Facile Assembly of Fused Benzo[4,5]furo Heterocycles

Liu, Jing; Fitzgerald, Anne E.; Mani, Neelakandha S.

doi:10.1021/jo8000595

Cited by 87 publications

(45 citation statements)

References 14 publications

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“…Treatment of 4 with an excess amount of ethyl triflate furnished ammonium salt 5, which was subsequently transformed into the acetylated product 6. Demethylation of 6 followed by the formation of benzofuran structure via intramolecular Ullmann condensation 22 provided the target compound, BINDY.…”

Section: Synthesis Of Bindymentioning

confidence: 99%

Design and synthesis of a potent inhibitor of class 1 DYRK kinases as a suppressor of adipogenesis

Masaki

Kii

Sumida

et al. 2015

Bioorganic & Medicinal Chemistry

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Dysregulation of dual-specificity tyrosine-phosphorylation-regulated kinase 1A (DYRK1A) has been demonstrated in several pathological conditions, including Alzheimer's disease and cancer progression. It has been recently reported that a gain of function-mutation in the human DYRK1B gene exacerbates metabolic syndrome by enhancing obesity. In the previous study, we developed an inhibitor of DYRK family kinases (INDY) and demonstrated that INDY suppresses the pathological phenotypes induced by overexpression of DYRK1A or DYRK1B in cellular and animal models. In this study, we designed and synthesized a novel inhibitor of DYRK family kinases based on the crystal structure of the DYRK1A/INDY complex by replacing the phenol group of INDY with dibenzofuran to produce a derivative, named BINDY. This compound exhibited potent and selective inhibitory activity toward DYRK family kinases in an in vitro assay. Furthermore, treatment of 3T3-L1 pre-adipocytes with BINDY hampered adipogenesis by suppressing gene expression of the critical transcription factors PPARγ and C/EBPα. This study indicates the possibility of BINDY as a potential drug for metabolic syndrome.

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Section: Synthesis Of Bindymentioning

confidence: 99%

Design and synthesis of a potent inhibitor of class 1 DYRK kinases as a suppressor of adipogenesis

Masaki

Kii

Sumida

et al. 2015

Bioorganic & Medicinal Chemistry

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“…In 2008, the Suzuki–Miyaura monoarylation of 2,4,5,6‐tetrachloropyrimidine ( 480 ) was investigated by Yang et al 172…”

Section: Cross‐coupling Reactions Of Polyhalogenated Six‐membered Hmentioning

confidence: 99%

“…Worthy of note is that the first and only example of a selective Suzuki–Miyaura monoarylation of a dihalogenated quinoxaline was described in 2008 by Liu et al.,172 who found that the Pd(OAc) 2 /PPh 3 ‐catalyzed reaction between 1.5 equiv. of 2,3‐dichloroquinoxalime ( 492 ) and 5‐fluoro‐2‐methoxyphenylboronic acid ( 493 ) in a 4:1 mixture of MeCN and water at 60 °C in the presence of 3.0 equiv.…”

Section: Cross‐coupling Reactions Of Polyhalogenated Six‐membered Hmentioning

confidence: 99%

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

2012

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The palladium-catalyzed Suzuki-Miyaura reaction of multiply halogenated, electron-rich and electron-deficient heteroarenes is one of the most reliable and environmentally friendly tools for installing a wide range of non-functionalized and functionalized carbon substituents onto heteroaromatic systems with exquisite chemo-and site-selectivity. For substrates with different halogen groups the chemoselectivity of the Suzuki-Miyaura reactions has been found to be dependent on the reactivity difference between the halogens. However, the hardest achievement of selectivity in Suzuki-Miyaura monocouplings involving polyhalogenated heteroarenes with identical halogen atoms has been shown to be dominated by steric and electronic effects and the presence of directing groups at positions neighbouring the reaction sites. Moreover, in the case of symmetrically substituted dihaloheteroarenes with identical halogen atoms, highly selective monocoupling reactions have often been achieved only after a careful optimization of reaction parameters including the catalyst precursor, base, solvent, and the molar ratio between electrophile and organoboron reagent. This critical review with 341 references covers developments on the chemo-and site-selective Suzuki-Miyaura monocoupling reactions of polyhalogenated heteroarenes with different or identical halogen atoms. It also includes the synthesis of polysubstituted heteroarenes, not easily accessible by other means, via consecutive monocoupling reactions and/ or a more synthetically valuable approach involving one-pot polycoupling reactions.

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“…Liu and co-workers [47] developed a concise synthesis of fused benzo [4,5]furo heterocycles 169 that are a common structural motif in biologically active compounds and drug candidates (Scheme 32). One of the key reactions is a chemo/regioselective Suzuki coupling.…”

Section: Synthesis Of Oxygen-bearing Heterocyclic Compoundsmentioning

confidence: 99%

Recent advances in application of intramolecular Suzuki cross-coupling in cyclization and heterocyclization

Heravi

Hashemi

2012

Monatsh Chem

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Facile Assembly of Fused Benzo[4,5]furo Heterocycles

Cited by 87 publications

References 14 publications

Design and synthesis of a potent inhibitor of class 1 DYRK kinases as a suppressor of adipogenesis

Design and synthesis of a potent inhibitor of class 1 DYRK kinases as a suppressor of adipogenesis

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

Recent advances in application of intramolecular Suzuki cross-coupling in cyclization and heterocyclization

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