Selective synthesis, structural studies and antitumor evaluation of some novel unsymmetrical 1-hetaryl-4-(2-chloroquinolin-3-yl)azines

Abstract

A series of novel unsymmetrical 1-hetaryl-4-(2-chloroquinolin-3-yl) azines 4-9 was selectively synthesized in a three-step procedure starting from acetanilide (1). The molecular structures of 4-9 were established by elemental analyses, spectral data, hybrid density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations. Molecular conformation analysis for compounds 4-9, performed using DFT calculations utilizing the energy functional 3-Parameter (Exchange), Lee, Yang and Parr (B3LYP) and the full-electron basis set Density Gauss double-zeta with polarization functions (DGDZVP), on the synthesized azines considering the torsion angles (h 1 , h 2 , h 3 ) revealed 8 plausible conformers for each compound. Electronic and thermodynamic properties including the dipole moment and the thermodynamic energy values of the Frontier occupied and virtual molecular orbitals, HOMO and LUMO, respectively, were calculated for the most stable conformer for each compound. Furthermore, TD-DFT calculations coupled with the polarizable conductor calculation model (PCM), performed on the most stable conformers in DMF to account for the solvent effect, revealed that the optical properties including k max and oscillator strength performed on the most stable conformers were in excellent agreement with the experimental k max and molar extinction coefficient, which clearly validate the most stable molecular conformers identified for compounds 4-9. Comparison of the biological results to the calculated electronic and thermodynamic properties showed that the cytotoxicity is dependent on the low-lying

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

“…They are of particular importance in the development of light-based technology for communication and computing [14]. These compounds have pharmacological and biological properties and close relationships with their structures, which act as anti-inflammatory, analgesic, antibacterial, antifungal, antitumor, anti-HIV and antimicrobial agents [15][16][17][18][19]. Azines are also important for drug design, organocatalysis and synthesis of heterocyclic compounds [20][21] by undergoing different types of cyclo-addition reactions [21][22].…”

Transformation of Organostannanes Based on Photocleavage of C-Sn Bond via Single Electron Transfer Process

“…Based on the above experiment results and literature precedents 14 – 20 , a possible mechanism was proposed as shown in Fig. 6 .…”

Facile, mild and efficient synthesis of azines using phosphonic dihydrazide

“…lononitriles, via copper-catalyzed tandem cyclization, gave Condensation of a 2:1 mixture of 2-oxo-N'-arylpropanehy-1,2,4-triazolo [1,5-a]pyridines. [9] Azines exhibit various drazonoyl chlorides 1 and phosphonic dihydrazide (2) in [10] and act as antitumor, [11] antipharmacological activities boiling ethanol for 3 h gave bis(N'-arylpropanehydrazonoyl convulsant, [12] [13] and antimicrobial [14] antioxidant, agents.…”

“…The spectral data for 10a,b were in agree-ment with those reported. [36,37] Similarly, reaction of isatin (11) and 2 in ethanol under reflux for 3 h afforded (3Z,3'E)-3,3'-(hydrazine-1,2-diylidene)bis(indolin-2-one) (12) in 85% yield (Scheme 5). The Xray crystal structure of 12 is shown in Figure 6.…”