Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1H-benzimidazole derivatives as constrained stilbene bioisosteres

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 16, 2006, Pages 4169-4173

  Navarrete Vázquez, Gabriel ^a   Moreno Diaz, Hermenegilda ^a   Aguirre Crespo, Francisco ^a   León Rivera, Ismael ^b   Villalobos Molina, Rafael ^c   Muñoz Muñiz, Omar ^d   Estrada Soto, Samuel ^a  

^a UNIVERSIDAD AUTÓNOMA DEL ESTADO DE MORELOS   (Mexico)

^b CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^d UNIVERSIDAD VERACRUZANA   (Mexico)

Author keywords

Benzimidazole; Bioisosteric replacement; Spasmolytic; Stilbenoids

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; SPASMOLYTIC AGENT;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; ILEUM; MICROWAVE IRRADIATION; MUSCLE FUNCTION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SMOOTH MUSCLE;

ALDEHYDES; ANIMALS; BENZIMIDAZOLES; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; ILEUM; INHIBITORY CONCENTRATION 50; MICROWAVES; MODELS, CHEMICAL; PARASYMPATHOLYTICS; PHENYLENEDIAMINES; RATS; SOLVENTS; STILBENES;

EID: 33745713196     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.05.082     Document Type: Article

References (33)

1. Amorati R., Lucarini M., Mugnaini V., Pedulli G.F., Roberti M., and Pizzirani D. J. Org. Chem. 69 (2004) 7101
2. El-Mowafy A.M. Biochem. Biophys. Res. Commun. 291 (2002) 1218
3. Estrada-Soto S., López-Guerrero J.J., Villalobos-Molina R., and Mata R. Fitoterapia 77 (2006) 236
4. Orallo F., Álvarez E., Camina M., Leiro J.M., Gómez E., and Fernández P. Mol. Pharmacol. 61 (2002) 294
5. Hernández-Roméro Y., Rojas J.I., Castillo R., Rojas A., and Mata R. J. Nat. Prod. 67 (2004) 160
6. Bali A., Bansal Y., Sugumaran M., Singh-Saggu J., Balakumar P., Kaur G., Bansal G., Sharma A., and Singh M. Bioorg. Med. Chem. Lett. 15 (2005) 3962
7. Cheng J., Xie J., and Luo X. Bioorg. Med. Chem. Lett. 15 (2005) 267
8. Ueno H., Katoh S., Yokota K., Hoshi J., Hayashi M., Uchida I., Aisaka K., Hase Y., and Cho H. Bioorg. Med. Chem. Lett. 15 (2004) 4281
9. Navarrete-Vázquez G., Yepez-Mulia L., Hernández-Campos A., Tapia A., Hernández-Luis F., Cedillo R., González J., Martínez-Fernández M., Martínez-Grueiro M., and Castillo R. Bioorg. Med. Chem. 11 (2003) 4615
10. Özden S., Atabey D., Yi{dotless}ldi{dotless}z S., and Göker H. Bioorg. Med. Chem. 13 (2005) 1587
11. Andrzejewska M., Yépez-Mulia L., Cedillo-Rivera R., Tapia A., Vilpo L., Vilpo J., and Kazimierczuk Z. Eur. J. Med. Chem. 37 (2002) 973
12. Terzioglu N., van Rijn R., Bakker R.A., De Esch I.J.P., and Leurs R.. Bioorg. Med. Chem. Lett. 14 (2004) 5251
13. Küçükbay H., Durmaz R., Orhan E., and Günal S. Farmaco 58 (2003) 431
14. Estrada-Soto, S.; Villalobos-Molina, R.; Aguirre-Crespo F.; Vergara-Galicia, J.; Moreno-Díaz, H.; Torres-Piedra, M.; Navarrete-Vázquez, G. Life Sci., in press. doi:10.1016/j.lfs.2006.01.019.
15. Navarrete-Vázquez G., Cedillo R., Hernández-Campos A., Yepez-Mulia L., Hernández-Luís F., Valdez J., Morales R., Cortes R., Hernandez M., and Castillo R. Bioorg. Med. Chem. Lett. 11 (2001) 187
16. Thompson L.K., Ramaswamy B.S., and Seymour E.A. Can. J. Chem. 55 (1977) 878
17. Göker H., Ku C., Boykin D.W., Yildiz S., and Altanar N. Bioorg. Med. Chem. 10 (2002) 2589
18. Ben-Alloum A., Bakkas S., and Soufiaoui M. Tetrahedron Lett. 39 (1998) 4481
19. Verner E., Katz B.A., Spencer J.R., Allen D., Hataye J., Hruzewicz W., Hui H.C., Kolesnikov A., Li Y., Luong C., Martelli A., Radika K., Rai R., She M., Shrader W., Sprengeler P.A., Trapp S., Wang J., Young W.B., and Mackman R.L. J. Med. Chem. 44 (2001) 2753
20. Lombardy R.L., Tanious F.A., Ramachandran K., Tidwell R.R., and Wilson W.D. J. Med. Chem. 39 (1996) 1452
21. Trivedi R., De S.K., and Gibbs R.A. J. Mol. Catal. A: Chem. 245 (2006) 8
22. Gogoi P., and Konwar D.. Tetrahedron Lett. 47 (2006) 79
23. Lin S., and Yang L. Tetrahedron Lett. 46 (2005) 4315
24. Mavandadi F., and Lidström P. Curr. Top. Med. Chem. 4 (2004) 773
25. Yu H., Kawanishi H., and Koshima H. Heterocycles 60 (2003) 1457
26. Su Y.S., Lin M.J., and Sun M.C. Tetrahedron Lett. 46 (2005) 177
27. Boufatah N., Gellis A., Maldonado J., and Vanelle P. Tetrahedron 60 (2004) 9131
28. Bendale P.M., and Sun C.M. J. Comb. Chem. 4 (2002) 359
29. Chen X., and Wang W. Annu. Rep. Med. Chem. 38 (2003) 333
30. Olesen P.H. Curr. Opin. Drug Discovery Dev. 4 (2001) 471l
31. General method of synthesis of 2-(Alkyloxyaryl)-1H-benzimidazoles 1-17. Microwave irradiation conditions: A mixture of 1,2-phenylenediamine (0.0313 mol), 1.01 equivalents of appropriate aldehyde, and 1.01 equivalents of sodium metabisulfite was mixed and introduced in an open Erlenmeyer flask. The mixture was irradiated in a household microwave oven (Samsung MW1446WC, 1000 W) for 24-60 s. After irradiation, the mixture was poured onto cold water. The precipitate was collected by filtration, washed with water, dried, and recrystallized. Classical conditions: A mixture of 1,2-phenylenediamine (0.0313 mol), 1.01 equivalents of appropriate aldehyde, and 1.01 equivalents of sodium metabisulfite in 10 mL DMF was heated to reflux for 3-4.5 h. After cooling, water (20 mL) was added and the mixture was extracted with AcOEt (3 × 15 mL). The organic layer was dried over magnesium sulfate and removed under vacuum. Purification was done by chromatography on silica gel eluting with chloroform and recrystallization from adequate solvent.
32. 2: 240.0898. Found: 240.0900.
33. ® 6.0). The statistical significance (p < 0.05) of differences between means was assessed by an analysis of variance (ANOVA).