Synthesis, spectral analysis and study of antimicrobial activity of 2,5-diformyl-1H-pyrrole bis(methan-1-yl-1-ylidene)dimalonohydrazone

Rawat, Poonam; Singh, R.N.

doi:10.1016/j.arabjc.2014.10.050

Cited by 16 publications

(8 citation statements)

References 27 publications

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“…The infrared (IR) spectra were recorded in KBr disc using a Nicolet MX-1 FTIR spectrophotometer. On a Bruker spectrometer, 1 H NMR spectra were acquired at 300 MHz (in DMSO-d 6 or methanol solvent), and chemical shifts were reported in parts per million (ppm) units relative to an internal standard, TMS. The UV−vis spectra were recorded using a Shimadzu UV 2100 UV−vis recording spectrophotometer in the 200−800 nm range.…”

Section: Methodsmentioning

confidence: 99%

“…The global electrophilicity index (ω = 5.994 eV) of (3C) shows that it behaves as a strong electrophile. ECT is calculated as 0.524 for reactant molecules (1) and (2A), which indicates that charge flows from (2) to (1). Therefore, (1) acts as the electron acceptor (electrophile) and (2) acts as the electron donor (nucleophile).…”

Section: Global Reactivity Descriptorsmentioning

confidence: 99%

“…Hydrazones display a range of biological spectra. 1 − 7 The chemical structures of materials and their variety of biological effects are scientifically significant and have been responsible for the development of many technologically relevant fields of interest.…”

Section: Introductionmentioning

confidence: 99%

“…Difference in nature of nitrogen atoms provides capability to react with electrophilic and nucleophilic reagents; hence, majority of the hydrazine derivatives are used in the synthesis of heterocyclic compounds and nitrogen-containing organic compounds. Hydrazones display a range of biological spectra. − The chemical structures of materials and their variety of biological effects are scientifically significant and have been responsible for the development of many technologically relevant fields of interest.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Structural Variation on Spectral, NLO Properties, and Biological Activity of Pyrrole Hydrazones

et al. 2022

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This paper describes spectral, non-linear optical (NLO), and biological activity variation of pyrrole hydrazones as a result of structural variation. In order to study structure–property variation, pyrrole hydrazones ( 3A , 3B , and 3C ) were synthesized in both solid and solution phases. The grinding solvent-free method becomes rapid, easy, convenient, useful, sustainable, and eco-friendly green synthesis as compared to the classical solution phase reactions. The structure of pyrrole hydrazones has been elucidated by microanalysis and quantum chemical calculations. The intense emission at λ em 521 nm ( 3A and 3B ) and 617 nm ( 3C ) in the visible (green and orange) region with Stokes shifts at 195, 160, and 282 nm reveals that the studied compounds work as good photoluminescent materials. All compounds show strong n−π* and charge transfer (π–π*) transitions in the UV–vis region with high extinction coefficients. In the studied systems ( 3A , 3B , and 3C ), the orbital overlap between σ(NH–O) → σ*(NH–O) is found due to intra-molecular charge transfer. The first hyperpolarizabilities were found to be 48.83 × 10 –30 esu for 3B and 63.89 × 10 –30 esu for 3C, showing variation with structure. Their high values indicate more suitability for NLO application. Incorporation and/or change in position of electron-withdrawing groups increase the β 0 values of 3B and 3C compared to 3A . The β value also increases monotonically as the polarity of the solvents increases. The red shift in N–H and C=O stretching Fourier-transform infrared bonds is due to the formation of dimers. The synthesized 3A , 3B , and 3C show good antimicrobial activity and are predicted to be potential antibacterial and antifungal drugs. The 3B has more molar refractivity (122.16 esu) than 3A and 3C and correlates well with the calculated binding affinity and experimental antimicrobial data.

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Section: Methodsmentioning

confidence: 99%

Section: Global Reactivity Descriptorsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effect of Structural Variation on Spectral, NLO Properties, and Biological Activity of Pyrrole Hydrazones

et al. 2022

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“…However, the most valuable property of aroylhydrazones is their great physiological activity due to the presence of the active pharmacophore (C‚NANHACOA) and provides a wide range of application in medicinal and pharmaceutical fields with various biological applications. Therefore, a number of hydrazone derivatives have been used for the treatment of diseases such as convulsant (Dimmock et al, 2000), malaria (Melnyk et al, 2006), HIV, cancer (Savini et al, 2004), microbial (Rallas et al, 2002;Gursoy et al, 1997;Ajani et al, 2010;Rawat and Singh, 2014a, 2015a, 2015b and tuberculosis (Zheng et al, 2009;Richardson and Bernhardt, 1999;Bedia et al, 2006;Darnell and Richardson, 1999;Murukan and Mohanan, 2007). Many of hydrazones are used as prospective new materials for the development of potential chemosensors (Yu et al, 2007), opto-electronic (Szczesna and Lipkowska, 2001) and nonlinear optical (NLO) (Vijayakumar et al, 2010(Vijayakumar et al, , 2011Shirota and Kageyama, 2007;Blau, 1987;Vogt et al, 2008;Genger et al, 2008) applications.…”

Section: Introductionmentioning

confidence: 98%

Synthesis and study on aroylhydrazones having cyanovinylpyrrole

Rawat

Singh

2019

Arabian Journal of Chemistry

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A series of C-cyanovinylpyrrole containing aroylhydrazones (3a-c), derived from ethyl 2-cyano-3-(5-formyl-1H-pyrrol-2-yl)-acrylate and acid hydrazides: salicylhydrazide, isoniazid and 3,5-dinitrobenzohydrazide have been characterized by various spectroscopic techniques ( 1 H NMR, 13 C NMR, Mass, UV-Visible, Emission, FT-IR) and quantum chemical calculations. TD-DFT has been used to calculate the various electronic excitations and their nature. The emission spectra show that (3a-c) are good photoluminescent material due to intense emission at higher wavelength in yellow, green and blue region with high Stoke's shift in the region 80-328 nm. The molar refractivity (MR) for (3a-c) is calculated as 109.28, 102.96, 119.14 esu, respectively. Natural bond orbital (NBO) analysis has been carried out to explore the various conjugative and hyperconjugative interactions within molecule and their second order stabilization energy (E (2) ). Global electrophilicity index (x = 5.41-8.11 eV) shows that (3a-c) molecules work as strong electrophiles. The local reactivity descriptors analyses such as Fukui functions (f k + , f k À ), local softnesses (s k + , s k À ) and electrophilicity indices (x k + , x k À ) have been performed to determine the reactive sites within molecules. The first hyperpolarizabilities (b 0 ) of (3a-c) have been computed and found to increase with electron withdrawing substituents. ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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Synthesis, Thermal Stability and Antifungal Evaluation of Two New Pyrrole Esters

Gao,

Fan,

Zhang

et al. 2024

Chemistry & Biodiversity

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To develop new chemicals that are stable at high temperatures with biological activity, a pyrrole intermediate was firstly synthesized using glucosamine hydrochloride as raw materials through cyclization and oxidation. Further, two novel pyrrole ester derivatives were prepared via Steglich esterification from pyrrole intermediate with vanillin and ethyl maltol, respectively. Nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high resolution mass spectrometry (HRMS) were used to confirm the target compounds. Thermal behavior of the compounds was investigated by thermogravimetry (TG), differential scanning calorimeter (DSC) and the pyrolysis‐gas chromatography/mass spectrometry (Py‐GC/MS) methods. The plausible pyrolytic mechanism was proposed. Additionally, their biological activities against the pathogens Fusarium graminearum, Fusarium oxysporum, Fusarium moniliforme, Phytophthora nicotianae, and Rhizoctonia solani were assessed. These target compounds showed outstanding antifungal activities and the highest inhibitor rates of 62.50% and 68.75% against R. solani with EC50 values of 0.0296 and 0.0200 mg mL‐1, respectively. SDHI protein sequence was molecularly docked to identify the binding mechanisms in the active pocket and examine the interactions between both the molecules and the SDHI protein.

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Synthesis, spectral analysis and study of antimicrobial activity of 2,5-diformyl-1H-pyrrole bis(methan-1-yl-1-ylidene)dimalonohydrazone

Cited by 16 publications

References 27 publications

Effect of Structural Variation on Spectral, NLO Properties, and Biological Activity of Pyrrole Hydrazones

Effect of Structural Variation on Spectral, NLO Properties, and Biological Activity of Pyrrole Hydrazones

Synthesis and study on aroylhydrazones having cyanovinylpyrrole

Synthesis, Thermal Stability and Antifungal Evaluation of Two New Pyrrole Esters

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