Synthesis of new symmetrical bis-steroidal pyrazine analogues from diosgenin

Khaled Q Shawakfeh; Naim H Al-Said

doi:10.1016/j.steroids.2010.10.002

Synthesis of new symmetrical bis-steroidal pyrazine analogues from diosgenin

Steroids. 2011 Feb;76(3):232-7. doi: 10.1016/j.steroids.2010.10.002. Epub 2010 Oct 15.

Authors

Khaled Q Shawakfeh¹, Naim H Al-Said

Affiliation

¹ Department of Applied Chemical Sciences, Jordan University of Science and Technology, Irbid, Jordan. shawakfa@just.edu.jo

PMID: 20951717
DOI: 10.1016/j.steroids.2010.10.002

Abstract

New symmetrical bis-steroidal pyrazine dimers that are cephalostatins/ritterazines analogues have been prepared easily from a cheap, readily available natural steroid (diosgenin). These dimers were obtained by classical, condensation of α-amino ketones in order to construct the pyrazine rings. The three dimers differ in the functionalized diosgenin: (25R)-5α,6β-dihydroxy-5α-spirosta-3-one, (25R)-4,5α-epoxy-5β-spirosta-3,6-dione and (25R)-5α-hydroxy-5α-spirosta-3,6-dione respectively.

MeSH terms

Dimerization
Diosgenin / chemistry*
Ketones / chemistry
Models, Molecular
Pyrazines / chemical synthesis*
Pyrazines / chemistry

Substances

Ketones
Pyrazines
Diosgenin