1376686-97-3

Basic information

• Product Name: 3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
• Synonyms: 3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
• CAS NO: 1376686-97-3
• Molecular Weight: 389.386
• Mol File: 1376686-97-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione(1376686-97-3)
• EPA Substance Registry System: 3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione(1376686-97-3)

Safety Data

• Hazardous Substances Data: 1376686-97-3(Hazardous Substances Data)

Upstream product

• 766-98-3 1-ethynyl-4-fluorobenzene 
• 1062639-43-3 3-azido-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione, 3-azido-nor-β-lapachone 
• 84-79-7 Lapachol 
• 15297-99-1 nor-lapachol 
• 83280-64-2 3-bromo-2,3-dihydro-2,2-dimethylnaphtho[1,2-b]furan-4,5-dione 

Relevant articles and documents

Benzo[a]phenazine derivatives: Promising scaffolds to combat resistant Mycobacterium tuberculosis

The continuous emergence of resistant Mycobacterium tuberculosis keeps tuberculosis (TB) treatment options still insufficient, and new therapeutic alternatives are urgently needed. Considering the antimycobacterial activity of phenazine derivatives previously reported by our research group, we aimed to explore possible applications to circumvent the resistance in M. tuberculosis. Firstly, we evaluated the antimicrobial activity of seven benzo[a]phenazine derivatives against eleven M. tuberculosis strains: ten resistant and one susceptible (H37Rv). Then, we determined the cytotoxicity of benzo[a]phenazine derivatives and investigated the possible mechanism of action of the most promising compound. Among them, compound 10 was the only one active against all strains evaluated, with a minimum inhibitory concentration between 18.3 and 146.5?μM. For some resistant strains, this compound showed antimicrobial activity higher than rifampicin and it was also active against MDR strains, indicating an absence of cross-resistance with anti-TB drugs. Also, 10 showed a pharmacological safety for further in vivo studies and its mechanism of action seems to be related to oxidative stress. Thus, our findings indicate that benzo[a]phenazine derivatives are promising scaffolds for the development of new anti-TB drugs, mainly focusing on the treatment of resistant TB cases.

Potent antileukemic action of naphthoquinoidal compounds: Evidence for an intrinsic death mechanism based on oxidative stress and inhibition of DNA repair

The current study describes that nor-β-lapachone and its arylamino derivatives, iodinated and methylated naphthoquinones and nor-β-lapachone- based 1,2,3-triazoles exhibited pronounced cytotoxic effects against four human leukemia cell lines (HL-60, K562, Molt-4 and Jurkat). Nor-β-lapachones arylamino substituted with potent activity were identified, revealing themselves as potential prototypes against tumor cell lines. Moreover, cells treated with these compounds showed DNA damage according to the standard comet assay, a finding that was, at least in part, due to increased intracellular levels of ROS. HL-60 cells were chosen to study the underlying molecular mechanisms of cytotoxicity. Drug-induced apoptosis in HL-60 cells was observed by flow cytometry analyses. Strains of Saccharomyces cerevisiae were used for a preliminary investigation into the mechanism of drug action on DNA topoisomerases. These results suggested that the cytotoxicity of these compounds apparently does not involve topoisomerase inhibition, but that treatment impairs DNA repair activity, thus triggering cell death. Considering their pro-oxidant properties, we investigated the ability of these compounds to induce apoptosis and chromosomal aberrations as micronuclei in Chinese hamster lung fibroblasts (V79 cells). Morphological apoptotic nuclei and micronuclei induction following drug treatment were observed, suggesting a correlation between DNA damage and apoptosis.

On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions

Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-β-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream