A general protocol for the solvent- and catalyst-free synthesis of 2-styrylquinolines under focused microwave irradiation

Synlett

Volumn , Issue 17, 2011, Pages 2577-2579

  Staderini, Matteo ^a   Cabezas, Nieves ^a   Bolognesi, Maria Laura ^a   Menendez, J Carlos ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b Dipto di Scienze Farmaceutiche   (Italy)

Author keywords

aldol condensations; heterocycles; microwave assisted synthesis; quinolines

Indexed keywords

2 (4 FLUOROSTYRYL) 6 METHOXYQUINOLINE; 2 STYRYLQUINOLINE DERIVATIVE; 6 CHLORO 2 (4 PHENYLBUTA 1,3 DIENYL)QUINOLINE; 7 CHLORO 2 (4 METHOXYSTYRYL)QUINOLONE; ACETIC ANHYDRIDE; BENZALDEHYDE DERIVATIVE; CARBON; CINNAMALDEHYDE DERIVATIVE; QUINALDINE DERIVATIVE; QUINOLINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; STEREOCHEMISTRY;

EID: 80054080438     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260330     Document Type: Article

References (33)

1. For reviews of quinoline-related compounds, see:, Michael J P., Nat. Prod. Rep. 2008 25 166
2. Michael J P., Nat. Prod. Rep. 2007 24 223
3. Kouznetsov V V., VargasMéndez L Y., MeléndezGomez C M., Curr. Org. Chem. 2005 9 141
4. Michael J P., Nat. Prod. Rep. 2004 21 650
5. Michael J P., Nat. Prod. Rep. 2005 22 627
6. Bongarzone S, Bolognesi M L., Curr. Opin. Drug Discovery Dev. 2011 6 251
7. For reviews of the potential of integrase inhibitors as anti-HIV agents, see:, Makhija M T., Curr. Med. Chem. 2006 13 2429
8. Pommier Y, Johnson A A., Marchand C, Nat. Rev. Drug Discovery 2005 4 236
9. Andréola M L., DeSoultrait V R., Fournier M, Parissi V, Desjobert C, Litvak S, Expert Opin. Ther. Targets 2002 6 433
10. dAngelo J, Mouscadet J.-F, Desmaële D, Zouhiri F, Leh H, Pathol. Biol. 2001 49 237
11. Raltegravir, an integrase inhibitor, has recently reached the market as an anti-AIDS agent. For a study of its clinical efficacy, see:, Steigbigel R T., Cooper D A., Kumar P N., Eron J E., Schechter M, Markowitz M, Loutfy M R., Lennox J L., Gatell J M., Rockstroh J K., Katlama C, Yeni P, Lazzarin A, Clotet B, Zhao J, Chen J, Ryan D M., Rhodes R R., Killar J A., Gilde L R., Strohmaier K M., Meibohm A R., Miller M D., Hazuda D J., Nessly M L., DiNubile M J., Isaacs R D., Nguyen B.-Y, Teppler H, N. Engl. J. Med. 2008 359 339
12. Normand-Bayle M, Bénard C, Zouhiri F, Mouscadet J.-F, Leh H, Thomas C.-M, Mbemba G, Desmaële D, dAngelo J, Bioorg. Med. Chem. Lett. 2005 15 4019
13. Bénard C, Zouhiri F, Normand-Bayle M, Canet M, Desmaële D, Leh H, Mouscadet J.-F, Mbemba G, Thomas C.-M, Bonnenfant S, LeBret M, dAngelo J, Bioorg. Med. Chem. 2004 14 2473
14. Mousnier A, Leh H, Mouscadet J.-F, Dargemont C, Mol. Pharmacol. 2004 66 783
15. Polanski J, Zouhiri F, Jeanson L, Desmaële D, dAngelo J, Mouscadet J.-F, Gieleciak R, Gasteiger J, LeBret M, J. Med. Chem. 2002 45 4647
16. Yuan H, Parrill A L., Bioorg. Med. Chem. 2002 10 4169
17. Oulali M, Labulais C, Leh H, Gill D, Desmaële D, Mekouar K, Zouhiri F, dAngelo J, Auclair C, Mouscadet J.-F, LeBret M, J. Med. Chem. 2002 43 1949
18. dAngelo J, Mouscadet J.-F, Desmaele D, Zouhiri F, Leh H, Pathol. Biol. 2001 49 237
19. Zouhiri F, Mouscadet J.-F, Mekouar K, Desmaële D, Savouré D, Leh H, Subra F, LeBret M, Auclair C, dAngelo J, J. Med. Chem. 2000 43 1533
20. Ouali M, Laboulais C, Leh H, Gill D, Desmaele D, Mekouar K, Zouhiri F, dAngelo J, Auclair C, Mouscadet J.-F, LeBret M, J. Med. Chem. 2000 43 1949
21. Mekouar K, Mouscadet J.-F, Desmaële D, Subra F, Leh H, Savouré D, Auclair C, dAngelo J, J. Med. Chem. 1998 41 2846
22. Bonnenfant S, Thomas C M., Vita C, Subra C, Deprez E, Zouhiri F, Desmaële D, dAngelo J, Mouscadet [nl]J.-F, Leh H, J. Virol. 2004 78 5728
23. Li Q, Min J, Ahn Y.-H, Namm J, Kim E M., Lui R, Kim H Y., Ji Y, Wu H, Wisniewski T, Chang Y.-T, ChemBioChem 2007 8 1679
24. Dabiri M, Salehi P, Baghbanzadeh M, Nikcheh [nl]M S., Tetrahedron Lett. 2008 49 5366
25. Leonard J T., Roy K, Eur. J. Med. Chem. 2008 43 81
26. Makhija [nl]M T., Curr. Med. Chem. 2006 13 2429
27. Bonnenfant S, Thomas C.-M, Vita C, Subra C, Deprez E, Zouhiri F, Desmaele D, dAngelo J, Mouscadet J.-F, Leh H, [nl] J. Virol. 2004 78 5728
28. Yuan H B., Parrill A L., Bioorg. Med. Chem. 2002 10 4169
29. For a discussion, see:, Kappe A O., Angew. Chem. Int. Ed. 2004 43 6250
30. Musiol R, Podeszwa B, Finster J, Niedbala H, Polansli J, Monatsh. Chem. 2006 137 1211
31. For the preparation of these starting materials, see:, Sridharan V, Avendaño C, Menéndez J C., Tetrahedron 2007 63 673
32. Fedoryak O D., Dore T M., Org. Lett. 2002 4 3419
33. Chen X.-Y, Shi J, Li [nl]Y.-M, Wang F.-L, Wu X, Guo Q.-X, Liu L, Org. Lett. 2009 11 4426