50739-39-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(Bromomethyl)-6-chlorobenzothiazole is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with antimicrobial properties. Its unique structure allows for the creation of compounds that can target specific pathogens or diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 2-(Bromomethyl)-6-chlorobenzothiazole is employed as an intermediate in the production of agricultural chemicals, such as pesticides and herbicides. Its antimicrobial properties make it a valuable component in creating effective solutions for crop protection and disease management.
Used in Organic Chemistry as a Reagent:
2-(Bromomethyl)-6-chlorobenzothiazole is utilized as a reagent in organic chemistry reactions due to its reactive bromomethyl group. This allows for the formation of new compounds and the modification of existing ones, expanding the scope of chemical research and development.

Upstream product

• 4146-24-1 6-chloro-2-methylbenzo[d]thiazole 
• 59280-70-5 4'-chloro-2'-fluoroacetanilide 
• 57946-56-2 2-fluoro-4-chloroaniline 
• 23474-98-8 2-amino-5-chlorobenzenethiol 
• 113071-97-9 6-chloro-2-chloromethyl-benzothiazole 

Relevant academic research and scientific papers

CYCLOPENTYLBENZAMIDE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF PSYCHOTIC AND COGNITIVE DISORDERS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein n, L, X, Ra, Rb, R1, R2 and R3 their preparation, pharmaceutical compositions containing them and their use in therapy.

Highly selective aldose reductase inhibitors. II. Optimization of the aryl part of 3-(arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic acids

Accumulation of intracellular sorbitol, the product of glucose reduction catalyzed by aldose reductase (AR) [EC 1.1.1.21], is thought to be the main culprit in the development of diabetic complications. A series of 3- arylalkyl-2,4,5-trioxoimidazolidine-1-acetic acids was prepared and tested for inhibitory activities towards AR and aldehyde reductase (ALR) [EC 1.1.1.2]. These derivatives showed strong inhibitory activity against AR without markedly inhibiting ALR. In particular, the compounds with 3- nitrophenyl, 4-chloro-3-nitrophenyl, and chloro-substituted benzothiazolyl groups as the aryl part showed powerful AR-inhibitory activity. The chloro- substituted benzothiazolyl compound showed an AR selectivity of more than 5000 fold.

Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (zopolrestat) and congeners

A new working hypothesis that there is a hitherto unrecognized binding site on the aldose reductase (AR) enzyme with strong affinity for benzothiazoles was pursued for the design of novel, potent aldose reductase inhibitors (ARIs). The first application of this hypothesis led to a novel series of 3,4-dihydro-4-oxo-3-(benzothiazolylmethyl)-1-phthalazineacetic acids. The parent of this series (207) was a potent inhibitor of AR from human placenta (IC50 = 1.9 x 10-8 M) and was orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications (ED50 = 18.5 mg/kg). Optimization of this lead through medicinal chemical rationale, including analogy from other drug series, led to more potent congeners of 207 and culminated in the design of 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (216, CP-73,850, zopolrestat). Zopolrestat was found to be more potent than 207, both in vitro and in vivo. Its IC50 against AR and ED50 in the acute test were 3.1 x 10-9 M and 3.6 mg/kg, respectively. Its ED50s in reversing already elevated sorbitol accumulation in rat sciatic nerve, retina, and lens in a chronic test were 1.9, 17.6, and 18.4 mg/kg, respectively. It was well absorbed in diabetic patients, resulting in high blood level, showed a highly favorable plasma half-life (27.5 h), and is undergoing further clinical evaluation. An assortment of synthetic methods used for the construction of benzothiazoles, including an efficient synthesis of zopolrestat, is described. Structure-activity relationships in the new series are discussed.