18892-39-2

Usage

InChI:InChI=1/C9H5ClN2O2/c10-5-6(11)8(13)4-2-1-3-12-7(4)9(5)14/h1-3H,11H2

Upstream product

• 6541-19-1 6,7-dichloroquinoline-5,8-dione 
• 1023880-02-5 6-azido-7-chloro-5,8-quinolinedione 
• 1228299-80-6 6-(benzhydryl-amino)-7-chloro-5,8-quinolinequinone 
• 148-24-3 8-quinolinol 

Downstream Products

• 58372-39-7 N-(7-chloro-5,8-dioxo-5,8-dihydro-6-quinolinyl)acetamide 
• 132624-34-1 2-phenyl-thiazolo[4,5-g]quinoline-4,9-dione 
• 91426-36-7 6-amino-7-methylsulfanyl-5,8-quinolinequinone 
• 132624-33-0 2-(2-hydroxy-phenyl)-thiazolo[4,5-g]quinoline-4,9-dione 
• 98000-21-6 2-methyl-3-phenyl-3H-imidazo[4,5-g]quinoline-4,9-dione 

Relevant academic research and scientific papers

Use of naphthoquinone derivative as inhibitor for IDO1 and/or TDO

The invention discloses a use of a naphthoquinone derivative as an inhibitor for IDO1 and/or TDO. The derivative is shown as a general formula (I), and the definition of each substituent is detailed in the specification. The compound represented by the general formula (I) has an inhibitory effect on indoleamine-2,3-dioxygenase 1 (IDO1) and/or tryptophan-2,3-dioxygenase (TDO), and can be used for treating diseases with IDO1- and/or TDO-mediated tryptophan metabolism as pathological features, including but not limited to tumors, autoimmune diseases, infectious diseases, Alzheimer's disease, depression, and anxiety disorder.

Design, synthesis and biological evaluation of novel naphthoquinone derivatives as IDO1 inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) mediated kynurenine pathway of tryptophan degradation is identified as an appealing and novel target in immunotherapy for the treatment of cancer. In this study, a novel series of naphthoquinone derivatives were synthesized, characterized and evaluated for their inhibitory activities against IDO1, and their structure?activity relationship was investigated. Among them, compounds T16, T44, T47, T49, T53 and T54 displayed potent IDO1 inhibitory activities with IC50 values ranging between 18 and 61 nM, which are more potent than INCB024360 undergoing clinical trial III evaluation. In addition, compounds T28, T44 and T53 decreased the kynurenine levels in rat plasma by 30%–50%. Compounds exhibiting excellent IDO1 inhibitory activities were also evaluated for their inhibitory activities against tryptophan 2,3-dioxygenase (TDO). Of which, compound T28 (IDO1 IC50 = 120 nM) showed promising TDO inhibition (IC50 72 nM) and was identified as an IDO1/TDO dual inhibitor.

The anti-cancer, anti-inflammatory and tuberculostatic activities of a series of 6,7-substituted-5,8-quinolinequinones

A variety of 6,7-substituted-5,8-quinolinequinones were synthesised and assessed for their anti-tumour and anti-inflammatory activities, and their ability to inhibit the growth of Mycobacterium bovis BCG. In particular, the introduction of a sulfur group

The regioselectivity in the reaction of 6,7-dihaloquinoline-5,8-diones with amine nucleophiles in various solvents

The regioselectivity in the reaction of 6,7-dihaloquinoline-5,8-diones with amine nucleophiles was described. In this reaction the solvent played an important role. (C) 2000 Elsevier Science Ltd.

Synthesis and cytotoxicity of 2-methyl-1-substituted-imidazo[4,5-g]quinoline-4,9-dione and 7,8-dihydro-10H-[1,4]oxazino[3',4':2,3]imidazo[4,5-g]quinoline-5,12-dione derivatives

2-Methyl-1-substituted-imidazo[4,5-g]quinoline-4,9-diones and 7,8-dihydro-10H-[1,4]oxazino -[3',4':2,3]imidazo[4,5-g]quinoline-5,12-dione (19) derivatives have been synthesized from 6,7-dichloro-5,8-quinolinedione for developing the new anticancer drugs. Our study on the cytotoxicity of imidazoquinolinedione derivatives has revealed that 7,8-dihydro-10H-[1,4]oxazino-[3',4':2,3]imidazo[4,5-g]quinoline-5,12-dione (19), a tetracyclic heteroquinone analogue, exhibited high cytotoxicity on human colon tumor cell (HCT 15) in vitro SRB assay. The IC50 value of this compound was 0.026μg/mL whereas those of doxorubicin and cisplatin were 0.023μg/mL and 1.482μg/mL, respectively. Meanwhile compounds 5-7 and 12 in the series of 1-substituted-imidazoquinolinediones showed relatively good activity on human brain tumor cell lines (XF 498). Copyright (C) 2000 Elsevier Science Ltd.