110704-18-2

Basic information

• Product Name: 2-(BROMOMETHYL)-6-METHOXYBENZOTHIAZOLE
• Synonyms: 2-(BROMOMETHYL)-6-METHOXYBENZOTHIAZOLE;2-(bromomethyl)-6-methoxybenzo[d]thiazole
• CAS NO: 110704-18-2
• Molecular Formula: C₉H₈BrNOS
• Molecular Weight: 258.13
• Mol File: 110704-18-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(BROMOMETHYL)-6-METHOXYBENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(BROMOMETHYL)-6-METHOXYBENZOTHIAZOLE(110704-18-2)
• EPA Substance Registry System: 2-(BROMOMETHYL)-6-METHOXYBENZOTHIAZOLE(110704-18-2)

Safety Data

• Hazardous Substances Data: 110704-18-2(Hazardous Substances Data)

Upstream product

• 103-90-2 4-acetaminophenol 
• 2941-72-2 6-methoxy-2-methylbenzothiazole 

Relevant articles and documents

Aniline derivatives having herbicidal activity, their preparation and their use

Compounds of formula (I): STR1 (wherein: R1 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy, or optionally substituted alkylthio; R2 is hydrogen, optionally substituted alkyl, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or a group of formula --YR7 ; R3 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro or a group of formula --COR8, wherein R8 is hydrogen, alkyl, cycloalkyl or alkoxy; R4 and R5 are each hydrogen atom or alkyl; R6 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro, or a group of formula --COR8, as defined above; A, Q and X are each oxygen or sulfur; Y is a group of formula --CO--, --COO--, --CH2 O--, --CH2 S--, --CH2 CH2 O--, --CH2 CH2 S--, --CH2 CO--, --CH2 COO--, --CH(Me)COO--, --CH2 CH2 CO--, --CH2 OCO--, CH2 OCOO-- and --CH2 CH2 OCO--; R7 is optionally substituted alkyl group, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted aralkyl, or an optionally substituted heterocycle; and m and n are each an integer from 0 to 4; and herbicidally acceptable addition salts thereof) are useful as herbicides.

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.