170953-74-9

Usage

Uses

Used in Pharmaceutical Industry:
METHYL-3-ETHOXYISOTHIAZOLE-5-CARBOXYLATE is used as a chemical intermediate for the synthesis of GABAA agonist photoaffinity labels, which are important for studying the structure and function of GABAA receptors in the central nervous system. This helps in understanding the role of GABAA receptors in various neurological disorders and the development of potential therapeutic agents targeting these receptors.

Upstream product

• 74-96-4 ethyl bromide 
• 100241-89-2 methyl 3-hydroxyisothiazole-5-carboxylate 

Downstream Products

• 170953-78-3 3-ethoxy-5-chloromethylisothiazole 

Relevant academic research and scientific papers

Synthesis and receptor binding of 5-amino[3H]2methyl-3-isothiazolol ([3H]thiomuscimol), a specific GABA(A) agonist photoaffinity label

The synthesis of tritium labelled thiomuscimol (5-amino[3H]2methyl-3-isothiazolol) (7c), a specific and high-affinity agonist photoaffinity label for GABA(A) receptors, is described. The synthesis of 7c is based on a procedure for the preparation of 5-amino[2H]2methyl-3-isothiazolol (7b). Methyl 3-ethoxyisothiazole-5-carboxylate (3), synthesized from 3-hydroxyisothiazole-5-carboxamide (1) via the corresponding methyl ester (2), was reduced with sodium borotritide to give 3-ethoxy-5-hydroxy[3H]2methyl-3-isothiazole (4c). 3-Ethoxy-5-phthalimido[3H]2-methylisothiazole (6c), synthesized from the 5-chloro[3H]2methyl analogue (5c) of (4c), was deprotected by treatment with concentrated hydrochloric acid to give 7c with a specific radioactivity of 29 Ci/mmol. In pilot binding assays, 7c was shown to bind to membranes from rat forebrain in a saturable manner and with K(D) and B(max) values of 28 ± 6 nM and 50 ± 4 fmol/mg original tissue, respectively.