Synthesis, structural studies and antituberculosis evaluation of new hydrazone derivatives of quinoline and their Zn(II) complexes

Mandewale, Mustapha C.; Thorat, Bapu R.; Nivid, Y.; Jadhav, R. G.; Nagarsekar, Aarti; Yamgar, Ramesh

doi:10.1016/j.jscs.2016.04.003

Cited by 61 publications

(26 citation statements)

References 29 publications

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“…Numerous examples of Cu (II) and Zn (II) complexes have been explored for their significant antimicrobial activity [20]. Based on these facts, supported by literature [21] Figure 1 and in continuation of our current research interest in the field of synthesis and antimicrobial study of heterocyclic compounds [22][23][24][25][26], we have synthesized and screened the antimicrobial activity of series of transition metal complexes of new Schiff base ligands derived from ethyl 5-aminobenzofuran-2carboxylate.…”

Section: Introductionmentioning

confidence: 83%

Synthesis, characterization and antibacterial activity of Cu (II) and Zn (II) complexes of 5-aminobenzofuran-2-carboxylate Schiff base ligands

Nazirkar

Mandewale

Yamgar³

2019

Journal of Taibah University for Science

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The ever-increasing spread of bacterial infection with rising antibacterial drug resistance has become a matter of global concern in the modern times. Therefore, such serious infections leading to high mortality rate has necessitated the search for new classes of effective antibacterial agents with minimum toxicity. Herein, we report the synthesis and identification of a new class of benzofuran based Schiff ligands (6a-6e) and their Cu/Zn complexes (7a-7j) via sequential reactions starting with Salicylaldehyde. Compounds 6a, 7c and 7e exhibit activity in the low microgram range against M. tuberculosis, showing the minimum inhibitory concentrations (MICs) of 1.6 µg/mL. The compounds 6e and 7b also show interesting antibacterial activity against S. Aureus, E. coli and B. Subtilis with comparable area of inhibition of standard drugs under study. This research suggests that benzofuran based compounds can serve as a promising lead scaffold in developing new drugs to combat microbial infections.

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Section: Introductionmentioning

confidence: 83%

Synthesis, characterization and antibacterial activity of Cu (II) and Zn (II) complexes of 5-aminobenzofuran-2-carboxylate Schiff base ligands

Nazirkar

Mandewale

Yamgar³

2019

Journal of Taibah University for Science

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“…Unicam UV-VIS UV2 spectrometer was used to measure the electronic spectra. 1 H-NMR spectra in d 6 -DMSO was were recorded on a Varian Gemini WM-200 MHz spectrometer. Thermogravimetric analysis performed using an automatic recording Thermo balance, type 951 DuPont; heating rate of 10 °C/min (25-800 °C) in N 2 .…”

Section: Instrumentationmentioning

confidence: 99%

“…Supplementary Material (23) 125.263 N(12)-N(11)-C (9) 124.077 O(10)-C(9)-C (8) 114.086 C(9)-C(8)-N (7) 122.517 117.214 C(9)-C(8)-N (7) 125.795 C(8)-N(7)-C (6) 119.876 N(7)-C(6)-N (5) 116.154 N(7)-C(6)-C(1) 120.795…”

Section: Page | 752mentioning

confidence: 99%

“…Ligands derived from substituted hydrazone have played an important part in revealing the preferred coordination geometries of metal complexes and have a valuable contribution in the coordination chemistry due to their preparative accessibility, diversity and structural variability. The hydrazones and their complexes with transition metal ions have been well documented in the literature as good therapeutic, antimicrobial, anticonvulsant, pharmacological and catalytic agents [5][6][7]. The ligands that contain an amidic bond are capable of keto-enol tautomerism thus providing numerous modes of chelation to a metal ion either in neutral or deprotonated form as quinquedentates, via hydrazone nitrogen and carbonyl oxygen atoms depending upon the metal ion, pH of the medium, the reaction conditions and the nature of the hydrazones [8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

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Mononuclear Cr(III), Mn (II), and Fe(III) complexes derived from new ONO symmetrical flexible hydrazone: synthesis, spectral characterization, optical band gap and DFT computational study

2019

Lett Appl NanoBioSci

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New mononuclear Mn (II), Cr (III) and Fe (III) complexes of flexible symmetrical 2-(2-(2-hydroxy-3-methoxybenzylidene) hydrazinyl)-2-oxo-N-(pyridine-2-yl) acetamid (H 4 MPA) were isolated and characterized. IR spectra proved that the hydrazone coordinates as ONO dibasic or monobasic in keto and enol forms. The density functional theory (DFT) based quantum chemical calculations were accomplished at B3LYP/6-level of theory. Muilikan atomic charge in a companion with global and local reactivities and various energitic values have been calculated at the selected atoms, and the reactive sites have been assigned on the surface of the molecules through molecular electrostatic potential (MEP) map. The stability of all compounds was examined by TGA and DrTGA and the associated kinetic parameters were determined. Also, the optical band gap values were evaluated and found to be comparable with those obtained by DFT suggesting the possibility of using the title compounds in solar cells.

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“…Extensive biochemical and pharmacological studies have confirmed that these molecules are effective against various strains of microorganisms. Based on recent literature and in continuation of our research 14,15,16,17,18,19,20,21 for more potent antibacterial agents, we synthesized and screened quinolinobenzimidazole derivatives (3a-3h). The compounds (3a-3h) were prepared using reported methodology 22 by using o-phenylene diamines and various substituted quinolone aldehydes in presence of catalytic NH 4 Cl in ethanol.…”

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confidence: 99%

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2020

IJPSR

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A series of some quinolino-benzimidazole/thiazole derivatives (3a-3h) have been synthesized from2-hydroxyquinoline-3formaldehyde derivatives (1a-1d) and 1, 2-phenylenediamines/2aminothiophenols (2a-2c). The synthesized compounds were characterized by FTIR, 1 H-NMR and Mass Spectrometry. All the compounds were screened in-vitro for their antibacterial activity against Mycobacterium tuberculosis (H37 RV strain) ATCC No-27294. Among the compounds tested, compounds 3e showed potent antitubercular activity against M. tuberculosis at MIC 6.25 µg/mL. We extended our study to explore the inhibition mechanism by conducting molecular docking analysis by using Schrödinger. INTRODUCTION: Heterocyclic chemistry is one of the largest classical divisions of organic chemistry. Moreover, they are of immense importance not only both biologically and industrially but to the functioning of any developed human society as well. Their participation in a wide range of areas cannot be underestimated. The majority of pharmaceutical products that mimic natural products with biological activity are heterocycles. Most of the significant advances against disease have been made by designing and testing new structures, which are often heteroaromatic derivatives. Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole.

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Synthesis, structural studies and antituberculosis evaluation of new hydrazone derivatives of quinoline and their Zn(II) complexes

Cited by 61 publications

References 29 publications

Synthesis, characterization and antibacterial activity of Cu (II) and Zn (II) complexes of 5-aminobenzofuran-2-carboxylate Schiff base ligands

Synthesis, characterization and antibacterial activity of Cu (II) and Zn (II) complexes of 5-aminobenzofuran-2-carboxylate Schiff base ligands

Mononuclear Cr(III), Mn (II), and Fe(III) complexes derived from new ONO symmetrical flexible hydrazone: synthesis, spectral characterization, optical band gap and DFT computational study

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