132903-89-0

Upstream product

• 1516-60-5 4-nitrophenyl azide 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 100-01-6 4-nitro-aniline 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 130-15-4 [1,4]naphthoquinone 

Relevant academic research and scientific papers

Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC50 (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.

Small molecule compound having an IDO1/TDO double target, preparation method and applications thereof

The invention belongs to the field of chemical medicine, and particularly relates to a small molecule compound having an IDO1/TDO double target, wherein the general formula is defined in the specification. According to the present invention, the embodiment schemes prove that the small molecule compound can simultaneously inhibit two enzymes IDO1 and TDO so as to reduce the immune evasion of tumorcells, achieve self-cure of tumor diseases, achieve good medicinal potential and provides new potential choice for clinical medication; the preparation method has characteristics of simpleness, mild reaction condition, convenient operation, convenient control, low energy consumption, high yield and low cost, and is suitable for industrial production; and the prepared compound has advantages of high biological activity, strong selectivity to tumor cells, remarkable drug-like properties, and good application prospects in the pharmaceutical industry.

Tuning the biological activity of cationic anthraquinone analogues specifically toward Staphylococcus aureus

Development of new antibacterial agents against drug resistant bacteria is an imminent task, especially against methicillin-resistant Staphylococcus aureus (MRSA). While MRSA can still be treated with broad spectrum antibiotics, the use of which often leads to the disruption of normal microbial flora leading to Clostridium difficile infection (CDI). Herein, a new class of antibacterial agent, cationic anthraquinone analogues specifically against MRSA, has been developed. Through the variation and optimization of substituents, these agents are selective toward MRSA, and not Gram negative bacteria which may avoid the problem of CDI. In addition, newly discovered lead compounds also show significantly reduced cytotoxicity against normal mammalian cells than cancerous cells. This interesting finding can alleviate the toxicity and side effect problems often associate with the use of antibiotics.

DBU catalyzed metal free synthesis of fused 1,2,3-triazoles through [3+2] cycloaddition of aryl azides with activated cyclic C–H acids

DBU catalyzed synthesis of fused 1,2,3-triazoles by [3+2] cycloaddition of aryl azides with activated cyclic C–H acids such as dimedone, cyclohexane-1,3-dione, 5-methylcyclohexane-1,3-dione, and 2-hydroxynaphthalene-1,4-dione in PEG-400 has been reported

Efficient TMG catalyzed synthesis of 1,2,3-triazoles

A practical and efficient method for the synthesis of 1,2,3-triazoles via the cycloaddition reaction of azides and CH-acids in the presence of 1,1,3,3-tetramethylguanidine (TMG) in ethanol at 30 C has been reported. The simple experimental procedure, shor

Thermal Reactivity of Tricyclic 4,5-Diacyltriazolines Resulting from Addition of Aryl Azides to 1,4-Naphthoquinone and 2-Methyl-1,4-naphthoquinone

Reaction of 4-methoxyphenyl azide 1a with 1,4-naphthoquinone 10 at 15-100 deg C in benzene, dimethyl sulphoxide, or nitromethane leads mainly to the ring-contracted enamine 18a, the ring-expanded 2-benzazepine-1,5-dione 20a, and the aziridine 16a, the decomposition products of an intermediate triazoline 12a, to an extent largely independent of the solvent polarity and the temperature employed.However, the triazole 15a appears to be the main decomposition product of the triazoline 12a produced in hexamethylphosphoric triamide.A comparable chemical trend is observed with thermal additions of 4-nitrophenyl azide 1b to the quinone 10.Cycloaddition of the azide 1a to 2-methyl-1,4-naphthoquinone 11 leads regioselectively to the formation of the triazoline adduct 13a, which undergoes preferential isomerization to an isolable diazo dione 23a.On the other hand the azide 1b leads to a mixture of the regioisomeric triazolines 13b and 14b.The triazoline 13b, analogously to 13a, rearranges to the ring-opened diazo dione 23b, whereas the triazoline 14b is converted into a mixture of the ring-contracted and ring-expanded products 24b and 21b.The possible reaction mechanisms involved in the decomposition of the triazolines 12a and 12b, 13a and 13b and 14b are discussed.