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A Facile Synthesis of Two Brucine-Steroid Derivatives
Corresponding Author(s) : Lauro Figueroa-Valverde
Asian Journal of Chemistry,
Vol. 25 No. 4 (2013): Vol 25 Issue 4
Abstract
In this study, two brucine-steroid derivative were synthesized. In first stage, the brucine-androsterone derivative was development by the reaction of N1-(2,3-dimethoxystrychnidin-10-yliden)-ethane-1,2-diamine and androsteronehemisuccinate using as catalyst a carbodiimide derivative. The second stage was achieved by the reaction of N1-(2,3-dimethoxystrychnidin-10-yliden)-ethane-1,2-diamine with b-estradiol 17-hemisuccinate to form the brucine-estradiol conjugatein presence of a carbodiimide derivative. In conclusion, in this study we show a facile procedure for synthesis of two brucine-steroid derivatives.
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- K. Zahn, N. Eckstein, C. Tränkle, W. Sadée and K. Mohr, J. Pharm. Exp. Ter., 301, 2720 (2002).
- A. Black and P. Vogel, Helv. Chim Acta, 67, 1612 (1984).
- H.Y. Kim, H.-J. Shih, W.E. Knabe and K.S. Oh, Angew. Chem., 121, 7556 (2009).
- J. Show and T. Hooker, Can. J. Chem., 56, 1222 (1978).
- N. Birdsall, T. Farries, P. Gharagozloo, S. Kobayashi, S. Lazareno and M. Sugimoto, Mol. Pharm., 55, 778 (1999).
- S. Findlay, J. Am. Chem. Soc., 73, 3008 (1951).
- K. Záruba and V. Král, Tetrahedron Asym., 13, 2567 (2002).
- S. Graham, U. Wemuth and J. White, Acta Cryst., C62, o353 (2006).
- K. Záruba, J. Králová, Pa. Rezanka, P. Poucková, L. Veverková and V. Král, Org. Biomol. Chem., 8, 3202 (2010).
- L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos, E. GarcíaCervera and E. Pool Gómez, Asian J. Chem., 25, 1405 (2013).
- L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos, E. GarcíaCervera, E. Pool Gómez and R. Torres-Cutz, Asian J. Chem., 24 2321 (2012) .
- L. Figueroa, F. Díaz, A. Camacho, E. Díaz and M. Marvin, Biomédica, 29, 625 (2009).
- A. Medvedeva, M. Andreev, L. Safronova and G. Sarapulova, Arkivoc, 143 (2001).
- D. Levin, Org. Process. Res. Dev., 1, 182 (1997).
- N. DeSilva, Am. J. Respir. Cell. Mol. Biol., 29, 757 (2003).
- L. Figueroa-Valverde, F. Díaz-Cedillo, L. Tolosa, G. Maldonado and G. Ceballos-Reyes, J. Mex. Chem. Soc., 50, 42 (2006).
References
K. Zahn, N. Eckstein, C. Tränkle, W. Sadée and K. Mohr, J. Pharm. Exp. Ter., 301, 2720 (2002).
A. Black and P. Vogel, Helv. Chim Acta, 67, 1612 (1984).
H.Y. Kim, H.-J. Shih, W.E. Knabe and K.S. Oh, Angew. Chem., 121, 7556 (2009).
J. Show and T. Hooker, Can. J. Chem., 56, 1222 (1978).
N. Birdsall, T. Farries, P. Gharagozloo, S. Kobayashi, S. Lazareno and M. Sugimoto, Mol. Pharm., 55, 778 (1999).
S. Findlay, J. Am. Chem. Soc., 73, 3008 (1951).
K. Záruba and V. Král, Tetrahedron Asym., 13, 2567 (2002).
S. Graham, U. Wemuth and J. White, Acta Cryst., C62, o353 (2006).
K. Záruba, J. Králová, Pa. Rezanka, P. Poucková, L. Veverková and V. Král, Org. Biomol. Chem., 8, 3202 (2010).
L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos, E. GarcíaCervera and E. Pool Gómez, Asian J. Chem., 25, 1405 (2013).
L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos, E. GarcíaCervera, E. Pool Gómez and R. Torres-Cutz, Asian J. Chem., 24 2321 (2012) .
L. Figueroa, F. Díaz, A. Camacho, E. Díaz and M. Marvin, Biomédica, 29, 625 (2009).
A. Medvedeva, M. Andreev, L. Safronova and G. Sarapulova, Arkivoc, 143 (2001).
D. Levin, Org. Process. Res. Dev., 1, 182 (1997).
N. DeSilva, Am. J. Respir. Cell. Mol. Biol., 29, 757 (2003).
L. Figueroa-Valverde, F. Díaz-Cedillo, L. Tolosa, G. Maldonado and G. Ceballos-Reyes, J. Mex. Chem. Soc., 50, 42 (2006).