Gold mediated sp³αC-H functionalization of steroidal diglycoside and their anti-cancer evaluation

Abstract

C(sp³)-H alkylation at α-position of methyl-keto group on D-ring of Steroidal diglycoside (SG) with (i) C=N of Schiff base imines to form amine derivatives and (ii) C=C of acrylate Michael acceptors to form Markovnikov ester products using AuCl₃/NHC as pre-catalyst and Ag(I) salts as co-catalyst was described. The original form of SG (1) and its derivatives (3b-f & 5a-d) were screened for in vitro anti-cancer activity specifically on two breast cancer cell lines (i.e. MCF-7, MDA-MB-231) and deduced the structure-activity-relationship with the support of molecular docking studies. Among these compounds 3b, 3f, 5b & 5d have shown more potent anticancer activity than standard drug cisplatin with considerable IC50 values.

Graphical Abstract

Keywords:

• Steroidal diglycoside
• gold-NHC
• C-H functionalization
• markovnikov
• anti-cancer activity

Acknowledgements

One of the authors Dr. S. Kankala is thankful to CSIR, New Delhi for the award of Research Associate.

Disclosure statement

The authors have no conflicts of interest in this work.

Additional information

Funding

Council of Scientific & Industrial Research (CSIR).