title: Design and synthesis of four steroid-oxirane derivatives using some chemical tools.
abstract: This study involved the synthesis of several new derivatives of progesterone, 11a-hydroxyprogesterone, 11a-t-butyldimethylsilanyloxyprogesterone, and andrenosterone. The new derivatives were prepared by condensation of the 4-en-3-one moiety of the four steroids with 2-hydroxy-1-naphthaldehyde to afford a series of 4-(R)-hydroxy-(2-hydroxynaphtalen-1-yl) adducts. These adducts were further modified by cyclization reactions of the dihydroxynaphthalenyl moieties with succinic acid, and the resulting cyclic succinates were then condensed with ethylenediamine to form imine derivatives at all available carbonyl groups. These compounds were then derivatized by N-acylation of the 11- and 17-imine nitrogens with chloroacetyl chloride and the resulting chloroacetamides were then condensed with 2-hydroxy-1-napthaldehyde in Darzens-type reactions forming the corresponding epoxy acetamides in the side chains. In addition, the chemical structure of steroid derivatives was confirmed by NMR spectroscopic data.
authors.affiliation: 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., 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, C.P. 11340 México, D.F., Mexico.
authors.forename: Díaz-Cedillo
authors.initials: DC
authors.lastname: Francisco
authors.affiliation: 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., Mexico.
authors.forename: Ortega-Morales
authors.initials: OM
authors.lastname: Otto
authors.affiliation: 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., Mexico.
authors.forename: García-Cervera
authors.initials: GC
authors.lastname: Elodia
authors.affiliation: Facultad de Nutrición, Universidad Veracruzana, Médicos y Odontólogos s/n, C.P. 91010 Xalapa, Veracruz, Mexico.
authors.forename: Rosas-Nexticapa
authors.initials: RN
authors.lastname: Marcela
authors.affiliation: 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., Mexico.
authors.forename: Pool-Gómez
authors.initials: PG
authors.lastname: Eduardo
authors.affiliation: 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., Mexico.
authors.forename: Lopéz-Ramos
authors.initials: LR
authors.lastname: Maria
authors.affiliation: 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., Mexico.
authors.forename: Rodriguez-Hurtado
authors.initials: RH
authors.lastname: Fernanda
authors.affiliation: 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., Mexico.
authors.forename: Chan-Salvador
authors.initials: CS
authors.lastname: Marissa
mesh_terms: D000085:Acetates / Q000737:chemistry; D005027:Ethylene Oxide / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D011374:Progesterone / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*
chemical_list: D000085:Acetates; D009281:Naphthalenes; D013256:Steroids; D011374:Progesterone; C062247:2-hydroxy-1-naphthaldehyde; D005027:Ethylene Oxide; C045557:chloroacetyl chloride
keywords: Chloroacetyl chloride; Oxirane ring; Progesterone; Steroid derivatives