One pot synthesis of biologically active pregnane derivatives, their single crystal structures, spectroscopic characterization and theoretical calculations

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• 作者：Arun Sethi ; Akriti Bhatia ; Gitika Bhatia ; Atul Shrivastava ; Rohit Prakash
• 关键词：DFT ; Crystal structure ; Anti-hyperlipidemic and anti-oxidant activity ; Allylic oxidation ; HOMO&ndash ; LUMO
• 刊名：Journal of Molecular Structure
• 出版年：2013
• 出版时间：25 November, 2013
• 年：2013
• 卷：1052
• 期：Complete
• 页码：76-84
• 全文大小：1355 K

文摘

One pot allylic oxidation of 3¦Â-acetoxypregna-5,16-diene-20-one (2) and nucleophilic addition at C-16 position of 3¦Â-hydroxypregna-5,16-diene-20-one (3) yielded 3¦Â-acetoxypregna-5,16-diene-7,20-dione (4) and 3¦Â-hydroxy-16¦Á-(5¡ä-hydroxypentyloxy)-pregn-5-ene-20-one (5) respectively in high yield. A detailed theoretical study supported by X-ray analysis of compounds 4 and 5 has been carried out. Conformational analysis of compounds 4 and 5 was done with the help of crystal structure, which crystallize out in orthorhombic form having P2₁2₁2₁ space group. Structural characterization of compounds 4 and 5 was done with the aid of ¹H, ¹³C NMR, IR, UV, ESI-MS and ESI-HRMS. The molecular geometries and vibrational frequencies for compounds 4 and 5 in the ground state were calculated using the Density functional theory (DFT) with 6-31G(d,p) basis set and compared with experimental data. ¹H and ¹³C nuclear magnetic resonance magnetic shifts of 4 and 5 were calculated using GIAO method and compared with the experimental data. UV-Vis spectra of both the compounds were recorded and electronic properties such as HOMO-LUMO energies were calculated by time dependent TD-DFT approach. The compounds were screened for their anti-hyperlipidemic and anti-oxidant activity.