Vinyl sulfone synthesis via copper-catalyzed three-component decarboxylative addition

2021 ◽  
Vol 19 (36) ◽  
pp. 7827-7831
Author(s):  
Seunghwan An ◽  
Kwang Ho Song ◽  
Sunwoo Lee
Keyword(s):  
Boronic Acids ◽  
Vinyl Sulfone ◽  
Sulfone Derivatives

The synthesis of vinyl sulfone derivatives via the reaction of arylpropiolic acids, K2S2O5, and aryl boronic acids is reported.

scholarly journals Identification of Vinyl Sulfone Derivatives as EGFR Tyrosine Kinase Inhibitor: In Vitro and In Silico Studies

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2211
Author(s):  
Thitinan Aiebchun ◽  
Panupong Mahalapbutr ◽  
Atima Auepattanapong ◽  
Onnicha Khaikate ◽  
Supaphorn Seetaha ◽  
...  
Keyword(s):  
Tyrosine Kinase ◽  
Inhibitory Activity ◽  
In Silico ◽  
Kinase Inhibitor ◽  
Kinase Assay ◽  
Vinyl Sulfone ◽  
Egfr Tyrosine Kinase ◽  
In Silico Studies ◽  
Sulfone Derivatives

Epidermal growth factor receptor (EGFR), overexpressed in many types of cancer, has been proved as a high potential target for targeted cancer therapy due to its role in regulating proliferation and survival of cancer cells. In the present study, a series of designed vinyl sulfone derivatives was screened against EGFR tyrosine kinase (EGFR-TK) using in silico and in vitro studies. The molecular docking results suggested that, among 78 vinyl sulfones, there were eight compounds that could interact well with the EGFR-TK at the ATP-binding site. Afterwards, these screened compounds were tested for the inhibitory activity towards EGFR-TK using ADP-Glo™ kinase assay, and we found that only VF16 compound exhibited promising inhibitory activity against EGFR-TK with the IC50 value of 7.85 ± 0.88 nM. In addition, VF16 showed a high cytotoxicity with IC50 values of 33.52 ± 2.57, 54.63 ± 0.09, and 30.38 ± 1.37 µM against the A431, A549, and H1975 cancer cell lines, respectively. From 500-ns MD simulation, the structural stability of VF16 in complex with EGFR-TK was quite stable, suggesting that this compound could be a novel small molecule inhibitor targeting EGFR-TK.

Visible-Light-Induced Chemoselective Synthesis of α-Chloro and Vinyl Sulfones by Sulfonylation of Alkenes

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 364-368 ◽  
Author(s):  
Teng-fei Niu ◽  
Bang-qing Ni ◽  
Dan Lin ◽  
Lin-shuang Xue ◽  
Ding-yun Jiang
Keyword(s):  
Visible Light ◽  
Electronic Properties ◽  
Room Temperature ◽  
Sulfonyl Chloride ◽  
Vinyl Sulfone ◽  
Chemoselective Synthesis ◽  
High Yields ◽  
Sulfone Derivatives

Direct sulfonylation between alkenes and sulfonyl chloride was achieved at room temperature by a visible-light-induced photo­redox process. This method allows the chemoselective synthesis of α-chloro and vinyl sulfone derivatives with moderate to high yields. The selectivity of the reaction was fully controlled by the electronic properties of the alkenes.

Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde

2020 ◽  
Vol 18 (18) ◽  
pp. 3527-3535
Author(s):  
Fuhong Xiao ◽  
Yangling Hu ◽  
Huawen Huang ◽  
Fen Xu ◽  
Guo-Jun Deng
Keyword(s):  
Vinyl Sulfone ◽  
Metal Free ◽  
Selectivity Control ◽  
Sulfone Derivatives

A tuneable metal-free protocol for the selective preparation of α-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. The base played an important role in the selectivity control of transformation.

A Mild and Simple Method for Making MIDA Boronates

2020 ◽  
Author(s):  
Aidan Kelly ◽  
Peng-Jui (Ruby) Chen ◽  
Jenna Klubnick ◽  
Daniel J. Blair ◽  
Martin D. Burke
Keyword(s):  
Organic Synthesis ◽  
Boronic Acids ◽  
Simple Method ◽  
Direct Preparation ◽  
Synthesis Procedure ◽  
Harsh Conditions

<div> <div> <div> <p>Existing methods for making MIDA boronates require harsh conditions and complex procedures to achieve dehydration. Here we disclose that a pre-dried form of MIDA, MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in labs that do not specialize in organic synthesis. </p> </div> </div> </div>

Neoglycopeptide Synthesis by Suzuki-Miyaura Couplings between Glycosyl Aryl Boronic Acids and Iodopeptides

2014 ◽  
Vol 21 (10) ◽  
pp. 1004-1010
Author(s):  
Guohua Chen ◽  
Xiangying Gu ◽  
Lin Chen ◽  
Xin Wang ◽  
Yue-Lei Chen ◽  
...  
Keyword(s):  
Boronic Acids
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