Synthesis of novel steroids using Mizoroki-Heck reaction, their spectroscopic analysis, anticancer activity against cervical cancer and DFT studies

Publication date: Available online 4 December 2019Source: Journal of Molecular StructureAuthor(s): Arun Sethi, Praveer Singh, Neera Yadav, Rohit Prakash, Ranvijay Pratap Singh, Priyanka Yadav, Monisha BanerjeeAbstractTwo novel steroids, 3β, 25R-spirost-5-en-3yl 3-(4-propionylphenyl)but-2-enoate(3a) and 3β, 25R-spirost-5-en-3yl 3-(4-nitrophenyl) but-2-enoate (3b) have been synthesized using a palladium catalyzed Mizoroki-Heck reaction in a two-step synthesis using diosgenin as a starting material. A new strategy was adopted involving conversion of diosgenin (compound 1) into compounds, 3β, 25R-spirost-5-en-3yl 2-chloroacetate (Compound 2), 3β, 25R-spirost-5-en-3yl trans-but-2-enoate (Compound 3) and 3β, 25R-spirost-5-en-3yl-trans-cinnamate (Compound 4) via Steglich esterification using an ionic liquid (NMP+HSO4). The synthesized compounds were then treated with 4-bromopropiophenone and 1-bromo-4-nitrobenzene using [Pd(PPh3)4] as a catalyst and K2CO3 as a base in DMF; only compound 3 underwent reaction yielding compounds (3a) and (3b). Structure elucidation of all the synthesized compounds was done by 1H NMR, 13C NMR, NOESY, IR, UV–Vis spectroscopic techniques and mass spectrometry. Stereochemistry of compound 2 was established by a single crystal X-ray structural analysis. These compounds 2, 3, 3a, 3b and 4 were investigated for cytotoxicity and apoptosis through MTT assay and Mitochondrial staining respectively, of cervical cancer cell line HeLa; the compounds showed s...
Source: Journal of Molecular Structure - Category: Molecular Biology Source Type: research