127406-55-7Relevant articles and documents
Pd(ii) complexes of N,S-heterocyclic carbenes with pendant and coordinated allyl function and their Suzuki coupling activities
Yen, Swee Kuan,Koh, Lip Lin,Huynh, Han Vinh,Hor, T. S. Andy
, p. 3952 - 3958 (2007)
3-(2-Propenyl)benzothiazolium bromide (A) provides a direct and simple entry to Pd(ii) complexes with N,S-heterocyclic carbene (NSHC) ligands functionalized with an allyl pendant with hemilabile potential. Addition of salt A to Pd(OAc)2 eliminates HOAc and affords the bis(carbene) complexes cis-[PdBr2(NHSC)2] (cis-1, NSHC = 3-(2-propenyl) benzothiazolin-2-ylidene) and trans-[PdBr2(NHSC)2] (trans-1) along with the monocarbene complexes [PdBr2(NSHC)] (2) and trans-[PdBr2(benzothiazole-κN)(NSHC)] (3) as minor side products. Salt-metathesis of cis-1 with AgO2CCF3 yields the mixed dicarboxylato-bis(carbene) complex cis-[Pd(O2CCF 3)2(NSHC)2] (4). Complexes cis-1, trans-1 and 4 were characterized by multinuclear NMR spectroscopies, ESI mass spectrometry and elemental analysis. The molecular structures of complexes cis-1, 2 and 3 have been determined by X-ray single crystal diffraction. Complexes cis-1 and 4 as well as an in situ mixture of Pd(OAc)2 and salt A are active toward Suzuki-Miyaura coupling of aryl bromides and activated aryl chlorides giving good conversions. The Royal Society of Chemistry.
Generation of 3-Pyridyl Biaryl Systems Via Palladium-Catalyzed Suzuki Cross-Couplings of Aryl Halides with 3-Pyridylboroxin
Cioffi, Christopher L.,Spencer, William T.,Richards, Justin J.,Herr, R. Jason
, p. 2210 - 2212 (2004)
The synthesis of 3-pyridyl biaryl systems can be readily achieved by means of palladium-catalyzed Suzuki cross-coupling reactions between aryl halides and 3-pyridyl-boroxin. A series of cross-couplings were conducted in order to investigate the scope and limitations of this protocol.
One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
Jong, Howard,Eey, Stanley T.-C.,Lim, Yee Hwee,Pandey, Sangeeta,Iqbal, Nurul Azmah Bte,Yong, Fui Fong,Robins, Edward G.,Johannes, Charles W.
supporting information, p. 616 - 622 (2017/02/23)
A methodology for a sequential palladium-catalyzed cross-coupling procedure consisting of borylation, the Suzuki reaction and amination has been developed for the assembly of molecules with multi-aryl backbones. The linchpin of this development is the meta-terarylphosphine ligand, Cy*Phine, which has been employed as an air- and moisture-stable precatalyst, Pd(Cy*Phine)2Cl2, to improve the efficiency of one-pot borylation–Suzuki reactions. Additionally, the reactivity of the Pd-Cy*Phine system could be tuned to furnish a one-pot, borylation–Suzuki reaction–amination (BSA) cross-coupling treble. The methodology successfully integrated complementary conditions for three distinctly different and modular reactions. Average yields of 74–94% could be achieved for each segment that cumulatively afforded 50–84% yield over the entire three-step sequence in a single pot. (Figure presented.).
VP1 crystal structure-guided exploration and optimization of 4,5-dimethoxybenzene-based inhibitors of rhinovirus 14 infection
Da Costa, Laurène,Roche, Manon,Scheers, Els,Coluccia, Antonio,Neyts, Johan,Terme, Thierry,Leyssen, Pieter,Silvestri, Romano,Vanelle, Patrice
, p. 453 - 462 (2016/04/19)
Human rhinoviruses (HRV) are the predominant cause of common colds and flu-like illnesses, but are also responsible for virus-induced exacerbations of asthma and chronic obstructive pulmonary disease. However, to date, no drug has been approved yet for clinical use. In this study, we present the results of the structure-based lead optimization of a class of new small-molecule inhibitors that we previously reported to bind into the pocket beneath the canyon of the VP1 protein. A small series of analogues that we designed based on the available structure and interaction data were synthesized and evaluated for their potency to inhibit the replication of HRV serotype 14. 2-(4,5-Dimethoxy-2-nitrophenyl)-1-(4-(pyridin-4-yl)phenyl)ethanol (3v) was found to be a potent inhibitor exhibiting micromolar activity (EC50 Combining double low line 3.4 ± 1.0 μM) with a toxicity for HeLa cells that was significantly lower than that of our previous hit (LPCRW-0005, CC50 Combining double low line 104.0 ± 22.2 μM; 3v, CC50 > 263 μM).
