Synthesis, antimicrobial, and mosquito larvicidal activity of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6, 10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 20, 2010, Pages 6052-6055

  Rajanarendar, E ^a   Reddy, M Nagi ^a   Murthy, K Rama ^a   Reddy, K Govardhan ^a   Raju, S ^a   Srinivas, M ^a   Praveen, B ^b   Rao, M Srinivasa ^b  

^a KAKATIYA UNIVERSITY   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Antibacterial activity; Antifungal activity; Biginelli reaction; Isoxazolyl pyrimidoquinolines; Mosquito larvicidal test

Indexed keywords

1 ARYL 4 METHYL 3,6 BIS (5 METHYLISOXAZOL 3 YL) 2 THIOXO 2,3,6,10B TETRAHYDRO 1H PYRIMIDO[5,4 C]QUINOLIN 5 ONE; ACETOACETIC ACID; ALDEHYDE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ISOXAZOLE; LARVICIDAL AGENT; THIOUREA; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACILLUS SPHAERICUS; BACILLUS SUBTILIS; BACTERIAL STRAIN; BIGINELLI REACTION; CHROMOBACTERIUM VIOLACEUM; CONTROLLED STUDY; CULEX QUINQUEFASCIATUS; CURVULARIA LUNATA; CYCLIZATION; DRUG SYNTHESIS; FUNGAL STRAIN; FUSARIUM MONILIFORME; KLEBSIELLA AEROGENES; LARVA; NONHUMAN; ONE POT SYNTHESIS; PSEUDOMONAS AERUGINOSA; RHIZOPUS ORYZAE; STAPHYLOCOCCUS AUREUS;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS; ANTIFUNGAL AGENTS; BACTERIA; BACTERIAL INFECTIONS; CULEX; CULICIDAE; FUNGI; HUMANS; ISOXAZOLES; LARVA; MICROBIAL SENSITIVITY TESTS; MYCOSES; PYRIMIDINES; QUINOLONES;

BACTERIA (MICROORGANISMS); CULEX PIPIENS QUINQUEFASCIATUS;

EID: 77956900492     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.060     Document Type: Article

References (33)

1. K. Coleman Drug Discov. Today Ther. Strateg. 1 2004 455
2. E. Nakayama, M. Miyanchi, K. Fugimoto, and J. Idle J. Antibiot. 43 1990 1122
3. P.B. Reddy, S.M. Reddy, E. Rajanarendar, and A.K. Murthy Indian Phytopathol. 37 1984 369
4. R.P. Clausen, E.K. Moltzen, J. Perregaard, S.M. Lenz, C. Sanchez, E. Falch, B. Frolund, T. Bolvig, A. Sarup, O.M. Larsson, A. Schousboe, and P. Krogsgaard-Larsen Bioorg. Med. Chem. 3 2005 895
5. H. Kano, I. Adachi, R. Kido, and K. Hirose J. Med. Chem. 10 1967 411
6. J. Getal Antibiotics 28 1975 91
7. G.G. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, J.D. Dimarco, J.Z. Gougoutas, A. Hedberg, M.F. Malley, J.P. McCarthy, R. Zhang, and S. Moreland J. Med. Chem. 38 1995 119
8. S. Noll, M. Kralj, L. Suman, H. Stephan, and I. Piantanida Eur. J. Med. Chem. 44 2009 1172
9. H.I. Ali, N. Ashida, and T. Nagamatsu Bioorg. Med. Chem. 15 2007 6336
10. P.G. Baraldi, M.G. Pavani, M. Nunez, P. Brigidi, B. Vitali, R. Gambari, and R. Romagnoli Bioorg. Med. Chem. 10 2002 449
11. S.M. Sondhi, M. Johar, S. Rajvanshi, S.G. Dastidar, R. Shukla, R. Raghubir, and J.W. Lown Aust. J. Chem. 54 2001 69
12. L.B. Narayana, R.R.A. Rao, and S.P. Rao Eur. J. Med. Chem. 44 2009 1369
13. G. Mangalagiu, M. Ungnreanu, G. Grosu, I. Mangalagiu, and M. Petrovanu Ann. Pharm. Fr. 59 2001 139
14. M.T. Chhabria, and M.H. Jani Eur. J. Med. Chem. 44 2009 3837
15. R.C. Elderfield, and E.F. LeVon J. Org. Chem. 25 1960 1576
16. R. Musiol, J. Jampilek, V. Buchta, L. Silva, H. Niedbala, B. Podeszwa, A. Palka, K. Majerz-Maniecka, B. Oleksyn, and J. Polanksi Bioorg. Med. Chem. 14 2006 3592
17. C. Benard, F. Zouhiri, M. Normand-Bayle, M. Danet, D. Desmaele, H. Leh, J.-F. Mouscadet, G. Mbemba, C.-M. Thomas, S. Bonnenfant, M. Le Bret, and J. d'Angelo Bioorg. Med. Chem. Lett. 14 2004 2473
18. P. Garrouste, M. Pawlowski, T. Tonnaire, S. Sicsic, P. Dumy, E. De Rosny, M. Reboud-Ravanx, P. Fulcrand, and J. Martinez Eur. J. Med. Chem. 33 1998 423
19. J. Desrivot, C. Herrenknecht, G. Ponchel, N. Garbi, E. Prina, A. Fournet, C. Bories, B. Figadere, R. Hocquemiller, and P.M. Loiseau Biomed. Pharmacother. 61 2007 441
20. A. Borioni, C. Mustazza, I. Sestili, M. Sbraccia, L. Turchetto, and M.F. Del Gindice Arch Pharm. 340 2007 17
21. A. Sprecher, M. Gerspacher, A. Beck, S. Kinmel, H. Wiestner, G.P. Anderson, U. Niederhauser, N. Subramanian, and M.A. Bray Bioorg. Med. Chem. Lett. 8 1998 965
22. S. Manohar, S.I. Khan, and D.S. Rawat Bioorg. Med. Chem. Lett. 20 2010 322
23. E. Rajanarendar, G. Mohan, P. Ramesh, and D. Karunakar Tetrahedron Lett. 47 2006 4957
24. E. Rajanarendar, G. Mohan, P. Ramesh, and M. Srinivas J. Heterocycl. Chem. 44 2007 215
25. E. Rajanarendar, P. Ramesh, E. Kalyan Rao, G. Mohan, and M. Srinivas Arkivoc XIV 2007 266
26. E. Rajanarendar, M. Srinivas, and K. Ramu Synth. Commun. 33 2003 3077
27. S. Narasimha Swamy, A. Krishna Murthy, and E. Rajanarendar Indian J. Heterocycl. Chem. 12 2003 357
28. General procedure for the synthesis of ethyl-3-aryl-4-(2-chlorophenyl)-6- methyl-1-(5-methylisoxazol-3-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5- carboxylates (4a-h): A mixture of o-chloro benzaldehyde 1 (1 mmol), ethyl acetoacetate 2 (1 mmol), isoxazolyl thiourea 3 (1 mmol), and ceric ammonium nitrate (10 mol %) in ethanol (10 mL) were heated at 100 °C, while stirring for 3 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled and poured in to ice water. The separated solid was filtered and recrystallized from ethanol to give pure product (4a-h).
29. 2 atmosphere. The progress of the reaction was monitored by TLC. After the completion of the reaction, the solvent was removed by vacuum distillation and the contents are poured in ice cold water. The separated solid was filtered and recrystallized from ethanol to give the pure product (6a-h).
30. National Committee for Clinical Laboratory (NCCLS), Standard methods for dilution antimicrobial susceptibility tests for bacteria which grows aerobically, Nat Comm Clini Lab stands, Villanova, 1982, p 242.
31. Margery, E. Practical. Introduction of Microbiology; E and F N Spon Ltd, UK, 1962; p 177.
32. Murthy, U. S. N.; Jamil, K. International pest control 1986, 29, 8.
33. WHO: Instruction for determining the susceptibility or resistance of mosquito larvae to insecticides. Mimeographed document WHO/VBC/1975, 583.