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• W2993272643 abstract "Abstract Two 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 significant anticancer activity. The molecular geometry of the compounds was optimized by density functional theory using (DFT/B3LYP) method with 6–31G (d, p) basis set and compared it with experimental data. From the low value of HOMO-LUMO energy gap, compound 3b was found to have high chemical reactivity. Nucleophilic and electrophilic sites within molecules were obtained by electrostatic potential surfaces. From global reactivity descriptors, 3b exhibited greater global electrophilicity index value (5.83eV), suggesting it to be a good electrophile. The high value of first hyperpolarizability (15.99 × 10−30 esu) for compound 3 suggested it to be ideal for non linear optical (NLO) application. From AIM (Atoms in Molecule) approach, it is found that compound 3 was more stable in comparison to other compounds." @default.
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• W2993272643 date "2020-03-01" @default.
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• W2993272643 title "Synthesis of novel steroids using Mizoroki-Heck reaction, their spectroscopic analysis, anticancer activity against cervical cancer and DFT studies" @default.
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• W2993272643 doi "https://doi.org/10.1016/j.molstruc.2019.127512" @default.
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