139601-75-5

Usage

Structure

Contains an oxadiazole ring, a thione functional group, and a hydrochloride salt attached to the aminoethyl side chain

Pharmaceuticals

Due to its unique structure and properties

Organic Synthesis

As a building block or intermediate in chemical reactions

Oxadiazole Ring

A five-membered heterocyclic ring with two nitrogen atoms and one oxygen atom

Thione Functional Group

A sulfur-containing group with a C=S bond

Aminoethyl Side Chain

A two-carbon chain with an amine (NH2) group attached

Monohydrochloride Salt

A single hydrogen chloride (HCl) molecule attached to the compound, increasing its solubility and stability

Drug Discovery and Development

The presence of the oxadiazole and thione groups could make 1,3,4-Oxadiazole-2(3H)-thione, 5-(2-aminoethyl)-, monohydrochloride useful in the development of new drugs

Research and Industry

The compound has potential for various applications in both research and industrial settings due to its unique properties and structure

Upstream product

• 843619-52-3 [2-(5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

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.