16091-26-2Relevant articles and documents
Synthesis of polyaramids in γ-valerolactone-based organic electrolyte solutions
Winters, Jonas,Bolia, Raheed,Dehaen, Wim,Binnemans, Koen
, p. 1228 - 1239 (2021/02/26)
The current synthetic procedures for polyaramids mainly involve the use of amide solvents such asN-methylpyrrolidone andN,N-dimethylacetamide. However, these solvents are suspected to be teratogenic and are considered ‘Substances of Very High Concern’ by the European Commission. Here we propose a benign alternative solvent system: an Organic Electrolyte Solution (OES) consisting of γ-valerolactone (GVL) and a small amount of the ionic liquid 1-methyl-3-octylimidazolium chloride, [C8MIm][Cl]. Three commercially relevant polyaramids were synthesized: poly-p-phenylene terephthalamide (PPTA), poly-m-phenylene isophthalamide (PMIA) and copoly(p-phenylene/3,4′-diphenylether terephthalamide) (ODA/PPTA). PMIA was successfully synthesized in the OES containing [C8MIm][Cl] in a molar fraction ofxIL= 0.043, achieving an inherent viscosity ofηinh= 1.94 ± 0.064 dL g?1, which is on par with the current industrial standard and the benchmark lab scale synthesis. The reaction mixture could also be directly used for the wet spinning of polyaramid fibers, and all components of the solvent could be recycled in good yields by a series of evaporation and distillation steps. ODA/PPTA could be synthesized, but only rather low inherent viscosities were achieved. The reaction mixture was too viscoelastic to be spun by our small-scale spinning setup. PPTA always instantly precipitated and could not be synthesized from a [C8MIm][Cl]/GVL OES. α-Picoline, the organic base which was added to capture the released HCl during the reaction, was found to play a pivotal role in the polymerization reaction. By undergoing an acid-base reaction with HCl, it forms a protic ionic liquidin situwhich increases the solubility of the polymer.
Probing 2H-Indazoles as Templates for SGK1, Tie2, and SRC Kinase Inhibitors
Schoene, Jens,Gazzi, Thais,Lindemann, Peter,Christmann, Mathias,Volkamer, Andrea,Nazaré, Marc
, p. 1514 - 1527 (2019/08/07)
The broader and systematic application of a novel scaffold is often hampered by the unavailability of a short and reliable synthetic access. We investigated a new strategy for the design and synthesis of an array of N2-substituted aza-2H-indazole derivatives as potential kinase inhibitors. Guided by a rational ligand alignment approach to qualify the so-far underrepresented aza-2H-indazole scaffold, indazoles were connected at the N2 position with a phenyl spacer and an arylsulfonamide or amide linkage. Initial profiling against a panel of 30 kinases confirmed the in silico predicted selectivity bias. A synthesized focused library of 52 different aza-2H-indazole derivatives showed good initial selective inhibition against SGK1, Tie2, and SRC kinases, with the best representatives having IC50 values in the range of 500 nm. In a comparative computational study, these data were analyzed and rationalized in light of docking studies.
Discovery of arylamide-5-anilinoquinazoline-8-nitro derivatives as VEGFR-2 kinase inhibitors: Synthesis, in vitro biological evaluation and molecular docking
Zhao, Yongqiang,Liu, Feifei,He, Guojing,Li, Ke,Zhu, Changcheng,Yu, Wei,Zhang, Conghai,Xie, Mingjin,Lin, Jun,Zhang, Jihong,Jin, Yi
, (2019/11/11)
Herein, we embarked on a structural optimization campaign aiming at the discovery of novel anticancer agents with our previously reported XL-6f as a lead compound. A library of 23 compounds has been synthesized based on the highly conserved active site of VEGFR-2. Several title compounds exhibited selective inhibitory activities against VEGFR-2, which also displayed selective anti-proliferation potency against HepG2 cell. All synthesized compounds were evaluated for anti-angiogenesis capability. Compound 7o showed the most potent anti-angiogenesis ability, the efficient cytotoxic activities (in vitro against HUVEC and HepG2 cell lines with IC50 values of 0.58 and 0.23 μM, respectively). The molecular docking analysis revealed 7o is a Type-II inhibitor of VEGFR-2 kinase. In general, these results indicated these arylamide-5-anilinoquinazoline-8-nitro derivatives are promising inhibitors of VEGFR-2 for the potential treatment of anti-angiogenesis.
