22049-19-0Relevant articles and documents
Intermolecular interactions in the solid state structures of neutral and N-protonated 5-alkoxymethyl-8-hydroxyquinolines
Schulze, Mathias M.,B?hme, Uwe,Schwarzer, Anke,Weber, Edwin
, p. 307 - 319 (2017)
A series of five different alkoxymethyl substituted derivatives of 8-hydroxyquinoline was synthesised both in protonated (1a-1e) and neutral (2a-2e) form. The alkoxymethyl groups are MeO (1a, 2a), EtO (1b, 2b), n-PrO (1c, 2c), iso-PrO (1d, 2d), n-BuO (1e, 2e). The compounds were characterised by single crystal X-ray diffraction and spectroscopic methods. Hirshfeld surface analysis was performed to analyse the crystal packing quantitatively. Topological analysis of the electron density distribution delivers information about the strength of the hydrogen bonds. The overall results reveal a main difference between the charged (1a-1d) and uncharged (2a-2e) compounds in the orientation of the hydroxyl group resulting in a different cyclic dimer formation. In both cases the structures are dominated by hydrogen bonding (1a-1d: O[sbnd]H?Cl, N[sbnd]H?Cl and 2a-2e: O[sbnd]H?N). Furthermore, all crystal structures show π involved interactions though taking only a minor part in the packing of the molecules.
Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes
Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma
, p. 1121 - 1126 (2018/08/17)
Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.
Design, synthesis and structure-activity relationship studies of novel survivin inhibitors with potent anti-proliferative properties
Xiao, Min,Wang, Jin,Lin, Zongtao,Lu, Yan,Li, Zhenmei,White, Stephen W.,Miller, Duane D.,Li, Wei
, (2015/07/15)
The anti-apoptotic protein survivin is highly expressed in most human cancer cells, but has very low expression in normal differentiated cells. Thus survivin is considered as an attractive cancer drug target. Herein we report the design and synthesis of a series of novel survivin inhibitors based on the oxyquinoline scaffold from our recently identified hit compound UC-112. These new analogs were tested against a panel of cancer cell lines including one with multidrug-resistant phenotype. Eight of these new UC-112 analogs showed IC50 values in the nanomole range in anti-proliferative assays. The best three compounds among them along with UC-112 were submitted for NCI-60 cancer cell line screening. The results indicated that structural modification from UC-112 to our best compound 4g has improved activity by four folds (2.2 μM for UC-112 vs. 0.5 μM for 4g, average GI50 values over all cancer cell lines in the NCI-60 panel).Western blot analyses demonstrated the new compounds maintained high selectivity for survivin inhibition over other members in the inhibition of apoptosis protein family. When tested in an A375 human melanoma xenograft model, the most active compound 4g effectively suppressed tumor growth and strongly induced cancer cell apoptosis in tumor tissues. This novel scaffold is promising for the development of selective survivin inhibitors as potential anticancer agents.
