Record Details

<strong>Expeditious synthesis of isolated Steroids-Fluorine prodrugs, their single crystal  X-ray crystallography, DFT studies and mathematical modeling</strong>

Online Publishing @ NISCAIR

View Archive Info
 
 
Field Value
 
Authentication Code dc
 
Title Statement <strong>Expeditious synthesis of isolated Steroids-Fluorine prodrugs, their single crystal  X-ray crystallography, DFT studies and mathematical modeling</strong>
 
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
 
Uncontrolled Index Term Fluorine-prodrugs, hydrocortisone, X-ray crystallography, Reactivity descriptors, NLO.
 
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.
 
Publication, Distribution, Etc. Indian Journal of Chemistry (IJC)
2022-08-16 12:31:01
 
Electronic Location and Access application/pdf
application/pdf
http://op.niscair.res.in/index.php/IJC/article/view/65025
 
Data Source Entry Indian Journal of Chemistry (IJC); ##issue.vol## 61, ##issue.no## 8 (2022): Indian Journal of Chemistry - (IJC)
 
Language Note en