Design and Synthesis of Estrogen Derivative

L. Figueroa-Valverde; F. Diaz-Cedillo; E. Garcia-Cervera; E. Pool Gomez; M. Rosas-Nexticapa; R. Mendoza-L&oacute;pez4; M. Lopez-Ramos; I. May-Gil

doi:10.14233/ajchem.2014.15744

Issue

Vol. 26 No. 4 (2014): Vol 26 Issue 4

Issue Published : February 15, 2014

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

Design and Synthesis of Estrogen Derivative

https://doi.org/10.14233/ajchem.2014.15744

L. Figueroa-Valverde

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

F. Diaz-Cedillo

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

E. Garcia-Cervera

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

E. Pool Gomez

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

M. Rosas-Nexticapa

Facultad de Nutrición, Universidad Veracruzana, Médicos y Odontólogos s/n, 91010, Xalapa, Veracruz, México4Unidad de Servicios de Apoyo en Resolucion Analitica, Universidad Veracruzana, Luis Castelazo Ayala s/n, Col. Industrial Animas, 91190, Xalapa, Veracruz, Mexico

R. Mendoza-López4

1Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P. 24039 Campeche Cam., México 2Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala s/n Col. Santo Tomas, México, D.F. C.P. 11340. 3Facultad de Nutrición, Universidad Veracruzana, Médicos y Odontólogos s/n, 91010, Xalapa, Veracruz, México 4Unidad de Servicios de Apoyo en Resolución Analítica, Universidad Veracruzana, Luis Castelazo Ayala s/n, Col. Industrial Animas, 91190, Xalapa, Veracruz, México *Corresponding author: E-mail: lauro_1999@yahoo.com

M. Lopez-Ramos

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

I. May-Gil

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

Corresponding Author(s) : L. Figueroa-Valverde

lauro_1999@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 4 (2014): Vol 26 Issue 4
Article Published : February 14, 2014

Abstract

In this study, an estrogen derivative was synthesized. The first stage involves the synthesis of 17-(2-amino-ethylimino)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[ a]phenanthren-3-ol (3) by the reaction of estrone with ethylenediamine using boric acid as catalyst. The second stage was achieved by reaction of compound 3 with chloroacetyl chloride in presence of triethylamine to form N-{2-[(3-chloro-2-oxo-cyclobutyl)-(3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-amino]ethylcarbamic chloride (5). The third stage was achieved by reaction of compound 5 with thiourea to form 2-[(2-amino-ethyl)-(3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16-17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)amino]-4-chloro-cyclobutanone (7) in methanol. The structures of compounds obtained were confirmed by spectroscopically.

Keywords

Estrogen Estrone Thiourea Ethylenediamine

Figueroa-Valverde, L., Diaz-Cedillo, F., Garcia-Cervera, E., Pool Gomez, E., Rosas-Nexticapa, M., Mendoza-López4, R., … May-Gil, I. (2014). Design and Synthesis of Estrogen Derivative. Asian Journal of Chemistry, 26(4), 1007–1010. https://doi.org/10.14233/ajchem.2014.15744

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References

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M. Hania, E-J. Chem., 6, 629 (2009); doi:10.1155/2009/104058.
L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos, E. García-Cervera and E. Pool Gómez, Asian J. Chem., 24, 2173 (2012).
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References

J.A. Katzenellenbogen, R.J. McGorrin, T. Tatee, R.J. Kempton, K.E. Carlson and D.H. Kinder, J. Med. Chem., 24, 435 (1981); doi:10.1021/jm00136a013.

L. Luyt, H. Bigott, M. Welch and J. Katzenellenbogen, Bioorg. Med. Chem. Lett., 11, 4977 (2003); doi:10.1016/j.bmc.2003.09.004.

S. Schwarz, I. Thieme, M. Richter, B. Undeutsch, H. Henkel and W. Elger, Steroids, 61, 710 (1996); doi:10.1016/S0039-128X(96)00200-0.

M. Leese, S. Newman, A. Purohit, M.J. Reed and B.V.L. Potter, Bioorg. Med. Chem. Lett., 14, 3135 (2004); doi:10.1016/j.bmcl.2004.04.027.

H. Ali and J.E. van Lier, Bioorg. Med. Chem. Lett., 12, 2847 (2002);doi: 10.1016/S0960-894X(02)00634-0.

S. Top, H. El Hafa, A. Vessières, M. Huché, J. Vaissermann and G. Jaouen, Chem. Eur. J., 8, 5241 (2002); doi:10.1002/1521-3765(20021115)8:22<5241::AID-CHEM5241>3.0.CO;2-M.

L. Prokai, S.-M. Oon, K. Prokai-Tatrai, K.A. Abboud and J.W. Simpkins, J. Med. Chem., 44, 110 (2001);doi:10.1021/jm000280t.

M. Adamczyk, D.D. Johnson and R.E. Reddy, Bioconjug. Chem., 9, 403 (1998); doi:10.1021/bc970203l.

B. Barlaam, J. Boivin, L. Elkaim, S. Elton-Farr and S.Z. Zard, Tetrahedron, 51, 1675 (1995); doi:10.1016/0040-4020(94)01034-W.

L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos, E. García-Cervera and E. Pool-Gómez, Afr. J. Pharm. Pharmacol., 14, 1703 (2011).

H. Ali, J. Rousseau and J.E. van Lier, J. Med. Chem., 36, 3061 (1993); doi:10.1021/jm00073a004.

S. Hussey S. MuddanaB. Peterson. S.L. Hussey, S.S. Muddana and B.R. Peterson, J. Am. Chem. Soc., 125, 3692 (2003); doi:10.1021/ja0293305.

V. Perron, D. Rabouin, E. Asselin, S. Parent, R. Gaudreault and G. Bérubé, Bioorg.Chem.,33, 1 (2005);doi:10.1016/j.bioorg.2004.06.009.

H. Enginar, P. Unak, F. Lambrecht and Z. Biber, J. Radioanal. Nucl. Chem., 260, 339 (2004);doi: 10.1023/B:JRNC.0000027107.43043.37.

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

D. Jean -Noël uppiah, M. Gupta Bhowon and Jhaumeer Laulloo, E-J. Chem., 6, S195 (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, M. López-Ramos, E. García-Cervera and E. Pool Gómez, Asian J. Chem., 24, 2173 (2012).

G.A. Hiegel, T.J. Hogenauer and J.C. Lewis, Synth. Commun., 35, 2099 (2005);doi: 10.1081/SCC-200066703.

A. Katritzky, S. Majumder and R. Jain, ARKIVOC, 74 (2003); doi:10.3998/ark.5550190.0004.c09.

A. Harte and T. Gunnlaugsson, Tetrahedron Lett., 47, 6321 (2006); doi:10.1016/j.tetlet.2006.06.090.

S. Katke, S. Amrutkar, R. Bhor and M. Khairnar, Int. J. Pharm. Sci. Res., 2, 148 (2011).

W. Steglich and H.-G. Batz, Angew.Chem. Intern.10, , 10, 75 (1971); doi:10.1002/anie.197100752.

J. Glass, M. pelzing and C. Pande, Int. J. Pept. Protein Res., 28, 13 (1979).

M. MasakiT. KitaharaH. KuritaM. Ohta. M. Masaki, T. Kitahara, H. Kurita and M. Ohta, J. Am. Chem. Soc., 90, 4508 (1968); doi:10.1021/ja01018a088.

M. Bertolini and C.P.J. Glaudemans, Carbohydrate Res., 15, 263 (1970);doi:10.1016/S0008-6215(00)88010-6.

Issue

Vol. 26 No. 4 (2014): Vol 26 Issue 4

Design and Synthesis of Estrogen Derivative

Corresponding Author(s) : L. Figueroa-Valverde

Abstract

Keywords

Full Article

Download Citation

References

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