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•We are synthesized novel organic ligands and their metal complexes.•Characterization of ligands and metal complexes were carried out by various spectral techniques.•α-Glucosidase ...inhibitory activity, antioxidant activity, antimicrobial activity were carried out for our novel ligands and metal complexes.
Present work reviews that, the synthesis of (E)-N′-((7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene)benzohydrazide L ligand and their metal complexes. The colored complexes were prepared of type M2+LX2, where M2+=Mn, Co, Ni, Cu, Sr and Cd, L=(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene)benzohydrazide, X=Cl−. Ligand derived from the condensation of 8-formyl-7-hydroxy-4-methylcoumarin and benzohydrazide in the molar ratio 1:1 and in the molar ratio 1:2 for metal complexes have been prepared. The chelation of the ligand to metal ions occurs through the both oxygen groups, as well as the nitrogen atoms of the azomethine group of the ligand. Reactions of the Schiff base ligand with Manganese(II), Cobalt(II), Nickel(II), Copper(II), Strontium(II), and Cadmium(II) afforded the corresponding metal complexes. The structures of the obtained ligand and their respective metal complexes were elucidated by infra-red, elemental analysis, Double beam UV–visible spectra, conductometric measurements, magnetic susceptibility measurements and also thermochemical studies. The metal complex exhibits octahedral coordination geometrical arrangement. Schiff base ligand and their metal complexes were tested against antioxidants, antidiabetic and antimicrobial activities have been studied. The Schiff base metal complexes emerges effective α-glucosidase inhibitory activity than free Schiff base ligand.
In the present paper a series of triphenylphosphine complexes containing mixed ligands like 2-aminothiazole (Ath) and 2-aminotriazole (Atz) have been prepared. The complexes are of the formula MCl
3
...((Pph
3
)(Ath)
2
and MCl
3
((Pph
3
)(Atz)
2
, M = Ru(III), Ce(III) and La(III). These complexes were characterized by different spectral techniques. Additionally, the computational study has been performed using density functional theory (DFT) and the calculation is used to examine the electronic structure of the synthesized complexes. The biological activities of all the synthesized complexes were evaluated and the comparative account in properties between the triphenylphosphine metal complexes containing 2-aminothiazole and 2-aminotriazole ligands has been made. The DNA-binding property of these metal complexes was investigated using electronic absorption spectroscopy and fluorescence spectroscopy. The antibacterial and antifungal activity against bacterial species (Gram −ve bacteria:
Escherichia coli
,
Salmonella typhi
) and (Gram +ve bacteria: (
Staphylococcus aureus
and
Bacillus subtilis
) and fungi (
Aspergillus niger
and
Candida albicans
). The antioxidant study was carried out against the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH
·
) which showed that the metal complexes are good antioxidant, as compared to BHT. Further, the in-silico molecular docking study was performed to predict the possible binding sites of the metal complexes.
Schiff bases being biological moieties possess diverse biological and pharmaceutical applications. Metal ions play an important role in various functions of the biological system as well as the human ...body. The importance of Schiff base and their metal complexes have been acknowledged in the field of bioinorganic chemistry. The current investigation hence focuses on the synthesis and characterization of a bidentate indole-based ligand(Z)-
N'
((1H-indol-3-yl)methylene)nicotinohydrazide
(L)
derived from indole-3-carboxaldehyde
(1)
, nicotinic acid hydrazide
(2)
and their metal complexes of Mn(II), Co(II), Ni(II) and Cu(II),
(4a–d)
in 2:1 stichiometric ratio. All the synthesized ligand and complexes were characterized by IR, UV–Visible,
1
H NMR,
13
C NMR, Mass, Powder XRD analysis. Further, the ligand and their metal complexes were screened for antimicrobial, antioxidant and DNA cleavage studies. Among the synthesized complexes, Ni(II)
(4c)
showed highest antimicrobial activity against tested Gram −ve and Gram +ve bacterial strains and fungal microorganism, better than the ligand
(L)
. The antioxidant activity results showed that the metal complexes
(4a–d)
were observed to be more active than the parent ligand. Furthermore, the ligand
(L)
and their respective metal (II) complexes
(4a–d)
were found to cleave the pBR322 DNA, during gel electrophoresis studies.
A new class of functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds (4a–q) was synthesized by a four step reaction in good yields. Initially, o-alkyl derivative of ...salicyaldehyde (1) readily furnished corresponding 2-acetyl benzofuran (2) on treatment with potassium tert-butoxide (t-BuOK) in the presence of molecular sieves. Further, Claisen–Schmidt condensation reaction with 4-methoxy benzaldehyde and hydrazine hydrate followed by coupling of benzoyl chlorides afforded target compounds (4a–q). Representative of the synthesized compounds was characterized by IR, 1H NMR, 13C NMR, mass, elemental analysis and evaluated for antimicrobial and antioxidant activities. The results gathered are allowed to conclude that, all newly synthesized analogues exhibit a certain degree of antimicrobial and antioxidant activities. Among the analogues, compounds (4h) and (4j) showed an excellent antimicrobial activity in the well plate method. Meanwhile, compounds (4e–f), (4l) and (4p) showed good antioxidant activity, whereas compound (4g) and (4q) displayed dominant antioxidant efficacy compared to standard butylated hydroxy anisole (BHA).
•The new 1,3-thiazole derived 1,2,3-triazole were synthesized and characterized.•Profiling of In vivo anti anxiety and anti inflammatory activity was carried out•Compounds (6h) and (6i) have strong ...anti-anxiety effect against tested mice.•The compounds (6e, 6g, 6h, and 6k) were found good anti-inflammatory agents against carrageenan induced acute inflammation in rats.•Further, a molecular docking study was performed on lead compounds to identify important binding modes responsible for anti anxiety activity.
Heterocyclic rings such as thiazole and triazole are considered as privileged moieties, since they constitute several drugs for biological treatment. In this work, a novel series of 1, 3-thiazole linked 1,2,3-triazole derivatives were designed and synthesized according to convenient synthetic procedures. All the synthesized compounds are characterized by 1H NMR, 13C NMR and LCMS techniques. The molecular docking was studied to illustrate the binding interactions of target molecules with GABAA receptor. The synthesized compounds containing 1,3-thiazole and 1,2,3-triazole ring, the presence of these rings in each molecule may lead to have potential in vivo anti-anxiety and anti-inflammatory properties. The in vivo activity result revealed that some of the compounds possessed statistical significant therapeutic efficacy. Anti-anxiety screening on mice indicated that all the target compounds (5mg/kg) exhibited certain extent of an anxiolytic effect by increasing time spent on open arms and the percentage of open arm entries as compared to controlled group. More importantly, among the newly synthesized compounds (6h) and (6i) have strong anti-anxiety against mice. The non steroidal anti-inflammatory activity drugs (NSAIDs) are plays a very important role to prevent the growth of cyclooxygenase enzymes which are responsible for inflammation and pain. The results show that the following compounds 6e, 6g, 6h, and 6k are having maximum anti inflammatory activity against carrageenan induced acute inflammation in rats comparable to diclofenac as reference drug. Molecular docking simulations were employed to find out the important binding modes responsible for the anti anxiety activity, thus supporting their effective anti-anxiety efficacy.
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Benzofuran fused phenyl pyrimidine/pyrazole schiff base derivatives 8(a-e) and 9(a-e) have been synthesized by a three step reaction. The structures of the synthesized compounds were established ...based on the analytical and spectral data. The in-vitro anticancer and antimicrobial activity of compounds against MCF-7 and HeLa cancer cell lines and microbes were studied. The compounds 8c and 9c showed significant levels of anticancer activity compared to the standard. Molecular docking studies were performed on the active site of transferase (PDB ID: 4ANM) with the synthesized ligands 8(a-e) and 9(a-e) for the optimization of the investigated compounds as potential cancer cell inhibitors. The antimicrobial activity was performed by using well diffusion method, compounds 8d and 9d showed maximum inhibition effect against the tested microbial pathogens, respectively.
•A new Schiff base fluorescent turn-off sensor NF1 has been synthesized and developed.•Global reactivity descriptors and excited state properties were calculated by DFT/TD-DFT.•Sensor NF1 exhibits ...high selectivity towards Cu2+ over other studied metal ions.•Fluorescence quenching and hypsochromic shift mechanism was observed for NF1 with inclusion of Cu2+ ions.•S-V analysis was performed to estimate the binding affinity.
Herein, we report a novel Schiff base receptor (Z)-N'-((1H-indol-3-yl) methylene) nicotinohydrazide (NF1) as a fluorescent chemosensor for the selective detection of Cu2+ in buffer solution (20 mM HEPES, pH 7.5, 1:4 (v:v) water: DMSO) in the presence of other competitive metal ions (Na+, Mg2+ Cd2+, Ni2+, Co2+). The probe NF1 was synthesized and characterized by spectroscopic and single crystal X-ray diffraction studies. The fluorescence binding studies was performed by adding different concentration of Cu2+ metal ions to the solution of NF1 (6.4 × 10−4 M). The successive addition of Cu2+ ions (0-20 mM), results in a decrease in the fluorescence intensity of NF1 due to chelation enhanced fluorescence quenching, which is attributed to the paramagnetic nature of transition metal ion Cu2+. The fluorescence quenching of NF1 after adding different concentrations of Cu2+ ions (0 to 20 equivalents) along with a large blue shift of 65 nm in emission wavelength observed are the evidence for the formation of the NF1-Cu2+ complex. The results of Job's plot and mass spectroscopic analysis, altogether indicated the 1:1 stoichiometry of the NF1-Cu2+ complex. The shift in vibrational modes of C=O and N-C modes was observed in FT-IR studies, and also these could be ascribed for the complex formation. The association and dissociation constants of the NF1-Cu2+ complex were calculated by using the Stern-Volmer plot. The photophysical properties such as quantum yield and fluorescence lifetimes were calculated for NF1 and NF1 with 1 equivalent of Cu2+. The proposed complex structure was optimized by applying the DFT method. The highest occupied molecular orbital/lowest unoccupied molecular orbital energy gap was calculated for probe NF1 and NF1-Cu2+ complex. Theoretical calculations were performed using the TD-DFT method to calculate the excited state properties of the molecule NF1 and NF1-Cu2+ complex and compared with experimental results. All the theoretical and experimental findings strongly suggest that NF1 can be a good candidate for copper sensing applications.
•Several 5-substituted-1,3,4-oxadiazole-2-thiol hybrids 4(a-m) were synthesized and evaluated as anti-inflammatory and anti-cancer agent.•The molecular structure of all the synthesized compounds were ...validated by 1H NMR, 13C NMR, LC-MS spectral analysis.•Different substituents (EWG and EDG) and their respective positions on the attached phenyl ring of the 1,3,4-oxadiazole-2-thiol hybrids show amazing variations of anti-inflammatory and anti-cancer activity.•All the tested derivatives display certain degree of activity but compound 4f exhibited the good anti-inflammatory activity in vivo, while compound 4e demonstrated the most potent anticancer activity against a breast cancer cell line.•Molecular docking studies were used to determine the binding interactions between synthesised compounds and the target protein.
A series of novel substituted 5-phenyl-methyl (Z)-2-(1-amino-2-((1,3,4-oxadiazol-2-yl)thio)ethylidene)hydrazine-1-carboxylate scaffolds 4(a-m) have been synthesized to assess their potential as anti-inflammatory and anticancer agents. The structures of the synthesized derivatives were established by employing 1H- NMR, 13C- NMR, and LC-MS analysis. In particular, thirteen derivatives were evaluated for their in vivo anti-inflammatory activity by making use of carrageenan-induced paw edema in SD rats and in vitro anticancer activity towards the BT474 female breast cancer cell line. Among the tested derivatives, Compound 4f emerged as a key lead and showed significant inhibition in paw edema volume in vivo (81 %), and compound 4e exhibited interesting ability to inhibit cellular proliferation in vitro (IC50=3.78 µM for BT474) compared to Doxorubicin (IC50 = 6.795 μM). Based on the structure-activity relationship, the presence of electron-donating substituents along with oxadiazole nucleus seems favorable for biological activities. A docking study was performed to understand the molecular interactions of the synthesized compounds which revealed that the compounds perfectly docked into the active sites of the protein.
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The bio-active Co(II), Ni(II) and Cu(II) complexes derived from new (2-((1H-benzodimidazol-2-yl)methylthio)-1H-benzodimidazol-5-yl)(phenyl)methanone were synthesized in good yield. The structure of ...these metal complexes have been characterized using IR, Uv–visible, mass spectra,1H NMR, TGA and powder XRD techniques. The spectral data of the Co(II) and Ni(II) complex indicated the tri-dentate bonding mode with the ligand and that of the Cu(II) complex is in bi-dentate bonding mode. The electrocatalytic activity of the Co(II) complex was studied by cyclic voltammeter using modified GCE towards various concentration of dopamine (DA, 3,4-dihydroxyphenethylamine). The obtained Ip value linearly increased with increasing scan rates, indicating the oxidation process of dopamine (DA) which occurred by modified Co(II) complex/GCE through diffusion controlled process. The antimicrobial, antioxidant and cytotoxicity studies of the ligand and its metal complexes were performed, the obtained results showed that the complexes are more potent bio-active as compared with uncoordinated ligand. The DNA binding property of the metal complexes were performed on double strand calf thymus DNA using electronic absorption and fluorescence emission methods, in addition, photo induced DNA cleavage activity also studied on pBR322 DNA. The molecular docking of the Co(II) complex on 6-bp DNA (PDB code: 1Z3F) and C-KIT Tyrosive kinases (TRKs) (PDB code: 1t46), further confirms the inhibition ability of the metal complex. The experimental results and the drug likeness property of the metal complexes suggest the possible applications of metal complex which, could be developed as a potent drug in the near future.
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•The ligand BIPM used to synthesize Co(II), Ni(II) and Cu(II) complexes. The electrocatalytic activity of the Co(II) complex was studied by cyclic voltammeter using modified GCE towards various concentration of dopamine (DA).•The antimicrobial, antioxidant, cytotoxicity, DNA binding and DNA cleavage activity studies of the ligand and metal complexes were performed.•The molecular docking of the Co(II) complex on 6-bp DNA (PDB code: 1Z3F) and C-KIT Tyrosive kinases (TRKs) (PDB code: 1t46).
The study has been achieved the efficient synthesis of vanillin derived piperidin-4-one oxime esters (5a–m) via four step reaction involved Mannich reaction of vanillin, acetone and ammonium acetate ...to obtain 2,6-bis(4-hydroxy-3-methoxyphenyl)-piperidin-4-one 2 followed by N-methylation and oximation. Further, to enhance the biological activity of vanillin derived piperidin-4-one oxime core, esterification of 4 with substituted benzoyl chlorides in the presence of strong organic base t-BuOK accomplished a series of vanillin derived piperidin-4-one oxime esters (5a–m). The synthesized analogues are screened for their antioxidant and antimicrobial studies and the preponderant effect of the phenyl ester substituents on the biological activity of piperidin-4-one oxime core was demonstrated. Among the tested compounds, 5i and 5j are emerged as outperformed antioxidants than standard Butylated hydroxy anisole (BHA) whereas, compounds 5b and 5d manifested potent antibacterial and antifungal activity than standard streptomycin and fluconazole respectively.
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