Crystal Structure of 2-[2-hydroxy-3-methoxyphenyl]-3-[2-hydroxy-3-methoxybenzylamino]-1,2-dihydroquinazolin-4(3H)-one and the Synthesis, Spectral and Thermal Investigation of its Transition Metal Complexes

Gudasi, Kalagouda B.; Patil, Siddappa A.; Vadavi, Ramesh S.; Shenoy, Rashmi V.; Nethaji, Munirathinam

doi:10.1007/s11243-006-0034-0

Cited by 80 publications

(24 citation statements)

References 14 publications

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“…In the present complexes, due to rotation about the N–N bond, the ligand changes its conformation to facilitate the coordination in ONN fashion as in the case of Cd(II) complex as reported earlier [14]. The antibacterial activity of the ligand is enhanced on complexation, whereas no distinct change is observed in case of antifungal activity.…”

Section: Discussionsupporting

confidence: 63%

Antimicrobial Study of Newly Synthesized Lanthanide(III) Complexes of 2‐[2‐hydroxy‐3‐methoxyphenyl]‐3‐[2‐hydroxy‐3‐methoxybenzylamino]‐1,2‐dihydroquinazolin‐4(3H)‐one

et al. 2007

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New lanthanide(III) complexes with 2-[2-hydroxy-3-methoxyphenyl]-3-[hydroxyl-3-methoxybenzylamino]-1,2-dihydroquin- azoline-4(3H)-one (Hmpbaq) have been synthesized and characterized by elemental analysis, conductance measurements, magnetic susceptibilities, spectroscopic (IR, NMR, UV, EPR), and thermal studies. Molar conductance studies indicate 1 : 1 electrolytic behavior for these complexes. IR spectra indicate that Hmpbaq acts as a tridentate ligand coordinating through carbonyl oxygen, benzyl amine nitrogen, and deprotonated phenolic oxygen. TG and DTA studies of La(III) and Pr(III) complexes indicate the presence of two coordinated water molecules. Based on these studies, the complexes have been formulated as [La(mpbaq)2(H2O)2]·NO3, where Ln = La(III), Pr(III), Nd(III), Sm(III), Eu(III), Gd(III), Th(III), Dy(III), and Y(III). The ligand, lanthanide(III) salts, and the corresponding complexes have been simultaneously screened for their antibacterial and antifungal activities and compared with the drugs in use.

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Section: Discussionsupporting

confidence: 63%

Antimicrobial Study of Newly Synthesized Lanthanide(III) Complexes of 2‐[2‐hydroxy‐3‐methoxyphenyl]‐3‐[2‐hydroxy‐3‐methoxybenzylamino]‐1,2‐dihydroquinazolin‐4(3H)‐one

et al. 2007

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“…Both compounds (A and B) were synthesized by using a similar procedure as previously described, with a few modifications 46 47 ( Fig. 12 ).…”

Section: Methodsmentioning

confidence: 99%

Synthesis, characterization and apoptotic activity of quinazolinone Schiff base derivatives toward MCF-7 cells via intrinsic and extrinsic apoptosis pathways

Zahedifard

Faraj

Paydar

et al. 2015

Sci Rep

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The current study investigated the cytotoxic effect of 3-(5-chloro-2-hydroxybenzylideneamino)-2-(5-chloro-2-hydroxyphenyl)-2,3-dihydroquinazolin-41(H)-one (A) and 3-(5-nitro-2-hydroxybenzylideneamino)-2-(5-nitro-2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (B) on MCF-7, MDA-MB-231, MCF-10A and WRL-68 cells. The mechanism involved in apoptosis was assessed to evaluate the possible pathways induced by compound A and B. MTT assay results using A and B showed significant inhibition of MCF-7 cell viability, with IC50 values of 3. 27 ± 0.171 and 4.36 ± 0.219 μg/mL, respectively, after a 72 hour treatment period. Compound A and B did not demonstrate significant cytotoxic effects towards MDA-MB-231, WRL-68 and MCF-10A cells. Acute toxicity tests also revealed an absence of toxic effects on mice. Fluorescent microscopic studies confirmed distinct morphological changes (membrane blebbing and chromosome condensation) corresponding to typical apoptotic features in treated MCF-7 cells. Using Cellomics High Content Screening (HCS), we found that compound A and B could trigger the release of cytochrome c from mitochondria to the cytosol. The release of cytochrome c activated the expression of caspases-9 and then stimulated downstream executioner caspase-3/7. In addition, caspase-8 showed remarkable activity, followed by inhibition of NF-κB activation in A-and B-treated MCF-7 cells. The results indicated that A and B could induce apoptosis via a mechanism that involves either extrinsic or intrinsic pathways.

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“…The empirical factor f = g /A cm −1 is an index of tetragonal distortion, and its value may vary from 105 to135 for small to extreme distortions in square planar complexes [32], and it depends on the nature of the coordinated atoms [33]. The f value for the Cu(II) complex is found to be 122, indicating significant distortion from planarity ( Figure S4).…”

Section: Esr Spectra a Powder Esr Spectrum Of Copper(ii)mentioning

confidence: 99%

Synthesis, Characterization, and Biological Activity of Some Transition Metal Complexes Derived from Novel Hydrazone Azo Schiff Base Ligand

Anitha¹,

Sumathi²,

Tharmaraj³

et al. 2011

International Journal of Inorganic Chemistry

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A series of metal(II) complexes ML where M = VO(II), Co(II), Ni(II), Cu(II), and Zn(II) have been synthesized from azo Schiff base ligand (N′E)-N′-(5-((4-chlorophenyl)diazenyl)-2-hydroxybenzylidene)-2-hydroxybenzohydrazide and characterized on the basis of elemental analyses, electronic, IR, and 1H NMR spectra, magnetic susceptibility and also by aid of scanning electron microscopy (SEM), X-ray powder diffraction, fluorescence spectral studies, and molar conductivity measurements. Conductivity measurements reveal that the complexes are nonelectrolytes. Spectroscopy and other analytical studies reveal distorted square planar geometry for copper, square-pyramidal geometry for oxovanadium, and tetrahedral geometry for other complexes. Redox behavior of the copper(II) complex has been studied with cyclic voltammetry, and the biological activities of the ligand and metal complexes have been studied against several microorganisms by the well diffusion method. All synthesized compounds can serve as potential photoactive materials as indicated from their characteristic fluorescence properties. The second harmonic generation (SHG) efficiency of the ligand was measured and found to be higher than that of urea and KDP. The SEM image of the copper(II) complex implies that the size of the particles is 50 nm.

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Crystal Structure of 2-[2-hydroxy-3-methoxyphenyl]-3-[2-hydroxy-3-methoxybenzylamino]-1,2-dihydroquinazolin-4(3H)-one and the Synthesis, Spectral and Thermal Investigation of its Transition Metal Complexes

Cited by 80 publications

References 14 publications

Antimicrobial Study of Newly Synthesized Lanthanide(III) Complexes of 2‐[2‐hydroxy‐3‐methoxyphenyl]‐3‐[2‐hydroxy‐3‐methoxybenzylamino]‐1,2‐dihydroquinazolin‐4(3H)‐one

Antimicrobial Study of Newly Synthesized Lanthanide(III) Complexes of 2‐[2‐hydroxy‐3‐methoxyphenyl]‐3‐[2‐hydroxy‐3‐methoxybenzylamino]‐1,2‐dihydroquinazolin‐4(3H)‐one

Synthesis, characterization and apoptotic activity of quinazolinone Schiff base derivatives toward MCF-7 cells via intrinsic and extrinsic apoptosis pathways

Synthesis, Characterization, and Biological Activity of Some Transition Metal Complexes Derived from Novel Hydrazone Azo Schiff Base Ligand

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