A detailed investigation of the multicomponent reaction of salicylaldehyde, ethyl acetoacetate and isocyanides under microwave heating

Amanpour, Tayebeh; Zangger, Klaus; Belaj, Ferdinand; Bazgir, Ayoob; Dallinger, Doris; Kappe, C. Oliver

doi:10.1016/j.tet.2014.12.002

Cited by 13 publications

(8 citation statements)

References 63 publications

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“…In an initial study, a typical Knoevenagele Doebner condensation procedure was performed, which involved heating under reflux for a few hours an equimolar quantity of the furochromone carbaldehyde ( 1 ), Curcumin ( 2 ) and a base such as pipredine (a few drops) in pyridine as a solvent [ 18 , 19 ]. Compound 3 ( Scheme 1 ) was thus obtained and identified by spectral data such as its IR spectrum, which showed the disappearance of (CHO gp) and the appearance of (OH gp).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

et al. 2018

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Curcumin, a widely utilized flavor and coloring agent in food, has been shown to demonstrate powerful antioxidant, antitumor promoting and anti-inflammatory properties in vitro and in vivo. In the present work, synthesis of new heterocyclic derivatives based on Curcumin was studied. Compound 3 was synthesized via the reaction of furochromone carbaldehyde (1) with Curcumin (2) using pipredine as catalyst. Also, novel, 4,9-dimethoxy-5H-furo [3, 2-g] chromen-5-one derivatives 4a–d, 6a–d, 7, 8a–d, 9 and 10 were synthesized by the reactions of furochromone carbaldehyde (1) with different reagents (namely: appropriate amine 3a–d, appropriate hydrazine 5a–d, hydroxylamine hydrochloride, urea/thiourea, malononitrile, malononitrile with hydrazine hydrate). The structure of the synthesized products had been confirmed from their spectroscopic data (IR, 1H-NMR, 13C-NMR and mass spectra). In the present investigation, the newly synthesized products were screened using the MTT colorimetric assay for their in vitro inhibition capacity in two human cancer cell lines (hepatocellular carcinoma (HEPG2) and breast cancer (MCF-7) as well as the normal cell line (human normal melanocyte, HFB4) in comparison to the known anticancer drugs: 5-flurouracil and doxorubicin. The anticancer activity results indicated that the synthesized products 4c and 8b showed growth inhibition activity against HEPG2 cell line and synthesized products 4b and 8a showed growth inhibition activity against MCF-7, but with varying intensities in comparison to the known anticancer drugs, 5-flurouracil and doxorubicin. Cyclin dependent kinase 2 (CDK2), a major cell cycle protein, was identified as a potential molecular target of Curcumin. Furthermore, Curcumin induced G1 cell cycle arrest, which is regulated by CDK2 in cancer cells. Therefore, we used molecular modelling to study in silico the possible inhibitory effect of CDK2 by Curcumin derivatives as a possible mechanism of these compounds as anticancer agents. The molecular docking study revealed that compounds 4b, 8a and 8b were the most effective compounds in inhibiting CDk2, and, this result was in agreement with cytotoxicity assay.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

et al. 2018

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“…126 Furthermore, 3-acetylcoumarin 1 was reacted with isocyanide 294 in toluene under microwave irradiation to furnish 2-aminofuran 295, This combined very rapidly with triplet oxygen to afford hydroperoxide 296, in addition the ketoamide 297 as well as the 5-hydroxy-pyrrolidone 298 was formed when the same reaction in refluxing ethanol was repeated (Scheme 52). 127 Scheme 52. Reaction of 1 with sodium cyanide and isocyanide…”

Section: Reaction With Sodium Cyanide and Isocyanidementioning

confidence: 99%

3-Acyl(aroyl)coumarins as synthon in heterocyclic synthesis

Hamama¹,

Berghot²,

Baz³

et al. 2019

Org.Commun.

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“…While chromanone-fused γ-hydroxyγ-butyrolactams were obtained in a standard open vessel, 5-hydroxy-2-iminofuran-fused coumarins were synthesized in a closed vessel. 58…”

Section: Scheme 27 Reaction Between αβ-Unsaturated Ketones and Isocymentioning

confidence: 99%

Strategies To Access γ-Hydroxy-γ-butyrolactams

Mardjan

Parrain²,

Comméiras

2018

Synthesis

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α,β-Unsaturated γ-hydroxy-γ-butyrolactams are of a great interest due to their presence in designed pharmaceutical molecules and numerous natural products displaying a broad spectrum of biological activities. In addition, these five-membered heterocyclic compounds are also relevant and versatile building blocks in organic synthesis. In this context, strategies for the construction of these scaffolds has triggered considerable attention and this review highlights the progress in the formation of α,β-unsaturated γ-hydroxy-γ-butyrolactams (5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones).1 Introduction2 Intramolecular Routes3 Intermolecular Routes4 Oxidation of Heterocyclic Compounds5 Miscellaneous6 Conclusion

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A detailed investigation of the multicomponent reaction of salicylaldehyde, ethyl acetoacetate and isocyanides under microwave heating

Cited by 13 publications

References 63 publications

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

3-Acyl(aroyl)coumarins as synthon in heterocyclic synthesis

Strategies To Access γ-Hydroxy-γ-butyrolactams

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