Synthesis and biological evaluation of N-antipyrine-4-substituted amino-3-chloromaleimide derivatives

Mahle, F.; Guimarães, Tatiana da Rosa; Meira, Aleandra V.; Corrêa, Rogério; Cruz, Ramón; Cruz, Alexandre Bella; Nunes, Ricardo José; Cechinel‐Filho, Valdir; Buzzi, Fátima de Campos

doi:10.1016/j.ejmech.2010.07.040

Cited by 31 publications

(13 citation statements)

References 20 publications

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“…Antipyrine (N‐heterocyclic compound) and its derivatives exhibit a wide range of biological activities like analgesic, antibacterial, antifungal, anti‐inflammatory, antiviral, antiarrhythmic, antipyretic and antioxidant activities . Also, chromone derivatives, compounds with aromatic planar structure, have been of special interest in organic synthesis due to their biological activities such as anticonvulsant, antioxidant, antibacterial, antifungal, anticancer, anti‐HIV, antiulcer and anti‐inflammatory activities …”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, molecular docking studies and in vitro screening of new metal complexes with Schiff base as antimicrobial and antiproliferative agents

Pahontu

Proks

Shova³

et al. 2019

Applied Organom Chemis

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A series of Cu(II), Co(II), Pd(II), Pt(II), Zn(II), Cd(II) and Fe(III) complexes were designed and synthesized using Schiff base 1‐phenyl‐2,3‐dimethyl‐4‐(N‐3‐formyl‐6‐methylchromone)‐3‐pyrazolin‐5‐one (HL). The new metal complexes were investigated using various physicochemical techniques including elemental and thermal analyses, molar electric conductivity and magnetic susceptibility measurements, as well as spectroscopic methods. Also, the crystal structures of ligand HL and the Pd(II) complex were determined using single‐crystal X‐ray diffraction analysis. For all compounds, the antimicrobial activity was studied against a series of standard strains: Staphylococcus aureus, Bacillus cereus, Enterococcus faecalis, Escherichia coli, Acinetobacter baumannii, Candida albicans, Candida krusei and Cryptococcus neoformans. The in vitro antiproliferative activity of the ligand and complexes was evaluated against ten cancer cell lines: MSC, A375, B16 4A5, HT‐29, MCF‐7, HEp‐2, BxPC‐3, RD, MDCK and L20B. At 10 μM concentration a significant cytotoxic effect of the Co(II), Pd(II) and Cd(II) complexes was observed against B16 4A5 murine melanoma cells. The Zn(II) complex is active against HEp‐2, RD and MDCK cancer cell lines, where IC50 values vary between 1.0 and 77.6 and for BxPC‐3 the activity index versus doxorubicin is 3.7 times higher.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, molecular docking studies and in vitro screening of new metal complexes with Schiff base as antimicrobial and antiproliferative agents

Pahontu

Proks

Shova³

et al. 2019

Applied Organom Chemis

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“…The antipyrine nucleus has been utilized as a useful precursor for the construction of many biologically important heterocycles [1,2]. Antipyrine derivatives are of great interest in medicine as a result of their broad range of pharmacological activity and clinical applications, including antibacterial [3], analgesic [4], and anti-inflammatory [4,5] as well as antitumor activity [6,7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Modeling Study and Antioxidants Activity of New Heterocycles Derived from 4-Antipyrinyl-2-Chloroacetamidothiazoles

Abu‐Melha

2018

Applied Sciences

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The present work reports the preparation of twelve new heterocyclic scaffolds containing an antipyrinyl-thiazole hybrid through the reaction of 4-antipyrinyl-2-chloroacetamido-thiazoles 1 and 6 with various types of nucleophiles, namely; ethyl thioglycolate, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, ammonium thiocyanate, malononitrile, and salicylaldehyde. The constructed compounds were characterized by conventional spectroscopic techniques (IR, 1H NMR, 13C NMR, and mass analysis). A DFT method (material studio package) was used to predict the geometry, bond lengths, bond angles, and dipole moments as well as other global chemical reactivities of the constructed antipyrinyl-thiazole compounds. Also, their semi-core pseudopods calculations (dspp) were carried out with DNP (double numerical basis sets plus polarization functional) to predict the properties of materials. In addition, the antioxidant activity of these antipyrinyl-thiazole scaffolds has been screened by the ABTS method. The results indicated that 2-(4-antipyrinylthiazolylamino)-5-substituitedbenzylidene-thiazol-4(5H)-ones 10b and 10c exhibited the best antioxidant activity with a percentage inhibition of 85.74% and 83.51%, respectively.

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“…Antipyrine (1‐phenyl‐2,3‐dimethylpyrazol‐5‐one) 1 and its derivatives play an important role in heterocyclic synthesis as they are of great biological and medicinal value . They are important pyrazolone derivatives and have been widely used for a long time in medicine as antipyretic , analgesic , sedative , antimicrobial , antiviral , antioxidant , anticancer , and anti‐inflammatory drugs .…”

Section: Introductionmentioning

confidence: 99%

Synthetic Routes to Selected Heterocycles Containing Antipyrine Moiety

El‐Taweel

Elmaaty

2015

Journal of Heterocyclic Chem

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This review deals with the synthetic potentiality and utility of antipyrine and its derivatives in the synthesis of 4-substituted antipyrine and other heterocycles containing antipyrine moiety such as thiazole, pyrazolopyridines, pyrazolopyrimidines, and pyrazolotriazines. The reactions that cover the methods of synthesizing the aforementioned heterocycles such as addition, condensation, and cyclization were also reviewed.

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Synthesis and biological evaluation of N-antipyrine-4-substituted amino-3-chloromaleimide derivatives

Cited by 31 publications

References 20 publications

Synthesis, characterization, molecular docking studies and in vitro screening of new metal complexes with Schiff base as antimicrobial and antiproliferative agents

Synthesis, characterization, molecular docking studies and in vitro screening of new metal complexes with Schiff base as antimicrobial and antiproliferative agents

Synthesis, Modeling Study and Antioxidants Activity of New Heterocycles Derived from 4-Antipyrinyl-2-Chloroacetamidothiazoles

Synthetic Routes to Selected Heterocycles Containing Antipyrine Moiety

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