331850-17-0

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 1904-58-1 anthranilic acid hydrazide 

Downstream Products

• 361996-35-2 3-[1-(2-hydroxyphenyl)ethylidenamino]-2-phenyl-1,2-dihydroquinazolin-4(3H)-one 

Relevant academic research and scientific papers

Dimer formation by symbiotic donor-acceptor interaction between two molecules of a specially designed dioxomolybdenum(VI) complex containing both donor and acceptor centers - A structural, spectroscopic and DFT study

This work presents a model study for the formation of a dimeric dioxomolybdenum(VI) complex [MoO2L]2, generated by simultaneous satisfaction of acceptor and donor character existing in the corresponding monomeric Mo(VI) complex MoO2L. This mononuclear complex is specially designed to contain a coordinatively unsaturated Mo(VI) acceptor centre and a free donor group, (e.g. -NH2 group) strategically placed in the ligand skeleton [H2L = 2-hydroxyacetophenonehydrazone of 2-aminobenzoylhydrazine]. Apart from the dimer [MoO2L]2, complexes of the type MoO2L·B (where B = CH3OH, γ-picoline and imidazole) are also reported. All the complexes are characterized by elemental analysis, spectroscopic (UV-Vis, IR, 1H NMR) techniques and cyclic voltammetry. Single crystal X-ray structures of [MoO2L]2 (1), MoO 2L·CH3OH (2), and MoO2L.(γ-pic) (3) have been determined and discussed. DFT calculation on these complexes corroborates experimental data and provides clue for the facile formation of this type of dimer not reported previously. The process of dimer formation may also be viewed as an interaction between two molecules of a specially designed complex acting as a monodentate ligand. This work is expected to open up a new field of design and synthesis of dimeric complexes through the process of symbiotic donor-acceptor (acid-base) interaction between two molecules of a specially designed monomer.

Synthesis, characterization, and cytotoxic and antimicrobial activities of mixed-ligand hydrazone complexes of variable valence VO: Z + (z = 2, 3)

Two sets of mixed-ligand complexes were synthesized and characterized, namely, [VIVO(L1-4)(phen)] (1-4) and [VVO(L1-4)(hq)] (5-8) incorporating 2-aminobenzoylhydrazone of 2-hydroxyacetophenone (H2Lsu

A study of anti-inflammatory and analgesic activity of new 2,3-disubstituted 1,2-dihydroquinazolin-4(3H)-one derivative and its transition metal complexes

A new 2,3-disubstituted 1,2-dihydroquinazolin-4(3H)-one derivative namely 2-hydroxy-2-ethyl-(3-carboxylideneamino)-3-(2-(4-methyl-phenyl))-1, 2-dihydroquinazolin-4(3H)-one (HECMDQ) is synthesized employing a modified method in higher yield and is complexed with Co(II), Ni(II), Cu(II) and Zn(II) metal ions in order to study its coordinating behavior. All the complexes were characterized by various physicochemical (analytical, IR, NMR, Electron Paramagnetic Resonance (EPR), mass, Thermogravimetric Analysis Differential Thermogravimetric Analysis (TGA-DTA)) methods. The molar conductivity measurements in N,N-dimethylformamide (DMF) solution indicate the non-electrolytic nature of complexes. IR spectral analysis reveal that coordination takes place through the deprotonated hydroxyl group, azomethine nitrogen and carbonyl oxygen. Four coordinated geometry was assigned to all the complexes on the basis of spectral studies. The anti-inflammatory activities of compounds are moderate. Co(II) complex exhibited highest activity among all the complexes. At lower dose level activity of Ni(II) and Cu(II) complexes is more compared to that of ligand. The analgesic activity of ligand has enhanced on complexation with Co(II), Ni(II) and Zn(II) metal ions. Among the compounds studied Co(II) complex has shown highest activity and is comparable with standard used.

Simultaneous formation of non-oxidovanadium(iv) and oxidovanadium(v) complexes incorporating phenol-based hydrazone ligands in aerobic conditions

A new family of non-oxidovanadium(iv) [VIV(L)2] (1-4) complexes along with methoxy bonded oxidovanadium(v) [VVO(L)(OCH3)] (5 and 6) and [VVO(L)(OCH3)]2 (7 and 8) complexes have been synthesized by refluxing [VIVO(aa)2] [aa- being the deprotonated form of acetylacetone (Haa)] with a family of hydrazone ligands (H2L1-4, general abbreviation H2L, obtained by the condensation of 2-aminobenzoylhydrazide with 2-hydroxyacetophenone and its 5-substituted derivatives) using laboratory grade methanol as a solvent in the presence of air in ～30% yield. The DFT calculated changes in Gibbs free energy (ΔG), enthalpy (ΔH) and internal energy (ΔE) for the reaction to form complexes 1-4 in methanol: 2H2L + [VIVO(aa)2] + ?O2 + CH3OH → [VIV(L)2] + 2Haa + CH3OH + ?O2 are on average ～10, ～5 and ～14 kcal mol-1 respectively, while these values for the reaction in methanol to form complexes 5-8: 2H2L + [VIVO(aa)2] + ?O2 + CH3OH → [VVO(L)(OCH3)] + H2L + 2Haa + ?H2O are on average ～-16, ～-20 and ～-12 kcal mol-1 respectively, suggesting that the formation of 1-4 is not thermodynamically feasible through this method. In practice, however, these complexes are also formed probably due to their very low solubility in methanol along with complexes 5-8. The complexes were characterized by analytical and spectral methods. The structures of the H2L2 and H2L3 ligands and complexes 3 and 5-8 were determined by X-ray diffraction. Complexes 1-4 display quasi-reversible one-electron oxidation and reduction peaks in the potential windows of 0.66-0.70 and -0.22 to -0.39 V respectively while complexes 5-8 exhibit quasi-reversible one-electron reduction peaks in the 0.15-0.22 V region. The EPR spectral parameters indicate that the odd electron in complexes 1-4 is present in the dxy orbital, a suggestion which is also supported by a DFT study. The substituents in the aryloxy ring of the hydrazone ligands exhibited a significant effect on λmax for the LMCT transition, A‖, E1/2, ESOMO/EHOMO and ELUMO of the complexes. Complexes 1, 3, and 5-7 showed a wide range of toxicity in a dose dependent manner against lung cancer cells and they kill the cells through apoptosis. The binding ability of the complexes with CT DNA has been determined by a fluorescence emission study and the binding constant value obtained by this method was supported by a molecular docking study.

Syntheses and structural investigation of some alkali metal ion-mediated LVVO2- (L2- = tridentate ONO ligands) species: DNA binding, photo-induced DNA cleavage and cytotoxic activities

Eight alkali metal ion-mediated dioxidovanadium(v), [{VVO 2L1-6}A(H2O)n]∝, complexes for A = Li+, Na+, K+ and Cs +, containing tridentate aroylhydrazonate ligands coordinating via ONO donor atoms, are described. All the synthesised ligands and the metal complexes were successfully characterised by elemental analysis, IR, UV-Vis and NMR spectroscopy. X-ray crystallographic investigation of 3, 5-7 shows the presence of distorted NO4 coordination geometries for LVO 2- in each case, and varying μ-oxido and/or μ-aqua bridging with interesting variations correlated with the size of the alkali metal ions: with small Li+, no bridging-O is found but four ion aggregates are found with Na+, chains for K+ and finally, layers for Cs+. Two (5) or three-dimensional (3, 6 and 7) architectures are consolidated by hydrogen bonding. The dioxidovanadium(v) complexes were found to exhibit DNA binding activity due to their interaction with CT-DNA by the groove binding mode, with binding constants ranging from 103 to 104 M-1. Complexes 1-8 were also tested for DNA nuclease activity against pUC19 plasmid DNA which showed that 6 and 7 had the best DNA binding and photonuclease activity; these results support their good protein binding and cleavage activity with binding constants ranging from 104 to 105 M-1. Finally, the in vitro antiproliferative activity of all complexes was assayed against the HeLa cell line. Some of the complexes (2, 5, 6 and 7) show considerable activity compared to commonly used chemotherapeutic drugs. The variation in cytotoxicity of the complexes is influenced by the various functional groups attached to the aroylhydrazone derivative.

Synthesis, characterization, anti-inflammatory and analgesic activity of transition metal complexes of 3-[1-(2-hydroxyphenyl) ethylideamino]-2-phenyl-3, 4-dihydroquinazolin-4(3H)-one

A new quinazolinone derivative, 3-[1-(2-hydroxyphenyl)ethylideamino]-2- phenyl-3,4-dihydroquinazolin-4(3H)-one (LH) was synthesized by the condensation of 2-hydroxyacetophenone-2-aminobenzoylhydrazone and benzaldehyde. The cyclization to form 1,2-dihydroquinazolinone was confirmed by IR, 1D and 2D HETCOR studies. Coordination compounds of Co(II), Ni(II), Cu(II) and Zn(II) of LH were synthesized and characterized using various physico-chemical studies like stoichiometric, conductivity, magnetic moment measurements and spectral techniques such as IR, NMR, UV-vis and EPR spectroscopy. The elemental analysis and thermal studies suggested a general stoichiometry [M(HEPDQ)Cl] for all the complexes. A four-coordinate geometry was assigned to all the complexes. The complexes along with the parent ligand were screened for their anti-inflammatory activity, using carrageenan-induced rat paw edema, and for their analgesic activity by Eddy's hot plate method. The activity of the ligand was enhanced on complexation with metal ions. This enhanced activity was attributed to the increased lipophilic nature of the complexes. Notable anti-inflammatory activity was observed for Ni(II), Cu(II) and Zn(II) complexes. The analgesic activity of the ligand was greater than the standard at 60 min. and at a 10 mg kg -1 dose, whereas the activity of Ni(II) and Cu(II) complexes at 10 mg kg-1 dose was comparable with the standard used.

SYNERGISTIC FUNGICIDAL COMPOSITIONS INCLUDING HYDRAZONE DERIVATIVES AND COPPER

The present invention relates to the use of mixtures containing hydrazone compounds and copper for controlling the growth of fungi.