Efficient and fast Heck vinylation of 2-bromo-6-methyl pyridines with methylacrylate. Application to the synthesis of 6-methyl cyclopenta[b]pyridinone

Robert, Nicolas; Hoarau, Christophe; Célanire, Sylvain; Ribereau, P.; Godard, Alain; Quéguiner, G.; Marsais, Francis

doi:10.1016/j.tet.2005.03.008

Cited by 14 publications

(11 citation statements)

References 36 publications

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“…To synthesize these analogues, 2-hydroxy-5-methyl pyridine 27 was brominated to afford compound 28 . 41 N -oxidation of 28 with m-CPBA gave product 29 in 70% yield. Rearrangement of 29 , facilitated by TFAA afforded compound 30 .…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Novel Small-Molecule Inhibitors of the Hypoxia Inducible Factor Pathway

Mooring

Jin

Devi³

et al. 2011

J. Med. Chem.

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Hypoxia, a reduction in partial oxygen pressure, is a salient property of solid tumors. Hypoxia drives malignant progression and metastasis in tumors and participates in tumor resistance to radio- and chemotherapies. Hypoxia activates the hypoxia-inducible factor (HIF) family of transcription factors, which induce target genes that regulate adaptive biological processes such as anaerobic metabolism, cell motility and angiogenesis. Clinical evidence has demonstrated that expression of HIF-1 is strongly associated with poor patient prognosis and activation of HIF-1 contributes to malignant behavior and therapeutic resistance. Consequently, HIF-1 has become an important therapeutic target for inhibition by small molecules. Herein, we describe the design and synthesis of small molecules that inhibit the HIF-1 signaling pathway. Many of these compounds exhibit inhibitory activity in the nanomolar range. Separate mechanistic studies indicate that these inhibitors do not alter HIF-1 levels, but interfere with the HIF-1α/HIF-1β/p300/CBP complex formation by interacting with p300 and CBP.

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Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Novel Small-Molecule Inhibitors of the Hypoxia Inducible Factor Pathway

Mooring

Jin

Devi³

et al. 2011

J. Med. Chem.

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“…2-Bromo-6-methylpyridin-3-ol. The 2-bromo-6-methylpyridin-3-ol was obtained by the same method as previously reported [20]. Bromine (14 ml, 270 mmol) was slowly added to a soln.…”

Section: Experimental Partmentioning

confidence: 99%

Metal‐Ion Sensing Europium(III) Complexes with Bidentate Phosphine Oxide Ligands Containing a 2,2′‐Bipyridine Framework

Hasegawa

Hieda

Nakagawa

et al. 2009

Helvetica Chimica Acta

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“…[45][46][47][48][49] In particular, structural elaboration on heterocyclic compounds with terminal alkynyl/alkenyl functionalities using Sonogashira and Heck coupling reactions is quite interesting. [50][51][52][53][54][55][56] However, attempts are not made to investigate the structural elaboration of cyanopyridine derivatives using Pd-mediated Sonogashira and Heck coupling reactions via a one-pot multicomponent reaction (MCR).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

2014

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Efficient and fast Heck vinylation of 2-bromo-6-methyl pyridines with methylacrylate. Application to the synthesis of 6-methyl cyclopenta[b]pyridinone

Cited by 14 publications

References 36 publications

Design and Synthesis of Novel Small-Molecule Inhibitors of the Hypoxia Inducible Factor Pathway

Design and Synthesis of Novel Small-Molecule Inhibitors of the Hypoxia Inducible Factor Pathway

Metal‐Ion Sensing Europium(III) Complexes with Bidentate Phosphine Oxide Ligands Containing a 2,2′‐Bipyridine Framework

Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

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