36209-50-4

Basic information

• Product Name: 4-amino-5-p-nitrophenyl-1,2,4-triazole-3 thione
• Synonyms: 4-amino-5-p-nitrophenyl-1,2,4-triazole-3 thione
• CAS NO: 36209-50-4
• Molecular Weight: 237.242
• Mol File: 36209-50-4.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 4-amino-5-p-nitrophenyl-1,2,4-triazole-3 thione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-5-p-nitrophenyl-1,2,4-triazole-3 thione(36209-50-4)
• EPA Substance Registry System: 4-amino-5-p-nitrophenyl-1,2,4-triazole-3 thione(36209-50-4)

Safety Data

• Hazardous Substances Data: 36209-50-4(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 62-23-7 4-nitro-benzoic acid 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 2231-57-4 Thiocarbohydrazide 
• 84459-83-6 potassium 2-(4-nitrobenzoyl)hydrazinecarbodithioate 
• 99-77-4 ethyl 4-nitrobenzoate 
• 23766-30-5 5-(p-nitrophenyl)-2-mercapto-1,3,4-oxadiazole 

Downstream Products

• 172844-93-8 4-{[1-(2-Chloro-5-nitro-phenyl)-meth-(E)-ylidene]-amino}-5-(4-nitro-phenyl)-4H-[1,2,4]triazole-3-thiol 
• 882687-75-4 7-bromo-naphtho[1,2-b]pyran-4-one 
• 144140-05-6 4-{[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-5-(4-nitro-phenyl)-4H-[1,2,4]triazole-3-thiol 
• 1185732-15-3 2-(4-aminophenyl)-5-(4-nitrophenyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1262223-05-1 6-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-3-(4-nitrophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1325203-58-4 C₁₄H₁₈N₆O₃S 
• 1325203-59-5 C₁₆H₂₂N₆O₃S 
• 1325203-61-9 C₁₆H₂₂N₆O₃S 
• 1325203-62-0 C₁₈H₂₆N₆O₃S 
• 1325203-63-1 C₁₅H₂₀N₆O₃S 
• 1325203-64-2 C₁₅H₁₈N₆O₃S 
• 1325203-66-4 C₁₆H₂₀N₆O₃S 
• 1325203-67-5 C₂₂H₂₄N₆O₃S 
• 1325203-68-6 C₂₁H₂₃N₇O₃S 

Relevant articles and documents

New heparanase-inhibiting triazolo-thiadiazoles attenuate primary tumor growth and metastasis

Compelling evidence ties heparanase, an endoglycosidase that cleaves heparan sulfate side (HS) chains of proteoglycans, with all steps of tumor development, including tumor initiation, angiogenesis, growth, metastasis, and chemoresistance. Moreover, heparanase levels correlate with shorter postoperative survival of cancer patients, encouraging the development of heparanase inhibitors as anti-cancer drugs. Heparanase-inhibiting heparin/heparan sulfate-mimicking compounds and neutralizing antibodies are highly effective in animal models of cancer progression, yet none of the compounds reached the stage of approval for clinical use. The present study focused on newly synthesized triazolo–thiadiazoles, of which compound 4-iodo-2-(3-(p-tolyl)-[1,2,4]triazolo[3,4b][1,3,4]thiadiazol-6-yl)phenol (4-MMI) was identified as a potent inhibitor of heparanase enzymatic activity, cell invasion, experimental metastasis, and tumor growth in mouse models. To the best of our knowledge, this is the first report showing a marked decrease in primary tumor growth in mice treated with small molecules that inhibit heparanase enzymatic activity. This result encourages the optimization of 4-MMI for preclinical and clinical studies primarily in cancer but also other indications (i.e., colitis, pancreatitis, diabetic nephropathy, tissue fibrosis) involving heparanase, including viral infection and COVID-19.

Synthesis and biological activities of cyclanone O-(2-(3-aryl-4- amino-4H-1,2,4-triazol-3-yl)thio)acetyl)oxime derivatives

Twelve cyclanone O-(2-(3-aryl-4-amino-4H-1,2,4-triazol-3-yl)thio)acetyl)oxime derivatives were synthesized and their structures were confirmed by spectroscopy (IR, 1H NMR, 13C NMR, 19F NMR) and elemental analysis. Their antifungal and antibacterial activities were evaluated against six fungi (Gibberella zeae, Fusarium oxysporum, Clematis mandshurica, Phytophthora infestans, Paralepetopsis sasakii, Sclerotinia sclerotiorum) and two bacteria (Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas citri subsp. Citri (Xcc)). The results indicated that most of the title compounds exhibited good antibacterial activities. Among them, compounds 6d, 6g, 6h, and 6j showed better antibacterial activities against Xoo and Xcc than that of the commercial agent thiodiazole-copper.

A process for preparing 3 - substituted - 6 - ferrocenyl methylene - 1, 2, 4 - triazolo [3.4 - b] - 1, 3, 4 - thiadiazole method

The invention relates to a method for preparing 3-substituted-6-ferrocenylmethylene-1,2,4-triazolo[3.4-b]-1,3,4-thiadiazole. The method comprises the following steps: 1) adding A mmol of ferrocenyl acetic acid, B mmol of 3-substituted-4-amino-5-sulfhydryl