Multicomponent synthesis of antibacterial dihydropyridin and dihydropyran embelin derivatives

Journal of Organic Chemistry

Volumn 78, Issue 16, 2013, Pages 7977-7985

  Peña, Rosalyn ^a,b   Jiménez Alonso, Sandra ^a,b   Feresin, Gabriela ^c   Tapia, Alejandro ^c   Méndez Alvarez, Sebastián ^a,d   Machín, Félix ^b,d   Ravelo, Ángel G ^a,b   Estévez Braun, Ana ^a,b  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b Madrid Spain   (Spain)

^c UNIVERSIDAD NACIONAL DE SAN JUAN   (Argentina)

^d HOSPITAL UNIVERSITARIO NUESTRA SEÑORA DE CANDELARIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CLINICAL ISOLATES; DIHYDROPYRAN; GRAM-POSITIVE BACTERIUM; MULTICOMPONENT SYNTHESIS; NITROGEN ATOM; ONE-POT PROTOCOL; STAPHYLOCOCCUS AUREUS; THREE COMPONENT REACTIONS;

BACTERIA;

POLYOLS;

9 (3 FLUORO 4 METHOXYPHENYL) 2 HYDROXY 6,6 DIMETHYL 3 UNDECYL 5,6,7,9 TETRAHYDROXANTHENE 1,4,8 TRIONE; 9 (3 FLUOROPHENYL) 2 HYDROXY 3 UNDECYL 6,7,9,10 TETRAHYDRO 5H ACRIDINE 1,4,8 TRIONE; 9 (3 FLUOROPHENYL) 2 HYDROXY 6,6 DIMETHYL 3 UNDECYL 5,6,7,9 TETRAHYDROXANTHENE 1,4,8 TRIONE; 9 (4 BROMOPHENYL) 2 HYDROXY 3 UNDECYL 6,7,9,10 TETRAHYDRO 5H ACRIDINE 1,4,8 TRIONE; 9 (4 BROMOPHENYL) 2 HYDROXY 6,6 DIMETHYL 3 UNDECYL 5,6,7,9 TETRAHYDROXANTHENE 1,4,8 TRIONE; 9 (4 CHLOROPHENYL) 2 HYDROXY 3 UNDECYL 6,7,9,10 TETRAHYDRO 5H ACRIDINE 1,4,8 TRIONE; 9 (4 FLUOROPHENYL) 2 HYDROXY 3 UNDECYL 6,7,9,10 TETRAHYDRO 5H ACRIDINE 1,4,8 TRIONE; 9 (4 FLUOROPHENYL) 2 HYDROXY 6,6 DIMETHYL 3 UNDECYL 5,6,7,9 TETRAHYDROXANTHENE 1,4,8 TRIONE; 9 (4 NITROPHENYL) 2 HYDROXY 6,6 DIMETHYL 3 UNDECYL 5,6,7,9 TETRAHYDROXANTHENE 1,4,8 TRIONE; 9 ETHYL 2 HYDROXY 3 UNDECYL 6,7 DIHYDROACRIDINE 1,4,8 (5H,9H,10H)TRIONE; ALDEHYDE; ANTIINFECTIVE AGENT; DIHYDROPYRAN EMBELIN DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; EMBELIN; NITROGEN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIUM ISOLATE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; ONE POT SYNTHESIS; OXYGENATION; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; BENZOQUINONES; DIHYDROPYRIDINES; MOLECULAR STRUCTURE; PYRANS; STEREOISOMERISM;

EID: 84882344019     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401189x     Document Type: Article

References (45)

1. Hui, Y.; Khim Chng, E. L.; Lin Chng, C. Y.; Poh, H. L.; Webster, R. D. J. Am. Chem. Soc. 2009, 131, 1523
2. Ogawa, M.; Koyanagi, J.; Sugaya, A.; Tsuda, T.; Ohguchi, H.; Nakayama, K.; Yamamoto, K.; Tanaka, A. Biosci. Biotechnol. Biochem. 2006, 70, 1009
3. Thomson, R. H. Naturally Occurring Quinones IV. Recent Advances; Blackie: London, 1997.
4. Marcos, I. S.; Conde, A.; Moro, R. F.; Basabe, P.; Diez, D.; Urones, J. Mini-Rev. Med. Chem 2010, 7, 230
5. Marco-Contelles, J.; Molina, M. T. Curr. Org. Chem. 2003, 7, 1433
6. Kumamoto, T.; Ishikawa, T.; Omura, S. Yuki Gosei Kagaku Kyokaishi 2004, 62, 49
7. Liu, J.-K. Chem. Rev. 2006, 106, 2209
8. Ravelo, A. G.; Estévez-Braun, A.; Chávez-Orellana, H.; Pérez-Sacau, E.; Mesa-Siverio, D. Curr. Top. Med. Chem. 2004, 4, 241
9. Ferreira, I. C. F. R.; Vaz, J. A.; Vasconcelos, M. H.; Martins, A. Mini-Rev. Med. Chem. 2010, 10, 424
10. Dandawate, P. R.; Vyas, A. C.; Padhye, S. B.; Singh, M. W.; Baruah, J. B. Mini-Rev. Med. Chem. 2010, 10, 436
11. Stasiuk, M.; Kozubek, A. Global J. Biochem. 2011, 2, 262
12. Feresin, G. E.; Tapia, A.; Sortino, M.; Zacchino, S.; de Arias, A. R.; Inchausti, A.; Yaluff, G.; Rodriguez, J.; Theoduloz, C.; Schmeda-Hirschmann, G. J. Ethnopharmacol. 2003, 88, 241
13. Githiori, J. B.; J. Hoglund, P. J; Waller, R.; Leyden, B. Vet. Parasitol. 2003, 118, 215
14. Githui, E. K.; Makawiti, D. W.; Midiwo, J. O. Contraception 1991, 44, 311
15. Chitra, M.; Sukumar, E.; Suja, V.; Devi, C. S. Chemotherapy 1994, 40, 109
16. Sreepriya, M.; Bali, G. Fitoterapia 2005, 76, 549
17. Xu, M.; Cui, J.; Fu, P.; Proksch, W.; Lin, M. Li Planta Med. 2005, 71, 944
18. Lamblin, M.; Sallustrau, A.; Commadeur, C.; Cresteil, T.; Felpin, F. X.; Dessolin, J. Tetrahedron 2012, 68, 4655
19. Viault, G.; Grée, D.; Das, S.; Yadav, J. S.; Grée, R. Eur. J. Org. Chem. 2011, 1233
20. Chen, J.; Nikolovska-Coleska, Z.; Wang, G.; Qiu, Su; Wang, S. Bioorg. Med. Chem. Lett. 2006, 16, 5805
21. Jiménez-Alonso, S.; Estévez-Braun, A.; Zárate, R.; Ravelo, A. G.; López, M. Tetrahedron 2007, 63, 3066
22. Jiménez-Alonso, S.; Chávez-Orellana, H.; Estévez-Braun, A.; Ravelo, A. G.; Feresin, G.; Tapia, A. Tetrahedron 2008, 64, 8938
23. Jiménez-Alonso, S.; Chávez-Orellana, H.; Estévez-Braun, A.; Ravelo, A. G.; Pérez-Sacau, E.; Machín, F. J. Med. Chem. 2008, 51, 6761
24. Jiménez-Alonso, S.; Pérez-Lomas, A. L.; Estévez-Braun, A.; Muñoz-Martinez, F.; Chávez-Orellana, H.; Ravelo, A. G.; Gamarro, F.; Castanys, S.; López, M. J. Med. Chem. 2008, 51, 7132
25. Jiménez-Alonso, S.; Guasch, J.; Estévez-Braun, A.; Ratera, I.; Veciana, J.; Ravelo, A. G. J. Org. Chem. 2011, 76, 1634
26. Guedes, G.; López-Rodríguez, M.; Ravelo, A. G.; Estévez-Braun, A. Eur. J. Org. Chem. 2012, 5757
27. Spanish patent application (P201130432). Peña, R.; Jiménez-Alonso, S.; Méndez-álvarez, S.; Machín, F.; Ravelo, A. G.; Estévez-Braun, A.
28. Costantino, L.; Barlocco, D. Curr. Med. Chem. 2006, 13, 763
29. Wetzel, S.; Bon, R. S.; Kumar, K.; Waldmann, H. Angew. Chem., Int. Ed. 2011, 50, 10800
30. Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18, 9160
31. Quinone Methides; Rokita, S. E., Ed.; Wiley: New York, 2009.
32. Van der Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367
33. Pathak, T. P.; Sigman, M. S. J. Org. Chem. 2011, 76, 9210
34. Jiang, B.; Li, Y.; Tu, M. T.; Wang, S. L.; Tu, S. J.; Li, G. J. Org. Chem. 2012, 77, 7497
35. Wu, X.-J.; Xu, X.-P.; Su, X.-M.; Chen, G.; Zhang, Y.; Ji, S.-J. Eur. J. Org. Chem. 2009, 4963
36. Tu, S.; Zhang, Y.; Jiang, B.; Jia, R.; Zhang, J.; Ji, S. Synthesis 2006, 22, 3874
37. Wang, H.; Li, L.; Lin, Xu,P.; Huang, Z.; Shi, D. Org. Lett. 2012, 14, 4598
38. Li, J.; Yu, Y.; Tu, M. T.; Jiang, B. M.; Wang, S. L.; Tu, S. J. Org. Biomol. Chem. 2012, 10, 5361
39. Elassar, A. Z.; El-khair, A. A. Tetrahedron 2003, 59, 8643
40. Negri, G.; Kascheres, C.; Kascheres, A. J. J. Heterocycl. Chem. 2004, 41, 461
41. Al-Mousawi, S.; Abdelkhalik, M. M.; John, E.; Elnagdi, M. H. J. Heterocycl. Chem. 2003, 40, 689
42. Paira, M.; Misra, R.; Roy, S. C. Indian J. Chem. 2008, 47B, 966
43. Boucher, H. W.; Corey, G. R. Clin. Infect. Dis. 2008, 46, S344-9
44. Perrin, D. D.; Amarego, W. L. F. Purification of Laboratory Chemicals, 3 rd ed.; Pergamon Press: Oxford, 1988.
45. Casero, C.; Estévez-Braun, A.; Ravelo, A. G.; Demo, M.; Méndez-álvarez, S.; Machín, F. Phytomedicine 2013, 20, 133