Design and synthesis of a new furan-steroid-propanone derivative using some chemical strategies

Figueroa-Valverde Lauro; Rosas-Nexticapa Marcela; Lopez-Ramos Maria; Diaz Cedillo Francisco; Garcimarero-Espino E Alejandra; Mateu-Armand Virginia; Ortiz-Ake Yazmin

doi:10.1016/j.steroids.2020.108654

Design and synthesis of a new furan-steroid-propanone derivative using some chemical strategies

Steroids. 2020 Aug:160:108654. doi: 10.1016/j.steroids.2020.108654. Epub 2020 May 18.

Authors

Figueroa-Valverde Lauro¹, Rosas-Nexticapa Marcela², Lopez-Ramos Maria³, Diaz Cedillo Francisco⁴, Garcimarero-Espino E Alejandra⁵, Mateu-Armand Virginia⁶, Ortiz-Ake Yazmin³

Affiliations

¹ Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Ex Hacienda Kalá s/n, 24085 San Francisco de Campeche, Mexico. Electronic address: lfiguero@uacam.mx.
² Facultad de Nutrición, Universidad Veracruzana. Médicos y Odontólogos s/n, 91010 Xalapa, Veracruz, Mexico. Electronic address: rosasnm@yahoo.com.
³ Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Ex Hacienda Kalá s/n, 24085 San Francisco de Campeche, Mexico.
⁴ Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala s/n Col, Santo Tomas, D.F. C.P. 11340, Mexico.
⁵ Facultad de Medicina, Universidad Veracruzana. Médicos y Odontólogos s/n, 91010 Xalapa, Veracruz, Mexico.
⁶ Facultad de Nutrición, Universidad Veracruzana. Médicos y Odontólogos s/n, 91010 Xalapa, Veracruz, Mexico.

PMID: 32439408
DOI: 10.1016/j.steroids.2020.108654

Abstract

There are several reports for the preparation of furan derivatives using some protocols which requires special conditions. In this way, the aim of this study was to synthesize a new furan-steroid-propanone derivative from both 17α-ethynylestradiol and 2-nitro-17α-ethynylestradiol using some series of reactions such as aldolization, 2 + 2 addition and etherification. The chemical structure was evaluated through both ¹H NMR and ¹³C NMR spectroscopic analysis. The results showed a good yielding from furan-steroid derivative. In conclusion, this investigation provides a facile synthesis of a new furan-steroid-propanone derivative, using some reagents which are not expensive and do not require special conditions for handling.

Keywords: Derivative; Estradiol; Furan; Nitroestradiol; Steroid.

MeSH terms

Chemistry Techniques, Synthetic*
Drug Design
Furans / chemistry*
Molecular Structure
Propane / analogs & derivatives*
Propane / chemistry*
Steroids / chemistry*

Substances

Furans
Steroids
Propane
furan