100241-89-2

Usage

Uses

1. Used in Organic Synthesis:
5-Isothiazolecarboxylic acid, 2,3-dihydro-3-oxo-, methyl ester (9CI) is used as a synthetic intermediate for the development of various chemical compounds. Its application in this field is due to its unique chemical structure, which allows for further reactions and modifications to create a wide range of products.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Isothiazolecarboxylic acid, 2,3-dihydro-3-oxo-, methyl ester (9CI) is used as a building block for the synthesis of novel drug candidates. Its unique chemical properties make it a valuable component in the development of new medications, particularly those targeting specific biological pathways or receptors.
3. Used in Agrochemical Industry:
5-Isothiazolecarboxylic acid, 2,3-dihydro-3-oxo-, methyl ester (9CI) is also utilized in the agrochemical industry for the synthesis of various pesticides and other agricultural chemicals. Its role in this industry is to provide a starting material for the development of compounds that can help protect crops from pests and diseases.
4. Used in Material Science:
In the field of material science, 5-Isothiazolecarboxylic acid, 2,3-dihydro-3-oxo-, methyl ester (9CI) is employed in the development of new materials with specific properties. Its unique chemical structure allows for the creation of materials with tailored characteristics, such as improved strength, flexibility, or chemical resistance.
5. Used in Dye and Pigment Industry:
5-Isothiazolecarboxylic acid, 2,3-dihydro-3-oxo-, methyl ester (9CI) is used as a key component in the synthesis of dyes and pigments for various applications, including textiles, plastics, and printing inks. Its role in this industry is to provide a versatile building block for the creation of a wide range of colorants with different properties and performance characteristics.

InChI:InChI=1/C5H5NO3S/c1-9-5(8)3-2-4(7)6-10-3/h2H,1H3,(H,6,7)

Upstream product

• 67-56-1 methanol 
• 62020-63-7 3-hydroxyisothiazole-5-carboxamide 

Downstream Products

• 1240402-72-5 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl ester 
• 170953-74-9 methyl 3-ethoxyisothiazole-5-carboxylate 

Relevant academic research and scientific papers

AMPA receptor agonists: Synthesis, protolytic properties, and pharmacology of 3-isothiazolol bioisosteres of glutamic acid

A number of 3-isothiazolol bioisosteres of glutamic acid (1) and analogs of the AMPA receptor agonist, (RS)-2-amino-3-(3-hydroxy-5-methylisoxazol-4- yl)propionic acid (AMPA, 2a), including (RS)-2-amino-3-(3-hydroxy-5- methylisothiazol-4-yl)propionic acid (thio-AMPA, 2b), were synthesized. Comparative in vitro pharmacological studies on this series of 3-isothiazolol and the corresponding 3-isoxazolol amino acids were performed using a series of receptor binding assays (IC50 values) and the electrophysiological rat cortical slice model (EC50 values). Whereas 2a (IC50 = 0.04 ± 0.005 μM, EC50 = 3.5 ± 0.2 μM) is markedly more potent than the tert-butyl analog ATPA (3a) (IC50 = 2.1 ± 0.16 μM, EC50 = 34 ± 2.4 μM) in [3H]AMPA binding and electrophysiological studies, 2b (IC50 = 1.8 ± 0.13 μM, EC50 = 15.0 ± 2.4 μM) was approximately equipotent with thio-ATPA (3b) (IC50 = 0.63 ± 0.07 μM, EC50 = 14 ± 1.3 μM). (RS)-2-Amino-3-(3- hydroxyisoxazol-5-yl)propionic acid (HIBO, 4a) was approximately equipotent with its thio analog 4b, whereas 4-Br-HIBO (5a) (IC50 = 0.65 ± 0.12 μM, EC50 = 22 ± 0.6 μM) turned out to be much more potent than the corresponding 3-isothiazolol 5b (IC50 = 17 ± 2.2 μM, EC50 = 500 ± 23 μM), 2b (ED50 = 130 μmol/kg) was more potent than 2a (220 μmol/kg) as a convulsant after subcutaneous administration in mice. The protolytic properties of 2a,b-4a,b were determined using 13C NMR spectroscopy. For each pair of compounds, the α-amino acid groups showed similar protolytic properties, whereas the 3-isoxazolol moieties typically showed pK(a) values 2 units lower than those of the 3-isothiazolols. Accordingly, calculations of ionic species distributions revealed pronounced differences between 3- isoxazolol and 3-isothiazolol amino acids. No simple correlation between activity as AMPA agonists in vitro and pK(a) values of these compounds was apparent. On the other hand, the relative potencies of AMPA (2a) and thio- AMPA (2b) in vitro and in vivo may reflect that these compounds predominantly penetrate the blood-brain barrier as net uncharged diprotonated ionic species.

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.