Design and synthesis of new thiobarbituric acid metal complexes as potent protease inhibitors: spectral characterization, thermal analysis and DFT calculations

Nassar, Mostafa Y.; El‐Shwiniy, Walaa H.; El-Sharkawy, Abdel-Azem M.; El-Desoky, Salsabiel

doi:10.1007/s13738-017-1229-3

Cited by 9 publications

(10 citation statements)

References 37 publications

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“…i.e. respectively for L 1 , L 2 , L 3 . From shifting to higher and lower frequency values for ν(C=N), the coordination between the ligand molecule and Zr(IV) through the nitrogen atom of hydrazono group was confirmed.…”

Section: Resultsmentioning

confidence: 79%

“…These changes of the IR spectra suggest that L 1 , L 2 , L 3 are coordinated to the Zr(IV) via two nitrogen atoms of amino (N‐H) and hydrazono (C=N) groups. The ν(O‐H) vibration of the water molecules in the prepared complexes were found at 3397–3402 cm ‐1 also, the ν(C=O) was found at 1599–1615 cm −1 .…”

Section: Resultsmentioning

confidence: 88%

“…A group of new bands with different intensities was found which characteristics for ν(M‐N). The ν(M‐N) bands observed at 544, 492 cm −1 for Zr(IV)‐L 1 , 638, 539 cm −1 for Zr (IV)‐L 2 and 593 and 543 cm −1 for Zr(IV)‐L 3 , which are absent in the spectra of L 1 , L 2 and L 3 . From the above mentioned result the coordination of L 1, L 2, and L3 was done through two C=N and N‐H groups (Scheme ).…”

Section: Resultsmentioning

confidence: 91%

“…Upon coordination to Zr(IV) the electron density on the nitrogen atom was decreased this lead to a decrease in the electron repulsion between the nitrogen lone pair and the double bond electrons and as a result C=N bond became a strong band with a higher frequency . A lower frequency value (3390, 3400 and 3399 cm −1 ) for the shifting of ν(N‐H) indicated a decrease of the N‐H bond strength upon coordination .…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, the values of protons of ‐CH aliphatic (methyl) observed in δ : 1.91 ppm (s, 3H, –CH 3 ), that of aromatic ring are in δ : 7.51–7.60 ppm (m, 4H, Aromatic–H),the proton of ( = CH‐Ar) group observed in δ : 6.51 ppm (S, 1H, = CH‐Ar) and protons of (N (CH 3 ) 2 ) group observed in δ : 3.71 ppm (s, 6H, ‐N (CH 3 ) 2 ) increased and the intensity of signals is increased, as shown in Table . From 1 HNMR and FT‐IR results, it was proposed that the L 3 coordinated to the central metal ion as bidentate ligand through the two nitrogen atom of pyrazolone …”

Section: Resultsmentioning

confidence: 99%

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Synthesis and cytotoxic evaluation of some substituted pyrazole zirconium (IV) complexes and their biological assay

El‐Shwiniy

Shehab

Mohamed

et al. 2018

Applied Organom Chemis

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Pyrazole and their derivatives are found to have intense biological efficiency. In the present work some substituted pyrazole derivatives were synthesized and used as ligands (4‐[2‐vinylthiophene]‐3‐methyl pyrozolin‐5(4H) ‐ one (L1), 4‐[4‐chloro benzylidine]‐3‐methyl pyrozolin‐5(4H) ‐ one (L2) and 4‐[4‐dimethylnitro benzylidine]‐3‐methylpyrozolin‐5(4H) ‐ one (L3)) to prepare the zirconium (IV) complexes. The synthesized ligands and their complexes were obtained as colored powdered materials and were characterized using magnetic measurements, melting point, molar conductance, infrared, electronic, 1HNMR, mass spectra and thermogravimetric analyses. All of the tested compounds showed good microbial activity against pathogenic microorganisms. The tested compounds exhibited considerable antitumor activity and cytotoxic specificity towards human colon carcinoma cell line (HCT‐116).

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Section: Resultsmentioning

confidence: 79%

Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis and cytotoxic evaluation of some substituted pyrazole zirconium (IV) complexes and their biological assay

El‐Shwiniy

Shehab

Mohamed

et al. 2018

Applied Organom Chemis

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Synthesis, characterization, thermal, anticancer studies, and density functional theory for potentially active pyrimidine‐based complexes

Abouzayed,

Mostafa,

Hammad

et al. 2024

Applied Organom Chemis

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This work aimed to create and characterize some new bioactive chelates of bis azodye ligand, 5‐((2‐hydroxy‐4,6‐dioxo‐1,4,5,6‐tetrahydropyrimidin‐5‐yl)diazenyl)naphthalen‐1‐yl)diazenyl) pyrimidine 2,4,6 (1H,3H,5H)‐trione. Except for the Sm(III) chelate, which exhibited a (3M:1L) molar ratio, all chelates had a (2M:1L) stoichiometry. According to Fourier transform infrared spectroscopy (FT‐IR), azo groups were not included in chelating with all ions except Sm(III), where just one azo group was coordinated. With the Ni(II) and Zn(II) ions, the ligand behaved as OON‐tridentate moiety; with the Co(II) and Cu(II) ions, it behaved as ON‐bidentate moiety. Co(II) and Cu(II) chelates had square planar structure, and Ni(II) and Zn(II) chelates had square pyramidal geometry. The chelates had greater thermal stability than the uncoordinated ligand due to the chelate's structure. [Sm3(H4L)(OH)7(NO3)2.H2O].4.5EtOH exhibited the maximum thermal stability, which may be due to the large number of solvent molecules and the high number of chelate rings. With the exception of the Sm(III) chelate, all of the examined chelates were more cytotoxic against MCF‐7 and Hep‐G2 cells than their parent ligand. With the exception of the Zn(II) chelate, which demonstrated activity on Hep‐G2 rather than MCF‐7, the effects of each metal chelate on the two cells were nearly equivalent. All of the studied chelates, especially Zn(II) and Co(II), were potent as antioxidants more than the native ligand. To support experimental findings, density functional theory (DFT) studies were performed via the CAM‐B3LYP/LanL2DZ method, and the geometry of the ligand and its chelates had been validated.

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Characterization of orthogonal hydrogen and halogen bonds in thiobarbituric acid complexes with halogen molecules (X = I₂, Br₂, and Cl₂): Structural and spectroscopic study

Alosaimi

Aljehani

Ibrahim

et al. 2021

J Chinese Chemical Soc

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The molecular complexes between thiobarbituric acid (TBA) and halogen molecules (X2 = I2, Br2, and Cl2) in different solvents are explored. Density functional theory (DFT) calculations at rwb97xd/lanl2dz were used to corroborate the experimental electronic and optical properties of the molecular adducts. Experimental results (Fourier transform infrared spectroscopy) show the stability of the complexes by halogen bonding (XB) and competitive hydrogen bonding (HB), which was supported by the DFT calculations. The molecular electrostatic potential and the frontier orbital calculations supported engagement of the thione group in XB rather than the carbonyl group. Based on the Hirshfeld atomic population, noncovalent interaction, and natural bond orbital analysis, the stability of TBAX2 adducts increases in the order TBACl2 > TBABr2 > TBAI2, where the larger charge transfer and highest stabilization energy were calculated for TBACl2 adducts.

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Design and synthesis of new thiobarbituric acid metal complexes as potent protease inhibitors: spectral characterization, thermal analysis and DFT calculations

Cited by 9 publications

References 37 publications

Synthesis and cytotoxic evaluation of some substituted pyrazole zirconium (IV) complexes and their biological assay

Synthesis and cytotoxic evaluation of some substituted pyrazole zirconium (IV) complexes and their biological assay

Synthesis, characterization, thermal, anticancer studies, and density functional theory for potentially active pyrimidine‐based complexes

Characterization of orthogonal hydrogen and halogen bonds in thiobarbituric acid complexes with halogen molecules (X = I₂, Br₂, and Cl₂): Structural and spectroscopic study

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Design and synthesis of new thiobarbituric acid metal complexes as potent protease inhibitors: spectral characterization, thermal analysis and DFT calculations

Cited by 9 publications

References 37 publications

Synthesis and cytotoxic evaluation of some substituted pyrazole zirconium (IV) complexes and their biological assay

Synthesis and cytotoxic evaluation of some substituted pyrazole zirconium (IV) complexes and their biological assay

Synthesis, characterization, thermal, anticancer studies, and density functional theory for potentially active pyrimidine‐based complexes

Characterization of orthogonal hydrogen and halogen bonds in thiobarbituric acid complexes with halogen molecules (X = I2, Br2, and Cl2): Structural and spectroscopic study

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Characterization of orthogonal hydrogen and halogen bonds in thiobarbituric acid complexes with halogen molecules (X = I₂, Br₂, and Cl₂): Structural and spectroscopic study