A quick microwave preparation of isatin hydrazone schiff base conjugated organosilicon compounds: Exploration of their antibacterial, antifungal, and antioxidative potentials

Singh, Gurjaspreet; Kalra, Pooja; Singh, Akshpreet; Sharma, Geetika; Sanchita, .; Pawan, -; Mohit, .; Espinosa, Cristóbal; Esteban, María Ángeles

doi:10.1016/j.jorganchem.2021.122051

Cited by 18 publications

(15 citation statements)

References 54 publications

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“…(i) The vanishing of stretching frequency bands of hydrazonic NH, oximatic hydroxyl and carbonyl groups referring to the covalency bonding of enolic carbonyl and deprotonated oximato groups with Cu 2+ , Mn 2+ , Zn 2+ , Fe 3+ , and VO 2+ ions. (ii) a negative shift of the stretching frequency bands of hydrazonic and oximatic azomethine groups by 19 referring to the participation of oximatic moiety in chelation via the nitrogen atom rather than the oxygen atom. 58 Second, hydrazone-oxime (H 2 L,1) can also interact as a mono-negative tridentate chelator with negative shift of the stretching frequency bands of hydrazonic and oximatic azomethine groups by 14-33 and 5-30 cm À1 correspondingly.…”

Section: Distorted Octahedralmentioning

confidence: 99%

“…These chelators and their synthetic complex derivatives have enormous benefit to acquire varied applications in several fields. They have shown considerable antimalarial, 1 anti-insecticidal, 2 anticancer, 3 anticholinesterase, 4 antitumor, 5,6 anti-tuberculosis, 7 antifungal, [8][9][10][11] antibacterial, 8-11 antihyperglycemic, 12,13 anti-infective, 14 antiradical, 15 antioxidant, [16][17][18] antimicrobial, 19,20 antitrypanosome, 21 antidiabetic, anti-inflammatory, 22,23 antiviral, [23][24][25] antidepressant and nootropic, 26 and gastroprotective activities. 27 Furthermore, They act as enzyme inhibitors, 23,[28][29][30] catalysts in various reactions, [31][32][33] and excellent anticorrosion to protect the metals and alloys as steel.…”

Section: Introductionmentioning

confidence: 99%

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Metal complexes of hydrazone–oxime derivative as promising in vitro antimicrobial agents against some fungal and bacterial strains

Hassan

Ebrahium

2022

Applied Organom Chemis

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In this study, Cu2+, Co2+, Ni2+, Mn2+, Zn2+, Fe3+, VO2+, and UO22+ complexes derived from a NNO tridentate chelating hydrazone–oxime, namely, N′‐((2E,3Z)‐3‐(hydroxyimino)butan‐2‐ylidene)benzohydrazide (H2L,1) were prepared. The elemental, thermo‐gravimetric, spectral, molar conductivity, and magnetic measurements were applied to elucidate the compositions and structures of these new compounds. In addition to the density functional theory (DFT), studies were employed to acquire optimal structures and quantum chemical parameters. The analyses indicate that the chelator reacted as a neutral or mononegative tridentate ligand bonded to the metal ions via the enolic/ketonic carbonylic oxygen, protonated/deprotonated oximatic nitrogen, and azomethine nitrogen atoms adopting square planar or distorted octahedral geometry. The structural characterization of hydrazone–oxime and its complexes was supported by DFT calculations according to the DFT‐B3LYP procedure and 6‐311+G(d,p) basis set. The theoretical data revealed that the reactivity of the complexes is greater than the free hydrazone–oxime (H2L,1), and there is a good agreement between the practical and theoretical data. The thermogravimetric investigation shows that the complexes break down in two to four decomposing steps in temperature range extended from 50 to 1000°C. In vitro antimicrobial activity data demonstrated an increase in activity of the hydrazone–oxime (H2L,1), upon chelation, and some metal complexes show enhanced antibacterial and antifungal agents.

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Section: Distorted Octahedralmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Metal complexes of hydrazone–oxime derivative as promising in vitro antimicrobial agents against some fungal and bacterial strains

Hassan

Ebrahium

2022

Applied Organom Chemis

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“…Isatins are regarded as highly useful heterocyclic moieties and explored as starting materials for the synthesis of various other heterocycles. Because of that, they have found a plethora of applications in general laboratory chemistry for ring expansion reactions, Friedel–Crafts reaction, aldol condensation reactions, and so forth. , In the pharmaceutical industry, isatins are used for the synthesis of various anti-cancer, anti-HIV, anti-diabetic, anti-tubercular, anti-bacterial, anti-fungal, anti-protozoal, antioxidant, anti-inflammatory, and neuroprotective agents. − They are also useful as precursors to anti-corrosive agents and fluorescence sensors in the dye industry . Synthesis of isatin and its derivatives are extensively found in the literature, but the isolation of the same and C2 or C3 di-indolyl indolones with iron-catalyst only with slight variation in reaction conditions is still not explored .…”

Section: Introductionmentioning

confidence: 99%

Fe₂O₃ Nanocatalysts Supported on Zeolite-Y for the Selective Synthesis of C2 Di-Indolyl Indolones and Isatins

Baruah

Dutta

Biswas

et al. 2022

ACS Appl. Nano Mater.

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Iron-oxide (Fe 2 O 3 ) nanoparticles in the dimension of ∼2.3 nm supported on zeolite-Y appeared as an excellent, reusable heterogeneous catalyst for the chromatography-free selective synthesis of 2,2-di(3-indolyl)-3-indolones, a C2-trimerized product. The zeolite-Y-supported Fe-oxide nanocatalyst showed the catalytic activity better than the Pd-and Au-based catalysts in the synthesis of C2 di-indolyl indolones under the prevailing reaction conditions. Besides, this low-cost catalyst displayed the ability to synthesize the pharmaceutically significant isatin molecules with high selectivity. The nature of the solvent and oxidant played a crucial role in the regioselective trimerization of indoles. The selective formation of the C2-trimerized product was accomplished in acetonitrile with peroxymonosulfate (oxone) as the oxidant, while in a water/acetonitrile mixture, it led to the formation of isatin. Compared to many other high-cost catalysts, the cheaper zeolite-Y-supported iron oxide catalyst promoted the reaction at room temperature with high selectivity. The products were obtained within 15−30 min with ≤95% yield. Different pieces of spectroscopic and electrochemical evidence supported by density functional theory (DFT) studies provided strong evidence for the proposed reaction mechanism. The kinetics of the reaction was studied through UV−vis spectroscopy and found to follow first-order kinetics. The UV−vis spectrum of the C2-trimerized product was further evaluated through time-dependent DFT calculations. The CO 2temperature programmed desorption study indicated the presence of strong basic sites in the Fe 2 O 3 -Y catalyst, favoring the interaction of the acidic indole molecule with the catalyst surface.

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“…The introduction of Schiff bases into 1,3,4-thiadiazoleis is interesting to study, and the 1,3,4-thiadiazole Schiff base derivatives also have biological activities [ 61 , 62 ]. For example, compound V in Figure 2 were found to exhibit obvious fungicidal activity [ 63 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

et al. 2022

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A series of novel indole Schiff base derivatives (2a–2t) containing a 1,3,4-thiadiazole scaffold modified with a thioether group were synthesized, and their structures were confirmed using FT-IR, 1H NMR, 13C NMR, and HR-MS. In addition, the antifungal activity of synthesized indole derivatives was investigated against Fusarium graminearum (F. graminearum), Fusarium oxysporum (F. oxysporum), Fusariummoniliforme (F.moniliforme), Curvularia lunata (C. lunata), and Phytophthora parasitica var. nicotiana (P. p. var. nicotianae) using the mycelium growth rate method. Among the synthesized indole derivatives, compound 2j showed the highest inhibition rates of 100%, 95.7%, 89%, and 76.5% at a concentration of 500 μg/mL against F. graminearum, F. oxysporum, F.moniliforme, and P. p. var. nicotianae, respectively. Similarly, compounds 2j and 2q exhibited higher inhibition rates of 81.9% and 83.7% at a concentration of 500 μg/mL against C. lunata. In addition, compound 2j has been recognized as a potential compound for further investigation in the field of fungicides.

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A quick microwave preparation of isatin hydrazone schiff base conjugated organosilicon compounds: Exploration of their antibacterial, antifungal, and antioxidative potentials

Cited by 18 publications

References 54 publications

Metal complexes of hydrazone–oxime derivative as promising in vitro antimicrobial agents against some fungal and bacterial strains

Metal complexes of hydrazone–oxime derivative as promising in vitro antimicrobial agents against some fungal and bacterial strains

Fe₂O₃ Nanocatalysts Supported on Zeolite-Y for the Selective Synthesis of C2 Di-Indolyl Indolones and Isatins

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

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A quick microwave preparation of isatin hydrazone schiff base conjugated organosilicon compounds: Exploration of their antibacterial, antifungal, and antioxidative potentials

Cited by 18 publications

References 54 publications

Metal complexes of hydrazone–oxime derivative as promising in vitro antimicrobial agents against some fungal and bacterial strains

Metal complexes of hydrazone–oxime derivative as promising in vitro antimicrobial agents against some fungal and bacterial strains

Fe2O3 Nanocatalysts Supported on Zeolite-Y for the Selective Synthesis of C2 Di-Indolyl Indolones and Isatins

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

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Fe₂O₃ Nanocatalysts Supported on Zeolite-Y for the Selective Synthesis of C2 Di-Indolyl Indolones and Isatins