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.
Keywords: C-H functionalization; Steroidal diglycoside; anti-cancer activity; gold-NHC; markovnikov.