Azo Schiff Base Research Articles

Synthesis, biological evaluation, molecular docking analyses, and ADMET study of azo derivatives containing 1-naphthol against MβL-producing S. maltophilia

Stenotrophomonas maltophilia is a model organism exhibiting intrinsic antibiotic resistance, primarily due to its production of Mβ-lactamase enzymes that inactivate β-lactam antibiotics. This study aims to synthesize an azo derivative containing an oxazepine ring as a potential inhibitor of Mβ-lactamase. The molecular docking results revealed that the binding energies of the Mβ-lactamases ranged from − 5.95 to − 6.09 kcal/mol, indicating favourable interactions with the synthesized compounds. Two compounds were prepared: the first via aldol condensation of (A1) with p-hydroxybenzaldehyde to form (K1) and the second through Azo-Schiff base formation from 3,5-dimethylaniline, resulting in (L2) and (L18). Characterization of these compounds was conducted via FT-IR, CHN, 1H NMR, and 13C NMR spectroscopy. Antimicrobial activity was assessed through minimum inhibitory concentration (MIC) and minimum bacterial concentration (MBC) tests, which yielded values ranging from 1.19 ± 1 to 0.02 µg/mL and from 1.12 ± 1 to > 0.04 µg/mL, respectively. Notably, the MBC/MIC ratios indicated that L2 and L18 exhibited significant bactericidal activity. In silico analysis via MOE 2015 software allowed us to determine the binding poses and energies of the synthesized inhibitors against Mβ-lactamase (PDB ID: 6UAF). The most stable conformation from the docking results was selected for further evaluation. Compared with standard ceftazidime, the synthesized compounds significantly inhibited Mβ-lactamase activity. Additionally, ADMET analysis indicated favourable pharmacokinetic profiles and low toxicity, suggesting promising oral drug-like properties for the synthesized molecules.

Synthesis and characterization of some new Schiff base azo disperse dyes based on chromene moiety for simultaneous dyeing and antimicrobial finishing

New azo Schiff base disperse dyes based on a chromene moiety were synthesized by reacting (2-amino-7-hydroxy-4-(4-methoxyphenyl)-4 H-chromene-3 carbonitrile) and(2-amino-4-(3,4-dimethoxyphenyl)-7-hydroxy-4 H-chromene-3-carbonitrile), with vanillin and ninhydrin, producing new chromene Schiff base derivatives, which in turn were coupled with 2-chloro-4-nitroaniline diazonium salt to give new 4 azo disperse dyes (1–4). The structures of the prepared dyes were confirmed using elemental analysis, 1HNMR spectroscopy, mass spectrometry, and IR. The synthesized dyes were applied to polyester and nylon fabrics using different dyeing techniques: high temperature- high pressure, and ultrasonic dyeing methods. The highest K/S values for all investigated dyes were achieved usinga high temperature-high pressure dyeing technique. Also, the color reflectance of all synthesized dyes with different dyeing shades (1%, 2%, and 3%) was obtained. The fastness properties of the dyed samples using the investigated dyes showed good color fastness toward light, washing, rubbing, and perspiration fastness. The presence of a chromene moiety and Schiff base in the investigated dyes promotes a higher antimicrobial activity on nylon and polyester fabrics against all tested bacteria (E. coli gram-negative and Staphylococcus aureus gram-positive) and two fungi, Aspergillus Niger and Candida albicans.

Synthesis, Characterisation and Biological Evaluation of Metal Complexes from Thiosemicarbazone

A new azo schiff base ligand, together with its metal complexes,was synthesized and characterized from a thiosemicarbazid moiety. The title (E)-2-((2-hydroxy-3-((E)-(3-nitrophenyl)diazenyl)naphthalen-1-yl)methylene)hydrazine-1-carbothioamide)(HL),was synthesized by reacting((-2-hydroxy-3-((3-nitrophenyl)diazenyl) withan thiosemicabazide in a 1:1 molar ratio,HL interacted with different metal ions (Cr,Mn,Co,Ni and Cu) to from monomerci coordination complexes .Arsng of spectroscopic and analytical techniques ,including conductance studies, H1 and C13-NMR,FT-IR, electronic and mass spectroscopy,magnetic susceptibility,and elemental micro-analysis,were used to extensivety characterize these complexes.Coordinate compounds with four and six-coordinate geometries were confirmed to from based on the characterization data .

New Semicarbazone-Schiff Base Coordination; Synthesis, Characterization and Biological Evaluation

The synthesis and characterisation of a new azo Schiff base ligand generated from a semicarbazone moiety are reported in this study, in addition to its metal complexes. The title ligand, (E)-2-((2-hydroxy-3-((E)-(2-nitrophenyl) diazenyl) naphthalen-1-yl) methylene) hydrazine-1-carboxamide (HL), was synthesised by reacting ((E)-2-hydroxy-3-((2-nitrophenyl) diazenyl)-1-naphthaldehyde) with semicarbazidein a 1:1 molar ratio. Afterward, the interplay between HL and other metal ions (CrШ, MnII, CoII, NiII and CuII) produced monomeric coordination complexes in a 1:1 ligand-to-metal ratio. A range of spectroscopic and analytical techniques, such as magnetic susceptibility, conductance tests, 1H and 13C-NMR, FT-IR, electronic and mass spectroscopy, and elemental microanalysis, were used to extensively characterize these complexes. The synthesis of coordination compounds with six-coordinate geometries was verified by the characterization data. The study also assessed the antimicrobial efficacy of the synthesised compounds against various bacterial and fungal species, revealing that After the complex formed, the ligand's antimicrobial activity was greatly increased.

Synthesis, theoretical studies, antibacterial, and antibiofilm activities of novel azo-azomethine chelates against the pathogenic bacterium Proteus mirabilis.

2-((1-(4-((2,4,6-trioxohexahydropyrimidin-5-yl)diazenyl) phenyl) ethylidene) amino) benzoic acid (H3L), and its V(IV), Co(II), Ni(II), Cu(II), Pd(II) and Ag(I) chelates were synthesized. They were defined usingmultiple spectral and analytical techniques. With the exception of Ag(I) chelate, all chelates possessed non-electrolytic character. Square pyramidal shape was proposed for V(IV) chelate and Square planar for the other chelates. The analysis of functional group bands of H3L and its coordination compounds alludes that H3L chelated as neutral tetradentate via nitrogen atoms of azo and azomethine groups, oxygen atom of carbonyl of barbituric acid and OH of the carboxylic group. TG/DTG predicted the thermal behaviors of all compounds. The antibacterial activity of H3L and its coordination compounds was conducted against Proteusmirabilis at concentrations of 250, 500, and 1000µg/mL. Ag(I) at 1000µg/mL, showed the most inhibiting potency against P.mirabilis and registered zone of inhibition of 28.33 ± 0.84mm and highest biofilm inhibition of 70.31%. At 50Gy of gamma irradiation, the reducing effect of Ag(I) chelate was improved. The protein interruption of P. mirabilis was greatly interrupted by increasing the concentration of the chaletes. Also, Ag(I) showed the highest cytotoxicity with IC50 value of 11.5 µg/ mL. The novelty of this study is the synthesis of a new azo-Schiff base and this is almost the first publication of the effect of azo-Schiff ligands against that bacterial strain P.mirabilis.

Linear and non-linear optical and dielectric properties of transition metals complexes films derived from Azo-Schiff base for photovoltaic applications

A novel azo-Schiff base, which incorporates a heterocyclic triazole nucleus known as 1H-1,2,4-triazol-5-yl)imino)methyl)-5-((2-nitrophenyl)diazenyl)phenol (H2ASB, 1), was formulated and synthesized. Furthermore, a series of Cu2+ complexes, derived from this azo-Schiff base, were prepared by a simple method with a molar ratio of 1 M Cu2+ to 1 M H2ASB. The synthesized compounds were thoroughly characterized using alternative analytical and spectral techniques. The obtained results confirmed that H2ASB bonded with the Cu2+ ions in a uni-negative/neutral bidentate manner, via the phenolic hydroxyl oxygen and azomethine nitrogen atom, thereby resulting in tetrahedral or octahedral geometries. Additionally, theoretical studies employing DFT/B3LYP/LanL2DZ were conducted, which included the assessment of global reactivity descriptors, dipole moment, molecular electrostatic potential image (MEP), optimized geometry, and the LUMO-HOMO energy gap to support the geometrical structure of the synthesized compounds. On the other side, the optical constants of H2ASB and its complexes have been studied over 300–1500 nm spectral range. The optical band gap (Eg) values of the present film's changes from 1.92 eV for H2ASB to 1.45 eV for CuHASB(5) film whereas the static index of refraction (n) takes a different behavior. The obtained values of n and Eg are the same as those recorded for many semiconductor materials. This means that, compared to the cost and ease of preparation, these films under study could replace many other semiconductors, such as CdTe with (Eg = 1.5 eV) which is the same value of CuHASB(4) film. With the help of n and extinction coefficient (k) values, the dielectric and non-linear optical parameters have been estimated and well discussed. Finally, the sheet resistance (Rs) and thermal emissivity (εth) changes due to the incident photon energy have been investigated. It was observed that, the change of Rs and εth with E is opposite to the change of other parameters such as the absorbance and optical conductivity.

Synthesis, Charecterization, Antibacterial and Cytotoxicity of Novel Metal Complexes Derived from Azomethine Ligand (Bis Azo-Schiff Base) In Vitro and In Silico

Background: Schiff bases, especially Azo-Schiff bases, are significant ligands in organic chemistry due to their coordination capabilities. They find applications in various industrial sectors and biological studies. Metal complexes of Schiff bases, particularly with tetradentate ligands, have gained attention for their potential pharmacological benefits. However, there is limited information on the biological activities of certain Schiff base complexes, such as 1H-indole-3-ethylenesalicyldamine derivatives. Method: The synthesis of bis azo-Schiff base ligands and their metal complexes, including Ni(II), Co(II), Pd(II), and Pt(IV) complexes, was conducted. Various analytical techniques were employed to characterize the compounds using FTIR, NMR, UV-Vis spectroscopy, mass spectrometry, and molar conductivity. Biological activities, including antibacterial and cytotoxicity studies, were evaluated. Results: The synthesized compounds demonstrated stability and structural characteristics consistent with the intended coordination geometries. IR spectra confirmed the coordination of metal ions with the ligands. The complexes were evaluated for the antimicrobial activity against two types strains of Gram-negative Escherichia coli and Gram-positive bacteria Staphylococcus aureus and showed good significant against these bacteria. The Pd(II) complex demonstrated higher efficacy against cancer cells compared to normal cells, highlighting its potential as an anticancer agent. The cytotoxicity of the Pd (II) complex on human malignant melanoma A375 and Normal cell WRL-68 were IC50 23.83 and IC50 153.7, respectively. Molecular docking studies provide insights into the interaction of the complexes with target proteins, offering potential modes of action. Conclusion: The study successfully synthesized and characterized bis azo-Schiff base ligands and their metal complexes, demonstrating their stability and promising biological activities.

Synthesis, characterization, medical activity, and docking prediction of new heterocyclic Azo-Schiff base ligand derived from 2-Amino-5-methyl thiazol and Cr(III), Ni(II), and Cu(II) metal ions

A new heterocyclic Azo-Schiff base dye named 3- (((Z)-4-(dimethylamino) benzylidene) amino)-4-((E)-(5-methylthiazol-2-yl) diazenyl) phenol (HL) 3-aminophenol is produced when 2-amino-5-methyl thiazole reacts with (dimethylamino) benzaldehyde. The azo-Schiff base ligand reacted with some metal ions like Cr(III), Ni (II), and Cu(II) forming a chelate complex. Elements were analyzed by UV, FT-IR, H1-NMR, 13C NMR, molar conductance, mass spectra, GA, X-ray, and FESEM elemental analysis. Spectra reveal the complex's [M:L] ratio was 1:2. This investigation comprised antibacterial and antifungal activities against Escherichia coli (Gram-negative), Streptococcus (Gram-positive), and penicillin. Some complexes have good activity. Azo ligand and Ni(II) complex inhibit HepG2 cancer cells. The results indicated that it can be used as an anti-cancer drug in the fields of medicine and pharmacy. The DPPH test was also used to demonstrate that ligands and their complexes are antioxidants. The docking portion was used to determine cancer cells' physical characteristics and inhibitory activity. The order of inhibition is Ni-Complex > HL > Cr-Complex > Cu-Complex.

Ligational behavior of bidentate NO-donor, 2-(((1H-1,2,4-triazol-5-yl)imino)methyl)-4-(o-tolyldiazenyl)phenol towards VO2+, Fe3+, Ru3+, Co2+, Mn2+, Ni2+, Cu2+ Zn2+ and ions preparation, experimental, theoretical characterization, and microbicidal investigation

Novel bidentate chelator, 2-(((1H-1,2,4-triazol-5-yl)imino)methyl)-4-(o-tolyldiazenyl)phenol was employed for designing and preparation of transition metallic complexes. The synthetics were characterized based on various analytical, spectral, and theoretical tools. Based on the various analysis data, the azo-Schiff base chelator (H2L) linked with metallic cations as a neutral/uni-negative bidentate chelator via the protonated/deprotonated hydroxyl oxygen and azomethine nitrogen atoms adopted a distorted octahedral, tetrahedral, or square planar geometry. The mass spectroscopy confirmed that the molecular weights of azo-Schiff base and some of its complexes closely match with that of the estimated m/z values. Additionally, the structure of the azo-Schiff base ligand and some metallic complexes were studied by Density functional theory (DFT) calculations to assess the molecular orbitals (LUMO&HOMO) as well as the molecules electrostatic potential (MEP) to complete the picture. The synthetics were evaluated for their in vitro activity against Escherichia coli, Aspergillus niger, and Bacillus subtilis. According to this research, unbound ligand molecules are inactive while their metallic complexes have low to moderate activity.

Synthesis and Characterization of a Novel Azo-Dye Schiff Base and Its Metal Ion Complexes Based on 1,2,4-Triazole Derivatives

The study focused on producing and examining the properties of the 2-(((3-mercapto-5-(4-nitrophenyl)-4H-1,2,4-triazol-4-yl)imino)methyl)-4-(((4-mercaptophenyl) diazenyl)phenol) ligand (L) and its complexes with three transition metal ions, namely Ni(II), Co(II), and Cu(II). The ligand was formed through diazotization and coupling reactions between 4-aminobenzenethiol and a coupling Schiff base derived from 1,2,4-triazole. The characterization of the ligand and its metal ion complexes was carried out using analytical techniques such as FTIR, 1H- and 13C-NMR, UV-visible spectroscopy, and thermal analysis (TGA and DTG). Various physical methods were employed to synthesize and analyze the properties of the three mononuclear Co(II), Ni(II), and Cu(II) complexes with the azo-dye Schiff's base ligand. Based on the microanalysis and spectroscopic results, it was determined that the coordination between the azo Schiff base ligand and the central metal ion occurred through the NOS-donating atoms of the ligand. The analysis of the electronic spectra revealed that the synthesized Co(II) and Ni(II) complexes exhibited an octahedral geometry, while the Cu(II) complex had a distorted octahedral geometry. The implications of the finding regarding the octahedral and distorted-octahedral geometries include expanding the structural diversity in coordination chemistry, providing insights into ligand-metal interactions, and understanding the influence of geometry on properties.

Tetradentate azo Schiff base Ni(II), Pd(II) and Pt(II) complexes: Synthesis, spectral properties, antibacterial activity, cytotoxicity and docking studies

A new complexes of Ni(II), Pd(II), and Pt(II) have been synthesized from the reaction of Azo-Schiff base ligand (L1) that was prepared by the condensation firstly of salicylaldehyde with ethylene diamine in a 1:2 molar ratio and the prepared imine compound (S1) reacted with 2,5-dichloro aniline, and were employed in the preparation of complexes containing the metal ions Ni(II), Pd(II), and Pt(II). The structural characteristics of the synthesized compounds were investigated using UV-Vis, IR and NMR, molar conductance, elemental analysis, and mass spectroscopy. The results of the elemental analysis point to a 1:1 [M:L] stoichiometry. According to molar conductance studies, none of the prepared end products are electrolytic in nature. The complexes of Ni(II), Pd(II), and Pt(II) may have square planer geometry, according to spectral investigations. Then Pd(II), Ni(II), and Pt(II) complexes were evaluated for antimicrobial activity against different types strains of Gram-negative [Escherichia coli (ATCC 25922)] and positive bacteria [Staphylococcus aureus (ATCC 25923)] and showed good significant against these bacteria. The cytotoxic effect of the palladium complex on the prostatic malignant cell was examined via the PC3 cell line studied against normal cell WRL-68. The molecular docking of target microorganisms of these complexes will be studied by using MOE software.
 KEY WORDS: Salen ligand, Nickel(II), Palladium(II), Platinum(II), Complexes, bis azo-Schiff base
 Bull. Chem. Soc. Ethiop. 2024, 38(1), 99-111. DOI: https://dx.doi.org/10.4314/bcse.v38i1.8

Synthesis and Spectral identifications of new azo – Schiff base ligand(4Cl-2DIBP) derived from (para-aminobenzylamine) with its some metallic complexes

The New Heterocyclic ligand 4-chloro-2-(((4-((4,5-diphenyl-1H-imidazol-2-yl) diazenyl ) benzyl)imino)methyl) phenol (4Cl-2DIBP) was prepared from the condensation of para-aminobenzylamine with 4,5-diphenyl imidazole, followed by the condensation of the resulting compound with 5- chloro-2- hydroxy benzaldehyde. Different analytical and characterization techniques including (Mass,1HNMR, FT-IR and UV-Vis. spectroscopy and C.H.N elemental analysis) in the investigation of Newly prepared ligand. A series of Novel solid metal complexes of this ligand with Co (II), Ni (II), Cu (II), Zn ((II), Cd (II), and Hg (II) were prepared and all complexes were characterization by techniques above, excluding the Mass and the 1H-NMR spectroscopy of some prepared solid metal complexes and the use of flame atomic absorption spectroscopy to determine the percentages of metal ions in the prepared complexes also studied the magnetic susceptibility and molar conductivity of the metal complexes dissolved in DMSO at 1 × 10-3 M concentration laboratory temperature. The results of this studies showed that the coordination sites for the new Azo-Schiff base ligand with Co (II), Ni (II), Cu (II), Zn ((II) , Cd (II) and Hg(II) were to be through nitrogen of the imidazole ring, and the nitrogen of azo group,. The Electronic spectral and magnetic measurement data predict octahedral structure of the complexes. All complexes showed that Non-electrolytes properties.

Novel star-shaped liquid crystal macromolecules based on conjugated structures of azo and Schiff bases: synthesis and properties

ABSTRACT In this paper, a series of novel liquid crystal units (ASE-n, n = 4, 6, 8) of azo Schiff bases with sulphonic acid (-SO3H) as terminal substituents and different alkyl chain lengths were designed and synthesised. Nine star-shaped liquid crystal macromolecules with different central groups (ASE-P-n, ASE-T-n, ASE-G-n, n = 4, 6, 8) were synthesised by esterification of three novel azo Schiff base liquid crystal units (ASE-n, n = 4, 6, 8) with phloroglucinol, pentaerythritol and glucose. The structure of the synthesised compounds were analysed by infrared spectroscopy and 1H NMR. The results showed that all the compounds were consistent with the molecular structure design. The properties of liquid crystal such as phase transition temperature and liquid crystal mesophase range were characterised by POM and DSC. The effects of alkyl chain length and branched degree on the properties of liquid crystal were studied. The maximum absorption spectrum of the compound was determined by UV-Vis spectrophotometry. The photoisomerisation reaction of the compound was also studied. Under ultraviolet light (λ = 365 nm) irradiation, the effect of different duration on the cis-absorption percentage of azo (-N=N-) bond in the compound was studied.

Synthesis, physicochemical characterisation and DNA binding study of a novel azo Schiff base Ni(II) complex

The azo Schiff base ligand was synthesised, along with its Ni(II) complex, by diazotisation of salicylaldehyde with 4-nitroaniline in accordance with the accepted literature approach. Using a variety of spectroscopic techniques, the resulting complex is analysed both quantitatively and qualitatively (Elemental analysis, FT-IR spectroscopy, UV-VIS spectroscopy, 1H NMR, etc.). Spectral measurements of the complex revealed a mole ratio of 1:1. The non-electrolytic nature of the complex is confirmed by molar conductance investigation. The unique azo compound had a tetrahedral shape as a result of the tetra coordination of two phenolic oxygen and two imine nitrogen. The ability of the metal complexes to bind DNA was examined using absorption spectroscopy, fluorescence spectroscopy, viscosity tests, and thermal denaturation methods. Experimental research suggests that complexes bind to DNA through intercalation.

Bivalent Metal Chelates with Pentadentate Azo-Schiff Base Derived from Nicotinic Hydrazide: Preparation, Structural Elucidation, and Pharmacological Activity.

Azo-Schiff base ligand (N'-((E)-2-hydroxy-5-((E)-(2-hydroxyphenyl)diazenyl)benzylidene)nicotinohydrazide) and its Mn(II), Co(II), Ni(II), Cu(II), Zn(II) and Pd(II) chelates were prepared and elucidated. The geometrical structures of the prepared chelates were characterized by several spectroanalytical techniques and thermogravimetric analysis. The obtained data revealed that the chelates have (1M:1L), (1M:2L), (1M:3L), and (1M:4L) molar ratios. The infrared spectra displayed that the H2 L ligand behaves in a pentacoordinate fashion in chelates of Mn(II), Ni(II), and Cu(II) ions. However, in Zn(II) and Pd(II) chelates, the ligand is coordinated as a tetradentate species (NONO) through nitrogen atoms of azomethine and azo groups as well as oxygen atoms of phenolic hydroxy, and carbonyl groups. Besides, it was concluded that the oxygen atoms of carbonyl and hydroxy groups along with the azomethine nitrogen atom of the ligand are bounded with Co(II) ion in metal chelate (2). According to the measured molar conductance values, the chelates of Cu(II), Zn(II), and Pd(II) are weak electrolytes, but Mn(II), Co(II), and Ni(II) chelates are ionic. The azo-Schiff base ligand and its prepared metal chelates were tested for their antioxidant and antibacterial properties. The Ni(II) chelate was found to be considered an effective antioxidant agent. In addition, the available antibacterial data suggest that the Ni(II) and Co(II) chelates may be employed as inhibitor agents against Proteus vulgaris, Escherichia coli, and Bacillus subtilis bacteria. Furthermore, the data showed that, in comparison to the ligand and other metal chelates, copper(II) chelate (4) exhibited higher action against Bacillus subtilis bacteria.

Synthesis of New Azo–Schiff Base Complexes and Study of their Antibacterial Activity

In this research, we synthesized new azo-schiff base derivatives (4-9). These derivatives of azo compounds (1-3) that synthesized from 4-ethoxyaniline and drivatives of aldehyde such as, 4-aminobenzaldehyde, 4- hydroxybenzaldehyde and 4-ethoxybenzaldehyse to produce azo compounds (1-3). The compounds (1-3) reacted with differents aldehyde such as, isonicotinic hydrazide to produce N'-[(Z)-{3-[(E)-(4-ethoxyphenyl)diazenyl]-4-subs.phenyl}-methylidene]pyridine-4-carbohydrazide derivatives (4-6) and 3-amino pyridine to produce 2-[(E)-(4-ethoxyphenyl)diazenyl]-4-{(E)-[(pyridin-3-yl)imino]-methyl}subsbenzene derivatives (7-9). These compounds were characterization by spectroscopy methods such as, FTIR and 1HNMR. Some compounds (4, 6 and 9) that synthesized tested as antibacterial via used differents types such as, E. coli, Bacillus subtilis, and S. aureus. The activities of these compounds with different bacteria are known by the excellent diffusion methodology applied and derivative (6) gives a more activites from other derivatives.

Single crystal structure of nitro terminated Azo Schiff base: DNA binding, antioxidant, enzyme inhibitory and photo-isomerization investigation

Novel azo schiff base compound, namely, 2‑hydroxy-5-[(E)-phenyldiazenyl] benzaldehyde (AzNP) was synthesized by reacting 2‑hydroxy-5-[(E)-phenyldiazenyl]benzaldehyde and 4-(4-nitrophenoxy)benzenamine under inert conditions. The synthesized compound AzNP was characterized by Fourier transform (FT-IR), Nuclear magnetic resonance (NMR) and Ultraviolet-visible (UV–vis) spectroscopy. The solid state structure was elucidated by single-crystal X-ray crystallography. The compound was crystallized in the Monoclinic system with P 1 21/c1 space group, having a = 6.4859(3 Å, b = 15.6673(7) Å, c = 19.7908(9) Å, β = 90.945(2), and Z = 4, showing only one intermolecular C21-H21...N2 interaction, with donor and acceptor distance of 3.5774(16) Å, responsible for the elegant 3D network of the structure. DFT calculations were performed for structure-property relationship information of AzNP. In order to comprehend the selectivity behavior of the compound, binding interaction with CT-DNA was examined using standard optical spectroscopy. The observed hypochromism in the binding studies indicated that ligand substantially interact via the groove binding mode (Kb =9.91×103 mol−1dm3) with the DNA. Further assessment of binding mode of AzNP with DNA was made through hydrodynamic measurement and molecular docking analysis which confirmed the major groove binding mode of the ligand. Additionally, the DPPH (2,2-diphenyl-1-picrylhydrazyl), the ferric reducing power, and the α-amylase inhibition assays were used to evaluate the biological significance. Analysis of Cis-Trans conformational changes was also done to investigate photoisomerization properties of synthesized compound AzNP.

Isoquinoline Containing Azo Schiff Derivatives as Potential Antitubercular Agents: Synthesis, Characterization, Molecular Docking, PASS Prediction and ADME Studies

A series of isoquinoline containing novel azo Schiff base derivatives (3a-l) were synthesized and characterized by FT-IR, NMR (1H NMR & 13C NMR) and mass spectral analysis. The synthesized title compounds were evaluated for in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H37Rv strain by microplate alamar blue assay (MABA) method. Among the synthesized series of compounds, the compounds 3a, 3b, 3c and 3d were emerged as excellent antitubercular agents. Compound 3b showed the lowest MIC value of 1.6 μg/mL with a potency equivalent to the standards, isoniazid and ethambutol. Compounds 3a & 3c showed MIC value of 3.125 μg/mL, which is equivalent to the activity of a reference standard pyrazinamide. Compound 3d showed significant activity with MIC of 6.25 μg/mL and other compounds showed good to moderate activity ranging from 12.5 to 50 μg/mL. The four potent components were further tested for in vitro cytotoxicity using MTT assay against MCF-7 and HeLa cell lines to check the selectivity index. Among the tested series, compound 3b possessed the highest cytotoxicity against both MCF-7 (IC50, 7.09 ± 0.41) and HeLa (IC50, 9.04 ± 0.34) cell lines. Additionally, in silico molecular docking was performed to study its binding interaction with Mycobacterium tuberculosis enoyl reductase (InhA) and drug-like features were studied using Swiss ADME tool. PASS analysis of all the compounds showed greater Pa than Pi value for the antituberculosis activity. The results suggested that the synthesized isoquinoline containing azo Schiff base derivatives becomes promising for developing new drugs to treat tuberculosis.

Synthesis and Spectral Identification of New Azo-Schiff base Ligand Derivative from Aminobenzylamine and its Novel Metal Complexes with Cu(II), Zn(II) and Hg(II)

Synthesis and Spectral Identification of New Azo-Schiff base Ligand Derivative from Aminobenzylamine and its Novel Metal Complexes with Cu(II), Zn(II) and Hg(II)

New Azo-Schiff Compounds and Metal Complexes Derived from 2-Naphthol Synthesis, Characterization, Spectrophotometric, and Study of Biological Activity

This research involved synthesizing two compounds as derivatives of 2-naphthol by the classical method. The azo coupling compound was prepared via diazonium salt of 4-amino acetophenone followed by 2-naphthole. The azo-Schiff molecule was synthesized through condensation of an azo compound with 5-amino salicylic acid in an acidic medium. Using spectrum approaches, the new compounds are characterized (13C-NMR, 1H-NMR, FT-IR). The acid-base characteristics were investigated at various pH levels (0.67-12), and the ionization and protonation constants were determined. Spectroscopic methods were used to identify new copper (II), nickel (II), and cobalt (II) complexes of the azo-Schiff base ligand. All the compounds were evaluated for antibacterial activity against bacteria such as Staphylococcus aureus (Gram-positive bacteria) and Escherichia coli (Gram-negative bacteria). It was found that the coordination complexes of Cu and Co had an antibacterial effect on both concentrations against Staphylococcus aureus.