<strong>Expeditious synthesis of isolated Steroids-Fluorine prodrugs, their single crystal X-ray crystallography, DFT studies and mathematical modeling</strong>
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Title Statement |
<strong>Expeditious synthesis of isolated Steroids-Fluorine prodrugs, their single crystal X-ray crystallography, DFT studies and mathematical modeling</strong> |
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Added Entry - Uncontrolled Name |
Sethi, Arun ; Department of Chemistry, University of Lucknow, Lucknow 226007, India Amandeep, Amandeep ; Department of Chemistry, University of Lucknow, Lucknow 226007, India Singh, Ranvijay Pratap; Department of Applied Science & Humanities, Faculty of Engineering & Technology, University of Lucknow, Lucknow-226031, India Pathak, Rachana ; Department of Applied Science & Humanities, Faculty of Engineering & Technology, University of Lucknow, Lucknow-226031, India Prakash, Rohit ; Faculty of Chemical Sciences, Institute of Natural Sciences and Humanities, Shri Ramswaroop Memorial University, Barabanki-225003, India Sharma, Sonia ; X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi-180006, India Kant, Rajni ; X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi-180006, India |
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Uncontrolled Index Term |
Fluorine-prodrugs, hydrocortisone, X-ray crystallography, Reactivity descriptors, NLO. |
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Summary, etc. |
In the present research article, we have synthesized novel steroidal-fluorine prodrugs using cholesterol (<strong>1</strong>), stigmasterol (<strong>4</strong>) and hydrocortisone acetate (<strong>7</strong>) isolated from the flowers of <strong><em>Allamanda violacea</em></strong>. These isolated compounds were converted into their fluorinated prodrugs Cholest-5-en-3β-yl-2-fluoro-benzoate<strong> (2)</strong>, Cholest-5-en-3β-yl-4-fluoro-benzoate<strong> (3)</strong>, 24α-ethylcholest-5, 22<em>E</em>-dien-3β-yl-2-fluoro benzoate<strong> (5)</strong>, 24α-ethylcholest-5, 22<em>E</em>-dien-3β-yl-4-fluoro benzoate<strong> (6)</strong>, 11, 17-dihydroxy-21-(2-fluoro benzoyloxy)-pregn-4-en-3, 20-dione<strong> (8)</strong> and 11, 17-dihydroxy-21-(4-fluoro benzoyloxy)-pregn-4-en-3, 20-dione<strong> (9)</strong>. We also synthesized fluorinated prodrugs 25R-spirost-5-en-3β-yl-2-fluoro-benzoate<strong> (11)</strong> and 25R-spirost-5-en-3β-yl-4-fluoro-benzoate<strong> (12)</strong> from diosgenin (<strong>10</strong>) a steroidal sapogenin. The structure and stereochemistry of 25R-spirost-5-en-3β-yl-4-fluoro-benzoate (<strong>12</strong>)<strong> </strong>was confirmed with help of single crystal X-ray crystallography. The characterization of compounds have been carried out with the help of <sup>1</sup>H, <sup>13</sup>C NMR, FT-IR spectroscopy and mass spectrometry. Density functional theory (DFT) with 6-31G (d, p) basis set and B3LYP functional has been used for the Quantum chemical calculations. Global reactivity descriptors have also been calculated to find the electrophilicity and nucleophilicity of a molecule. Dipole moment, polarizability and first static hyperpolarizability have been calculated to get NLO properties of synthesized prodrugs. Lastly a nonlinear mathematical model has been proposed and analyzed to study the effect of catalysts on these reactions. Local and global stability analysis of the mathematical model along with the persistence of the system was checked using theory of nonlinear ordinary differential equations. |
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Publication, Distribution, Etc. |
Indian Journal of Chemistry (IJC) 2022-08-16 12:31:01 |
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Electronic Location and Access |
application/pdf application/pdf http://op.niscair.res.in/index.php/IJC/article/view/65025 |
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Data Source Entry |
Indian Journal of Chemistry (IJC); ##issue.vol## 61, ##issue.no## 8 (2022): Indian Journal of Chemistry - (IJC) |
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Language Note |
en |
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