Detailed analytical studies of 1,2,4-triazole derivatized quinoline

The present study describes, the X-ray single crystal analysis of 4-((2-chloro-6-methoxyquinolin-3-yl)methyl)-2-phenyl-2H-1,2,4-triazol-3(4H)-one (TMQ). The crystal data for C19H15ClN4O2: monoclinic, space group P21/n (no. 14), a = 7.3314(15) Å, b = 12.459(3) Å, c = 18.948(4) Å, β = 98.322(9)°, V = 1712.5(6) Å3, Z = 4, T = 296.15 K, μ(MoKα) = 0.245 mm-1, Dcalc = 1.423 g/cm3, 5082 reflections measured (3.926° ≤ 2Θ ≤ 38.556°), 1428 unique (Rint = 0.0545, Rsigma = 0.0574) which were used in all calculations. The final R1 was 0.0423 (I >2σ(I)) and wR2 was 0.1145 (all data). The Density functional theory optimized molecular geometries in TMQ agree closely with those obtained from crystallographic studies. The Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energy levels and energy gap were calculated by experimental (UV absorption & Cyclic voltammetry) and theoretical studies in two different solvents. The natural bond orbital analysis was performed to understand the molecular interaction on the basis of stability of molecule arising from hyper-conjugative interaction and charge delocalization. Hirshfeld surface and their related fingerprint plots enabled the identification of significant intermolecular interaction. The molecular electrostatic potential analysis provides the visual image of the chemically active sites and comparable reaction of atoms

One-pot multicomponent synthesis of novel thiazol-2-imines <i>via</i> microwave irradiation and their antifungal evaluation

<p>Microwave-assisted green approach is developed for an efficient synthesis of thiazol-2-imines under catalyst-free conditions. The desired products are formed by one-pot three-component reaction which is an improvised method for Hantzsch thiazole synthesis. The microwave-assisted protocol gives excellent yields with high purity in just 10–15 min. All the synthesized compounds have been screened for antifungal activity and some of the derivatives show a broad spectrum against fungal pathogens.</p

X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone

This study is composed of X-ray diffraction and Density Functional Theory (DFT) based molecular structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (2PPT). Crystal data for C11H9N3O: Monoclinic, space group P21/c (no. 14), a = 7.8975(2) Å, b = 11.6546(4) Å, c = 11.0648(3) Å, β = 105.212(2)°, V = 982.74(5) Å3, Z = 4, T = 296.15 K, μ(MoKα) = 0.091 mm-1, Dcalc = 1.346 g/cm3, 13460 reflections measured (5.174° ≤ 2Θ ≤ 64.72°), 3477 unique (Rint = 0.0314, Rsigma = 0.0298) which were used in all calculations. The final R1 was 0.0470 (I > 2σ(I)) and wR2 was 0.1368 (all data). The experimentally determined data was supported by theoretically optimized calculations processed with the help of Hartree-Fock (HF) technique and Density Functional Theory with the 6-311G(d,p) basis set in the ground state. Geometrical parameters (Bond lengths and angles) as well as spectroscopic (FT-IR, 1H NMR, and 13C NMR) properties of 2PPT molecule has been optimized theoretically and compared with the experimentally obtained results. Hirshfeld surface analysis with 2D fingerprinting plots was used to figure out the possible and most significant intermolecular interactions. The electronic characterizations such as molecular electrostatic potential map (MEP) and Frontier molecular orbital (FMO) energies have been studied by DFT/B3LYP approach. The MEP imparted the detailed information regarding electronegative and electropositive regions across the molecule. The HOMO-LUMO energy gap as high as 5.3601 eV was found to be responsible for the high kinetic stability of the 2PPT

Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies

A new class of probes was synthesized using a simple and efficient synthetic protocol. These compounds (PTZ-6(a-e)) have the phenothiazine (PTZ) moiety as the electron donor (D) and substituted aldehydes along with the acrylonitrile group, which acts as the electron acceptor (A), thus making D-π-A push-pull system. The structures of the newly synthesized series of small organic target molecules PTZ-6(a-e) were investigated and confirmed by spectros-copic techniques. The optical/solvatochromic properties were studied in detail by UV-vis absorption and fluorescence spectroscopy, because the molecules have shown good solubility in organic solvents. The density functional theory (DFT) model with the CAM-B3LYP function is utilized to study the photophysical properties of the probes, as these probes exhibited orange-to-red emission. Optical band gap values ranged from 2.32 to 2.50 eV, and these probes exhibited good thermal stability with a melting temperature of 136 to 198 °C and a T5d temperature range from 335 to 354 °C. The cyclic voltammetry study confirms that the Eoxonset values of the target compounds are 0.80 eV. The quantum yields (Φ) of the probes are measured experimentally in ethanol and the Stokes shifts are observed to be in the range of 4846-9430 cm-1. The results displayed that novel (D-A-D) chromophores could play an important role in organic optoelectronics

Synthesis and evaluation of benzophenone oximes derivatized with sydnone as inhibitors of secretory phospholipase a(2) with anti-inflammatory activity

A series of benzophenone oximes appended with sydnone (3a-h) bearing different substituents on aroyl moiety were synthesized to evaluate in vivo and in vitro for their inhibitory activity against purified phospholipase A(2) (PLA(2)) enzymes from snake venom and human inflammatory pleural and ascites fluid. In vivo and in vitro inhibition studies were carried out against PLA(2) with respect to the modification of the pharmacophore (substituent) to analyze the specificity for PLA(2). The substituent at the aroyl ring was responsible for enhancing the inhibition towards PLA(2) enzymes. Most of the newly synthesized compounds inhibit the purified PLA(2) enzyme, and the inhibition was more in hydrophobic and aromatic substituents and less when no such substituents were present. The inhibitory effect of the compounds appeared to be due to the direct interaction of compounds with the enzyme. Inhibition is substrate dependent, and the inhibition competes with the substrate for the same binding site of the enzyme. The most active interacting compound 3h from in vitro inhibition of PLA(2) activity showed similar potency in the in vivo neutralization of PLA(2) induced mouse paw edema and hemolytic activity. Thus, the in vitro inhibition correlated well with the in vivo inhibition and hence the reported derivatives are therapeutically important anti-inflammatory drugs