73628-29-2

Usage

General Description

2-AMINO-3-CHLOROTHIOPHENOL is a chemical compound with the formula C4H4ClNOS. It is a derivative of thiophenol with a chlorine atom and an amino group attached to the thiophene ring. 2-AMINO-3-CHLOROTHIOPHENOL is used in the production of pharmaceuticals, dyes, and other organic chemicals. It is also known for its use as an intermediate in the synthesis of various organic compounds. 2-AMINO-3-CHLOROTHIOPHENOL is a yellowish solid that is sparingly soluble in water and is primarily used in laboratory research and development. It should be handled and stored with care due to its potential hazardous properties.

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Downstream Products

• 110704-21-7 2-Chloromethyl-4-fluoro-benzothiazole 
• 110821-57-3 (4-Bromo-phenyl)-(5-fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 121364-13-4 Biphenyl-4-yl-(5-fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 110821-54-0 (4-Chloro-phenyl)-(5-fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 159790-14-4 [4-(4-Bromo-2-fluoro-benzyl)-5-fluoro-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl]-acetic acid ethyl ester 
• 135517-93-0 (3,4-Dimethoxy-phenyl)-(5-fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 110821-55-1 (5-Fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-p-tolyl-methanone 
• 1219456-98-0 C₁₂H₈ClFN₂O₂S 
• 1169760-47-7 N-[3,4-dihydro-1,5-benzoxathiepin-3-yl]-3-(R)-[(2-amino-3-fluorophenyl)thio]-2-(S)-methylpropionamide 
• 110821-56-2 (5-Fluoro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-(4-methoxy-phenyl)-methanone 

Relevant academic research and scientific papers

Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications

Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective 3-[(benzothiazol-2-yl)methyl]indole-N-alkanoic acid aldose reductase inhibitors. The lead candidate, 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat, 9) inhibits aldose reductase with an IC50 of 5 nM, while being 5400 times less active against aldehyde reductase, a related enzyme involved in the detoxification of reactive aldehydes. It lowers nerve and lens sorbitol levels with ED50's of 1.9 and 4.5 mg/kg/d po, respectively, in the 5-day STZ-induced diabetic rat model. In a 3-month diabetic intervention model (1 month of diabetes followed by 2 months of drug treatment at 5 mg/kg/d po), it normalizes polyols and reduces the motor nerve conduction velocity deficit by 59% relative to diabetic controls. It has a favorable pharmacokinetic profile (F, 82%; t1/2, 5.6 h; Vd, 0.694 L/kg) with good drug penetration in target tissues (Cmax in sciatic nerve and eye are 2.36 and 1.45 μg equiv/g, respectively, when dosed with [14C] lidorestat at 10 mg/kg po).

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.

SYNTHESIS OF 2-AMINO-3-FLUOROBENZENETHIOL AND ITS CONVERSION INTO DIFFERENT HETEROCYCLES

Heterocycles containing fluorine possess a variety of biological applications and are useful drugs. 5-Fluorouracil and 5-fluorotryptamine are eefective drugs used in the treatment of cancer.