937366-54-6Relevant articles and documents
Ni-Catalyzed Traceless, Directed C3-Selective C-H Borylation of Indoles
Tian, Ya-Ming,Guo, Xiao-Ning,Wu, Zhu,Friedrich, Alexandra,Westcott, Stephen A.,Braunschweig, Holger,Radius, Udo,Marder, Todd B.
, p. 13136 - 13144 (2020)
A highly efficient and general protocol for traceless, directed C3-selective C-H borylation of indoles with [Ni(IMes)2] as the catalyst is reported. Activation and borylation of N-H bonds by [Ni(IMes)2] is essential to install a Bpin moiety at the N-position as a traceless directing group, which enables the C3-selective borylation of C-H bonds. The N-Bpin group which is formed is easily converted in situ back to an N-H group by the oxidative addition product of [Ni(IMes)2] and in situ-generated HBpin. The catalytic reactions are operationally simple, allowing borylation of a variety of substituted indoles with B2pin2 in excellent yields and with high selectivity. The C-H borylation can be followed by Suzuki-Miyaura cross-coupling of the C-borylated indoles in an overall two-step, one-pot process providing an efficient method for synthesizing C3-functionalized heteroarenes.
Design, synthesis and biological evaluation of pyrazolo[3,4-d]pyrimidine-based protein kinase D inhibitors
Gilles, Philippe,Kashyap, Rudra S.,Freitas, Maria Jo?o,Ceusters, Sam,Van Asch, Koen,Janssens, Anke,De Jonghe, Steven,Persoons, Leentje,Cobbaut, Mathias,Daelemans, Dirk,Van Lint, Johan,Voet, Arnout R.D.,De Borggraeve, Wim M.
supporting information, (2020/08/25)
The multiple roles of protein kinase D (PKD) in various cancer hallmarks have been repeatedly reported. Therefore, the search for novel PKD inhibitors and their evaluation as antitumor agents has gained considerable attention. In this work, novel pyrazolo[3,4-d]pyrimidine based pan-PKD inhibitors with structural variety at position 1 were synthesized and evaluated for biological activity. Starting from 3-IN-PP1, a known PKD inhibitor with IC50 values in the range of 94–108 nM, compound 17m was identified with an improved biochemical inhibitory activity against PKD (IC50 = 17–35 nM). Subsequent cellular assays demonstrated that 3-IN-PP1 and 17m inhibited PKD-dependent cortactin phosphorylation. Furthermore, 3-IN-PP1 displayed potent anti-proliferative activity against PANC-1 cells. Finally, a screening against different cancer cell lines demonstrated that 3-IN-PP1 is a potent and versatile antitumoral agent.
CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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Paragraph 0412; 0416, (2020/02/29)
A condensed cyclic compound and an organic light-emitting device including the same, the condensed cyclic compound being represented by the following Formula 1:
A traceless directing group for C - H borylation
Preshlock, Sean M.,Plattner, Donald L.,Maligres, Peter E.,Krska, Shane W.,Maleczka Jr., Robert E.,Smith III, Milton R.
supporting information, p. 12915 - 12919 (2014/01/06)
Not a trace: Borylation of the nitrogen in nitrogen heterocycles or anilines provides a traceless directing group for subsequent catalytic C - H borylation. Selectivities that previously required Boc protection can be achieved; furthermore, the NBpin directing group can be installed and removed in situ, and product yields are substantially higher. Boc=tert-butoxycarbonyl, pin=pinacolato. Copyright
Boc groups as protectors and directors for ir-catalyzed C-H borylation of heterocycles
Kallepalli, Venkata A.,Shi, Feng,Paul, Sulagna,Onyeozili, Edith N.,Maleczka Jr., Robert E.,Smith III, Milton R.
supporting information; experimental part, p. 9199 - 9201 (2010/03/02)
(Chemical Equation Presented) Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions β to N. The Boc group can be removed on thermolysis
Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: Regioselective synthesis of heteroarylboronates
Takagi, Jun,Sato, Kazuaki,Hartwig, John F,Ishiyama, Tatsuo,Miyaura, Norio
, p. 5649 - 5651 (2007/10/03)
The C-H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80-100°C in the presence of a 1/2[IrCl(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including pyridine and quinoline selectively occurred at the 3-position. Regioselective synthesis of bis(boryl)heteroaromatics was also achieved by using an almost equimolar amount of substrates and the diboron.
