Effect of substituents on 3(S)-amino-1-hydroxy-3,4-dihydroquinolin-2(1H)-one: a DFT study

PF04859989 is a potential novel drug designed to attenuate symptoms of Schizophrenia. We analyzed the substitution effect on PF04859989 using three functional, which included the long-range correction. The substituents were both donor and attractor electrons, in two positions of the fused-ring molec...

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Bibliographic Details
Published in:Theoretical chemistry accounts 2019, Vol.138 (1), p.1-13, Article 20
Main Authors: Lira, Jerónimo, Valencia, Diego, Barazorda, Haruna, Cárdenas-Garcia, Jaime, Gómez, Badhin
Format: Article
Language:English
Subjects:
Atomic/Molecular Structure and Spectra
Chemistry
Chemistry and Materials Science
CHITEL 2017 - Paris - France
Density functional theory
Hydrophobicity
Inorganic Chemistry
Isomers
Organic Chemistry
Physical Chemistry
Regular Article
Schizophrenia
Substitutes
Theoretical and Computational Chemistry
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Summary:PF04859989 is a potential novel drug designed to attenuate symptoms of Schizophrenia. We analyzed the substitution effect on PF04859989 using three functional, which included the long-range correction. The substituents were both donor and attractor electrons, in two positions of the fused-ring molecule, in positions six and seven. Global reactivity indices were analyzed, finding that it does not present more information except electrophilicity, when analyzed with respect to the Hammet parameter, representing a quadratic correlation closer to the unit. The hydrophobic capacity ( cLogP ) was considered, finding that the groups such as CH 3 , CN, Cl and COCH 3 increase hydrophobic capacity both in substitution in position six and seven. Additionally, we found that isomers conformations in position three of the amino group marked that equatorial isomers are more stable than the axial ones.
ISSN:1432-881X
1432-2234
DOI:10.1007/s00214-018-2403-0