Synthesis of New Spiro‐[isothiochromene‐3,5′‐isoxazolidin]‐4(1H)‐ones.

Bennani, Brahim; Jalbout, Abraham F.; Baba, Bouchra Filali; Larbi, Najib Ben; Boukir, Abdelatif; Kerbal, Abdelali; Mimouni, Mostafa; Hadda, Taîbi Ben; Trzaskowski, Bartosz

doi:10.1002/chin.200738136

Cited by 5 publications

(5 citation statements)

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“…The most frequently used pharmaceuticals for cancer treatment are natural products or their synthetic analogues. 8,9 Natural and nonnatural isoxazolines and spirocyclic isoxazoline derivatives have emerged as promising drug candidates due to their numerous biological activities 10 resulting in an overall antiproliferative effect on a variety of cancer cell lines. The natural product 11-deoxyfistularin-3 11 contains two spirocyclic isoxazoline moieties and is cytotoxic toward estrogen dependent MCF-7 breast cancer cells (LD 50 =17 mg/L).…”

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confidence: 99%

Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

Das

Omollo

Sitole

et al. 2015

Tetrahedron Letters

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A series of structurally diverse 4-bromo spiro-isoxazolines possessing a variety of aromatic and aliphatic substituents at the 3 position, were synthesized through a 1,3-dipolar cycloaddition followed by intramolecular cyclization of a pendant hydroxyl or carboxylic acid group. The biochemical antiproliferative activity was evaluated in vitro by using two breast cancer cell lines (MCF-7 and MDA-MB-231) and two prostate cancer cell lines (PC-3 and DU-145) using the MTT viability assay, and the IC50 values were obtained. Spiro-isoxazoline derivatives bearing a p-chloro or an o-dichloro aromatic substituent at the 3-position of the isoxazoline showed considerable antitumor activities in all four cell lines with IC50 value ranging from 43μM to 56μM.

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confidence: 99%

Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

Das

Omollo

Sitole

et al. 2015

Tetrahedron Letters

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“…Spiroisoxazolines synthesized in our laboratory in 2005 have been patented for their antituberculosis and anti-HIV properties 21,22 . Since then, we have been further developing these highly promising molecules 16,20 .…”

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confidence: 99%

Synthesis of new spiroheterocycles-fused isoxazoline from 2-arylidenes-3-phenyl-1-indanones through a regio-and diastereospecific 1,3-dipolar cycloaddition

Mahfoud¹,

Kerbal²,

Nakkabi³

et al. 2021

Mediterr.J.Chem.,

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<p>New spiroisoxazolines <strong>3</strong> have been synthesized by 1,3-dipolar cycloaddition of arylnitrile oxides with 2-arylidenes-3-phenyl-1-indanones. The reaction occurs in a regiospecific and diastereospecific manner and leads to one cycloadduct in all the cases. The proposed structure of the obtained cycloadducts was established based on spectroscopic data and confirmed by radiocrystallographic study. The spectral data were in favor of the observed regiochemistry and diastereoselectivity of this reaction.</p>

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“…1,2 We have recently investigated the antitubercular activity 3 and anti-breast cancer activity 4 of some spiroisoxazolines derivatives.…”

Section: Introductionmentioning

confidence: 99%

Drug design of new antitubercular agents: 1,3-dipolar cycloaddition reaction of arylnitriloxides and 3-para-methoxy-benzylidene-isochroman-4-ones

Houari¹,

Kerbal²,

Bennani³

et al. 2008

Arkivoc

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Five new 3',4'-substituted-spiro[isochromene-3,5'-isoxazolin]-4(1H)-ones 7-11 have been prepared in the reaction of p-R-benzadoxime 2-6 with 3-para-methoxy-benzylidene-isochroman-4-one 1. The reaction occurs by a 1,3-dipolar cycloaddition mechanism which leads to the regiospecific formation of various spiro-isoxazolines 7-11. It is concluded that rigid (O 1'group may be responsible for the biological activity observed in antitubercular test with these hyper inter-organised spiro-isoxazoline derivatives. However, subtle alteration by addition of a substituted aryl groups affecting the charge distribution of the terminal heteroatom O 1' confers significant improvements in biological effects.

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Synthesis of New Spiro‐[isothiochromene‐3,5′‐isoxazolidin]‐4(1H)‐ones.

Cited by 5 publications

References 1 publication

Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

Synthesis and investigation of novel spiro-isoxazolines as anti-cancer agents

Synthesis of new spiroheterocycles-fused isoxazoline from 2-arylidenes-3-phenyl-1-indanones through a regio-and diastereospecific 1,3-dipolar cycloaddition

Drug design of new antitubercular agents: 1,3-dipolar cycloaddition reaction of arylnitriloxides and 3-para-methoxy-benzylidene-isochroman-4-ones

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