66894-07-3

Upstream product

• 106-96-7 propargyl bromide 
• 3414-94-6 5-phenyl-1,2,4-triazole-3-thiol 
• 3414-94-6 3-phenyl-4,5-dihydro-1H-1,2,4-triazole-5-thione 
• 5351-66-6 benzoyl thiosemicarbazide 
• 613-94-5 benzoic acid hydrazide 
• 65-85-0 benzoic acid 
• 93-58-3 benzoic acid methyl ester 
• 3414-94-6 5-phenyl-4H-1,2,4-triazol-3-thiol 

Downstream Products

• 26542-69-8 2-phenyl-5-methylthiazolo-<3,2-b>-s-triazole 
• 64892-22-4 3-allenylthio-5-phenyl-s-triazole 

Relevant academic research and scientific papers

Regioselective synthesis of 6-benzylthiazolo[3,2-b]1,2,4-triazoles during Sonogashira coupling

The reaction of 3-mercaptopropargyl-1,2,4-triazoles with various iodobenzenes catalyzed by Pd-Cu leads to the regioselective formation of 6-benzylthiazolo[3,2-b]1,2,4-triazoles 4. The structure of 4d was confirmed by X-ray analysis.

Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction

Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.

First regioselective iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles

The regioselective iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles is described for the first time. The iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles using molecular iodine afforded diiodo-compound which on CuI-catalyzed intramolecular C-N coupling reaction gave six-membered 2-aryl-5H-[1,2,4]triazolo[5,1-b][1,3]thiazines, whereas, the five membered 3-aryl-5,6-dihydrothiazolo[2,3-c][1,2,4]triazoles were obtained exclusively when the iodocyclization reaction of 3-aryl-5-(prop-2-ynylthio)-1H-1,2,4-triazoles was carried out using NIS.

Acid catalyzed, regioselective synthesis of 2-substituted 5- methylthiazolo[3,2-b]-S-triazoles

The facile and regioselective synthesis of 2-substituted 5- methylthiazolo[3,2-b]triazoles has been performed by the catalytic action of H2SO4 on the corresponding propynylthio derivatives.

Sodium Hydroxide: A Mild and Inexpensive Catalyst for the Regioselective Synthesis of 2-Substituted 5-Methylthiazolo[3,2-A]-s-triazoles

The facile and regioselective synthesis of 2-substituted 5-methylthiazolo[3,2-b]-s-triazoles has been performed by the catalytic action of NaOH on 3-propynylthio-s-triazoles.