13229-01-1

Basic information

• Product Name: 4-Amino-5-p-tolyl-4H-[1,2,4]triazole-3-thiol
• Synonyms: 4-Amino-5-p-tolyl-4H-[1,2,4]triazole-3-thiol;4-amino-5-(4-methylphenyl)-4H-1,2,4-triazole-3-thiol(SALTDATA: FREE);4-amino-5-(4-methylphenyl)-2H-1,2,4-triazole-3-thione;4H-1,2,4-Triazole-3-thiol, 4-amino-5-(4-methylphenyl)-
• CAS NO: 13229-01-1
• Molecular Formula: C₉H₁₀N₄S
• Molecular Weight: 206.27
• Mol File: 13229-01-1.mol
• Article Data: 38

Chemical Properties

• Boiling Point: 321.3°Cat760mmHg
• Flash Point: 148.1°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.0003mmHg at 25°C
• Refractive Index: 1.731
• CAS DataBase Reference: 4-Amino-5-p-tolyl-4H-[1,2,4]triazole-3-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-5-p-tolyl-4H-[1,2,4]triazole-3-thiol(13229-01-1)
• EPA Substance Registry System: 4-Amino-5-p-tolyl-4H-[1,2,4]triazole-3-thiol(13229-01-1)

Safety Data

• Hazardous Substances Data: 13229-01-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H10N4S/c1-6-2-4-7(5-3-6)8-11-12-9(14)13(8)10/h2-5H,10H2,1H3,(H,12,14)

Upstream product

• 31130-15-1 5-(4-methylphenyl)-1,3,4-oxadiazoline-2(3H)-thione 
• 3619-22-5 p-toluic hydrazide 
• 38499-94-4 potassium 3-p-toluoyldithiocarbazate 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 99-94-5 p-Toluic acid 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 75-15-0 carbon disulfide 
• 1026393-29-2 C₈H₁₀N₂O₂ 
• 2231-57-4 Thiocarbohydrazide 
• 31130-15-1 2-mercapto-5-(4-methylphenyl)-1,3,4-oxadiazole 

Downstream Products

• 13228-88-1 3-p-tolyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6-thione 
• 3176-55-4 6-Amino-3-(4-tolyl)-s-triazolo<3,4-b><1,3,4>thiadiazole 
• 108222-53-3 3-(3-p-tolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl)-2H-chromen-2-one 
• 111828-02-5 (4-amino-5-p-methylphenyl-4H-1,2,4-triazol-3-ylsulphanyl)-methylenenitrile 
• 111828-08-1 (4-Amino-5-p-tolyl-4H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid methyl ester 
• 39876-09-0 3-p-tolyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-one 
• 85106-36-1 7H-6-Phenyl-3-(4-tolyl)-s-triazolo<3,4-b><1,3,4>thiadiazine 
• 13228-88-1 3-(4-Tolyl)-s-triazolo<3,4-b><1,3,4>thiadiazol-6(5H)-thione 
• 132818-38-3 7-Phenyl-3,6-di-p-tolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 132818-39-4 6-(4-Chloro-phenyl)-7-phenyl-3-p-tolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 111827-95-3 C₁₉H₂₀N₈S₂ 
• 153235-49-5 7-(4-Chloro-phenylsulfanyl)-6-phenyl-3-p-tolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 129330-26-3 7-(4-Chloro-phenoxy)-6-(4-chloro-phenyl)-3-p-tolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 129330-27-4 7-(4-Chloro-phenoxy)-3,6-di-p-tolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 

Relevant articles and documents

Synthesis, Antimicrobial, and Antioxidant Activities of Some Fused Heterocyclic [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole Derivatives

In the present work, we synthesized a series of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives (6a, 6b, 6c, 6d, 6e, 6f and 7a, 7b, 7c, 7d, 7e, 7f) by using simple starting materials, namely, β-amino acids and different aromatic acid hydrazides. The

Design, synthesis, biological activity, crystal structure and theoretical calculations of novel 1,2,4-triazole derivatives

Series of 1,2,4-triazole Schiff base (Ia-f) were designed and synthesized. Their in-vitro antifungal activity to pythium solani, gibberlla nicotiancola, fusarium oxysporium fs.p. niveum and gibberlla saubinetii were evaluated. The results showed compound If exhibited good activity with tested fungi, which indicated that 1,2,4-triazole scaffold with introduction of imidazole phenyl could keep the antifungal activity. In order to further research the compound If, the crystal structure was detected by X-ray diffraction. Meanwhile, the FT-IR, FT-Raman, natural bond orbital (NBO), HOMO-LUMO and MEP were calculated at B3LYP/6-311G+(d,p) level. All the results will be helpful for further drug design in 1,2,4-triazole analogues.

Design, synthesis, biological activities and DFT calculation of novel 1,2,4-triazole Schiff base derivatives

Series of 1,2,4-triazole Schiff bases (2a-2d, 2f-2h and 3a-3h) have been designed and synthesized. The structure of title compounds was confirmed on the basis of their spectral data and elemental analysis. All the target compounds were screened for their in vitro antifungal activity and antibacterial activity. Two of the tested compounds (2a and 2b) exhibited significant antifungal activity against most fungi, especially compound 2a showed better antifungal activity than triadimefon. Meanwhile, the antibacterial activity assay also indicated compound 2a exhibited excellent antibacterial activities comparable to chloramphenicol. The SAR manifested no substitution at position 5 of the triazole ring caused an increase in activity, and 3-phenoxy phenyl group introduced in 1,2,4-triazole scaffold can enhance the antibacterial activity. The DFT calculation indicated triazole ring, S atom and benzene ring in both of the 2a and 3a make a major contribution to the activity.

Synthesis of Triazole Based Novel Ionic Liquids and Salts

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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.

Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study

Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.