title: Novel synthesis of steroidal oximes and lactams and their biological evaluation as antiproliferative agents.
abstract: A novel three-step methodology to obtain 6a-aza-B-homo steroidal lactams has been developed starting from the easily available cholesterol and pregnenolone. In addition, a new procedure for the synthesis of a 6a-aza-B-homo steroidal lactam analog of vespertilin, starting from diosgenin has been established. In both synthetic pathways, the key intermediate is a hydroxyimino derivative obtained in a one- or two-step sequence from the starting materials. These methods avoid the use of hazardous oxidant agents in the process. The new steroidal oximes and lactams were examined for their antiproliferative activities against several tumor cell lines. The 6,23-dihydroxyimino derivative exhibited the highest activity with GI50values of 11-22µM.
authors.affiliation: Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, C.P. 72570, Puebla, Pue., Mexico.
authors.forename: Roxana
authors.initials: R
authors.lastname: Martínez-Pascual
authors.affiliation: Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, C.P. 72570, Puebla, Pue., Mexico.
authors.forename: Socorro
authors.initials: S
authors.lastname: Meza-Reyes
authors.affiliation: Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, C.P. 72570, Puebla, Pue., Mexico.
authors.forename: José Luis
authors.initials: JL
authors.lastname: Vega-Baez
authors.affiliation: Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, C.P. 72570, Puebla, Pue., Mexico.
authors.forename: Penélope
authors.initials: P
authors.lastname: Merino-Montiel
authors.affiliation: BioLab, Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/Astrofísico Francisco Sánchez 2, 38200 La Laguna, Tenerife, Spain.
authors.forename: José M
authors.initials: JM
authors.lastname: Padrón
authors.affiliation: Centro de Química-ICUAP, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, C.P. 72570, Puebla, Pue., Mexico.
authors.forename: Ángel
authors.initials: Á
authors.lastname: Mendoza
authors.affiliation: Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, C.P. 72570, Puebla, Pue., Mexico. Electronic address: maria.montiel@correo.buap.mx.
authors.forename: Sara
authors.initials: S
authors.lastname: Montiel-Smith
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D006801:Humans; D007769:Lactams / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010091:Oximes / Q000737:chemistry*; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D007769:Lactams; D010091:Oximes; D013256:Steroids
keywords: 6a-Aza-B-homo-steroids; Beckmann rearrangement; Nitrosation reaction