444112-59-8Relevant academic research and scientific papers
C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane
Lin, Xinxin,Zeng, Cuilian,Liu, Chengkou,Fang, Zheng,Guo, Kai
supporting information, p. 1352 - 1357 (2021/02/26)
An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale
Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile
Wen, Chunxia,Zhong, Ronglin,Qin, Zengxin,Zhao, Mengfei,Li, Jizhen
supporting information, p. 9529 - 9532 (2020/09/03)
The efficient regioselective C-H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O2 and N2 atmospheres, respectively. Using 2,2′-azobisisobutyronitrile (AIBN) as a radical precursor, the pr
Metal-Free Electrochemical Oxidative Dihalogenation of Quinolines on the C5 and C7 Positions Using N-Halosuccinimides
Hou, Jiahao,Wang, Kai,Zhang, Changjun,Wei, Tingting,Bai, Renren,Xie, Yuanyuan
supporting information, p. 6382 - 6386 (2020/10/19)
An efficient and convenient method for electrochemically oxidative dichlorination or dibromination of 8-aminoquinolines on C5 and C7 positions using N-halosuccinimides (NCS and NBS) as the halogen source was described. Substrates with various functional g
Catalyst- And oxidant-free electrochemical: para -selective hydroxylation of N -arylamides in batch and continuous-flow
Chen, Meng-Yi,Fang, Zheng,Guo, Kai,Lin, Xin-Xin,Liu, Cheng-Kou
supporting information, p. 6437 - 6443 (2020/11/09)
Hydroxyl compounds serve as key building blocks in the preparation of biologically active natural products and drugs. Traditionally, hydroxylation of the aromatic ring is achieved using stoichiometric amounts of oxidants, which leads to low atom-economy, undesired by-products, potential explosion risk and environmental pollution. Recently, electrosynthesis has attracted increasing attention as it employs clean electrical energy to promote redox reactions avoiding the use of oxidants. However, due to the poor mass and heat transfers of batch cells, low productivity and selectivity limit its further application. Herein, we develop a catalyst-, oxidant-, acidic solvent- and quaternary ammonium salt-free electrochemical para-selective hydroxylation of N-arylamides at room temperature in batch and continuous-flow. This proposal features excellent position control and water, air and functional group tolerance. Also, it is easy to scale up with higher productivity and selectivity using a flow electrolysis cell.
Visible light induced regioselective C5 halogenation of 8-aminoquinolines with 1,3-dihalo-5,5-dimethylhydantoin in continuous flow
Shu, Quan,Li, Yaming,Liu, Tong,Zhang, Siyu,Jiang, Linlin,Jin, Kun,Zhang, Rong,Duan, Chunying
supporting information, p. 3636 - 3642 (2019/05/29)
An efficient and convenient method for remote C5 halogenation of 8-aminoquinoline derivatives was developed in continuous flow at room temperature. This method employed inexpensive 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichlro-5,5-dimethylhyda
Co(II)/Cu(II)-cocatalyzed oxidative C-H/N-H functionalization of benzamides with ketones: A facile route to isoindolin-1-ones
Zhou, Xi,Xu, Hongyan,Yang, Qiaodan,Chen, Hua,Wang, Shoufeng,Zhao, Huaiqing
supporting information, p. 8603 - 8606 (2019/07/25)
A cobalt and copper catalyzed reaction protocol has been developed to achieve the oxidative C-H/N-H annulation of benzamides containing an 8-aminoquinoline moiety as the directing group with ketones. Structurally diverse isoindolin-1-ones were furnished by the reaction of various substituent benzamides with ketones.
Copper-mediated synthesis of quinazolin-4(3: H)-ones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides
Ban, Zihui,Cui, Xinfeng,Hu, Fangpeng,Lu, Guoqiang,Luo, Nan,Huang, Guosheng
supporting information, p. 12963 - 12966 (2019/08/28)
An efficient copper-mediated tandem C(sp2)-H amination to provide quinazolinones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides has been developed. It can afford rather complex products in a single step synthesis from easily availab
Synthesis and mechanistic studies of quinolin-chlorobenzothioate derivatives with proteasome inhibitory activity in pancreatic cancer cell lines
Hu, Shuai,Jin, Yi,Liu, Yanghan,Ljungman, Mats,Neamati, Nouri
, p. 884 - 895 (2018/09/29)
Inhibition of proteasome activity blocks the degradation of dysfunctional proteins and induces cancer cell death due to cellular stress. Thus, proteasome inhibitors represent an attractive class of anticancer agents, and bortezomib, carfilzomib and ixazomib have been FDA-approved to treat multiple myeloma. However, cancer cells acquire resistance to these inhibitors through point mutations in the proteasome catalytic subunit or induction of alternative compensatory mechanisms. In this study, we identified a quinolin-chlorobenzothioate, QCBT7, as a new proteasome inhibitor showing cytotoxicity in a panel of cancer cell lines. QCBT7 is a more stable derivative of quinoline-8-thiol that targets the regulatory subunit instead of the catalytic subunit of the proteasome. QCBT7 caused the accumulation of ubiquitylated proteins in the cancer cells, indicating its proteasome inhibitory activity. Additionally, QCBT7 increased the expression of a set of genes (PFKFB4, CHOP, HMOX1 and SLC7A11) at both nascent RNA and protein levels, similarly to the known proteasome inhibitors MG132 and ixazomib. Together, QCBT7 induces proteasome inhibition, hypoxic response, endoplasmic reticulum stress and glycolysis, finally leading to cell death. Importantly, we have identified PFKFB4 as a potential biomarker of proteasome inhibitors that can be used to monitor treatment response.
C5-Regioselective C-H fluorination of 8-aminoquinoline amides and sulfonamides with Selectfluor under metal-free conditions
Zhang, Yingchao,Wen, Chunxia,Li, Jizhen
supporting information, p. 1912 - 1920 (2018/03/23)
A novel and efficient regioselective C-H fluorination of 8-aminoquinoline amides and sulfonamides at the C5 position was achieved. Using Selectfluor as a "F" reagent and HOAc as an additive, the reaction proceeds smoothly via a radical pathway. This metho
Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids
Zhao, Donghong,Luo, Haofan,Chen, Binhui,Chen, Wenteng,Zhang, Guolin,Yu, Yongping
, p. 7860 - 7866 (2018/07/21)
We develop a palladium-catalyzed H/D exchange reaction with 8-aminoquinoline as the directing group as well as D2O as the source of deuterium atom and solvent. This reaction achieves selectively H/D exchange at the ortho-C-H of aromatic amides and the β-C-H of aliphatic amide. Ortho-deuterated aromatic acids and β-deuterated aliphatic acids are obtained by removal of the directing group. And a possible mechanism is also proposed.
