306935-43-3

Basic information

• Product Name: 4-BENZYL-5-(N-TERT-BUTOXYCARBONYLAMINOMETHYL)-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: 4-BENZYL-5-(N-TERT-BUTOXYCARBONYLAMINOMETHYL)-1,2,4-TRIAZOLE-3-THIOL;TERT-BUTYL N-[(4-BENZYL-5-MERCAPTO-4H-1,2,4-TRIAZOL-3-YL)METHYL]CARBAMATE;5-(Aminomethyl)-4-benzyl-1,2,4-triazole-3-thiol, N-BOC protected
• CAS NO: 306935-43-3
• Molecular Formula: C₁₅H₂₀N₄O₂S
• Molecular Weight: 320.41
• Mol File: 306935-43-3.mol

Chemical Properties

• Melting Point: 199-201
• Appearance: /
• Density: 1.24g/cm³
• Refractive Index: 1.61
• CAS DataBase Reference: 4-BENZYL-5-(N-TERT-BUTOXYCARBONYLAMINOMETHYL)-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYL-5-(N-TERT-BUTOXYCARBONYLAMINOMETHYL)-1,2,4-TRIAZOLE-3-THIOL(306935-43-3)
• EPA Substance Registry System: 4-BENZYL-5-(N-TERT-BUTOXYCARBONYLAMINOMETHYL)-1,2,4-TRIAZOLE-3-THIOL(306935-43-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 306935-43-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H20N4O2S/c1-15(2,3)21-14(20)16-9-12-17-18-13(22)19(12)10-11-7-5-4-6-8-11/h4-8H,9-10H2,1-3H3,(H,16,20)(H,18,22)

Upstream product

• 883004-39-5 C₁₅H₂₂N₄O₃S 

Downstream Products

• 1024058-55-6 5-aminomethyl-4-benzyl-2,4-dihydro-[1,2,4]triazol-3-thione 

Relevant articles and documents

Synthesis of GABAA receptor agonists and evaluation of their α-subunit selectivity and orientation in the GABA binding site

Drugs used to treat various disorders target GABAA receptors. To develop α subunit selective compounds, we synthesized 5-(4-piperidyl)-3-isoxazolol (4-PIOL) derivatives. The 3-isoxazolol moiety was substituted by 1,3,5-oxadiazol-2-one, 1,3,5-oxadiazol-2-thione, and substituted 1,2,4-triazol-3-ol heterocycles with modifications to the basic piperidine substituent as well as substituents without basic nitrogen. Compounds were screened by [3H]muscimol binding and in patch-clamp experiments with heterologously expressed GABAA αiβ 3γ2 receptors (i = 1-6). The effects of 5-aminomethyl-3H-[1,3,4]oxadiazol-2-one 5d were comparable to GABA for all α subunit isoforms. 5-piperidin-4-yl-3H-[1,3,4]oxadiazol-2-one 5a and 5-piperidin-4-yl-3H-[1,3,4]oxadiazol-2-thione 6a were weak agonists at α2-, α3-, and α5-containing receptors. When coapplied with GABA, they were antagonistic in α2-, α4-, and α6-containing receptors and potentiated α3-containing receptors. 6a protected GABA binding site cysteine-substitution mutants α1F64C and α1S68C from reacting with methanethiosulfonate-ethylsulfonate. 6a specifically covalently modified the α1R66C thiol, in the GABA binding site, through its oxadiazolethione sulfur. These results demonstrate the feasibility of synthesizing α subtype selective GABA mimetic drugs.