51079-10-8Relevant articles and documents
Photoactivatable caged prodrugs of VEGFR-2 kinase inhibitors
Pinchuk, Boris,Horbert, Rebecca,D?bber, Alexander,Kuhl, Lydia,Peifer, Christian
, (2016)
In this study, we report on the design, synthesis, photokinetic properties and in vitro evaluation of photoactivatable caged prodrugs for the receptor tyrosine kinase VEGFR-2. Highly potent VEGFR-2 inhibitors 1 and 3 were caged by introduction of a photoremovable protecting group (PPG) to yield the caged prodrugs 4 and 5. As expected, enzymatic and cellular proliferation assays showed dramatically diminished efficacy of caged prodrugs in vitro. Upon ultraviolet (UV) irradiation of the prodrugs original inhibitory activity was completely restored and even distinctly reinforced, as was the case for the prodrug 4. The presented results are a further evidence for caging technique being an interesting approach in the protein kinase field. It could enable spatial and temporal control for the inhibition of VEGFR-2. The described photoactivatable prodrugs might be highly useful as biological probes for studying the VEGFR-2 signal transduction.
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Nogrady,Doyle
, p. 485 (1964)
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Exploring of indole derivatives for ESIPT emission: A new ESIPT-based fluorescence skeleton and TD-DFT calculations
Ayd?n, Hatice Gülten,Ekmekci, Zeynep,Kaya, Serdal,Keskin, Selbi,Menges, Nurettin
, (2021/08/23)
Appropriate synthesis methods gave six different indole derivatives substituted at the C-2 or C-3 position. ESIPT emission capacities of these derivatives were investigated. It was concluded that the indole derivative containing the 1,2-dicarbonyl group at the C-2 position has ESIPT emission. Although adding water to the DMSO solution of the ESIPT-based molecule (9:1) resulted in ESIPT quenching, steady-state measurements in MeOH did not occur ESIPT quenching. TD-DFT calculation for uncovering the ESIPT mechanism emerged that the ESIPT mechanism occurred as a barrierless process. The X-ray analysis and DFT conformational analysis revealed that NH and CO groups involving proton transfer mechanisms are in the cis position. A mono-exponential decay was observed in DMSO and MeOH solutions, in which lifetimes were measured as 6.1 and 5.5 ns, respectively. pH studies revealed that acidic and basic solutions of molecule 7 did not influence ESIPT emission.
Copper-catalyzed carbonylative transformations of indoles with hexaketocyclohexane
Wang, Zechao,Yin, Zhiping,Wu, Xiao-Feng
supporting information, p. 4798 - 4801 (2018/05/23)
With hexaketocyclohexane octahydrate as the carbon monoxide source, a novel procedure for copper-catalyzed direct double carbonylation of indoles has been established. Using alcohols as reaction partners, moderate to good yields of the desired double carbonylation products have been obtained. Wide functional group tolerance and substrate scope can be observed.
Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters
Kumar, Yogesh,Jaiswal, Yogesh,Kumar, Amit
, p. 12247 - 12257 (2016/12/23)
A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.
