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http://dx.doi.org/10.5012/bkcs.2011.32.3.899

Eco-friendly Solventless Synthesis of 5-Indolylpyrimido[4,5-d]pyrimidinones and Their Antimicrobial Activity  

Gupta, Ragini (Department of Chemistry, Malaviya National Institute of Technology)
Jain, Anshu (Department of Chemistry, Malaviya National Institute of Technology)
Joshi, Rahul (Department of Chemistry, University of Rajasthan)
Jain, Meenakshi (Department of Chemistry, University of Rajasthan)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.3, 2011 , pp. 899-904 More about this Journal
Abstract
A series of 5-indolylpyrimido[4,5-d]pyrimidinones (4a-h) were obtained by multi-component reaction of 3-formylindole (1), thiobarbituric acid/barbituric acid (2) and thiourea/urea (3) under microwave irradiation in dry media. Secondly, grinding together neat reactants also gave the titled compounds in good yields. All the synthesized compounds have been characterized on the basis of elemental analyses and spectral data (IR, $^1H$ NMR and Mass). Representative compounds were also evaluated for their antimicrobial activity against Rhizopus stolonifer, Fusarium oxysporum, Escherichia coli, and Pseudomonas aeruginosa at different concentrations. Some of the compounds showed promising activity.
Keywords
5-Indolylpyrimido[4,5-d]pyrimidinones; Microwave irradiation on solid support; Grindstone technology; Biginelli reaction;
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1 Kidwai, M. Pure. Appl. Chem. 2001, 73, 147.   DOI   ScienceOn
2 Barthakur, M. G.; Gogoi, S.; Dutta, M.; Boruah, R. C. Steroids 2009, 74, 730.   DOI   ScienceOn
3 Kidwai, M.; Saxena, S.; Mohan, R.; Venkataramanan, R. J. Chem.Soc., Perkin Trans 1 2002, 1845.
4 Varma, R. S. Green. Chem. 1999, 1, 43   DOI   ScienceOn
5 Pathak, V. N.; Gupta, R.; Varshney, B. Indian J. Chem. B 2008,47, 434.
6 Vaca Ruiz, M. L.; Silva, P. G.; Laciar, A. L. Afr. J. Microbiol. Res.2009, 3, 319.
7 Robinson, B. Chem. Rev. 1969, 69, 227.   DOI
8 Joshi, K. C.; Pathak, V. N.; Chand, P. J. Prakt. Chem. 1978, 320,701.   DOI
9 Pete, B.; Parlagh, G. Tetrahedon Lett. 2003, 44, 2537.   DOI   ScienceOn
10 Walker, G. N.; Moore, M. A. J. Org. Chem. 1961, 26, 432.   DOI
11 Gangjee, A.; Zaware, N.; Raghavan, S.; Ihnat, M.; Shenoy, S.;Kisliuk, R. L. J. Med. Chem. 2010, 53, 1563.   DOI   ScienceOn
12 Santagati, A.; Granata, G.; Santagati, M.; Cutuli, V.; Mangano, N.G.; Caruso, A. Arzneimittel-Forschung 2002, 52, 448.
13 Romeo, G.; Materia, G.; Marucci, G.; Modica, M.; Pittala, V.;Salerno, L.; Siracusa, M. A.; Buccioni, M.; Angeli, P.; Minneman,K. P. Bioorg. Med. Chem. Lett. 2006, 16, 6200.   DOI   ScienceOn
14 Dotzauer, B.; Grunert, R.; Bednarski, P. J.; Lanig, H.; Landwehr,J.; Troschutz, R. Bioorg. Med. Chem. 2006, 14, 7282.   DOI   ScienceOn
15 Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
16 Kategaonkar, A. H.; Sadaphal, S. A.; Shelke, K. F.; Shingate, B.B.; Shingare, M. S. Ukr. Bioorg. Acta 1 2009, 3.
17 Sadanandam, Y. S.; Shetty, M. M.; Diwan, P. V. Eur. J. Med. Chem.1992, 27, 87.   DOI   ScienceOn
18 Wang, Z.-T.; Xu, L.-W.; Xia, C.-G.; Wang, H.-Q. Tetrahedron Lett. 2004, 45, 7951.   DOI   ScienceOn
19 Pathak, V. N.; Gupta, R.; Tiwari, R.; Gupta, R.; Sareen, V.; Varshney,B. Synth. Commun. 2007, 37, 977.   DOI   ScienceOn
20 Pathak, V. N.; Gupta, R.; Varshney, B. J. Heterocycl. Chem. 2008,45, 589.   DOI
21 Gupta, R.; Sharma, D.; Verma, P. S. Heteroat. Chem. 2009, 20,224.   DOI   ScienceOn
22 Srivastava, S. K.; Haq, W.; Chauhan, P. M. S. Bioorg. Med. Chem. Lett. 1999, 9, 965.   DOI   ScienceOn
23 Polshettiwar, V.; Varma, R. S. Chem. Soc. Rev. 2008, 37, 1546.   DOI   ScienceOn
24 Martínez-Palou, R. J. Mex. Chem. Soc. 2007, 51, 252.
25 Cave, G. W. V.; Raston, C. L.; Scott, J. L. Chem. Commun. 2001,2159.
26 Strauss, C. R. Aust. J. Chem. 2009, 62, 3.   DOI   ScienceOn
27 Taylor, E. C.; Knopf, R. J.; Meyer, R. F.; Holmes, A.; Hoefle,M. L. J. Am. Chem. Soc. 1960, 82, 5711.   DOI
28 Figueroa-Villar, J. D.;Carneiro, C. L.; Cruz, E. R. Heterocycles 1992, 34, 891.   DOI
29 Kitamura, N.; Onishi, A.; European Patent 163599, 1984
30 Kitamura, N.; Onishi, A., Chem. Abstr. 1984, 104, 186439.
31 Raddatz, P.; Bergmann, R.; Ger. Pat. 360731, 1988
32 Raddatz, P.; Bergmann, R., Chem. Abstr. 1988, 109, 54786.
33 Prajapati, D.; Gohain, M.; Thakur, A. J. Bioorg. Med. Chem. Lett.2006, 16, 3537.   DOI   ScienceOn
34 Delia, T. J.; Baumann, M.; Bunker, A. Heterocycles 1993, 35, 1397.   DOI
35 Chikvaidze, I. S.; Megrelishvili, N. S.; Samsoniya, S. A.; Suvorov,N. N.; Guskova, T. A.; Radkevich, T. P.; Baklanova, O. V. Pharm. Chem. J. 1998, 32, 29.   DOI   ScienceOn
36 Ryu, C. K.; Lee, J. Y.; Park, R. E.; Ma, M. Y.; Nho, J. H. Bioorg. Med. Chem. Lett. 2007, 17, 127.   DOI   ScienceOn
37 Giampieri, M.; Balbi, A.; Mazzei, M.; La Colla, P.; Ibba, C.;Loddo, R. Antiviral Res. 2009, 83, 179.   DOI   ScienceOn
38 Suvorov, N. N.; Chernov, V. A.; Velezheeva, V. S.; Ershova, Y.A.; Simakov, S. V.; Sevodin, V. P. Pharm. Chem. J. 1981, 15, 631.   DOI
39 Suvorov, N. N.; Chernov, V. A.; Velezheeva, V. S.; Ershova, Y. A.;Simakov, S. V.; Sevodin, V. P. Pharm. Chem. J. 1981, 15, 631.   DOI
40 Lauria, A.; Patella, C.; Dattolo, G.; Almerico, A. M. J. Med. Chem. 2008, 51, 2037.   DOI   ScienceOn
41 Lauria, A.; Patella, C.; Dattolo, G.; Almerico, A. M. J. Med. Chem.2008, 51, 2037.   DOI   ScienceOn
42 Ghosh, R.; Maiti, S.; Chakraborty, A. J. Mol. Catal. 2004, 217, 47.   DOI   ScienceOn
43 Coates, W. J., Chem. Abstr. 1990, 113, 40711
44 Srivastava, S. K.; Haq, W.; Chauhan, P. M. S. Bioorg. Med. Chem. Lett. 1999, 9, 965.   DOI   ScienceOn
45 Clercq, E. D.; Beraaerts, R. J. Biol. Chem. 1987, 262, 14905.
46 Coates, W. J. European Patent 351058, 1990
47 Ramsey, A. A. U.S. Patent 3830812 FMC Corp. 1974
48 Ramsey, A. A., Chem. Abstr. 1974, 81, 136174.