Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 17, 2012, Pages 5077-5084

  Concepcion Lozada M ^a   Soria Arteche, Olivia ^a   Teresa Ramírez Apan, Ma ^b   Nieto Camacho, Antonio ^b   Enríquez, Raúl G ^b   Izquierdo, Teresa ^a   Jiménez Corona, Arturo ^a  

^a DEPARTAMENTO DE SISTEMAS BIOLÓGICOS   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Amino acids; Amino derivatives; Antioxidants; Cytotoxic; Perezone

Indexed keywords

ACETYL TRYPTAMINE; ALPHA TOCOPHEROL; AMINO ACID DERIVATIVE; DOXORUBICIN; INDOLE DERIVATIVE; ISOPEREZONE; MELATONIN; METHYL 2 [4 HYDROXY 2 METHYL 5 (6 METHYLHEPT 5 EN 2 YL) 3,6 DIOXOCYCLOHEXA 1,4 DIENYLAMINO] 3 METHYLBUTANOIC ACID; METHYL 2 [4 HYDROXY 2 METHYL 5 (6 METHYLHEPT 5 EN 2 YL) 3,6 DIOXOCYCLOHEXA 1,4 DIENYLAMINO] 4 (METHYLTHIO)BUTANOIC ACID; METHYL 2 [4 HYDROXY 2 METHYL 5 (6 METHYLHEPT 5 EN 2 YL) 3,6 DIOXOCYCLOHEXA 1,4 DIENYLAMINO] 4 METHYLPENTANOIC ACID; METHYL 2 AMINO 3 [1 [4 HYDROXY 2 METHYL 5 (6 METHYLHEPT 5 EN 2 YL) 3,6 DIOXOCYCLOHEXA 1,4 DIENYL] 1H INDOL 3 YL]PROPANOIC ACID; N [2 [1 [4 HYDROXY 2 METHYL 5 (6 METHYLHEPT 5 EN 2 YL) 3,6 DIOXOCYCLOHEXA 1,4 DIENYL] 1H INDOL 3 YL]ETHYL]ACETAMIDE; N [2 [1 [4 HYDROXY 2 METHYL 5 (6 METHYLHEPT 5 EN 2 YL) 3,6 DIOXOCYCLOHEXA 1,4 DIENYL] 5 METHOXYL 1H INDOL 3 YL]ETHYL]ACETAMIDE; PEREZONE; PLANT EXTRACT; SULFORHODAMINE B; THIOBARBITURIC ACID REACTIVE SUBSTANCE; TRYPTOPHAN METHYL ESTER; UNCLASSIFIED DRUG;

ACOURTIA CUERNAVACANA; ADDITION REACTION; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHRONIC MYELOID LEUKEMIA; COLORECTAL CANCER; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LIPID PEROXIDATION; LUNG NON SMALL CELL CANCER; MALE; MEDICINAL PLANT; MYELOID LEUKEMIA; NONHUMAN; NUCLEOPHILICITY; PLANT ROOT; PROSTATE CANCER; PROTEIN STRUCTURE; RAT;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; BRAIN; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LIPID PEROXIDATION; MALE; RATS; RATS, WISTAR; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84865010570     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.07.027     Document Type: Article

References (38)

1. Noriega, J. M. (compilador). Escritos de Leopoldo Río de la Loza; Imprenta de Ignacio Escalante; México, 1911; pp 94-100.
2. F. Walls, J. Padilla, P. Joseph-Nathan, F. Giral, and J. Romo Tetrahedron Lett. 21 1965 1577
3. F. Walls, J. Padilla, P. Joseph-Nathan, F. Giral, M. Escobar, and J. Romo Tetrahedron 22 1966 2387
4. I.H. Sánchez, R. Yañez, R. Enríquez, and P. Joseph-Nathan J. Org. Chem. 46 1981 2818
5. R.G. Enríquez, B. Ortíz, E. Alducin, F. Walls, D. Gnecco, M. Yu, and W.F. Reynolds Nat. Prod. Res. 6 1995 103
6. F. Walls, M. Salmón, J. Padilla, P. Joseph-Nathan, and J. Romo Bol. Inst. Quim. Univ. Nac. Auton. Mex. XVII 1965 3
7. E.R. Wagner, R.D. Moss, R.M. Brooker, J.P. Heeschen, W.J. Potts, and M.L. Dilling Tetrahedron Lett. 47 1965 4233
8. D.A. Archer, and R.H. Thomson Chem. Commun. 14 1965 354
9. M. Soriano-García, R.A. Toscano, E. Flores-Valverde, F. Montoya-Vega, and I. López-Celis Acta Cryst. C42 1986 327
10. E. Cortés, M. Salmón, and F. Walls Bol. Inst. Quim. Univ. Autón. Méx. XVII 1965 19
11. I.H. Sánchez, S. Mendoza, M. Calderón, M.I. Larraza, and H.J. Flores J. Org. Chem. 50 1985 5077
12. E. García, V. Mendoza, and A. Guzmán J. Nat. Prod. 50 1987 1055
13. Hernández Magaña R.; Gally Jorda M. Plantas medicinales: usos y dosificación de las 184 plantas más usadas en América Latina. Ed. Pax: México, 2000.
14. F.J. Alarcón-Aguilar, R. Román-Ramos, M. Jiménez-Estrada, R. Reyes-Chilpa, B. González-Paredes, and J.L. Flores-Saenz J. Ethnopharmacol. 55 1997 171
15. A. De la Peña, R. Izaguirre, G. Baños, M. Viveros, R.G. Enríquez, and J.M. Fernández-G Phytomedicine 8 2001 465
16. J.F. Téllez, K. Carvajal, D. Cruz, A. Cárabez, and E. Chávez Life Sci. 65 1999 1615
17. R. Enríquez, J. Ortega, and X. Lozoya J. Ethnophamacol. 2 1980 389
18. X. García, G. Alcantara-Sarabia, L. Cartas-Heredia, and E. Gijón Gen. Pharmacol. 26 1995 1741
19. A. Carabez-T, and F. Sandoval-Z Arch. Biochem. Biophys. 260 1988 293
20. E. Chávez Archivos de cardiología de México 74 2004 S271
21. E. Burgueño-Tapia, L. Castillo, A. Gonzáles-Coloma, and P. Joseph-Nathan J. Chem. Ecol. 34 2008 766
22. Alonso D. Master Thesis, UAEM-UNAM, 2003.
23. L.E. Sánchez-Torres, J.A. Torres-Martínez, M. Godínez-Victoria, J.-M. Omar, and B. Velasco-Bejarano Phytomedicine 17 2010 614
24. R. Herrmann, W. Fayad, S. Schwarz, M. Berndtsson, and S. Linder J. Biomol. Screen. 13 2008 1
25. J.S. Gheeya, Q.R. Chen, C.D. Benjamin, A.T. Cheuk, P. Tsang, J.Y. Chung, B.B. Metaferia, T.C. Badgett, P. Johansson, J.S. Wei, S.M. Hewitt, and J. Khan Cancer Biol. Ther. 8 2009 2386
26. A. Galano, D. Tan, and R.J. Reiter J. Pineal Res. 51 2011 1
27. B. Di Giacomo, A. Bedini, G. Spadoni, G. Tarzia, F. Fraschini, M. Pannacci, and V. Lucini Bioorg. Med. Chem. 15 2007 4643
28. L. Lai, L. Yuan, Q. Chen, Ch. Dong, L. Mao, B. Rowan, T. Frasch, and S.M. Hill J. Pineal Res. 45 2008 476
29. S.R. Venkatachalam, A. Salaskar, A. Chattopadhyay, A. Barik, B. Mishra, R. Gangabhagirathi, and K.I. Priyadarsini Bioorg. Med. Chem. 14 2006 6414
30. G.L. Levit, L.V. Anikina, Y.B. Vikharev, A.M. Demin, V.A. Safin, T.V. Matveeva, and V.P. Krasnov Pharm. Chem. J. 36 2002 232
31. M.C. Lozada, R.G. Enríquez, C.E. Lobato, B. Ortíz, M. Soriano, D. Gnecco, and W.F. Reynolds Heterocycles 65 2005 49
32. A. Rodríguez-Hernández, H. Barrios, O. Collera, R.G. Enríquez, B. Ortíz, R. Sánchez-Obregón, F. Walls, F. Yuste, W.F. Reynolds, and M. Yu Nat. Prod. Lett. 4 1994 133
33. Y. Kanaoka, E. Sato, and Y. Ban Chem. Pharm. Bull. 15 1967 101
34. Y. Li, X.F. Li, D.S. Kim, H.D. Choi, and B.W. Son Arch. Pharm. Res. 26 2003 21
35. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo, and M. Boyd J. Natl. Cancer Inst. 83 1991 757
36. J.I. Rossato, L.A. Ketzer, F.B. Centuriao, S.J.N. Silva, D.S. Ludtke, G. Zeni, A.L. Braga, M.A. Rubin, and J.B.T. Rocha Neurochem. Res. 27 2002 297
37. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall J. Biol. Chem. 193 1951 265
38. H. Ohkawa, N. Ohishi, and K. Yagi Anal. Biochem. 95 1979 351