PIFA-mediated synthesis of novel pyrazoloquinolin-4-ones as potential ligands for the estrogen receptor

Christodoulou, Michael S.; Kasiotis, Konstantinos M.; Fokialakis, Nikolas; Tellitu, Imanol; Haroutounian, Serkos A.

doi:10.1016/j.tetlet.2008.09.098

Cited by 26 publications

(9 citation statements)

References 31 publications

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“…Haroutounian and co-workers [ 88 ] investigated a PIFA-mediated synthesis of spirocyclic lactam 54 as side product by treating substrate 52 with 1.5 equivalents of PIFA ( 31 ) in presence of 3.0 equivalents of TFA as an additive in dichloromethane ( Scheme 17 ). The fused tricyclic compound 53 was obtained as major product in 55% yield along with the spiro compound 54 as a minor product in 8% yield.…”

Section: Reviewmentioning

confidence: 99%

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

Singh¹,

Kole²,

Mangaonkar³

et al. 2018

Beilstein J. Org. Chem.

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Hypervalent iodine reagents have been developed as highly valuable reagents in synthetic organic chemistry during the past few decades. These reagents have been identified as key replacements of various toxic heavy metals in organic synthesis. Various synthetically and biologically important scaffolds have been developed using hypervalent iodine reagents either in stoichiometric or catalytic amounts. In addition, hypervalent iodine reagents have been employed for the synthesis of spirocyclic scaffolds via dearomatization processes. In this review, various approaches for the synthesis of spirocyclic scaffolds using hypervalent iodine reagents are covered including their stereoselective synthesis. Additionally, the applications of these reagents in natural product synthesis are also covered.

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Section: Reviewmentioning

confidence: 99%

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

Singh¹,

Kole²,

Mangaonkar³

et al. 2018

Beilstein J. Org. Chem.

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“…41 In this context, in collaboration with Haroutounian's group, it was decided to apply the I(III)-assisted aromatic amidation to the development of a new approach for the preparation of conformationally constrained quinoline-fused pyrazoles as candidates with selective estrogen receptor modulating activity. 42 Additionally, the synthetic plan included the generation of phenolic fragments resembling the structure of estradiol, an estrogen representative with similar pharmacological action.…”

Section: Synthesis Of Pyrazoloquinolinonesmentioning

confidence: 99%

The Application of [Bis(trifluoroacetoxy)iodo]benzene (PIFA) in the Synthesis of Nitrogen-Containing Heterocycles

Tellitu

Domı́nguez

2012

Synlett

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“…[19] Similarly to PKC, also RACK1 aberrant expression, pro-or antioncogenic effects, and contribution to the various stages of cell migration and invasion has been described in various cancers. [14,20,21] Continuing our research in the synthesis of anticancer compounds, [22][23][24][25][26][27][28][29] the aim of this work was the synthesis of chalcone derivatives containing electron-withdrawing or electron-donating substituents on both the aromatic rings, and the evaluation of their antiproliferative effects, and possible modulation of PKC and RACK1 expression in the human T-cell acute lymphoblastic leukemia-derived cell line CCRF-CEM.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia‐derived cells: Role of PKCβ

Corsini

Facchetti

Esposito

et al. 2020

Archiv der Pharmazie

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A series of twenty chalcone derivatives was synthetized and their anti-proliferative activity was tested against the human T-cell acute lymphoblastic leukemia-derived cell line (CCRF-CEM).Based on the structural features of the most active compounds a new library of chalcone derivatives, according to SAR design, was synthetized and their antiproliferative activity was tested on the same cancer cell line. Four of them (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 M), were selected for further investigation regarding the modulation of the protein expression of receptor for activated C kinase (RACK1), PKCα and PKCβ, and their action at cell cycle level.Cell cycle analysis indicated a block in G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in S phase, with no indication of apoptosis (subG0/G1 phase). Compounds 4 and 8 showed a statistical significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ as assessed by treating cells with a selective PKCβ activator, indicated that the antiproliferative effect observed is likely to be mediated through PKCβ induction.

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PIFA-mediated synthesis of novel pyrazoloquinolin-4-ones as potential ligands for the estrogen receptor

Cited by 26 publications

References 31 publications

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

The Application of [Bis(trifluoroacetoxy)iodo]benzene (PIFA) in the Synthesis of Nitrogen-Containing Heterocycles

Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia‐derived cells: Role of PKCβ

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