Synthesis and Antiproliferative Activity of Some Dihydro-1H-furo[2,3-c]pyrazole-Flavone Hybrids

Tangeti, Venkata Swamy; Vasundhara, D. E.; Satyanarayana, Kamani; Kumar, Kaja Srinivas Pavan

doi:10.14233/ajchem.2017.20550

Cited by 4 publications

(4 citation statements)

References 2 publications

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“…Furopyrazol-substituted hybrids (44) with an antiproliferative effect were prepared in large quantities with different substituents in the aromatic ring and in the 2-phenyl group. On cell lines HEP-2 (human laryngeal carcinoma), A549 (human lung adenocarcinoma), and HeLa, IC50 = 2.5-10.0 µM values were obtained [30]. Furthermore, toxicity studies revealed that compound 44 specifically targets cancer cell lines.…”

Section: Heterocyclic Pharmacophoresmentioning

confidence: 99%

“…Amino acids containing apigenin (29) and quercetin derivatives (30) were also synthesized using protected amino acids. From the apigenin hybrids, the Lys-coupled molecule proved to be the best on the biological tests, having a sedative effect on mouse brain tissues (single dose 0.4 mg/g) passing through the blood-brain barrier [51].…”

Section: Flavone Hybrids With Amino Acidsmentioning

confidence: 99%

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Flavone Hybrids and Derivatives as Bioactive Agents

Hazai,

Zsoldos,

Halmai

et al. 2024

Applied Sciences

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Hybrid molecules can be defined as chemical entities with two or more structural domains, namely pharmacophores, having a specific biological effect. In many cases, when at least one of the components is biologically inactive, it is rather correct to call them “derivatives”, despite the fact that in the literature they are often mentioned also as hybrids. We have summarized such types of molecules, in which one of the components is mostly a real pharmacophore, i.e., flavone, which is one of the best-known natural bioactive substances. Structures, synthetic methods, medicinal indications, and more important activity data are presented.

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Section: Heterocyclic Pharmacophoresmentioning

confidence: 99%

Section: Flavone Hybrids With Amino Acidsmentioning

confidence: 99%

Flavone Hybrids and Derivatives as Bioactive Agents

Hazai,

Zsoldos,

Halmai

et al. 2024

Applied Sciences

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“…In a similar reaction using a pyridinium ylide instead of malononitrile, the dihydro-1 H -furo[2,3- c ]pyrazole system, consisting of an aromatic pyrazole ring fused with a five-membered 2,3-dihydrofuran ring, was formed [ 8 ]. Derivatives of the latter system are known for their antimicrobial [ 9 ] and antiproliferative activities [ 10 ]. Nevertheless, methods to access 2 H -furo[2,3- c ]pyrazoles, where both the fused pyrazole and furan moieties are aromatic, are still quite limited, and their chemistry and functional properties remain largely underexplored.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction

Milišiūnaitė¹,

Paulavičiūtė²,

Arbačiauskienė³

et al. 2019

Beilstein J. Org. Chem.

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Fused pyrazole ring systems are common structural motifs of numerous pharmaceutically important compounds. Nevertheless, access to derivatives of the aromatic 2H-furo[2,3-c]pyrazole ring system is still quite limited, and their chemistry and functional properties remain largely underexplored. The current study investigates routes to construct this system from easily accessible starting materials using metal-catalyzed reactions. A simple and efficient procedure to access the 2H-furo[2,3-c]pyrazole ring system was developed by employing the silver(I) ion-mediated ring-closure reaction of 4-alkynyl-3-hydroxy-1-phenyl-1H-pyrazoles as a key step. The required intermediate hydroxyalkynyl substrates for this reaction were prepared by a Pd-catalyzed coupling of 4-iodo-1-phenyl-1H-pyrazol-3-ol with ethyne derivatives. The structures of the obtained target compounds were unequivocally confirmed by detailed 1H, 13C and 15N NMR spectroscopic experiments, HRMS and a single-crystal X-ray diffraction analyses. This silver(I)-mediated 5-endo-dig cyclization of readily available 4-alkynyl-3-hydroxy-1H-pyrazoles can be used as an efficient method to access many novel 2,5-disubstituted 2H-furo[2,3-c]pyrazoles.

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“…Recently we have developed two new methodologies for the synthesis of C3-dihydrofuran substituted coumarins, dihydrofuro pyrazole by employing one pot multicomponent synthesis with pyridinium ylide. As part of our continued interest in the synthesis of diverse heterocyclic compounds of biological significance [18][19][20][21][22][23][24][25], we contemplated to synthesize novel tetrahydrofuro [3,2-c]pyridinone-2-carboxylate (5) by the one-pot four-component reaction of 6-methyl, 4-hydroxy pyran, aryl amine, aromatic aldehyde and pyridinium ylide to study their biological activity. Our previously developed methodology has been taken as a reference for developing furopyridone derivatives due to its slight structural similarity.…”

Section: Introductionmentioning

confidence: 99%

One Pot Multicomponent Synthesis of Anti-inflammatory Active Tetrahydrofuro[3,2-c]pyridinone-2-carboxylate Derivatives

Tangeti¹,

Reddy²,

Evangeline³

2018

Asian J. Chem.

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A novel, one-pot method has been developed for the synthesis of tetrahydrofuro[3,2-c]pyridine-2-carboxylate derivatives via cascade four-component condensation of 6-methyl, 4-hydroxy pyranone, aryl amines, aromatic aldehydes and pyridinium ylide, in presence of triethylamine as a catalyst under ethanol reflux conditions. It affords the corresponding product in high yield (78-92 %) with short reaction time (15-25 min).The anti-inflammatory activity of these compounds was determined. Out of the 17 synthesized compounds, compounds 5j, 5k, 5l, 5m and 5n were excellent inhibitors of TNF-α and IL-6, COX-2, β-glucuronidase.

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Synthesis and Antiproliferative Activity of Some Dihydro-1H-furo[2,3-c]pyrazole-Flavone Hybrids

Cited by 4 publications

References 2 publications

Flavone Hybrids and Derivatives as Bioactive Agents

Flavone Hybrids and Derivatives as Bioactive Agents

Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction

One Pot Multicomponent Synthesis of Anti-inflammatory Active Tetrahydrofuro[3,2-c]pyridinone-2-carboxylate Derivatives

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