41266-78-8

Basic information

• Product Name: 3-[(4-CHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-YLAMINE
• Synonyms: 5-[(4-chlorophenyl)methylthio]-2H-1,2,4-triazol-3-amine;ASISCHEM T79581;3-[(4-CHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-YLAMINE;3-[(4-CHLOROBENZYL)THIO]-1H-1,2,4-TRIAZOL-5-AMINE;AKOS BBS-00006599;5-(4-Chloro-benzylsulfanyl)-2H-[1,2,4]triazol-3-ylamine;3-[(4-chlorobenzyl)sulfanyl]-1H-1,2,4-triazol-5-amine;[5-[(4-chlorobenzyl)thio]-2H-1,2,4-triazol-3-yl]amine
• CAS NO: 41266-78-8
• Molecular Formula: C₉H₉ClN₄S
• Molecular Weight: 240.71
• Mol File: 41266-78-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 149-151°C
• Boiling Point: 488.6 °C at 760 mmHg
• Flash Point: 249.3 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 1.07E-09mmHg at 25°C
• Refractive Index: 1.699
• CAS DataBase Reference: 3-[(4-CHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(4-CHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-YLAMINE(41266-78-8)
• EPA Substance Registry System: 3-[(4-CHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-YLAMINE(41266-78-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 41266-78-8(Hazardous Substances Data)

Usage

General Description

3-[(4-CHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-YLAMINE is a chemical compound that falls under the category of triazole derivatives. It has a molecular formula C10H10ClN5S and a molecular weight of 261.74 g/mol. 3-[(4-CHLOROBENZYL)SULFANYL]-1H-1,2,4-TRIAZOL-5-YLAMINE is commonly used in medicinal chemistry and pharmaceutical research as a building block or intermediate in the synthesis of various bioactive molecules. Its structure consists of a triazole ring with an attached thiol group and a 4-chlorobenzyl moiety, and it is known for its potential biological activities, such as antimicrobial, antifungal, and anticancer properties. The compound's versatility and reactivity make it an important tool in the development of new drugs and chemical compounds.

InChI:InChI=1/C9H9ClN4S/c10-7-3-1-6(2-4-7)5-15-9-12-8(11)13-14-9/h1-4H,5H2,(H3,11,12,13,14)

Upstream product

• 84828-08-0 C₁₆H₁₂Cl₂N₂S₂ 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 16691-43-3 5-Amino-3-mercapto-1,2,4-triazole 
• 622-95-7 4-chlorobenzyl bromide 
• 16691-43-3 5-amino-3-mercapto-4H-[1,2,4]triazole 
• 118025-46-0 3-amino-1H-1,2,4-triazole-5-thiol 
• 16691-43-3 3-amino-5-thioxo-1,2,4-triazole 

Downstream Products

• 110984-69-5 N-[5-(4-Chloro-benzylsulfanyl)-2H-[1,2,4]triazol-3-yl]-acetamide 
• 110984-37-7 1-[5-Amino-3-(4-chloro-benzylsulfanyl)-[1,2,4]triazol-1-yl]-ethanone 
• 51646-16-3 2-(4-chlorobenzylthio)-5,7-dimethyl-1,2,4-triazolo<1,5-a>pyrimidine 
• 113967-65-0 5-Amino-2-(4-chlorobenzylthio)-6-ethoxycarbonyl-1,2,4-triazolo<1,5-a>pyrimidine 
• 111020-83-8 4-[5-Amino-3-(4-chloro-benzylsulfanyl)-[1,2,4]triazol-1-yl]-4-oxo-butyric acid methyl ester 
• 2247544-02-9 2-(5-((2-((4-chlorobenzyl)thio)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)thio)-1H-tetrazol-1-yl)-N,N-dimethylethan-1-amine hydrochloride 

Relevant articles and documents

Discovery of small-molecule enzyme activators by activity-based protein profiling

Activity-based protein profiling (ABPP) has been used extensively to discover and optimize selective inhibitors of enzymes. Here, we show that ABPP can also be implemented to identify the converse—small-molecule enzyme activators. Using a kinetically controlled, fluorescence polarization-ABPP assay, we identify compounds that stimulate the activity of LYPLAL1—a poorly characterized serine hydrolase with complex genetic links to human metabolic traits. We apply ABPP-guided medicinal chemistry to advance a lead into a selective LYPLAL1 activator suitable for use in vivo. Structural simulations coupled to mutational, biochemical and biophysical analyses indicate that this compound increases LYPLAL1’s catalytic activity likely by enhancing the efficiency of the catalytic triad charge-relay system. Treatment with this LYPLAL1 activator confers beneficial effects in a mouse model of diet-induced obesity. These findings reveal a new mode of pharmacological regulation for this large enzyme family and suggest that ABPP may aid discovery of activators for additional enzyme classes. [Figure not available: see fulltext.].

Discovery of the Triazolo[1,5- a]Pyrimidine-Based Derivative WS-898 as a Highly Efficacious and Orally Bioavailable ABCB1 Inhibitor Capable of Overcoming Multidrug Resistance

Targeting P-glycoprotein (ABCB1 or P-gp) has been recognized as a promising strategy to overcome multidrug resistance. Here, we reported our medicinal chemistry efforts that led to the discovery of the triazolo[1,5-a]pyrimidine derivative WS-898 as a highly effective ABCB1 inhibitor capable of reversing paclitaxel (PTX) resistance in drug-resistant SW620/Ad300, KB-C2, and HEK293/ABCB1 cells (IC50 = 5.0, 3.67, and 3.68 nM, respectively), more potent than verapamil and zosuquidar. WS-898 inhibited the efflux function of ABCB1, thus leading to decreased efflux and increased intracellular PTX concentration in SW620/Ad300 cells. The cellular thermal shift assay indicated direct engagement of WS-898 to ABCB1. Furthermore, WS-898 stimulated the ATPase activity of ABCB1 but had minimal effects on cytochrome P450 3A4 (CYP3A4). Importantly, WS-898 increased PTX sensitization in vivo without obvious toxicity. The results suggest that WS-898 is a highly effective triazolo[1,5-a]pyrimidine-based ABCB1 inhibitor and shows promise in reversing ABCB1-mediated PTX resistance.

Drug repurposing: Discovery of troxipide analogs as potent antitumor agents

Drug repurposing plays a vital role in the discovery of undescribed bioactivities in clinical drugs. Based on drug repurposing strategy, we for the first time reported a novel series of troxipide analogs and then evaluated their antiproliferative activity against MCF-7, PC3, MGC-803, and PC9 cancer cell lines and WPMY-1, most of which showed obvious selectivity toward PC-3 over the other three cancer cell lines and WPMY-1. Compound 5q, especially, could effectively inhibit PC3 with an IC50 value of 0.91 μM, which exhibited around 53-fold selectivity toward WPMY-1. Data indicated that 5q effectively inhibited the colony formation, suppressed the cell migration, and induced G1/S phase arrest in PC3 cells. Also, compound 5q induced cell apoptosis by activating the two apoptotic signaling pathways in PC3 cells: death receptor-mediated extrinsic pathway and mitochondria-mediated intrinsic pathway. Compound 5q up-regulated the expression of both pro-apoptotic Bax and P53, while down-regulated anti-apoptotic Bcl-2 expression. Besides, compound 5q significantly increased the expression of cleaved caspase 3/9 and cleaved PARP. Therefore, the successful discovery of compound 5q may further validate the feasibility of this theory, which will encourage researchers to reveal undescribed bioactivities in traditional drugs.