Convenient preparation of N-8-quinolinyl benzenesultams as novel NF-κB inhibitors

Xie, Yuning; Gong, Gangli; Liu, Yidong; Deng, Shi‐Xian; Rinderspacher, Alison; Branden, Lars; Landry, Donald W.

doi:10.1016/j.tetlet.2008.01.136

Cited by 30 publications

(28 citation statements)

References 8 publications

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“…The designs of the molecules were guided by the modifications based on already known inhibitors in the series. Pschorr reaction [28] was the key step in case of Figure 1 , whereas Buchwald coupling reaction [29] resulted in the synthesis of another set of molecules as shown in Figure 2 . All together ten new inhibitors were synthesized according to the scheme as shown in Figure 3 .…”

Section: Resultsmentioning

confidence: 99%

Efficacy of Cyclin Dependent Kinase 4 Inhibitors as Potent Neuroprotective Agents against Insults Relevant to Alzheimer’s Disease

et al. 2013

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Alzheimer’s disease (AD) is a progressive neurodegenerative disease with no cure till today. Aberrant activation of cell cycle regulatory proteins is implicated in neurodegenerative diseases including AD. We and others have shown that Cyclin dependent kinase 4 (Cdk4) is activated in AD brain and is required for neuron death. In this study, we tested the efficiency of commercially available Cdk4 specific inhibitors as well as a small library of synthetic molecule inhibitors targeting Cdk4 as neuroprotective agents in cellular models of neuron death. We found that several of these inhibitors significantly protected neuronal cells against death induced by nerve growth factor (NGF) deprivation and oligomeric beta amyloid (Aβ) that are implicated in AD. These neuroprotective agents inhibit specifically Cdk4 kinase activity, loss of mitochondrial integrity, induction of pro-apoptotic protein Bim and caspase3 activation in response to NGF deprivation. The efficacies of commercial and synthesized inhibitors are comparable. The synthesized molecules are either phenanthrene based or naphthalene based and they are synthesized by using Pschorr reaction and Buchwald coupling respectively as one of the key steps. A number of molecules of both kinds block neurodegeneration effectively. Therefore, we propose that Cdk4 inhibition would be a therapeutic choice for ameliorating neurodegeneration in AD and these synthetic Cdk4 inhibitors could lead to development of effective drugs for AD.

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Section: Resultsmentioning

confidence: 99%

Efficacy of Cyclin Dependent Kinase 4 Inhibitors as Potent Neuroprotective Agents against Insults Relevant to Alzheimer’s Disease

et al. 2013

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“…Biaryls embedded in cyclic sulfonamides (i.e., biaryl sultams; e.g., 3 and 4) have emerged as privileged structures in drug discovery because of their diverse enzyme inhibitory activity and active role in selective serotonin reuptake inhibition. [3][4][5] The structural simplicity of biaryl sultams belies their preparative complexity, and the quest for an efficient and convergent synthesis has captivated the attention of synthetic organic chemists.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Regio‐ and Chemoselective Reactions of 2‐Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven‐Membered Sultam

2015

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Molecules labeled with fluorine‐18 are used as radiotracers for positron emission tomography. An important challenge is the labeling of arenes not amenable to aromatic nucleophilic substitution (SNAr) with [18F]F−. In the ideal case, the 18F fluorination of these substrates would be performed through reaction of [18F]KF with shelf‐stable readily available precursors using a broadly applicable method suitable for automation. Herein, we describe the realization of these requirements with the production of 18F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [18F]KF/K222 and [Cu(OTf)2(py)4] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[18F]fluoro‐L‐DOPA, 6‐[18F]fluoro‐m‐tyrosine, and the translocator protein (TSPO) PET ligand [18F]DAA1106.

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“…Sulfonamides constitute one of the most important antibiotics developed from non-natural sources [ 1 , 2 ]. Benzosultams, a subclass of bicyclic sulfonamides, are found in numerous biologically active compounds, pharmaceuticals, as well as agricultural agents [ 3 , 4 , 5 , 6 , 7 ]. They exhibit a wide spectrum of promising bioactivities, such as antibacterial, antidiabetic, anticancer, and vitro HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitory activities, which have been widely utilized as inhibitors and drugs [ 8 , 9 , 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Catalytic Synthesis of Benzosultams

Zhao

2020

Molecules

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Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems for the efficient construction of benzosultam motifs over the past decades. Herein, in this review, we mainly summarize the recent advances in the field of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on the scopes and mechanisms of representative reactions.

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Convenient preparation of N-8-quinolinyl benzenesultams as novel NF-κB inhibitors

Cited by 30 publications

References 8 publications

Efficacy of Cyclin Dependent Kinase 4 Inhibitors as Potent Neuroprotective Agents against Insults Relevant to Alzheimer’s Disease

Efficacy of Cyclin Dependent Kinase 4 Inhibitors as Potent Neuroprotective Agents against Insults Relevant to Alzheimer’s Disease

Palladium‐Catalyzed Regio‐ and Chemoselective Reactions of 2‐Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven‐Membered Sultam

Recent Advances in Catalytic Synthesis of Benzosultams

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Convenient preparation of N-8-quinolinyl benzenesultams as novel NF-κB inhibitors

Cited by 30 publications

References 8 publications

Efficacy of Cyclin Dependent Kinase 4 Inhibitors as Potent Neuroprotective Agents against Insults Relevant to Alzheimer’s Disease

Efficacy of Cyclin Dependent Kinase 4 Inhibitors as Potent Neuroprotective Agents against Insults Relevant to Alzheimer’s Disease

Palladium‐Catalyzed Regio‐ and Chemo­selective Reactions of 2‐Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven‐Membered Sultam

Recent Advances in Catalytic Synthesis of Benzosultams

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Palladium‐Catalyzed Regio‐ and Chemoselective Reactions of 2‐Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven‐Membered Sultam