25219-78-7Relevant academic research and scientific papers
Use of naphthoquinone derivative as inhibitor for IDO1 and/or TDO
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Paragraph 0103-0106; 0111-0114, (2020/01/31)
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
Pan, Liangkun,Zheng, Qiang,Chen, Yu,Yang, Rui,Yang, Yanyan,Li, Zhongjun,Meng, Xiangbao
, p. 423 - 436 (2018/08/17)
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.
Micelles catalyzed one pot regio- and chemoselective synthesis of benzo[a]phenazines and naphtho[2,3-d]imidazoles 'in H2O'
Tandon, Vishnu K.,Verma, Manoj K.,Maurya, Hardesh K.,Kumar, Sandeep
, p. 6331 - 6334 (2014/12/10)
An efficient, novel, and concise one pot regio- and chemoselective synthesis of benzo[a]phenazines (4) and naphtho[2,3-d]imidazoles (8) has been accomplished in excellent yields by nucleophilic substitution reaction of 2,3-dichloro-1,4-naphthoquinone (1) with o-phenylenediamine (2) and benzamidines (7) respectively 'in H2O' using base and micelles (SDS) as catalyst. Analog reaction of 2,3-dichloro-1,4-naphthoquinone (1) with 2-aminobenzenethiol (9) under identical conditions led to formation of a mixture of benzo[b]phenothiazine (10), benzo[a]phenothiazine (11), and benzo[a]-1,4-benzothiazino-3,2-phenothiazine (12) in 17%, 23%, and 57% yields, respectively.
Facile synthesis of new imidazoles from direct reaction of 2,3-diamino-1,4-naphthoquinone with aldehydes
Aly, Ashraf A.,Hassan, Alaa A.,Brown, Alan B.,El-Shaieb, Kamal M.,Bedair, Tarek M. I.
experimental part, p. 787 - 791 (2011/09/16)
Figure represented. New imidazoles were easily prepared from 2,3-diamino-1,4-naphthoquinone and stoichiometric quantities of the appropriate aldehydes in dimethyl sulfoxide as a solvent. The reaction proceeded for few hours. The procedure can be generaliz
