Design and Synthesis of New Steroid-Derivatives with Antibacterial Activity on Salmonella typhi

L. Figueroa-Valverde; E. García-Cervera; F. Díaz-Cedillo; L. Hau-heredia; M. Rosas-Nexticapa; E. Pool-Gómez; M. López-Ramos; A. Camacho-Luis

doi:10.14233/ajchem.2016.19599

Issue

Vol. 28 No. 11 (2016): Vol 28 Issue 11

Issue Published : August 10, 2016

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

Design and Synthesis of New Steroid-Derivatives with Antibacterial Activity on Salmonella typhi

https://doi.org/10.14233/ajchem.2016.19599

L. Figueroa-Valverde

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

E. García-Cervera

Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences from 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, México, D.F. C.P. 11340

L. Hau-heredia

Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences from 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, XalapaVeracruz, México

E. Pool-Gómez

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

M. López-Ramos

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

A. Camacho-Luis

Facultad de Medicina y Nutrición, Universidad Juárez del Estado de Durango. Av. Universidad esq. Fany anitúa, C.P. 34000, Durango, México

Corresponding Author(s) : L. Figueroa-Valverde

lauro_1999@yahoo.com

Asian Journal of Chemistry, Vol. 28 No. 11 (2016): Vol 28 Issue 11
Article Published : August 11, 2016

Abstract

In this study, the following estrogen derivatives were synthesized; oxazin-estradiol-3,17-diol (6), oxazine-estradiol-3,17-diylbis-2-chloroacetate (8), chloro-acetic acid-estradiol ester (9), 3,17-bis-(tert-butyl-dimethyl-silanyloxy)-estradiol-1,2-diamine (10) and 3,17-bis-(tert-butyl-dimethyl-silanyloxy)-estradiol-chloro-acetamide (11) using several strategies. The structure of compounds obtained was confirmed by elemental analysis, spectroscopy and spectrometry data. On the other hand, antibacterial activity of compounds synthesized was evaluated on Salmonella typhi with broth dilution methods to determine the minimal inhibitory concentration using gentamycin, ciprofloxacin and cefotaxime as controls. The results indicate that only the compounds 6, 9, 10 and 11 decrease the growth of Salmonella typhi. The methods used for synthesis of estrogen derivatives offers some advantages such as simple procedure, low cost and ease of workup. In addition, the antibacterial activity showed the compounds 6, 9, 10 and 11 depend on chemical structure in comparison with the controls involved. These estrogenic derivatives could be used as a therapeutic alternative for treatment of infectious diseases induced by Salmonella typhi.

Keywords

Estrogen derivative Estradiol Chloroacetyl chloride Salmonella typhi

Figueroa-Valverde, L., García-Cervera, E., Díaz-Cedillo, F., Hau-heredia, L., Rosas-Nexticapa, M., Pool-Gómez, E., … Camacho-Luis, A. (2016). Design and Synthesis of New Steroid-Derivatives with Antibacterial Activity on Salmonella typhi. Asian Journal of Chemistry, 28(11), 2357–2364. https://doi.org/10.14233/ajchem.2016.19599

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References

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References

M.K. Bhan, R. Bahl and S. Bhatnagar, Lancet, 366, 749 (2005); doi:10.1016/S0140-6736(05)67181-4.

B. Rowe, L.R. Ward and E.J. Threlfall, Clin. Infect. Dis., 24(Suppl. 1), S106 (1997); doi:10.1093/clinids/24.Supplement_1.S106.

P. Roumagnac, F.-X. Weill, C. Dolecek, S. Baker, S. Brisse, N.T. Chinh, T.A.H. Le, C.J. Acosta, J. Farrar, G. Dougan and M. Achtman, Science, 314, 1301 (2006); doi:10.1126/science.1134933.

J. Wain, N.T.T. Hoa, N.T. Chinh, H. Vinh, M.J. Everett, T.S. Diep, N.P.J. Day, T. Solomon, N.J. White, L.J.V. Piddock and C.M. Parry, Clin. Infect. Dis., 25, 1404 (1997); doi:10.1086/516128.

P.D. Fey, T.J. Safranek, M.E. Rupp, E.F. Dunne, E. Ribot, P.C. Iwen, P.A. Bradford, F.J. Angulo and S.H. Hinrichs, N. Engl. J. Med., 342, 1242 (2000); doi:10.1056/NEJM200004273421703.

S. Sridhar, M. Saravanan and A. Ramesh, Eur. J. Med. Chem., 36, 615 (2001); doi:10.1016/S0223-5234(01)01255-7.

E. Konadu, J. Shilaoach, D. Bryla, J. Robbins and S. Szu, Infect. Immun., 64, 2709 (1996).

S.A. Khan, P. Kumar, R. Joshi, P.F. Iqbal and K. Saleem, Eur. J. Med. Chem., 43, 2029 (2008); doi:10.1016/j.ejmech.2007.12.004.

S.A. Khan, Eur. J. Med. Chem., 43, 2040 (2009); doi:10.1016/j.ejmech.2007.12.008.

S.A. Khan, N. Singh and K. Saleem, Eur. J. Med. Chem., 43, 2272 (2008); doi:10.1016/j.ejmech.2007.12.012.

H. Kim, K. Kwon, K. Kim and C. Lee, Bioorg. Med. Chem. Lett., 11, 3065 (2001); doi:10.1016/S0960-894X(01)00632-1.

L. Figueroa-Valverde, F. Díaz-Cedillo, M. López-Ramos and E. García-Cervera, Asian J. Chem., 23, 2157 (2011).

L. Figueroa-Valverde, F. Díaz-Cedillo, A. Camacho-Luis, M.L. Ramos, E.G. Cervera, Monatsh. Chem., 141, 373 (2010); doi:10.1007/s00706-010-0263-y.

C. Hocht, L. Opezzo and S. Gorzalczany, Rev. Argent. Cardiol., 67, 769 (1999).

Z. Turgut, E. Pelit and A. Köycü, Molecules, 12, 345 (2007); doi:10.3390/12030345.

D. Ondré, J. Wölfling, I. Tóth, M. Szécsi, J. Julesz and G. Schneider, Steroids, 74, 1025 (2009); doi:10.1016/j.steroids.2009.08.001.

H.A. Ahangar, G.H. Mahdavinia, K. Marjani and A. Hafezian, J. Iran. Chem. Soc., 7, 770 (2010); doi:10.1007/BF03246067.

P.Y. Johnson, R.B. Silver and M.M. Davis, J. Org. Chem., 38, 3753 (1973); doi:10.1021/jo00961a023.

R.M. McDonald and R.A. Krueger, J. Org. Chem., 31, 488 (1966); doi:10.1021/jo01340a032.

S.A. Guillén-Castellanos, J.S. Parent and R.A. Whitney, Macromolecules, 39, 2514 (2006); doi:10.1021/ma051898l.

V. Lillo, M.J. Geier, S.A. Westcott and E. Fernández, Org. Biomol. Chem., 7, 4674 (2009); doi:10.1039/b909341a.

F.-V. Lauro, D.-C. Francisco, G.-C. Elodia, P.-G. Eduardo, L.-R. Maria, R.-N. Marcela, H.-H. Lenin and S.-A. Beatriz, Orient. J. Chem., 30, 947 (2014); doi:10.13005/ojc/300305.

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

A.R. 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.

D. Phillipou, D. Bigham and R. Seamark, Steroids, 26, 516 (1975); doi:10.1016/0039-128X(75)90071-9.

Issue

Vol. 28 No. 11 (2016): Vol 28 Issue 11

Design and Synthesis of New Steroid-Derivatives with Antibacterial Activity on Salmonella typhi

Corresponding Author(s) : L. Figueroa-Valverde

Abstract

Keywords

Full Article

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