TY - JOUR
T1 - Spectroscopic investigations, NBO, HOMO-LUMO, NLO analysis and molecular docking of 5-(adamantan-1-yl)-3-anilinomethyl-2,3-dihydro-1,3,4-oxadiazole-2-thione, a potential bioactive agent
AU - Al-Omary, Fatmah A.M.
AU - Mary, Y. Sheena
AU - Panicker, C. Yohannan
AU - El-Emam, Ali A.
AU - Al-Swaidan, Ibrahim A.
AU - Al-Saadi, Abdulaziz A.
AU - Van Alsenoy, C.
N1 - Publisher Copyright:
© 2015 Published by Elsevier B.V.
PY - 2015/4/7
Y1 - 2015/4/7
N2 - The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-(adamantan-1-yl)-3-anilinomethyl-2,3-dihydro-1,3,4-oxadiazole-2-thione have been investigated experimentally and theoretically. The geometrical parameters are in agreement with XRD data. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The frontier molecular orbital analysis is used to determine the charge transfer within the molecule. As can be seen from the MEP map of the title molecule, the negative region are mainly localized over the CS and the CH2 group attached to the oxadiazole ring and the maximum positive region is localized near the NH group. The first and second order hyperpolarizability values are also calculated theoretically. The title compound forms a stable complex with PPARα as is evident from the binding affinity values and the results suggest that the compound might exhibit inhibitory activity against PPARα and this may result in development of new anti-diabetic (Type 2) agents.
AB - The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-(adamantan-1-yl)-3-anilinomethyl-2,3-dihydro-1,3,4-oxadiazole-2-thione have been investigated experimentally and theoretically. The geometrical parameters are in agreement with XRD data. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The frontier molecular orbital analysis is used to determine the charge transfer within the molecule. As can be seen from the MEP map of the title molecule, the negative region are mainly localized over the CS and the CH2 group attached to the oxadiazole ring and the maximum positive region is localized near the NH group. The first and second order hyperpolarizability values are also calculated theoretically. The title compound forms a stable complex with PPARα as is evident from the binding affinity values and the results suggest that the compound might exhibit inhibitory activity against PPARα and this may result in development of new anti-diabetic (Type 2) agents.
KW - Adamantane
KW - DFT
KW - FT-IR
KW - FT-Raman
KW - Molecular docking
UR - https://www.scopus.com/pages/publications/84929164687
U2 - 10.1016/j.molstruc.2015.03.049
DO - 10.1016/j.molstruc.2015.03.049
M3 - Article
AN - SCOPUS:84929164687
SN - 0022-2860
VL - 1096
SP - 1
EP - 14
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -