Structure–activity relationship study of a series of novel oxazolidinone derivatives as IL-6 signaling blockers

Singh, Sarbjit; Gajulapati, Veeraswamy; Gajulapati, Kondaji; Goo, Ja Il; Park, Yeon Hwa; Jung, Hwa Young; Lee, Sung Yoon; Choi, Jung Ho; Kim, Young Kook; Lee, Kyeong; Heo, Tae Hwe; Choi, Yongseok

doi:10.1016/j.bmcl.2016.01.016

Cited by 17 publications

(14 citation statements)

References 14 publications

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“…The increasing consumption of fossil resources has led to the excessive emission of CO 2 in the atmosphere, which is responsible for serious environmental problems such as the global greenhouse effect. − Therefore, how to reduce the content of CO 2 in the environment has become an urgent research topic for the scientific community. − On the other hand, CO 2 is also an abundant, cheap, nontoxic, and renewable C1 resource, and the transformation of CO 2 into high value-added chemicals is consistent with the development concept of green chemistry. − For example, as a kind of important oxygen–nitrogen heterocyclic equipped with hydrophobic, π–π, and electrostatic interactions, oxazole rings possess some special properties and tremendous application potential in many fields including medicine, pesticide, chemistry, physics, materials science, etc. − In particular, oxazolidinone compounds present effective biological activities by interacting with a variety of enzymes and receptors in organisms. − Therefore, they could be employed as important pharmaceutical intermediates used in the synthesis of many antimicrobial drugs. , However, most reported studies about the cycloaddition of CO 2 with aziridines were associated with homogeneous catalysts. − Although they have excellent catalytic performance, homogeneous catalysts are not easy to separate from the products, which will limit their recyclability and practical applications. Hence, it is necessary and important to find an effective heterogeneous catalyst.…”

Section: Introductionmentioning

confidence: 90%

Efficient Cycloaddition of CO₂ and Aziridines Activated by a Quadruple-Interpenetrated Indium–Organic Framework as a Recyclable Catalyst

et al. 2021

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On the basis of the global warming effect, it is of great significance to convert CO2 into the high value-added products oxazolidinones, but investigations on main-group-based metal–organic frameworks (MOFs) as heterogeneous catalysts still have not been reported so far. In this work, a quadruple-interpenetrated porous indium-based MOF, {[NH2(CH3)2][In(CPT)2]·3CH3CN·3DMA} n (1), is constructed from the organic ligand 3,5-bis(4′-carboxyphenyl)-1,2,4-triazole through solvothermal reactions, and N2 adsorption proves that the framework has a high Brunauer–Emmett–Teller surface areas with 2024 m2/g. The catalytic research on CO2 conversion reveals that compound 1 has high reactivity for the cycloaddition of CO2 with aziridines, and the product 3-ethyl-5-phenyloxazolidin-2-one can be obtained with a yield of 99% under mild conditions. In addition, 1 exhibits excellent activity for different kinds of substrates and can be reused at least five cycles without any significant deactivation, suggesting that 1 is a potential candidate for the chemical conversion of CO2 and aziridines. Mechanistic explorations indicate that the high efficiency of 1 is attributed to the indium center in the framework as a Lewis acid site, and the large porosity can enrich substrates. Importantly, 1 behaved as the first main-group MOF-based catalyst in the reported coupling reaction of CO2 with aziridines.

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Section: Introductionmentioning

confidence: 90%

Efficient Cycloaddition of CO₂ and Aziridines Activated by a Quadruple-Interpenetrated Indium–Organic Framework as a Recyclable Catalyst

et al. 2021

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“…Another small molecule inhibitor that has been shown to bind to gp130, LMT-28, was identified by screening a library of ~1,000 compounds ( 264 ). Computational docking suggested that LMT-28 binds to D1 of gp130, and the putative binding region in D1 of gp130 was supported using site-directed mutagenesis ( 265 ). Likewise, SPR showed that LMT-28 specifically bound gp130, with a dissociation constant ( K D ) of 7.4 μM, and LMT-28 was able to out-compete IL-6/IL-6Rα for gp130 binding ( 264 ).…”

Section: Therapeutic Targeting Of Il-6 Family Cytokine Signalingmentioning

confidence: 99%

Structural Understanding of Interleukin 6 Family Cytokine Signaling and Targeted Therapies: Focus on Interleukin 11

2020

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Cytokines are small signaling proteins that have central roles in inflammation and cell survival. In the half-century since the discovery of the first cytokines, the interferons, over fifty cytokines have been identified. Amongst these is interleukin (IL)-6, the first and prototypical member of the IL-6 family of cytokines, nearly all of which utilize the common signaling receptor, gp130. In the last decade, there have been numerous advances in our understanding of the structural mechanisms of IL-6 family signaling, particularly for IL-6 itself. However, our understanding of the detailed structural mechanisms underlying signaling by most IL-6 family members remains limited. With the emergence of new roles for IL-6 family cytokines in disease and, in particular, roles of IL-11 in cardiovascular disease, lung disease, and cancer, there is an emerging need to develop therapeutics that can progress to clinical use. Here we outline our current knowledge of the structural mechanism of signaling by the IL-6 family of cytokines. We discuss how this knowledge allows us to understand the mechanism of action of currently available inhibitors targeting IL-6 family cytokine signaling, and most importantly how it allows for improved opportunities to pharmacologically disrupt cytokine signaling. We focus specifically on the need to develop and understand inhibitors that disrupt IL-11 signaling.

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“…Another small molecule inhibitor that has been shown to bind to gp130, LMT-28, was identified by screening a library of ∼1,000 compounds (264). Computational docking suggested that LMT-28 binds to D1 of gp130, and the putative binding region in D1 of gp130 was supported using site-directed mutagenesis (265). Likewise, SPR showed that LMT-28 specifically bound gp130, with a dissociation constant (K D ) of 7.4 µM, and LMT-28 was able to out-compete IL-6/IL-6Rα for gp130 binding (264).…”

Section: Inhibitors Of Signaling Through Gp130mentioning

confidence: 99%

Modulating Cytokines as Treatment for Autoimmune Diseases and Cancer

Mortier¹,

Ma²,

Malynn³

et al. 2020

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Structure–activity relationship study of a series of novel oxazolidinone derivatives as IL-6 signaling blockers

Cited by 17 publications

References 14 publications

Efficient Cycloaddition of CO₂ and Aziridines Activated by a Quadruple-Interpenetrated Indium–Organic Framework as a Recyclable Catalyst

Efficient Cycloaddition of CO₂ and Aziridines Activated by a Quadruple-Interpenetrated Indium–Organic Framework as a Recyclable Catalyst

Structural Understanding of Interleukin 6 Family Cytokine Signaling and Targeted Therapies: Focus on Interleukin 11

Modulating Cytokines as Treatment for Autoimmune Diseases and Cancer

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Structure–activity relationship study of a series of novel oxazolidinone derivatives as IL-6 signaling blockers

Cited by 17 publications

References 14 publications

Efficient Cycloaddition of CO2 and Aziridines Activated by a Quadruple-Interpenetrated Indium–Organic Framework as a Recyclable Catalyst

Efficient Cycloaddition of CO2 and Aziridines Activated by a Quadruple-Interpenetrated Indium–Organic Framework as a Recyclable Catalyst

Structural Understanding of Interleukin 6 Family Cytokine Signaling and Targeted Therapies: Focus on Interleukin 11

Modulating Cytokines as Treatment for Autoimmune Diseases and Cancer

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Product

Resources

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Efficient Cycloaddition of CO₂ and Aziridines Activated by a Quadruple-Interpenetrated Indium–Organic Framework as a Recyclable Catalyst

Efficient Cycloaddition of CO₂ and Aziridines Activated by a Quadruple-Interpenetrated Indium–Organic Framework as a Recyclable Catalyst