FeCl3-catalyzed three-component reaction: a novel synthesis of tetrahydro-2,6-dioxopyrimidin-4-yl-2,3-dihydrophthalazine-1,4-dione derivatives under solvent-free conditions

Mudumala, Veeranarayana Reddy; Chinthaparthi, Radha Rani; Yeon, Tae Jeong

doi:10.1016/j.tet.2014.04.044

Cited by 21 publications

(4 citation statements)

References 62 publications

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“…Heterocyclic compounds have significant importance due to their therapeutic properties [ 24 ]. Also, heterocycles containing pyrazole scaffolds [ 25 , 26 ] exhibit some interesting biological activities.…”

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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“…This approach allows developing more complex molecular structures from simple and available reagents via a transformation with single step and does not require the isolation of intermediates products . MCRs have been one of the best approaches that meet the requirements of green chemistry as well as the library development of medicinal compounds .…”

Section: Introductionmentioning

confidence: 99%

One‐pot Three Component Synthesis of ω‐(oxathiolan‐2‐thion‐5‐yl)‐α‐oxazolidin‐2‐ones

Ghrab

Aroua

Beji

2017

Journal of Heterocyclic Chem

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We report a practical and one‐pot synthesis of novel series of ω‐(oxathiolan‐2‐thione‐5‐yl)‐α‐ oxazolidin‐2‐ones (3a‐h). The obtained compounds have been designed, synthesized via reaction of oligoethylene glycols diglycidyl ethers, isocyanate and carbon disulfide in the presence of catalytic amount of lithium bromide. A variety of important oxazolidinone derivatives can be obtained from simple starting materials in good yields and the biological activity of these new products will be investigated in complementary study.

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“…In one of these methods, 2,3-dihydrophthalazine-1 (4H ),4-dione ("phthalhydrazide") is used. This compound is commonly used as an intermediate in the synthesis of many molecules with a phthalazine moiety (17)(18)(19)(20)(21)(22).…”

Section: Introductionmentioning

confidence: 99%

Solvent-free organic salt media mono symmetrical aza-Michael: synthesis of new N-mono substituted phthalhydrazide derivatives

Soltanzadeh

Imanzadeh

Noroozi-Pesyan

et al. 2017

Green Chemistry Letters and Reviews

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In this paper, C-N bond formation between 2,3-dihydrophthalazine-1(4H),4-dione (phthalhydrazide) and α,β-unsaturated esters was investigated and a new series of phthalazine derivatives was synthesized using an efficient and simple method under solvent-free conditions. An aza-Michael addition of phthalhydrazide to both acrylic and fumaric esters led to N-monosubstituted phthalhydrazides (as mono-Michael adduct) in the presence of tetrabutylammonium bromide as a high polar media, and 1,4-diaza-bicyclo[2,2,2]octane as an available organic base. In this reaction, the N1,N2-bis-Michael adduct was not observed at all. Also, reactions were performed at 90°C and yields of products were good to excellent.

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FeCl3-catalyzed three-component reaction: a novel synthesis of tetrahydro-2,6-dioxopyrimidin-4-yl-2,3-dihydrophthalazine-1,4-dione derivatives under solvent-free conditions

Cited by 21 publications

References 62 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

One‐pot Three Component Synthesis of ω‐(oxathiolan‐2‐thion‐5‐yl)‐α‐oxazolidin‐2‐ones

Solvent-free organic salt media mono symmetrical aza-Michael: synthesis of new N-mono substituted phthalhydrazide derivatives

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