79707-04-3

Upstream product

• 100-39-0 benzyl bromide 
• 130-15-4 [1,4]naphthoquinone 
• 90-15-3 α-naphthol 
• 100-44-7 benzyl chloride 
• 622-79-7 benzyl azide 

Relevant academic research and scientific papers

Metal-free cycloaddition to synthesize naphtho[2,3-d][1,2,3]triazole-4,9-diones

A metal-free domino [3 + 2] cycloaddition is reported to construct naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives and provide an alternative approach to the azide-alkyne cycloadditions. The key features are easily available starting materials, mild reaction conditions, a good atom economy, eco-friendly characteristics and a broad substrate scope with high yields.

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.

Another Example of Organo-Click Reactions: TEMPO-Promoted Oxidative Azide–Olefin Cycloaddition for the Synthesis of 1,2,3-Triazoles in Water

The water-mediated, metal-free, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) promoted oxidative [3+2] cycloaddition of organic azides with electron-deficient terminal and internal olefins was explored. A library of 1,4-disubstituted and 1,4,5-trisubstitut

Synthesis of bioactive 1-alkyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-diones and N-aryl-2-aminomethylene-1,3-indanediones using water as the solvent

Through a [2+3] cycloaddition reaction, a new environmentally friendly method was developed to enable the synthesis of bioactive 1-alkyl-1H-naphtho[2, 3-d][1,2,3]triazole-4,9-diones and N-aryl-2-aminomethylene-1,3-indanediones using water as the solvent w

Safe and easy route for the synthesis of 1,3-dimethyl-1,2,3-triazolium salt and investigation of its anticancer activities

We have developed a new safe and easy route for the synthesis of 1,3-dimethyl-1,2,3-triazolium derivatives. We have reported the synthesis of 4,9-dioxo-1,3-dimethylnaphtho[2,3-d][1,2,3]triazol-3-ium chloride from methylation of 1-methyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione. The synthesis of 1-methyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione is inefficient as a significant amount of by-product is formed that is difficult to separate and also unsafe as it requires the use of hazardous methylazide as a starting material. It is, however, important to develop an improved method for the synthesis of 4,9-dioxo-1,3-dimethylnaphtho[2,3-d][1,2,3]triazol-3-ium salt due to its significant anticancer activities. Herein, we report a safe and convenient route for the synthesis of this compound, which lead to more detailed exploration of its profound anticancer activities. The improved method can be applicable for the synthesis of other 1,3-dimethyl-1,2,3-triazolium salts of interest without the use of potentially explosive methylazide. The compound synthesized in this new method shows significant anticancer activities against melanoma, colon cancer, non-small cell lung cancer and central nervous system (CNS) cancer with GI50 values ranging from low μM to nM.

One-pot synthesis of 1- and 2-substituted naphtho[2,3-d][1,2,3]triazole-4, 9-diones

(Chemical Equation Presented) A one-pot three-component [2+3] cycloaddition for the synthesis of 1-alkyl 1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione and 2-alkyl 2H-naphtho[2,3-d][1,2,3]triazole-4,9-dione has been developed. By taking the advantage of diffe

Divergent synthesis of three classes of aryl N-glycosides by solvent control

Aryl glycosides represent a group of molecules with immense biological applications and implications. While the syntheses of aryl C-glycosides and O-glycosides have been studied extensively, the preparation for aryl N-glycosides is relatively unexplored. By employing 1,4-naphthoquinone and glycosyl azides undergoing a [3 + 2] cycloaddition, we have developed a convenient method for constructing three different classes of aryl N-glycosides that include N-glycosylated 2-aminomethylene-1,3-indanedione, benzazepine-1,5-dione, and 9,10-anthraquinone derivatives via solvent control. It was found that conducting cycloaddition in DMF formed exclusively 9,10-anthraquinone derivatives, while less polar solvent such as toluene offered all three aryl N-glycosides. The synthesis of N-glycosylated 9,10-anthraquinone derivatives is of particular interest since no known example has been documented. The synthesis of these N-glycosylated heterocyclic compounds using traditional glycosylation methods could be challenging. Therefore, our diversity-oriented protocols can be viewed as an alternative and practical glycosylation approach. In addition, we have also demonstrated that alkyl azides can also undergo the same cycloaddition, further expanding the structural repertoire available for a broader interest. Initial anticancer assays have revealed that 19f and 19k exert mean growth percent of 17.58 and-5.95, respectively.