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X-ray crystal structure, NMR, DFT investigations, pharmaco-kinetic, and toxicity of sarcotrocheliol: A pyrane-based cemranoids of marine origin

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Title X-ray crystal structure, NMR, DFT investigations, pharmaco-kinetic, and toxicity of sarcotrocheliol: A pyrane-based cemranoids of marine origin
 
Creator El-Hefnawy, Mohamed E
Lasri, Jamal
Alsaihati, Zahraa A
Al-Footy, Khalid O
Hussien, Mostafa A
Ismail, Ali I
 
Subject Sarcotrocheliol
cembranoids
NMR
DFT
B3LYP
single crystal X-ray
 
Description 69-80
One of a recently discovered marine origin cembranoids has been studied experimentally and theoretically to obtain its
thorough structural, electronic, spectroscopic, and biochemical activity. The exact molecular structure of sarcotrocheliol
(C20H34O2) 1 has been determined for the first time using a single crystal X-ray diffraction analysis. Crystallography shows
that the molecule is crystalline as an orthorhombic, space group of P212121, with a = 9.20(4) Å, b = 10.80(4) Å, c = 19.99(9)
Å. 1H, 13C and DEPT-135 NMR measurements of sarcotrocheliol1have been measured in four different deuterated solvents:
CDCl3, CD3CN, MeOH-d4 and DMSO-d6. Theoretical calculations have been performed to find the main structural and
electronic properties of the compound and matched with the experimental properties. The density functional theory (DFT)
method at B3LYP/6-311++G(d,p) level of theory has been used for all computed properties. Vibrational frequencies have
been determined using DFT calculations and compared with the experimental values. Computed chemical shifts in the NMR
have been determined by the GIAO method. The correlation coefficients between the calculated and experimental NMR
chemical shifts have been found to be 0.92 and 0.998 for 1H and 13C NMR, respectively. Physicochemical parameters of the
compound versus reference drugs have been done. The isolated compound meets the main criteria of the employed rules
indicating a drug-like character. The molecular docking studies have been performed for the compound toward the breast
and prostate cancers.
 
Date 2022-02-01T10:53:21Z
2022-02-01T10:53:21Z
2022-01
 
Type Article
 
Identifier 2583-1321 (Online); 0019-5103 (Print)
http://nopr.niscair.res.in/handle/123456789/59037
 
Language en
 
Publisher NIScPR-CSIR, India
 
Source IJC Vol.61(01) [January 2022]