51493-17-5

Basic information

• Product Name: 3-(PROPYLTHIO)-1H-1,2,4-TRIAZOL-5-AMINE
• Synonyms: 3-(PROPYLTHIO)-1H-1,2,4-TRIAZOL-5-AMINE;ASISCHEM C66291;AKOS VGYB0000238;3-(propylthio)-1H-1,2,4-triazol-5-amine(SALTDATA: FREE)
• CAS NO: 51493-17-5
• Molecular Formula: C₅H₁₀N₄S
• Molecular Weight: 158.22
• Mol File: 51493-17-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 381.7°C at 760 mmHg
• Flash Point: 184.6°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 4.98E-06mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: 3-(PROPYLTHIO)-1H-1,2,4-TRIAZOL-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(PROPYLTHIO)-1H-1,2,4-TRIAZOL-5-AMINE(51493-17-5)
• EPA Substance Registry System: 3-(PROPYLTHIO)-1H-1,2,4-TRIAZOL-5-AMINE(51493-17-5)

Safety Data

• Hazardous Substances Data: 51493-17-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H10N4S/c1-2-3-10-5-7-4(6)8-9-5/h2-3H2,1H3,(H3,6,7,8,9)

Upstream product

• 540-54-5 1-Chloropropane 
• 118025-46-0 3-amino-1H-1,2,4-triazole-5-thiol 
• 16691-43-3 5-amino-3-mercapto-4H-[1,2,4]triazole 
• 16691-43-3 5-Amino-3-mercapto-1,2,4-triazole 

Downstream Products

• 79742-12-4 3-Amino-5-propylsulfanyl-[1,2,4]triazole-4-carboxylic acid phenylamide 

Relevant articles and documents

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.

Discovery of tofacitinib derivatives as orally active antitumor agents based on the scaffold hybridization strategy

In this work, a novel series of tofacitinib analogs were designed and synthesized based on the scaffold hybridization strategy and then evaluated for their antiproliferative activity toward three gastric cancer cell lines, leading to the identification of compound C18 which exhibited potent inhibitory activity against MGC-803 cell lines with an IC50 value of 2.68 μM. Compound C18 could effectively inhibit the colony formation, suppress the cell migration and induce apoptosis of MGC-803 cells through activating the p38 and JNK signaling pathways, while C18 showed no obvious effect on the cell cycle distribution in MGC-803 cells. In addition, C18 could initiate mitochondrial dysfunction of MGC-803 cells. Besides, in vivo antitumor studies indicated that C18 could inhibit gastric cancer tumor growth in vivo without obvious global toxicity.

Development of Highly Potent, Selective, and Cellular Active Triazolo[1,5- a]pyrimidine-Based Inhibitors Targeting the DCN1-UBC12 Protein-Protein Interaction

The cullin-RING ubiquitin ligases (CRLs) are responsible for about 20% of cellular protein degradation and regulate diverse cellular processes, and the dysfunction of CRLs is implicated in human diseases. Targeting the CRLs has become an emerging strategy for the treatment of human diseases. Herein, we describe the discovery of a hit compound from our in-house library and further structure-based optimizations, which have enabled the identification of new triazolo[1,5-a]pyrimidine-based inhibitors targeting the DCN1-UBC12 interaction. Compound WS-383 blocks the DCN1-UBC12 interaction (IC50 = 11 nM) reversibly and shows selectivity over selected kinases. WS-383 exhibits cellular target engagement to DCN1 in MGC-803 cells. WS-383 inhibits Cul3/1 neddylation selectively over other cullins and also induces accumulation of p21, p27, and NRF2. Collectively, targeting the DCN1-UBC12 interaction would be a viable strategy for selective neddylation inhibition of Cul3/1 and may be of therapeutic potential for disease treatment in which Cul3/1 is dysregulated.