Synthesis of Two Benzamide-Androgen Derivatives

Lauro Figueroa-Valverde; Francisco Díaz-Cedillo; Elodia García-Cervera; Eduardo  Pool-Gómez; Marcela Rosas-Nexticapa; Lenin Hau-Heredia; Betty Sarabia-Alcocer

doi:10.14233/ajchem.2015.17887

Issue

Vol. 27 No. 5 (2015): Vol 27 Issue 5

Issue Published : February 20, 2015

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

Synthesis of Two Benzamide-Androgen Derivatives

https://doi.org/10.14233/ajchem.2015.17887

Lauro Figueroa-Valverde

Laboratory 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

Francisco Díaz-Cedillo

Escuela 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, México

Elodia García-Cervera

Laboratory 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

Eduardo Pool-Gómez

Laboratory 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

Marcela Rosas-Nexticapa

Facultad de Nutrición, Universidad Veracruzana, Médicos y Odontologos s/n C.P. 91010, Unidad del Bosque, Xalapa, Veracruz, México

Lenin Hau-Heredia

Laboratory 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

Betty Sarabia-Alcocer

Faculty of Medicine, University Autonomous of Campeche, Av. Patricio Trueba de Regil s/n, Col Lindavista C.P.24090 Campeche Cam., México

Corresponding Author(s) : Lauro Figueroa-Valverde

lauro_1999@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 5 (2015): Vol 27 Issue 5
Article Published : February 20, 2015

Abstract

In this study, two benzamide-androgen derivatives (N-(3-butyl-1-cyclohexyl-4-cyclohexylimino-azetidin-2-ylidene)-N´-[2-(17-hydroxy-10,13-dimethyl-hexadecahydro-cyclo penta[a]phenanthren-3- ylideneamino)ethyl]-4-(naphtalen-2-yloxy)benzamide and N-(3-butyl-1-cyclohexyl-4- cyclohexyliminoazetidin-2-ylidene)-N´-[2-(3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ylideneamino)ethyl]-4-(naphtalen-2-yloxy)benzamide were synthesized using some strategies. The structure of the compounds was confirmed by elemental analysis, spectroscopy and spectrometry data. The proposed method offers some advantages such as simple procedure, low cost and ease of workup.

Keywords

Dihydrotestosterone androsterone Boric acid

Figueroa-Valverde, L., Díaz-Cedillo, F., García-Cervera, E., Pool-Gómez, E., Rosas-Nexticapa, M., Hau-Heredia, L., & Sarabia-Alcocer, B. (2015). Synthesis of Two Benzamide-Androgen Derivatives. Asian Journal of Chemistry, 27(5), 1781–1785. https://doi.org/10.14233/ajchem.2015.17887

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References

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References

M.I. Merlani, L.S. Amiranashvili, E.P. Kemertelidze, K. Papadopulos and E. Yannakopulu, Chem. Nat. Comp., 42, 313 (2006); doi:10.1007/s10600-006-0108-4.

S. Top, C. Thibaudeau, A. Vessieres, E. Brule, F. Le-Bideau, J. Joerger, M.-A. Plamont, S. Samreth, A. Edgar, J. Marrot, P. Herson and G. Jaouen, J. Organomet., 28, 1414 (2009); doi:10.1021/om800698y.

E. Mappus, C. Chambon, B. Fenet, M. Ravel, C. Grenot and C. Cuilleron, Steroids, 65, 459 (2000); doi:10.1016/S0039-128X(00)00106-9.

L. Figueroa-Valverde, F. Díaz-Cedillo, E. García-Cervera, E. Pool-Gómez, M. López-Ramos, M. Rosas-Nexticapa and R. Martinez-Camacho, Arch. Pharm. Res., 36, 1270 (2013); doi:10.1007/s12272-013-0166-7.

L. Figueroa-Valverde and F. Díaz-Cedillo, Int. J. ChemTech Res, 2, 1553 (2010).

L. Figueroa-Valverde and F. Díaz-Cedillo, Int. J. ChemTech Res, 2, 2163 (2010).

Y. Ling, J. Li, Y. Liu, K. Kato, G.T. Klus and A. Brodie, J. Med. Chem., 40, 3297 (1997); doi:10.1021/jm970337k.

P. Ács, B. Jakab, A. Takács and L. Kollár, Steroids, 72, 627 (2007); doi:10.1016/j.steroids.2007.04.004.

R. Waelchli, B. Bollbuck, C. Bruns, T. Buhl, J. Eder, R. Feifel, R. Hersperger, P. Janser, L. Revesz, H.-G. Zerwes and A. Schlapbach, Bioorg. Med. Chem. Lett., 16, 108 (2006); doi:10.1016/j.bmcl.2005.09.035.

H.F. Kung, R. Kasliwal, S. Pan, M.P. Kung, R.H. Mach and Y.Z. Guo, J. Med. Chem., 31, 1039 (1988); doi:10.1021/jm00400a027.

H.M. König, R. Abbel, D. Schollmeyer and A.F.M. Kilbinger, Org. Lett., 8, 1819 (2006); doi:10.1021/ol0603357.

X. Xu, D. Cheng, J. Li, H. Guo and J. Yan, Org. Lett., 9, 1585 (2007); doi:10.1021/ol070485x.

J. Beck, Tetrahedron, 34, 2057 (1978); doi:10.1016/0040-4020(78)89004-8.

T. Takekoshi, J.G. Wirth, D.R. Heath, J.E. Kochanowski, J.S. Manello and M.J. Webber, J. Polym. Sci., Polym. Phys. Ed., 18, 3069 (1980); doi:10.1002/pol.1980.170181016.

N. Kornblum and S. Boyd, J. Am. Chem. Soc., 92, 5784 (1970); doi:10.1021/ja00722a067.

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

D.J. Noel Uppiah, M.G. Bhowon and S. Jhaummer Laulloo, E-J. Chem., 6, S195 (2009); doi:10.1155/2009/636707.

Issue

Vol. 27 No. 5 (2015): Vol 27 Issue 5

Synthesis of Two Benzamide-Androgen Derivatives

Corresponding Author(s) : Lauro Figueroa-Valverde

Abstract

Keywords

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