TY - JOUR
T1 - Effect of substituents on 3(S)-amino-1-hydroxy-3,4-dihydroquinolin-2(1H)-one
T2 - a DFT study
AU - Lira, Jerónimo
AU - Valencia, Diego
AU - Barazorda, Haruna
AU - Cárdenas-Garcia, Jaime
AU - Gómez, Badhin
N1 - Publisher Copyright:
© 2019, Springer-Verlag GmbH Germany, part of Springer Nature.
PY - 2019/1/1
Y1 - 2019/1/1
N2 - 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 COCH3 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.
AB - 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 COCH3 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.
KW - CAM-B3LYP
KW - DFT
KW - Effect of substituents
KW - Schizophrenia
UR - http://www.scopus.com/inward/record.url?scp=85059700058&partnerID=8YFLogxK
U2 - 10.1007/s00214-018-2403-0
DO - 10.1007/s00214-018-2403-0
M3 - Article
AN - SCOPUS:85059700058
SN - 1432-881X
VL - 138
JO - Theoretical Chemistry Accounts
JF - Theoretical Chemistry Accounts
IS - 1
M1 - 20
ER -