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Expeditious synthesis of isolated steroids-fluorine prodrugs, their single crystal X-ray crystallography, DFT studies and mathematical modeling

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Title Expeditious synthesis of isolated steroids-fluorine prodrugs, their single crystal X-ray crystallography, DFT studies and mathematical modeling
 
Creator Sethi, Arun
Amandeep
Singh, Ranvijay Pratap
Pathak, Rachana
Prakash, Rohit
Sharma, Sonia
Kant, Rajni
 
Subject Fluorine-prodrugs
Hydrocortisone
X-ray crystallography
Reactivity descriptors
NLO
 
Description 831-841
In the present research article, we have synthesized novel steroidal-fluorine prodrugs using cholesterol (1),
stigmasterol (4) and hydrocortisone acetate (7) isolated from the flowers of Allamanda violacea. These isolated
compounds were converted into their fluorinated prodrugs Cholest-5-en-3β-yl-2-fluoro-benzoate (2), Cholest-5-en-3β-yl-
4-fluoro-benzoate (3), 24α-ethylcholest-5, 22E-dien-3β-yl-2-fluoro benzoate (5), 24α-ethylcholest-5, 22E-dien-3β-yl-4-
fluoro benzoate (6), 11, 17-dihydroxy-21-(2-fluoro benzoyloxy)-pregn-4-en-3, 20-dione (8) and 11, 17-dihydroxy-21-
(4-fluoro benzoyloxy)-pregn-4-en-3, 20-dione (9). We also synthesized fluorinated prodrugs 25R-spirost-5-en-3β-yl-2-
fluoro-benzoate (11) and 25R-spirost-5-en-3β-yl-4-fluoro-benzoate (12) from diosgenin (10) a steroidal sapogenin. The
structure and stereochemistry of 25R-spirost-5-en-3β-yl-4-fluoro-benzoate (12) was confirmed with help of single crystal
X-ray crystallography. The characterizations of compounds have been carried out with the help of 1H, 13C 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 is checked using theory of nonlinear ordinary
differential equations.
 
Date 2022-08-16T08:56:58Z
2022-08-16T08:56:58Z
2022-08
 
Type Article
 
Identifier 2583-1321 (Online); 0019-5103 (Print)
http://nopr.niscpr.res.in/handle/123456789/60301
https://doi.org/10.56042/ijc.v61i8.65025
 
Language en
 
Publisher NIScPR-CSIR,India
 
Source IJC Vol.61(08) [AUG 2022]