- Cobalt catalyzed electrochemical [4 + 2] annulation for the synthesis of sultams
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Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt catalyst, this electrochemical method avoided the utilization of stoichiometric amount of metallic oxidant, delivering H2 as the sole by-product. Moreover, this cobalt catalyzed electrochemical protocol proved to be practical and scalable. When the model reaction was scaled up to 5.0 mmol, 86% yield of product could still be obtained.
- Cao, Yangmin,Yuan, Yong,Lin, Yueping,Jiang, Xiaomei,Weng, Yaqing,Wang, Tangwei,Bu, Faxiang,Zeng, Li,Lei, Aiwen
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p. 1548 - 1552
(2020/03/26)
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- NEUROPROTECTIVE QUINOLINE SULFONAMIDES
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Disclosed herein are methods and compositions comprising compounds capable of activating and increasing protein SUMOylation. Disclosed herein are methods and compositions comprising compounds capable of showing neuroprotective and cytoprotective effects w
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Paragraph 0034
(2020/07/07)
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- Rhodium(i)-catalyzed mono-selective C-H alkylation of benzenesulfonamides with terminal alkenes
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The Rh(i)-catalyzed ortho-alkylation of benzenesulfonamides with alkenes with the aid of an 8-aminoquinoline directing group is reported. The reaction is applicable to a variety of benzenesulfonamide derivatives and various alkenes. Curiously, unactivated
- Rej, Supriya,Chatani, Naoto
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supporting information
p. 10503 - 10506
(2019/09/12)
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- Synthesis, molecular structure, anticancer activity, and QSAR study of N-(Aryl/heteroaryl)-4-(1h-pyrrol-1-yl)benzenesulfonamide derivatives
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A series of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)benzenesulfonamides were synthesized from 4-amino-N-(aryl/heteroaryl)benzenesulfonamides and 2,5-dimethoxytetrahydrofuran. All the synthesized compounds were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7 human tumor cell lines. Compound 28, bearing 8-quinolinyl moiety, exhibited the most potent anticancer activity against the HCT-116, MCF-7, and HeLa cell lines, with IC50 values of 3, 5, and 7 μM, respectively. The apoptotic potential of the most active compound (28) was analyzed through various assays: phosphatidylserine translocation, cell cycle distribution, and caspase activation. Compound 28 promoted cell cycle arrest in G2/M phase in cancer cells, induced caspase activity, and increased the population of apoptotic cells. Relationships between structure and biological activity were determined by the QSAR (quantitative structure activity relationships) method. Analysis of quantitative structure activity relationships allowed us to generate OPLS (Orthogonal Projections to Latent Structure) models with verified predictive ability that point out key molecular descriptors influencing benzenosulfonamide’s activity.
- ?o?nowska, Beata,S?awiński, Jaros?aw,Brzozowski, Zdzis?aw,Kawiak, Anna,Belka, Mariusz,Zielińska, Joanna,Baczek?, Tomasz,Chojnacki, Jaros?aw
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- Small molecule SUMOylation activators are novel neuroprotective agents
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Neuronal loss characterizes many of the most intractable nervous system diseases that deprive our ageing population of their quality of life. Neuroprotective pharmacological modalities are urgently needed to address this burgeoning population. Small ubiqu
- Krajnak, Katherine,Dahl, Russell
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p. 405 - 409
(2017/12/26)
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- Cobalt Catalyzed C-H and N-H Bond Annulation of Sulfonamide with Terminal and Internal Alkynes
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Chelate assisted cobalt catalyzed C-H and N-H annulation of aryl sulfonamide with terminal and internal alkynes is reported. Very high regioselectivity and excellent functional group tolerance were achieved using oxygen as a co-oxidant. The reaction is scalable under mild conditions.
- Kalsi, Deepti,Sundararaju, Basker
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supporting information
p. 6118 - 6121
(2016/01/09)
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- Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group
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The use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily prepared aryl sulfonamides and alkynes using 8-aminoquinoline as a directing group. The reaction shows broad substrate scope with products obtained in a highly regioselective manner in good to excellent isolated yields. Mechanistic insights suggest the formation of a Co(III)-aryl key species via a rate-determining arene C-H activation during the annulation reaction.
- Planas, Oriol,Whiteoak, Christopher J.,Company, Anna,Ribas, Xavi
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supporting information
p. 4003 - 4012
(2016/01/25)
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- From sensors to silencers: Quinoline- and benzimidazole-sulfonamides as inhibitors for zinc proteases
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Derived from the extensive work in the area of small molecule zinc(II) ion sensors, chelating fragment libraries of quinoline- and benzimidazole- sulfonamides have been prepared and screened against several different zinc(II)-dependent matrix metalloproteinases (MMPs). The fragments show impressive inhibition of these metalloenzymes and preferences for different MMPs based on the nature of the chelating group. The findings show that focused chelator libraries are a powerful strategy for the discovery of lead fragments for metalloprotein inhibition.
- Rouffet, Matthieu,De Oliveira, Cesar Augusto F.,Udi, Yael,Agrawal, Arpita,Sagi, Irit,McCammon, J. Andrew,Cohen, Seth M.
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supporting information; experimental part
p. 8232 - 8233
(2010/08/05)
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- Fluorescence sensing and binding behavior of aminobenzenesulfonamidoquinolino-β-cyclodextrin to Zn2+
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(Chemical Equation Presented) A water-soluble fluorescent zinc sensor which binds strongly to Zn2+ (log K = 12.4) was successfully synthesized under physiological conditions. This sensor exhibits a good fluorescence response to Zn2+ over a wide pH range in water. Under the same conditions, several metal ions commonly present in a physiological environment, such as Na+, K+, Ca2+, Mg2+, Mn 2+, Fe2+, and Co2+, showed little interference to the fluorescence response to Zn2+.
- Liu, Yu,Zhang, Ning,Chen, Yong,Wang, Li-Hua
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p. 315 - 318
(2008/02/03)
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