31568-91-9Relevant articles and documents
Synthesis and antiviral activity of a series of novel quinoline derivatives as anti-RSV or anti-IAV agents
Wang, Minghua,Zhang, Guoning,Zhao, Jianyuan,Cheng, Ningning,Wang, Yujia,Fu, Yuanhui,Zheng, Yanpeng,Wang, Juxian,Zhu, Mei,Cen, Shan,He, Jinsheng,Wang, Yucheng
, (2021/02/16)
We report herein the synthesis of a series of novel quinoline derivatives, based on the lead compound 1a, identified from a rRSV-mGFP high-throughput screening assay. Our results revealed that target compounds 1b, 1g-h, 1af and 1ah (IC50 = 3.10–6.93 μM) had good in vitro activity against RSV, which were better than 1a and ribavirin. In addition, we found that compound 1g displayed the lower cytotoxicity (CC50: 2490.33 μM) and the highest selective index (SI = 673.06), suggesting its promising potential as a candidate for further development. On the other hand, compounds 1a, 1m, 1v, 1ad-1af and 1ah-1ai (IC50s: 1.87–14.28 μM) were more active against IAV than or comparable to ribavirin (IC50: 15.36 ± 0.93 μM). Particularly, the most active compound 1ae (IC50: 1.87 ± 0.58 μM) was found to be 8.2-fold more potent than the reference drug, which could inhibit the virus transcription and replication cycle at an early stage.
Selenophenol quinoline derivative as well as preparation method and application thereof
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Paragraph 0095; 0102-0105, (2020/12/30)
The invention discloses a selenophenol quinoline derivative as well as a preparation method and application thereof. The structure of the selenophenol quinoline derivative is shown as a formula I, a formula II or a formula III, wherein R1 is hydrogen, a C1-6 alkyl group, a C1-6 alkoxy group, a substituted ketone group, a phenyl group, a benzyl group, a substituted phenyl group or a substituted benzyl group; R1 is a monovalent metal cation; R2 is one or more of hydrogen, halogen, a C1-4 alkyl group, a C1-4 alkoxy group or a C1-4 haloalkyl group; R3 is a substituted five-membered heterocyclicring or a substituted six-membered heterocyclic ring; and a heteroatom is one or more of N, O, S or Se. The compound disclosed by the invention is novel in structure, simple in preparation process and relatively good in inhibition effect on various cancer cells, particularly the compounds 34, 44, 45, 98, 104, 115 and 116 have excellent inhibition effects on various cancer cells, the effects of the compounds are equivalent to those of a positive control DDP, and the compounds can be used to prepare anti-cancer drugs to be applied under 5 [mu]M or below, so that the prospect is wide.
PRMT5 INHIBITORS AND USES THEREOF
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Paragraph 0359-0360, (2019/04/05)
Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.
Structure-activity relationships of anticancer ruthenium(II) complexes with substituted hydroxyquinolines
Havrylyuk, Dmytro,Howerton, Brock S.,Nease, Leona,Parkin, Sean,Heidary, David K.,Glazer, Edith C.
, p. 790 - 799 (2018/07/29)
8-Hydroxyquinolines (HQ), including clioquinol, possess cytotoxic properties and are widely used as ligands for metal-based anticancer drug research. The number and identity of substituents on the HQ can have a profound effect on activity for a variety of inorganic compounds. Ruthenium complexes of HQ exhibit radically improved potencies, and operate by a new, currently unknown, mechanism of action. To define structure-activity relationships (SAR), a family of 22 Ru(II) coordination complexes containing mono-, di- and tri-substituted hydroxyquinoline ligands were synthesized and their biological activity evaluated. The complexes exhibited promising cytotoxic activity against a cancer cell line, and the SAR data revealed the 2- and 7-positions as key sites for the incorporation of halogens to improve potency. The Ru(II) complexes potently inhibited translation, as demonstrated by an in-cell translation assay. The effects were seen at 2–15-fold higher concentrations than those required to observe cytotoxicity, suggesting that prevention of protein synthesis may be a primary, but not the exclusive mechanism for the observed cytotoxic activity.
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.
Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN
Qiao, Kai,Wan, Li,Sun, Xiaoning,Zhang, Kai,Zhu, Ning,Li, Xin,Guo, Kai
, p. 1606 - 1611 (2016/04/05)
A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.
PRMT5 INHIBITORS CONTAINING A DIHYDRO- OR TETRAHYDROISOQUINOLINE AND USES THEREOF
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Paragraph 00314, (2014/07/08)
Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5- mediated disorders are also described.
TAU IMAGING PROBE
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Paragraph 0217; 0218, (2013/09/12)
An object of the present invention is to provide a probe for imaging a β-sheet structure protein which can be used for the diagnosis of conformational diseases, particularly disease (tauopathy) having a cardinal symptom such as intracerebral accumulation of tau protein, for example, Alzheimer's disease. Another object of the present invention is to provide a compound which is highly specific to tau and can image tau with satisfactory sensitivity, and also has high brain transition, low or non-recognized bone-seeking properties and low or non-recognized toxicity. According to the present invention, the above problems are solved by providing a compound of a formula I (wherein A, R1, R2, R3, R4, R5, R6, Ra and Rb are as defined in the present description) or a pharmaceutically acceptable salt or solvate thereof.
Oxo-rhenium(V) complexes with 8-hydroxyquinoline derivatives
Sigouin, Olivier,Beauchamp, Andre L.
, p. 460 - 470 (2007/10/03)
Compounds of the types ReOCl2(L)(PPh3) and ReOCl(L)2 were prepared by reacting ReOCl3(PPh 3)2 with 8-hydroxyquinoline (HL) and its 2-methyl, 2-chloro, 5-chloro, 5-nitro, 5,7-dichloro, 5,7-dibromo, and 5,7-diiodo derivatives. With the bulky 2-phenyl-8-hydroxyquinoline, only ReOCl 2(L)(PPh3) could be isolated, whereas the still bulkier 2-tert-butyl derivative did not react. For ReOCl2(L)(PPh 3), the coordination of the quinoline oxygen trans to the Re=O bond and the cis-dichloro arrangement in the equatorial plane were established from crystallographic studies on the 2-chloro and the 5,7-dibromo complexes. From the combined data for these various derivatives, the 1H NMR signals could be fully assigned. With both series of compounds, a complex d-d absorption pattern is observed in the visible spectra, corresponding to the excitation of a d electron from the interaxial d orbital in the equatorial plane to the empty dxz and dyz orbitals, which are inequivalent in these low-symmetry systems. Deconvolution revealed the presence of two very weak low-energy components (～10 000 and ～12 000 cm-1), which are assigned to the two expected singlet-triplet transitions, whereas two stronger bands at higher energy (～14 000 and ～17 000 cm-1) originate from the two singlet-singlet transitions. These bands are not substantially displaced by substitution on the 8-hydroxyquinoline rings.
BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS
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Page 71, (2008/06/13)
Compounds of formula (I) are useful in the treatment of vanilloid-receptor-meditated diseases, such as inflammatory or neuropathic pain and diseases involving sensory nerve function such as asthma, rheumatoid arthritis, osteoarthritis, inflammatory bowel disorders, urinary incontinence, migraine and psoriasis.
