Computational Study of Solvent Effects on Characterizations of (E)‐3‐X‐Indoline‐2‐thiones Derivatives as Antivirus and Anticancer Compounds

Abstract

(E)-3-X-Indoline-2-thione derivatives (X = phenyl, furan-2-yl, 1H-pyrrole-2-yl, and thiophene-2-yl, I-IV, respectively) are considered as potent and selective inhibitors against different receptor tyrosine kinases. A particularly interesting issue for these biologically active compounds is how their stability is affected by solvation. Here we have tackled this issue using the self-consistent reaction field theory for I-IV, in the gas phase as well as solution including: toluene, CH 2 Cl 2 , MeOH, and H 2 O. The highest observed total free energy difference between liquid (l) and gas (g) phase (ΔE l-g ) relates to structure III in water, whereas the lowest ΔE l-g is associated with II in toluene. Thus, III is the most solvent sensitive and enjoys maximum stabilization in water. On the other extreme, II is the least solvent sensitive and its stability is least affected by solvation in toluene. Moreover, stability of each solute (I-IV) depends on the dielectric constant of the solvent and the possibility of the hydrogen bonding. In going from gas phase to different solvents, considerable changes of nucleophilicity as well as electrophilicity occur for scrutinized structures. The six-and fivemembered rings in indoline skeleton for all species show aromatic and nonaromatic property, respectively. Finally, the substituent rings appear the most aromatic property. These phenomena are confirmed by the succeeding geometrical parameters.

Solvent effect on cycloaddition of C20 nanofullerene with indoline‐2‐one, at density functional theory

“…[10] Theoretical investigation is an effective method for suggestion of organofullerene bearing a sixmember heterocycle from the [4 + 2] reaction of [20]fullerene with heterodienes. [11] Herein, we study exo and endo cycloaddition of C 20 nanocage as well as biologically active α,β-unsaturated diene in various media via selfconsistent reaction field (SCRF)-density functional theory (DFT) (Figure 1). [12] The SCRF theory has been relatively successful in describing the solvent effects on the molecules in solutions.…”