Synthesis and bioactivity of bis-steroidal pyrazine 23-deoxy-25-epi ritterostatin GN1N

[Display omitted] •Synthesis of ritterostatin, a hybrid analog of ritterazine and cephalostatin.•Ritterostatin synthesis involves reductive/oxidative modifications of hecogenin acetate.•Evaluation of the impact of C23 hydroxyl group on bioactivity of ritterostatin. Cephalostatins, ritterazines and t...

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Bibliographic Details
Published in:Steroids 2017-10, Vol.126, p.74-78
Main Authors: Kumar, Rayala Naveen, Lee, Seongmin
Format: Article
Language:English
Subjects:
Anticancer steroids
Cephalostatin
Ritterazine
Steroidal alkaloids
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Summary:[Display omitted] •Synthesis of ritterostatin, a hybrid analog of ritterazine and cephalostatin.•Ritterostatin synthesis involves reductive/oxidative modifications of hecogenin acetate.•Evaluation of the impact of C23 hydroxyl group on bioactivity of ritterostatin. Cephalostatins, ritterazines and their hybrid bis-steroidal pyrazine analogs such as 25-epi-rittereostatin GN1N show unusually high potency against a wide range of cancer cell lines. Herein, we report the synthesis and bioactivity of 23-deoxy-25-epi ritterostatin GN1N, which lacks the 23-hydroxyl group of 25-epi rittereostatin GN1N. The less oxygenated bis-steroidal pyrazine was ∼50- to 1000-fold less potent than 25-epi ritterostatin GN1N, highlighting the importance of the 23-hydroxyl group for the antiproliferative activity of the cephalostatin/ritterazine class of drugs.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2017.07.008