Design and Synthesis of Two Indol-Steroid Derivatives

L. Figueroa-Valverde; F. Díaz-Cedillo; E. García-Cervera; E.  Pool Gómez; M. Rosas-Nexticapa; M. López-Ramos

doi:10.14233/ajchem.2014.1626

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Issue Published : July 28, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Design and Synthesis of Two Indol-Steroid Derivatives

https://doi.org/10.14233/ajchem.2014.1626

L. Figueroa-Valverde

Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., México

F. Díaz-Cedillo

Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala s/n Col. Santo Tomas, D.F. C.P. 11340, México

E. García-Cervera

Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., México

E. Pool Gómez

Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., México

M. Rosas-Nexticapa

Facultad de Nutrición, Universidad Veracruzana. Médicos y Odontólogos s/n, 91010, Xalapa, Veracruz, México

M. López-Ramos

Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., México

Corresponding Author(s) : L. Figueroa-Valverde

lauro_1999@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 16 (2014): Vol 26 Issue 16
Article Published : July 28, 2014

Abstract

In this study two new indol-steroid derivatives were synthesized. The first stage involves the synthesis of 17-(2-amino-thiazol-5-yl)-10,13-dimethyl-1,2-6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (3) by the reaction of progesterone with thiourea using I₂ as catalyst. The second stage was achieved by reaction of a brucine derivative with the compound 3 to form the compound N-(2,3-dimethoxystrychnidin-10-ylenamino)-N'-[10,13-dimethyl-17(2-amino-thiazol-5-yl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta-[a]phenanthren-3-ylidene]-ethane-1,2-diamine using boric acid as catalyst. The third stage was achieved by reaction of compound 3 with brucine to form 10,13-dimethyl-17-[2-(2,3- dimethoxy-strychnidin-10-ylideneamino)-thiazol-5-yl]-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-onausing boric acid as catalyst. The structure of compounds obtained was confirmed by spectrometry data.

Keywords

Design Synthesis Indol-steroid

Figueroa-Valverde, L., Díaz-Cedillo, F., García-Cervera, E., Pool Gómez, E., Rosas-Nexticapa, M., & López-Ramos, M. (2014). Design and Synthesis of Two Indol-Steroid Derivatives. Asian Journal of Chemistry, 26(16), 4959–4962. https://doi.org/10.14233/ajchem.2014.1626

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References

M.C. Rodríguez-Argüelles, E.C. López-Silva, J. Sanmartín, P. Pelagatti and F. Zani, J. Inorg. Biochem., 99, 2231 (2005); doi:10.1016/j.jinorgbio.2005.07.018.
T.C. Leboho, J.P. Michael, W.A.L. van Otterlo, S.F. van Vuuren and C.B. de Koning, Bioorg. Med. Chem. Lett., 19, 4948 (2009); doi:10.1016/j.bmcl.2009.07.091.
R.C. Larock and E.K. Yum, J. Am. Chem. Soc., 113, 6689 (1991); doi:10.1021/ja00017a059.
S.-L. Cui, J. Wang and Y.-G. Wang, J. Am. Chem. Soc., 130, 13526 (2008); doi:10.1021/ja805706r.
M.C. Fagnola, I. Candiani, G. Visentin, W. Cabri, F. Zarini, N. Mongelli and A. Bedeschi, Tetrahedron Lett., 38, 2307 (1997); doi:10.1016/S0040-4039(97)00300-6.
D. Lee, C. Cho, J. Kim, Y. Youn, S. Shim and H. Song, Bull. Korean Chem. Soc., 17, 1132 (1996).
A. Yasuhara, Y. Kanamori, M. Kaneko, A. Numata, Y. Kondo and T. Sakamoto, J. Chem. Soc. Perkin Trans., 529 (1999); doi:10.1039/a808842j.
V.M.A. Moreira, T.S. Vasaitis, V.C.O. Njar and J.A.R. Salvador, Steroids, 72, 939 (2007); doi:10.1016/j.steroids.2007.08.004.
R. Haugland, J. Yguerabide and L. Stryer, Proc. Natl. Acad. Sci. USA, 63, 23 (1969); doi:10.1073/pnas.63.1.23.
J. Samu, J. Botyanszki, H. Duddeck and G. Snatzke, Liebigs Ann. Chem., 1225 (1993); doi:10.1002/jlac.1993199301198.
L. Figueroa-Valverde, F. Diaz-Cedillo and E. Garcia-Cerver, Bulgarian Chem. Comm., 44, 83 (2012).
L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos, E. García-Cervera and E. Pool-Gómez, Asian J. Chem, 24, 2173 (2012).
R. Mannhold and H. Van de Waterbeemd, J. Comput. Aided Mol. Des., 15, 337 (2001); doi:10.1023/A:1011107422318.
T. Österberg and U. Norinder, Eur. J. Pharm. Sci., 12, 327 (2001); doi:10.1016/S0928-0987(00)00189-5.
D. Boger and J. McKie, J. Org. Chem., 60, 1271 (1995); doi:10.1021/jo00110a034.
M. Gallant, J.T. Link and S.J. Danishefsky, J. Org. Chem., 58, 343 (1993); doi:10.1021/jo00054a015.
A. Shirayev, I. Moiseev and S. Karpeev, ARKIVOC, 199 (2004); doi:10.3998/ark.5550190.0006.416.
D. Jean-Noël Uppiah, M.G. Bhowon and J. Laulloo, E-J. Chem., 6, 195 (2009); doi:10.1155/2009/636707.
M. Hania, E-J. Chem., 6, 629 (2009); doi:10.1155/2009/104058.
L. Figueroa-Valverde, F. Díaz-Cedillo, E. García-Cervera, E. Pool-Gómez and M. López-Ramos, Bulgarian Chem. Comm., 45, 71 (2013).

References

M.C. Rodríguez-Argüelles, E.C. López-Silva, J. Sanmartín, P. Pelagatti and F. Zani, J. Inorg. Biochem., 99, 2231 (2005); doi:10.1016/j.jinorgbio.2005.07.018.

T.C. Leboho, J.P. Michael, W.A.L. van Otterlo, S.F. van Vuuren and C.B. de Koning, Bioorg. Med. Chem. Lett., 19, 4948 (2009); doi:10.1016/j.bmcl.2009.07.091.

R.C. Larock and E.K. Yum, J. Am. Chem. Soc., 113, 6689 (1991); doi:10.1021/ja00017a059.

S.-L. Cui, J. Wang and Y.-G. Wang, J. Am. Chem. Soc., 130, 13526 (2008); doi:10.1021/ja805706r.

M.C. Fagnola, I. Candiani, G. Visentin, W. Cabri, F. Zarini, N. Mongelli and A. Bedeschi, Tetrahedron Lett., 38, 2307 (1997); doi:10.1016/S0040-4039(97)00300-6.

D. Lee, C. Cho, J. Kim, Y. Youn, S. Shim and H. Song, Bull. Korean Chem. Soc., 17, 1132 (1996).

A. Yasuhara, Y. Kanamori, M. Kaneko, A. Numata, Y. Kondo and T. Sakamoto, J. Chem. Soc. Perkin Trans., 529 (1999); doi:10.1039/a808842j.

V.M.A. Moreira, T.S. Vasaitis, V.C.O. Njar and J.A.R. Salvador, Steroids, 72, 939 (2007); doi:10.1016/j.steroids.2007.08.004.

R. Haugland, J. Yguerabide and L. Stryer, Proc. Natl. Acad. Sci. USA, 63, 23 (1969); doi:10.1073/pnas.63.1.23.

J. Samu, J. Botyanszki, H. Duddeck and G. Snatzke, Liebigs Ann. Chem., 1225 (1993); doi:10.1002/jlac.1993199301198.

L. Figueroa-Valverde, F. Diaz-Cedillo and E. Garcia-Cerver, Bulgarian Chem. Comm., 44, 83 (2012).

L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos, E. García-Cervera and E. Pool-Gómez, Asian J. Chem, 24, 2173 (2012).

R. Mannhold and H. Van de Waterbeemd, J. Comput. Aided Mol. Des., 15, 337 (2001); doi:10.1023/A:1011107422318.

T. Österberg and U. Norinder, Eur. J. Pharm. Sci., 12, 327 (2001); doi:10.1016/S0928-0987(00)00189-5.

D. Boger and J. McKie, J. Org. Chem., 60, 1271 (1995); doi:10.1021/jo00110a034.

M. Gallant, J.T. Link and S.J. Danishefsky, J. Org. Chem., 58, 343 (1993); doi:10.1021/jo00054a015.

A. Shirayev, I. Moiseev and S. Karpeev, ARKIVOC, 199 (2004); doi:10.3998/ark.5550190.0006.416.

D. Jean-Noël Uppiah, M.G. Bhowon and J. Laulloo, E-J. Chem., 6, 195 (2009); doi:10.1155/2009/636707.

M. Hania, E-J. Chem., 6, 629 (2009); doi:10.1155/2009/104058.

L. Figueroa-Valverde, F. Díaz-Cedillo, E. García-Cervera, E. Pool-Gómez and M. López-Ramos, Bulgarian Chem. Comm., 45, 71 (2013).

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Design and Synthesis of Two Indol-Steroid Derivatives

Corresponding Author(s) : L. Figueroa-Valverde

Abstract

Keywords

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