3,5 DICARBOXYLATE; ETHYL 4 (4 ACETOXYPHENYL) 6 METHYL 1,2,3,4 TETRAHYDROPYRIMIDIN 2 ONE 5 CARBOXYLATE; ETHYL 4 (4 EPOXYMETHOXYPHENYL) 6 METHYL 1,2,3,4 TETRAHYDROPYRIMIDIN 2 ONE 5 CARBOXYLATE; ETHYL 4 (4 HYDROXYPHENYL) 6 METHYL 1,2,3,4 TETRAHYDROPYRIMIDIN 2 ONE 5 CARBOXYLATE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLOSIS; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ERYTHROCYTE; FUNGUS; HEMOLYSIS; HUMAN; HUMAN CELL; NONHUMAN; PATHOGENICITY; SPORE GERMINATION;

ANTIFUNGAL AGENTS; ASPERGILLOSIS; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; DIHYDROPYRIDINES; ERYTHROCYTES; HEMOLYSIS; HUMANS; HYDROXYLATION; MICROBIAL SENSITIVITY TESTS; MICROWAVES; MOLECULAR STRUCTURE; PYRIMIDINES;

ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; FUNGI;

EID: 30344485986     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.09.014     Document Type: Article

References (45)

1. M.M. McNeil, S.L. Nash, R.A. Hajjeh, M.A. Phelan, L.A. Conn, B.D. Plikaytis, and D.W. Warnock Clin. Infect. Dis. 33 2001 641
2. C. Beck-Sauge, and W.R. Jarvis J. Infect. Dis. 67 1993 1247
3. S.N. Banerjee, T.G. Emori, D.H. Culver, R.P. Gaynes, W.R. Jarvis, T. Horan, J.R. Edwards, J. Tolson, T. Henderson, and W.J. Martones Am. J. Med. 86 1989 668
4. R. Saral Rev. Infect. Dis. 13 1991 487
5. J.D. Meyer Semin. Oncol. 17 1990 10
6. J.R. Graybill Clin. Infect. Dis. 14 1992 170
7. J.E. Peacock, D.A. Herrington, and J.M. Cruz Infect. Dis. Clin. Pract. 2 1993 81
8. M.A. Fischer, G.H. Talbot, G. Maislin, B.P. Mackeon, K.P. Tynan, and B.L. Setrom Am. J. Med. 87 1989 547
9. K.L. Goa, and L.B. Barradell Drugs 50 1995 658
10. M.O. Gearhart Ann. Pharmacother. 28 1994 1177
11. J.D. Lazar, and K.D. Wilkner Rev. Infect. Dis. 12 1990 327
12. R. Guinet, J. Chanas, A. Gullier, G. Bonnefoy, and P. Ambroiise-Thomas J. Clin. Microbiol. 18 1983 443
13. M.A. Ghannoum, and L.B. Rice Clin. Microbiol. Rev. 12 1999 501
14. M. Cuenca-Estrella, E. Mellado, T.M. Diaz-Guerra, A. Monzon, and J.L. Tudela J. Antimicrob. Chemother. 46 2000 475
15. R.A. Janis, and D.J. Triggle J. Med. Chem. 26 1983 775
16. R.H. Bocker, and E.P. Guengerich J. Med. Chem. 29 1986 1596
17. M.F. Gordeev, D.V. Patel, and E.M. Gordon J. Org. Chem. 61 1996 924
18. C.E. Sunkel, M.F. Fau de Casa-Juana, L. Santos, A.G. Garcia, C.R. Artalijero, M. Villarroya, M.A. Gonzalez-Morales, M.G. Lopez, J. Cillero, S. Alonso, and J.G. Priego J. Med. Chem. 35 1992 2407
19. D. Vo, W.C. Matowe, M. Ramesh, N. Iqbal, M.W. Wolowyk, S.E. Howlett, and E.E.J. Knaus J. Med. Chem. 38 1995 2851
20. V. Klusa Drugs Fut. 20 1995 135
21. T. Godfraind, R. Miller, and M. Wibo Pharmacol. Rev. 38 1986 321
22. A. Sausins, and G. Duburs Heterocycles 27 1988 269
23. A.C. Gaudio, A. Korolkovas, and Y. Takahata J. Pharm. Sci. 83 1994 1110
24. K. Cooper, M.J. Fray, M.J. Parry, K. Richardson, and J. Steele J. Med. Chem. 35 1992 3115
25. J.S. Yadav, V.S. Reddy, and P.T. Reddy Synth. Commun. 31 2001 425
26. K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg, and B.C. O'Reilly J. Med. Chem. 34 1991 806
27. A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C. Debrosse, S. Mai, A. Trunch, D.J. Faulkner, B. Carte, A.L. Breen, R.P. Hertzberg, R.K. Johnson, J.W. Westley, and B.C. Potts J. Org. Chem. 60 1995 1182
28. B.B. Sinder, and Z. Shi J. Org. Chem. 58 1983 3828 and references cited therein
29. L.E. Overman, M.H. Rabinowitz, and P.A. Renhowe J. Am. Chem. Soc. 117 1995 2675 and references cited therein
30. C.O. Kappe, and M.F. Fabian Tetrahedron 53 1997 2803
31. E.W. Hurst, and R. Hull J. Med. Pharm. Chem. 3 1961 215
32. G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O'Reilly, J. Schwartz, and M.F. Malley J. Med. Chem. 35 1992 3254
33. H. Cho, M. Ueda, K. Shima, A. Mizuno, M. Hayashimatsu, Y. Ohnaka, M. Hamaguchi, K. Aisaka, T. Hidaka, M. Kawai, M. Takeda, T. Ishihara, K. Funahashi, F. Satoh, M. Morita, and T. Noguchi J. Med. Chem. 32 1989 2399
34. L.E. Hinkel, and W.R. Madel J. Chem. Soc. 1929 750
35. Semeraro C.; Micheli D.; Pieraccioli D.; Gaviraghi G.; Borthwick AD. USP 4,946,851, 1990.
36. R.A. Dommisse, J.A. Lepoivre, and F.C. Alderweireldt Bull. Chem. Soc. Belgium 86 1977 267
37. Mahendroo, N.; Khajuria, R. K.; Bedi, K. L.; Dhar, K. L.; Kapoor, V. K. WO 03/099790 A1, 2003.
38. A.J. Berson, and E. Brown J. Am. Chem. Soc. 77 1955 444
39. B.M. Khadilkar, and A.A. Chitnavis Indian J. Chem. 34B 1995 652
40. T. Shu-Jiang, Z. Jian-Feng, C. Pei-Jun, W. Hai, and F. Jun-Cai Synth. Commun. 32 2002 147
41. R. Dabur, and G.L. Sharma J. Ethnopharmacol. 80 2002 193
42. A. Riffel, L.F. Medina, V. Stefani, R.C. Santos, D. Bizani, and A. Brandelli Brazilian J. Med. Biol. Res. 35 2002 811
43. R. Iijima, S. Kurata, and S. Natori J. Biol. Chem. 268 1993 12055
44. C. Latoud, F. Peypoux, G. Michael, R. Genat, and J. Morgat Biochem. Biophys. Acta 35 1986 526
45. B. Cybulska, I. Gudomska, J. Mazerski, J. Grzybowska, E. Borowski, M. Cheron, and J. Bolard Acta. Biochim. Pol. 47 2000 121