110704-50-2

Usage

Uses

Used in Pharmaceutical Industry:
Benzothiazole, 2-(chloroMethyl)-5-(trifluoroMethyl)is used as an intermediate in the synthesis of pharmaceuticals for its potential role in the development of new medicines. Its antimicrobial and antifungal properties make it a promising candidate for creating treatments targeting various infections.
Used in Agrochemical Industry:
In the agrochemical industry, Benzothiazole, 2-(chloroMethyl)-5-(trifluoroMethyl)is utilized as an intermediate in the production of agrochemicals. Its antimicrobial and antifungal properties contribute to the development of pesticides and fungicides to protect crops and enhance agricultural productivity.
Used in Dye Production:
Benzothiazole, 2-(chloroMethyl)-5-(trifluoroMethyl)is used as a building block in the production of dyes. Its unique structure allows for the creation of dyes with specific color properties, making it valuable in the textile and other industries that rely on colorants.
Used in Polymer Production:
Benzothiazole, 2-(chloroMethyl)-5-(trifluoroMethyl)is also used in the production of polymers, where its chemical structure contributes to the development of polymers with specific properties. These polymers can be used in a variety of applications, including coatings, plastics, and adhesives.
Used in Organic Compounds Synthesis:
Benzothiazole, 2-(chloroMethyl)-5-(trifluoroMethyl)serves as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of organic compounds with diverse applications in different industries.
It is important to handle Benzothiazole, 2-(chloroMethyl)-5-(trifluoroMethyl)with care, as the chloromethyl and trifluoromethyl groups can pose hazards to human health and the environment. Proper safety measures should be taken during its production, use, and disposal to minimize potential risks.

Upstream product

• 51076-95-0 2-chloro-1,1,1-triethoxyethane 
• 19406-49-6 2-amino-4-trifluoromethylthiophenol 
• 4274-38-8 2-amino-4-(trifluoromethyl)benzenethiol hydrochloride 

Downstream Products

• 123895-42-1 2-bromomethyl-5-trifluoromethyl-benzothiazole 
• 139402-07-6 3-(5-trifluoromethylbenzothiazol-2-ylmethoxy)benzyl alcohol 
• 1355612-71-3 zopolrestat 
• 1355612-99-5 2-(iodomethyl)-5-(trifluoromethyl)benzo[d]thiazole 
• 140926-49-4 3,4-dihydro-4-oxo-5,6-cyclohexano-3-<<5-(trifluoromethyl)benzothiazol-2-yl>methyl>-1-pyridazineacetic acid 

Relevant academic research and scientific papers

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.

HETEROCYCLIC OXOPHTHALAZINYL ACETIC ACIDS

A heterocyclic oxophthalazinyl acetic acid having aldose reductast inhibitory activity of the formula, wherein X is oxygen or sulfur; Z is a covalent bond, O, S, NH or CH2 or CHR5Z is vinyl; R1 is hydroxy, or a prodrug group; R2 is a heterocyclic group, R3 and R4 are hydrogen or the same or a different substituent, and R5 is hydrogen, methyl or trifluoromethyl. The pharmaceutically acceptable acid addition salts of the above compounds wherein R1 is di(C1-C4)alkylamino or (C1-C4)alkoxy substituted by N-morpholino or di(Cl-C4)alkylamino and the pharmaceutically active base addition salts of the above compounds wherein R1 is hydroxy are also aldose reductase inhibitors

2-CHLORO-1,1,1-TRIETHOXYETHANE AND ITS USE IN A VERSATILE SYNTHESIS OF SUBSTITUTED, 2-CHLOROMETHYL HETEROCYCLES INCLUDING BENZOTHIAZOLE AND BENZOXAZOLE

An efficient procedure suitable for large scale preparation of 2-chloro-1,1,1-triethoxyethane and its use in a versatile synthesis of 2-chloromethyl derivatives of an assortment of heterocycles are described.

Process for preparing chloromethyl thiazoles or oxazoles, and intermediates for use therein

Chloromethyl group substituted heterocyclic compounds of the formulae STR1 wherein X is O or S; Y together with the two carbons to which Y is attached forms phenyl, pyridyl or pyrimidyl, each of which may be substituted by R; R is one of iodo or trifluoromethylthio or one or two of fluoro, chloro, bromo, (C1 -C4)alkyl, (C1 -C4)alkoxy, (C1 -C4)alkylthio, (C1 -C4)alkylsulfinyl, (C1 -C4)alkylsulfonyl or trifluoromethyl; and R1 is hydrogen or R, are prepared by reacting a bifunctional compound of the formulae STR2 with a 2-chloro-1,1,1-tri(C1 -C6)alkoxyethane. Most of the compounds of formulae I and II are novel. These compounds are intermediates of use in the preparation of compounds having pharmaceutical activity. The 2-chloro-1,1,1-tri(C1 -C6)alkoxyethanes are prepared from the corresponding tri(C1 -C6)alkoxyethanes by chlorination with N-chlorosuccinimide or with chlorine in pyridine and a chlorohydrocarbon cosolvent.