Voltar
Artigo Revisado por pares
BIBTEX RIS

Solvent-free microwave multicomponent regiospecific synthesis of pyrimido[4,5- c ]isoquinolines and evaluation In Vitro of their antifungal properties

2006; Wiley; Volume: 43; Issue: 2 Linguagem: Inglês

10.1002/jhet.5570430231

ISSN

1943-5193

Autores

Jairo Quiroga, Carlos Cisneros, Braulio Insuasty, Rodrigo Abonı́a, Manuel Nogueras, Maximiliano Sortino, Susana Zacchino,

Tópico(s)

Synthesis and Biological Evaluation

Resumo

Journal of Heterocyclic ChemistryVolume 43, Issue 2 p. 463-469 Article Solvent-free microwave multicomponent regiospecific synthesis of pyrimido[4,5-c]isoquinolines and evaluation In Vitro of their antifungal properties Jairo Quiroga, Jairo Quiroga Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali, ColombiaSearch for more papers by this authorCarlos Cisneros, Carlos Cisneros Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali, ColombiaSearch for more papers by this authorBraulio Insuasty, Braulio Insuasty Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali, ColombiaSearch for more papers by this authorRodrigo Abonía, Rodrigo Abonía Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali, ColombiaSearch for more papers by this authorManuel Nogueras, Manuel Nogueras Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, EspañaSearch for more papers by this authorMaximiliano Sortino, Maximiliano Sortino Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000), Rosario, ArgentinaSearch for more papers by this authorSusana Zacchino, Susana Zacchino Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000), Rosario, ArgentinaSearch for more papers by this author Jairo Quiroga, Jairo Quiroga Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali, ColombiaSearch for more papers by this authorCarlos Cisneros, Carlos Cisneros Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali, ColombiaSearch for more papers by this authorBraulio Insuasty, Braulio Insuasty Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali, ColombiaSearch for more papers by this authorRodrigo Abonía, Rodrigo Abonía Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali, ColombiaSearch for more papers by this authorManuel Nogueras, Manuel Nogueras Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, EspañaSearch for more papers by this authorMaximiliano Sortino, Maximiliano Sortino Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000), Rosario, ArgentinaSearch for more papers by this authorSusana Zacchino, Susana Zacchino Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, (2000), Rosario, ArgentinaSearch for more papers by this author First published: 13 March 2009 https://doi.org/10.1002/jhet.5570430231Citations: 8AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract The free-solvent multicomponent reaction under microwave irradiation of 6-aminopyrimidin-4(3H)-ones (1) with dimedone (2) and N,N-dimethylformamide dimethylacetal yields the pyrimido[4,5-c]isoquinolinones (5a-j). In this process, the intermediate of cyclization was isolated. The structure of the synthesized compounds was determined on the basis of nmr measurements, especially by 1H,1H-,1H,13C COSY, and DEPT. These compounds showed antifungal in vitro activity particularly against dermatophytes. References and Notes 1 B. Wong, B. Klei, T. Kozel, Inmunologic Approaches and Metabolite Detection. The Second NIAID Workshop in Medical Micology, University of Arizona, Northern Arizona University, Flagstaff, AZ, June 8–11, 1994. Google Scholar 2 A. Groll, T. De Lucca, T. Walsh, Trends in Microbiology, 6, 117 (1998). 10.1016/S0966-842X(97)01206-7 CASPubMedWeb of Science®Google Scholar 3 W. Timberlake, C. D'Enfert, W. Fonzi, Targets for Inhibiting Proliferaition of Virulence. The Second NIAID Workshop in Medical Micology, University of Arizona, Northern Arizona University, Flagstaff, AZ, June 8–11, 1994. Google Scholar 4 M. Ghannoum, L. Rice, Clin. Microbiol. Rev., 12, 501 (1992). PubMedWeb of Science®Google Scholar 5 T. White, K. Marr, R. Bowden, R. Clin. Microbiol. Rev., 11, 382 (1998) 10.1128/CMR.11.2.382 CASPubMedWeb of Science®Google Scholar 6 F. Marco, M. A. Pfaller, S. Messer, R. Jones, Antimicrob. Agents Chemother., 42, 161 (1998) 10.1093/jac/42.2.161 CASPubMedWeb of Science®Google Scholar 7 A. Rashid, E. M. Scott, M. D. Richardson, J. Am. Acad. Dermatol., 718 (1995) Google Scholar 8 P. H. Chandrasekar, E. K. Manavathu, Drugs of Today, 38, 829 (2002). 10.1358/dot.2002.38.12.820101 CASPubMedWeb of Science®Google Scholar 9a C. C. Cheng, Prog. Med. Chem., 6, 67 (1969). 10.1016/S0079-6468(08)70197-8 CASPubMedGoogle Scholarb J. Scherkenbeck, T. Himmler, S. Beohm, H. Hagemann, K. Stroecl, S. Dutzmann, H. W. Dehne, Haenssler, G. Ger. Often DE 4, 208, 050, 23rd Sep. 1993. Google Scholar Chem. Abstr. 120, 107033m (1994); Google Scholarc K. A. M. Walker, A. C. Braemer, S. Hitt, R. E. Jones, T. R. Mathews, J. Med. Chem., 21, 480 (1978). 10.1021/jm00203a016 PubMedWeb of Science®Google Scholard T. Obata, K. Fujii, K. Tsutsumiuchi, Y. Nakamoto, Eur. Pat. Appl. EP 543, 402, 26 May 1993. Google Scholar Chem. Abstr. 120, 107043q (1994). Google Scholare P. Wachtler, W. Paulus, Ludwig, Georg-Wilhelm, Eur. Pat. Appl. EP 559, 002; 8 September 1993. Google Scholar Chem. Abstr. 120, 107036q (1994). Google Scholarf S. Sakai, H. Hase, I. Narita, K. Hatano, H. Takunaga, JP 05, 294, 945/93, 294, 945. Google Scholar Chem. Abstr. 120, 217725w (1994); Google Scholarg S. Rollas, N. Kalyoncuoglu, D. Sur-Altiner, Yegenoglu, Y. Pharmazie 48, 308 (1993); CASPubMedWeb of Science®Google Scholarh A. Kreutzberger, A. Burger, Arch. Pharm. (Weinheim) 328, 473 (1993). 10.1002/ardp.19933260809 Web of Science®Google Scholar 10 B. K. Shoichet, R. M. Stroud, D. U. Santi, I. D. Kuntz, K. M. Perry, Science, 259, 1445 (1993). 10.1126/science.8451640 CASPubMedWeb of Science®Google Scholar 11 L. Pagano, L. Mele, L. Fianchi, L. Melillo, B. Martino, D. D'Antonio, M. Tosti, B. Posteraro, M. Sanguinetti, G. Trape, F. Equitani, F. Nobile, M. Carotenuto, G. Leone, Haematologica, 87, 535 (2002). PubMedWeb of Science®Google Scholar 12 J. Quiroga, A. Hormaza, B. Insuasty, A. J. Ortiz, A. Sánchez, M. Nogueras, J. Heterocyclic Chem., 35, 231 (1998). 10.1002/jhet.5570350142 CASWeb of Science®Google Scholar 13a A. Gangjee, J. K. Ohemeng, J. J. Tulachka, F.-T. Lin, A. A. Katoh, J. Heterocyclic Chem., 22, 1149 (1985); 10.1002/jhet.5570220449 CASWeb of Science®Google Scholarb A. Gangjee, J. K. O'Donnell, T. J. Bardos, T. I. Kalman, J. Heterocyclic Chem., 21, 873 (1984); 10.1002/jhet.5570210347 CASWeb of Science®Google Scholarc S. R. Stone, J. A. Montgomery, J. F. Morrison, Biochem. Pharmacol., 33, 175 (1984). 10.1016/0006-2952(84)90472-6 CASPubMedWeb of Science®Google Scholar 14a R. S. Varma, D. Kumar, Tetrahedron Lett., 40, 7665 (1999); 10.1016/S0040-4039(99)01585-3 CASWeb of Science®Google Scholarb K. Groebke, L. Weber, F. Mehlin, Synlett, 661 (1998); Google Scholarc C. O. Kappe, D. Kumar, R. S. Varma, Synthesis, 1799 (1999); Google Scholard L. Weber, K. Illegen, M. Almstetter, Synlett, 366 (1999); Google Scholare R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, T. A. Keating, Acc. Chem. Res., 29, 123 (1996). 10.1021/ar9502083 CASWeb of Science®Google Scholar 15a D. Dallinger, N. Y. Gorobets, C. O. Kappe, Org. Lett., 5, 1205 (2003); 10.1021/ol034085v CASPubMedWeb of Science®Google Scholarb U. Bora, A. Saikia, R. C. Boruah, Org. Lett., 5, 435 (2003); 10.1021/ol020238n CASPubMedWeb of Science®Google Scholarc J. F. Cheng, M. Chen, T. Arthenius, A. Nadzen, Tetrahedron Lett., 43, 6293 (2002); 10.1016/S0040-4039(02)01403-X CASWeb of Science®Google Scholard M. C. Bagley, J. W. Cale, J. Bower, Chem. Commun., 1682 (2002); Google Scholare V. Nair, A. U. Vinod, C. Rajesh, J. Org. Chem., 66, 4427 (2001); 10.1021/jo001714v CASPubMedWeb of Science®Google Scholarf R.V.A. Orru, M. de Greef, Synthesis, 1471 (2003). Google Scholar 16a A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, D. Mathe, Synthesis, 1213 (1998); Google Scholarb R. S. Varma, Green Chemistry, 43 (1999); Google Scholarc S. Deshayes, M. Liagre, A. Loupy, J.-L. Luche, A. Petit, Tetrahedron, 55, 10951 (1999); 10.1016/S0040-4020(99)00601-8 CASWeb of Science®Google Scholard R. S. Varma, Clean Products and Processes, 1, 132 (1999); Google Scholare R. S. Varma, Pure Appl. Chem., 73, 193 (2001); 10.1351/pac200173010193 CASWeb of Science®Google Scholarf J. Cossy, C. Willis, V. Bellosta, L. S. Jalmes, Synthesis, 951 (2002); Google Scholarg A. R. Katritzky, S. K. Singh, Arkivok, xiii, 68. Google Scholarh M. Nuchter, U. Müller, B. Ondruschka, A. Tied, W. Lautenschläger, Chem. Eng. Technol., 26, 1207 (2003); 10.1002/ceat.200301836 CASWeb of Science®Google Scholari A. de la Hoz, A. Díaz-Ortiz, A. Moreno, Chem. Soc. Rev., 34, 164 (2005). 10.1039/B411438H CASPubMedWeb of Science®Google Scholar 17 A. Bax and S. Subramanian, J. Magn. Reson., 65, 565 (1986). Google Scholar 18 A. Bax and M. F. Summers, J. Am. Chem. Soc., 108, 2093 (1986). 10.1021/ja00268a061 CASWeb of Science®Google Scholar 19a J. Quiroga, G. Viveros, B. Insuasty, M. Nogueras, A. Sánchez, J. Cobo, J. Heterocyclic Chem., 36, 501 (1999); 10.1002/jhet.5570360228 CASWeb of Science®Google Scholarb E. I. Al-Afaleq, Synthetic Commun., 30, 1985 (2000). 10.1080/00397910008087248 CASWeb of Science®Google Scholar 20 NCCLS, National Committee for Clinical Laboratory Standards, 2002, Method M27-A2, 2nd ed, Wayne Ed.; Vol. 22 (15), pp 1–29. NCCLS, National Committee for Clinical Laboratory Standards, 2002, Method M-38A, 2nd ed, Wayne Ed.; Vol. 22 (16), pp 1–27. Google Scholar 21 L. R. Wright, E. M. Scott, S. P. Gorman, J. Antimicrob. Chemother., 12, 317 (1983). 10.1093/jac/12.4.317 CASPubMedWeb of Science®Google Scholar Citing Literature Volume43, Issue2March/April 2006Pages 463-469 ReferencesRelatedInformation

Referência(s)