6275-26-9Relevant academic research and scientific papers
Nucleophilicity parameters for alkyl and aryl isocyanides
Tumanov, Vasily V.,Tishkov, Alexander A.,Mayr, Herbert
, p. 3563 - 3566 (2007)
How nucleophilic are isocyanides? The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable t
A Diarylacetonitrile as a Molecular Probe for the Detection of Polymeric Mechanoradicals in the Bulk State through a Radical Chain-Transfer Mechanism
Yamamoto, Takumi,Kato, Sota,Aoki, Daisuke,Otsuka, Hideyuki
, p. 2680 - 2683 (2021)
Since the beginning of polymer science, understanding the influence of mechanical stress on polymer chains has been a fundamental and important research topic. The detection of mechanoradicals generated by homolytic cleavage of the polymer chains in solut
Synthesis of difluoromethylated diarylmethanesviaFe(OTf)3-catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates
Yamamoto, Yoshihiko,Takase, Tomoya,Kuroyanagi, Eisuke,Yasui, Takeshi
supporting information, p. 3877 - 3880 (2021/04/26)
The Fe(OTf)3-catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates with electron-rich (hetero)arenes afforded difluoromethylated diarylmethanes. Control experiments showed that Fe(OTf)3behaves as the Lewis acid, an
Structure-based virtual screening, synthesis and biological evaluation of potential FAK-FAT domain inhibitors for treatment of metastatic cancer
Hiscox, Stephen E.,Jones, Samuel R.,Kandil, Sahar B.,Smith, Sonia,Westwell, Andrew D.
, (2020/08/28)
Focal adhesion kinase (FAK) is a tyrosine kinase that is overexpressed and activated in several advanced-stage solid cancers. In cancer cells, FAK promotes the progression and metastasis of tumours. In this study, we used structure-based virtual screening to filter a library of more than 210K compounds against the focal adhesion targeting FAK-focal adhesion targeting (FAT) domain to identify 25 virtual hit compounds which were screened in the invasive breast cancer line (MDA-MB-231). Most notably, compound I showed low micromolar antiproliferative activity, as well as antimigratory activity. Moreover, examination in a model of triple negative breast cancer (TNBC), revealed that, despite not effecting FAK phosphorylation, compound I significantly impairs proliferation whilst impairing focal adhesion growth and turnover leading to reduced migration. Further optimisation and synthesis of analogues of the lead compound I using a four-step synthetic procedure was performed, and analogues were assessed for their antiproliferative activity against three breast cancer (MDA-MB-231, T47D, BT474) cell lines and one pancreatic cancer (MIAPaCa2) cell line. Compound 5f was identified as a promising lead compound with IC50 values in the range of 4.59–5.28 μM in MDA-MB-231, T47D, BT474, and MIAPaCa2. Molecular modelling and pharmacokinetic studies provided more insight into the therapeutic features of this new series.
Different Selectivities in the Insertions into C(sp2)?H Bonds: Benzofulvenes by Dual Gold Catalysis Competition Experiments
Plajer, Alex J.,Ahrens, Lukas,Wieteck, Marcel,Lustosa, Danilo M.,Babaahmadi, Rasool,Yates, Brian,Ariafard, Alireza,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 10766 - 10772 (2018/08/03)
An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)?H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C?H positions. A bidirectional synthesis with two competing ortho-aryl C?H bonds in the selectivity-determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C?H bonds with a benzylic methyl group also showed perfect selectivity.
Switchable Stereoselectivity in Bromoaminocyclization of Olefins: Using Br?nsted Acids of Anionic Chiral Cobalt(III) Complexes
Jiang, Hua-Jie,Liu, Kun,Yu, Jie,Zhang, Ling,Gong, Liu-Zhu
supporting information, p. 11931 - 11935 (2017/09/20)
Br?nsted acids of anionic chiral CoIII complexes act as bifunctional phase-transfer catalysts to shuttle the substrates across the solvent interface and control stereoselectivity. The diastereomeric chiral CoIII-templated Br?nsted ac
The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes
Nambo, Masakazu,Yar, Muhammad,Smith, Joel D.,Crudden, Cathleen M.
supporting information, p. 50 - 53 (2015/07/28)
The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials. (Chemical Presented)
6-azabicyclo[3.2.1]octanes via copper-catalyzed enantioselective alkene carboamination
Casavant, Barbara J.,Hosseini, Azade S.,Chemler, Sherry R.
supporting information, p. 2697 - 2702 (2014/09/29)
Bridged bicyclic rings containing nitrogen heterocycles are important motifs in bioactive small organic molecules. An enantioselective copper-catalyzed alkene carboamination reaction that creates bridged heterocycles is reported herein. Two new rings are
Dual gold catalysis: Synthesis of polycyclic compounds via C-H insertion of gold vinylidenes
Wieteck, Marcel,Tokimizu, Yusuke,Rudolph, Matthias,Rominger, Frank,Ohno, Hiroaki,Fujii, Nobutaka,Hashmi, A. Stephen K.
supporting information, p. 16331 - 16336 (2015/01/09)
New and interesting polycyclic compounds have been synthesized from non-conjugated diyne systems by dual gold catalysis. A quaternary carbon center in the backbone and the accompanying Thorpe-Ingold effect enabled the unprecedented insertion of sp3 and sp2 C-H bonds that for the first time were incorporated within the backbone of the diyne system and allowed the construction of complex polycyclic carbon scaffolds inaccessible by previous approaches in which the C-H bonds for the insertion were situated at the other end of the alkyne.
Regio- and enantioselective aminofluorination of alkenes
Kong, Wangqing,Feige, Pascal,De Haro, Teresa,Nevado, Cristina
supporting information, p. 2469 - 2473 (2013/03/29)
Enantio- and regioselective: The intramolecular enantioselective aminofluorination of unactivated olefins was achieved by using a chiral iodo(III) difluoride salt. A highly regioselective aminofluorination of styrenes to access 2-fluoro-2-phenylethanamines was also developed. Copyright
