N-Phenyl-4-hydroxy-2-quinolone-3-carboxamides as selective inhibitors of mutant H1047R phosphoinositide-3-kinase (PI3Kα)

Sabbah, Dima A.; Simms, Neka; Wang, Wang; Dong, Yuxiang; Ezell, Edward L.; Brattain, Michael G.; Vennerstrom, Jonathan L.; Zhong, Haizhen A.

doi:10.1016/j.bmc.2012.09.059

Cited by 28 publications

(20 citation statements)

References 41 publications

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“…The significance of these binding residues has been validated by other computational 35,36,[44][45][46] and experimental studies. 12 The low docking score of 5 might be due to ion-dipole or ion-induced dipole interaction with Tyr836 (Fig.…”

Section: Introductionmentioning

confidence: 96%

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Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα)

Sabbah

Saada

Khalaf

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Section: Introductionmentioning

confidence: 96%

“…35 Novel N-Phenyl-4-hydroxy-2-quinolone-3-carboxamides were synthesized as selective H1047R PI3Ka inhibitors. 36 Recruiting ligand-based pharmacophore modeling for PI3Ka inhibitors and database searching against the National Cancer Institute (NCI) compound database 37 identified NSC 8082 (benzoin) (1) as a hit (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα)

Sabbah

Saada

Khalaf

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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“…57 Most of the compounds reported ( 182 ) were prepared via a multicomponent coupling reaction of two equivalents of aniline ( 181 ) with triethyl methane tricarboxylate ( 180 ).…”

Section: Pyridines Quinolines and Indolesmentioning

confidence: 99%

Recent syntheses of PI3K/Akt/mTOR signaling pathway inhibitors

Welker

Kulik

2013

Bioorganic & Medicinal Chemistry

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This review focuses on the syntheses of PI3K/Akt/mTOR inhibitors that have been reported outside of the patent literature in the last 5 years but is largely centered on synthetic work reported in 2011 and 2012. While focused on syntheses of inhibitors, some information on in vitro and in vivo testing of compounds is also included. Many of these reported compounds are reversible, competitive adenosine triphosphate (ATP) binding inhibitors, so given the structural similarities of many of these compounds to the adenine core, this review presents recent work on inhibitors based on where the synthetic chemistry was started, i.e. inhibitor syntheses which started with purines/pyrimidines are followed by inhibitor syntheses which began with pyridines, pyrazines, azoles, and triazines then moves to inhibitors which bear no structural resemblance to adenine: liphagal, wortmannin and quercetin analogs. The review then finishes with a short section on recent syntheses of phosphotidyl inositol (PI) analogs since competitive PI binding inhibitors represent an alternative to the competitive ATP binding inhibitors which have received the most attention.

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“…Several synthetic quinolinone derivatives have been also found to possess various pharmacological activities. [34][35] For instance compounds of type 1 and 2 are known to be selective Androgen receptor modulators and to have positive inotropic effects, respectively (Figure 1). 36 Linomide 3, a synthetic immunomodulator, has been also investigated in treatment of various types of cancers and autoimmune disorders (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Carbonylative annulation of unsaturated compounds using molybdenum hexacarbonyl: an efficient synthesis of 2(1H)-quinolones

Jafarpour¹,

Otaredi-Kashani²

2014

Arkivoc

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A ligand-and CO gas-free condition is developed in palladium-catalyzed three-component reaction of iodoanilines, unsaturated compounds and Mo(CO) 6 as a solid carbon monoxide source. The approach allows for smooth construction of biologically interesting 3,4-disubstituted (dihydro)quinolin-2(1H)-ones in presence of catalytic amounts of palladium and avoids the problematic use of gaseous carbon monoxide.

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N-Phenyl-4-hydroxy-2-quinolone-3-carboxamides as selective inhibitors of mutant H1047R phosphoinositide-3-kinase (PI3Kα)

Cited by 28 publications

References 41 publications

Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα)

Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα)

Recent syntheses of PI3K/Akt/mTOR signaling pathway inhibitors

Carbonylative annulation of unsaturated compounds using molybdenum hexacarbonyl: an efficient synthesis of 2(1H)-quinolones

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