title: Synthesis and antibacterial activity evaluation of two androgen derivatives.
abstract: In this study two androgen derivatives were synthesized using several strategies; the first stage an aza-steroid derivative (3) was developed by the reaction of a testosterone derivative (1) with thiourea (2) in presence of hydrogen chloride. The second step, involves the synthesis of an amino-steroid derivative (4) by the reaction of 1 with 2 using boric acid as catalyst. The third stage was achieved by the preparation of an aminoaza-androgen derivative (6) by the reaction of 3 with ethylenediamine using boric acid as catalyst. In addition, the compound 6 was made reacting with dihydrotestosterone to form a new androgen derivative (7) in presence of boric acid. The following step was achieved by the reaction of 7 with chloroacetyl chloride to synthesize an azetidinone-androgen derivative (8) using triethylamine as catalyst. Additionally, a thiourea-androgen derivative (9) was synthetized by the reaction of 4 with dihydrotestosterone using boric acid as catalyst. Finally, the compound 9 was made reacting with chloroacetyl chloride in presence of triethylamine to synthesize a new azetidinone-androgen derivative (10). On the other hand, antibacterial activity of compounds synthesized was evaluated on Gram negative (Escherichia coli and Vibrio cholerae) and Gram positive (Staphylococos aureus) bacteria. The results indicate that only the compound 3 and 8 decrease the growth bacterial of E. coli and V. cholerae. Nevertheless, growth bacterial of S. aureus was not inhibited by these compounds. These data indicate that antibacterial activity exerted by the compounds 3 and 8 depend of their structure chemical in comparison with the controls and other androgen derivatives that are involved in this study.
authors.affiliation: 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., Mexico. Electronic address: lauro_1999@yahoo.com.
authors.forename: Figueroa-Valverde
authors.initials: FV
authors.lastname: Lauro
authors.affiliation: 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, Mexico.
authors.forename: Díaz-Cedillo
authors.initials: DC
authors.lastname: Francisco
authors.affiliation: 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., Mexico.
authors.forename: García-Cervera
authors.initials: GC
authors.lastname: Elodia
authors.affiliation: 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., Mexico.
authors.forename: Pool-Gómez
authors.initials: PG
authors.lastname: Eduardo
authors.affiliation: 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., Mexico.
authors.forename: López-Ramos
authors.initials: LR
authors.lastname: Maria
authors.affiliation: Facultad de Nutrición, Universidad Veracruzana, Médicos y Odontologos s/n C.P. 91010, Unidad del Bosque, Xalapa, Veracruz, Mexico.
authors.forename: Rosas-Nexticapa
authors.initials: RN
authors.lastname: Marcela
authors.affiliation: 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., Mexico.
authors.forename: Hau-Heredia
authors.initials: HH
authors.lastname: Lenin
authors.affiliation: Faculty of Medicine, University Autonomous of Campeche, Av. PatricioTrueba de Regil s/n, Col. Lindavista, C.P. 24090 Campeche Cam., Mexico.
authors.forename: Sarabia-Alcocer
authors.initials: SA
authors.lastname: Bety
mesh_terms: D000728:Androgens / Q000138:chemical synthesis / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013211:Staphylococcus aureus / Q000187:drug effects; D014734:Vibrio cholerae / Q000187:drug effects
chemical_list: D000728:Androgens; D000900:Anti-Bacterial Agents
keywords: Androgen derivative; Bacteria; Boric acid; Testosterone