Synthesis, spectroscopic characterization, DFT study and antimicrobial activity of novel alkylaminopyrazole derivatives

Zălaru, Christina; Dumitraşcu, Florea; Drăghici, Constantin; Tarcomnicu, Isabela; Tatia, Rodica; Moldovan, Lucia; Chifiriuc, Mariana Carmen; Lazăr, Veronica; Marinescu, Maria; Nițulescu, George Mihai; Ferbinţeanu, Marilena

doi:10.1016/j.molstruc.2017.11.073

Cited by 19 publications

(13 citation statements)

References 35 publications

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“…The novel bases M-1-M-5 ( Fig. 3) were obtained by the classical Mannich reaction, at reflux temperature, as a three component condensation between benzimidazole B, aqueous 30% formaldehyde and an amine reagent [7]. The syntheses afford good yields (73-83%).…”

Section: Resultsmentioning

confidence: 99%

“…In the Mannich reaction, primary or secondary amines are nucleophilic reactants for the carbonyl group of the formaldehyde [7] are the signals corresponding to the methylene protons directly bonded to both amine nitrogen atom and heterocyclic nitrogen atom which appears in the range 5.1-6.01 ppm [74,75]. The most shielded methylene protons were observed in case of M-3 Mannich base due to the simultaneous presence of the two aromatic nuclei, linked by the amine group.…”

Section: Resultsmentioning

confidence: 99%

“…In the Mannich reaction, primary or secondary amines are nucleophilic reactants for the carbonyl group of the formaldehyde [ 7 ] and the Mannich bases M-1–M-5 or β-amino-carbonyl compounds are the final products of this condensation reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Mannich bases result from a three-component condensation between a substrate with acidic hydrogen, an aldehyde and an amine. Heterocycles Mannich bases are remarkable compounds with various medicinal properties such as: antimicrobial [1][2][3][4][5][6][7][8], anticancer [9,15], antiviral [9,10], analgesic [11][12][13], anticonvulsant [2,10] anti-inflammatory [11][12][13][14], anti-HIV [2,10], antimalarial [15], anti-Alzheimer [16,17], anthelmintic [15], antioxidant [16,17] and so forth. Recent studies show Mannich bases as multifunctional agents against Parkinson disease, with good in vitro anti-inflammatory and neuroprotective effects [18].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

et al. 2020

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The tri-component synthesis of novel chiral benzimidazole Mannich bases, by reaction between benzimidazole, aqueous 30% formaldehyde and an amine, the biological evaluation and DFT studies of the new compounds are reported here. The 1 H-NMR, 13 C-NMR, FTIR spectra and elemental analysis confirm the structures of the new compounds. All synthesized compounds were screened by qualitative and quantitative methods for their in vitro antibacterial activity against 4 bacterial strains. DFT studies were accomplished using GAMESS 2012 software and HOMO-LUMO analysis allowed the calculation of electronic and structural parameters of the chiral Mannich bases. The geometry of 1-methylpiperazine, the cumulated Mullikan atomic charges of the two heteroatoms and of the methyl, and the value of the global electrophilicity index (ω = 0.0527) of the M-1 molecule is correlated with its good antimicrobial activity. It was found that the presence of saturated heterocycles from the amine molecule, 1-methyl piperazine and morpholine, respectively, contributes to an increased biological activity, compared to aromatic amino analogs, diphenylamino-, 4-nitroamino-and 4-aminobenzoic acid. The planarity of the molecules, specific bond lengths and localization of HOMO-LUMO orbitals is responsible for the best biological activities of the compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

et al. 2020

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“…In the first step, pyrazoles reacted with a aqueous 30% formaldehyde solution to give the 1-(hydroxymethyl)pyrazole derivatives [3]. In the second step, the 1-hydroxymethyl-pyrazoles reacted with, aromatic amines giving pyrazole Mannich bases [4,5].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Spectral Characterization, and Anti-Tumor Activity of Some Pyrazole Derivatives

Zălaru

Marinescu

Dumitraşcu³

et al. 2020

The 16th International Symposium &Amp;ldquo;Priorities of Chemistry for a Sustainable Development” PRIOCHEM

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Molecular and Electronic Structures, Spectra, Electrochemistry and Anti‐bacterial Efficacy of Novel Heterocyclic Hydrazones of Phenanthrenequinone and Their Nickel(II) Complexes

et al. 2022

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A pair of tridentate ligands incorporating heterocyclic hydrazones of 9,10‐phenanthrenequinone viz,. pyridyl‐hydrazino‐phenathrenequinone HLPy 1a and benzothiazolyl‐hydrazino‐phenathrenequinone HLBenz 1b have been synthesized and both behave as monoanionic towards nickel(II), forming meridional octahedral complexes of type [Ni(LPy)2] 2a and [Ni(LBenz)2] 2b as evident from single crystal X‐ray diffraction studies. The complexes are electro‐active in solution and nature of redox orbitals has been analysed by theoretical means. They display two oxidative and two reductive responses that have been ascribed to the redox processes of coordinated ligands. The electronic absorption spectral patterns of two complexes are analogous barring the fact that lower energy transition for 2b is marginally bathochromically shifted relative to that of 2a and it has been clarified by TD‐DFT studies. Anti‐bacterial efficacy of the ligands HLPy 1a, HLBenz 1b and complexes [Ni(LPy)2] 2a, [Ni(LBenz)2] 2b against four Gram‐positive and four Gram‐negative strains has been explored. [Ni(LPy)2] 2a exhibits more pronounced efficacy than [Ni(LBenz)2] 2b and these are greater than those of the corresponding ligands. The mode of action of 2a is essential via DNA damage while protein leakage and membrane lipid damage were observed upon treatment with 2b.

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Synthesis, spectroscopic characterization, DFT study and antimicrobial activity of novel alkylaminopyrazole derivatives

Cited by 19 publications

References 35 publications

Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

Synthesis, Spectral Characterization, and Anti-Tumor Activity of Some Pyrazole Derivatives

Molecular and Electronic Structures, Spectra, Electrochemistry and Anti‐bacterial Efficacy of Novel Heterocyclic Hydrazones of Phenanthrenequinone and Their Nickel(II) Complexes

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