Antioxidant activity of some <i>N</i>-heterocycles derived from 2-(1-(2-oxo-2<i>H</i>-chromen-3-yl)ethylidene) hydrazinecarbothioamide

El‐Helw, Eman A. E.; Sallam, Hanan A.; Elgubbi, Amna S.

doi:10.1080/00397911.2019.1638938

Cited by 20 publications

(4 citation statements)

References 22 publications

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“…Thus, methyl 2-(4-oxothiazol-5(4H)-ylidene)acetate, which is easy to prepare, was chosen as the thiazole-containing fragment. This heterocyclic fragment is a well-known pharmacophore among the functional derivatives of which compounds with antitumor [69][70][71][72], antimicrobial [65,[73][74][75], antifungal [75], antiviral [76,77], antioxidant [65,78], anti-inflammatory [79], as well as anticoagulant [80] activity have been found.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Evaluation of New Hybrid Derivatives of 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one as Potential Dual Inhibitors of Blood Coagulation Factors Xa and XIa

Skoptsova,

Geronikaki,

Novichikhina

et al. 2024

Molecules

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Cardiovascular diseases caused by blood coagulation system disorders are one of the leading causes of morbidity and mortality in the world. Research shows that blood clotting factors are involved in these thrombotic processes. Among them, factor Xa occupies a key position in the blood coagulation cascade. Another coagulation factor, XIa, is also a promising target because its inhibition can suppress thrombosis with a limited contribution to normal hemostasis. In this regard, the development of dual inhibitors as new generation anticoagulants is an urgent problem. Here we report the synthesis and evaluation of novel potential dual inhibitors of coagulation factors Xa and XIa. Based on the principles of molecular design, we selected a series of compounds that combine in their structure fragments of pyrrolo[3,2,1-ij]quinolin-2-one and thiazole, connected through a hydrazine linker. The production of new hybrid molecules was carried out using a two-stage method. The reaction of 5,6-dihydropyrrolo[3,2,1-ij]quinoline-1,2-diones with thiosemicarbazide gave the corresponding hydrazinocarbothioamides. The reaction of the latter with DMAD led to the target methyl 2-(4-oxo-2-(2-(2-oxo-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1(2H)-ylidene)hydrazineyl)thiazol-5(4H)-ylidene)acetates in high yields. In vitro testing of the synthesized molecules revealed that ten of them showed high inhibition values for both the coagulation factors Xa and XIa, and the IC50 value for some compounds was also assessed. The resulting structures were also tested for their ability to inhibit thrombin.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Evaluation of New Hybrid Derivatives of 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one as Potential Dual Inhibitors of Blood Coagulation Factors Xa and XIa

Skoptsova,

Geronikaki,

Novichikhina

et al. 2024

Molecules

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“…In the last few years, the attention was oriented toward synthesis and pharmacological evaluation of coumarin derivatives as they exhibit interesting biological activities . So, cyclocondensation of the nitrile derivative 3 with salicylaldehyde and 2‐hydroxy‐1‐naphthaldehyde in dioxane and piperidine as a base at room temperature achieved the chromene and benzochromene derivatives 5 and 6 , respectively (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Design, synthesis, and pharmacological activities of pyrazole ring has been enriched in last decades, which is a core structure in various pharmaceuticals for example, antiviral, antitumor, insecticidal, plant growth regulation, anti‐biofilm, anti‐inflammatory, analgesic, and antioxidant (Figure ) . On the other hand, thiophene structure was found in various natural products and is also incorporated in many pharmacologically active skeletons .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of chromenone, pyrimidinone, thiazoline, and quinolone derivatives as prospective antitumor agents

El‐Helw

El‐Badawy

2020

Journal of Heterocyclic Chem

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Hydrazide‐hydrazone namely, 2‐cyano‐N′‐((1‐phenyl‐3‐[thiophen‐2‐yl]‐1H‐pyrazol‐4‐yl)methylene)acetohydrazide (3) underwent a series of reactions with some chemical reagents to construct new biologically active N‐heterocycles, for example, chromenone, benzochromenone, thiazoline, and quinolone derivatives. Treating the nitrile derivative 3 with 2,4‐dichlorobenzaldehyde and pyrazole aldehyde 1 afforded the corresponding condensed products. Some of the synthesized compounds were screened for their in vitro antitumor activities against two different human tumor cell lines including hepatocellular liver carcinoma (HepG2) and breast adenocarcinoma (MCF7) activities. Compound 3 was the most potent against the two tumors.

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“…Coumarin heterocyclic moiety is well regarded as a privileged structural motif in abundant natural products and synthetic organic compounds of various pharmacological properties. The 4H-pyran core is a rich source of biologically vital molecules possessing a broad spectrum of biological and pharmacological activities [7]. Pharmacological activities includes neuroprotective agents [8], antimicrobial agents [9,10], cardio preventive agents [11], antioxidant [12][13][14], anti-inflammatory agents [15] and antituberculating agents [16].…”

Section: Introductionmentioning

confidence: 99%

Novel synthesis of 3-(Phenyl) (ethylamino) methyl)-4-hydroxy-2H-chromen-2-one derivatives using biogenic ZnO nanoparticles and their applications

et al. 2022

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The present work describes the novel synthesis of 3, 3'-((phenyl) (ethylamino) methyl)-4-hydroxy-2H-chromen-2-one derivatives catalyzed by biogenic ZnO nanoparticles. The synthesized heterocyclic compounds were characterized by fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) andmass spectrometric techniques. Absorption, distribution, metabolism and excretion properties and various toxicities (ADMET) studies and in silico molecular docking studies were carried out for the synthesized compounds. The synthesized compounds were screened for their efficacy towards the antioxidant activity and were subjected to corrosion inhibition study towards the mild steel in acidic medium by weight loss method. Additionally, the recyclability of the employed catalyst was studied.

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Antioxidant activity of some N-heterocycles derived from 2-(1-(2-oxo-2H-chromen-3-yl)ethylidene) hydrazinecarbothioamide

Cited by 20 publications

References 22 publications

Design, Synthesis, and Evaluation of New Hybrid Derivatives of 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one as Potential Dual Inhibitors of Blood Coagulation Factors Xa and XIa

Design, Synthesis, and Evaluation of New Hybrid Derivatives of 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one as Potential Dual Inhibitors of Blood Coagulation Factors Xa and XIa

Synthesis of chromenone, pyrimidinone, thiazoline, and quinolone derivatives as prospective antitumor agents

Novel synthesis of 3-(Phenyl) (ethylamino) methyl)-4-hydroxy-2H-chromen-2-one derivatives using biogenic ZnO nanoparticles and their applications

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