55736-04-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Chloro-6-hydroxyphenyl)ethanone is used as a key intermediate for the synthesis and structure-activity relationship of novel spiropiperidine-based stearoyl-CoA desaturase-1 inhibitors. These inhibitors are being developed as potential therapeutic agents for the treatment of various metabolic disorders, such as obesity and type 2 diabetes, by modulating lipid metabolism and improving insulin sensitivity.
Used in Agrochemical Industry:
1-(2-Chloro-6-hydroxyphenyl)ethanone can also be utilized as a building block in the development of new agrochemicals, such as herbicides, insecticides, and fungicides. Its unique structure allows for the design of molecules with specific target sites and modes of action, leading to the creation of more effective and environmentally friendly products.

Preparation

Preparation by diazotization of 2-amino-6-chloro-acetophenone, followed by hydrolysis of the obtained diazonium salt (55%).

InChI:InChI=1/C8H7ClO2/c1-5(10)8-6(9)3-2-4-7(8)11/h2-4,11H,1H3

Upstream product

• 89999-90-6 3-chloro-2-cyanophenol 
• 75-16-1 methylmagnesium bromide 
• 108-43-0 3-monochlorophenol 
• 91105-99-6 1-chloro-3-(methoxymethoxy)benzene 
• 881883-32-5 1-(2-Chloro-6-methoxy-phenyl)-ethanone 
• 6575-10-6 2-Chlor-6-methoxybenzoesaeurenitril 
• 211449-30-8 2-acetyl-3-chlorophenyl diethylcarbamate 

Downstream Products

• 1227415-97-5 C₂₀H₁₅ClN₄O₃ 
• 1263427-05-9 tert-butyl 5-chloro-4-phenyl-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate 
• 1263427-06-0 5-chloro-4-phenylspiro[chromene-2,4'-piperidine] 
• 1263427-07-1 tert-butyl {5-[2-(5-chloro-4-phenyl-1'H-spiro[chromene-2,4'-piperidin]-1'-yl)-1,3-thiazol-5-yl]-2H-tetrazol-2-yl}acetate 
• 1263426-57-8 {5-[2-(5-chloro-4-phenyl-1'H-spiro[chromene-2,4'-piperidin]-1'-yl)-1,3-thiazol-5-yl]-2H-tetrazol-2-yl}acetic acid 
• 1354928-51-0 C₁₇H₁₁ClO₄ 
• 1354928-57-6 C₁₇H₁₁ClO₄ 
• 1441771-84-1 5-chloro-3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 1441774-34-0 C₁₈H₁₇ClO₅ 

Relevant academic research and scientific papers

Chromenones as potent bradykinin B1 antagonists

A series of fused 6,6-bicyclic chromenones was investigated for activity against the bradykinin B1 receptor. SAR studies based on a pharmacophore model revealed compounds with high affinity for both human and rabbit B1. These compounds demonstrated favorable pharmacokinetic properties and 5-chlorochromenone 15 was efficacious in a carrageenan-induced mechanical hyperalgesia model for chronic pain.

NOVEL SPIRO COMPOUNDS USEFUL AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE

Heteroaromatic compounds of structural formula (I) are selective inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD1) relative to other known stearoyl-coenzyme A desaturases. The compounds of the present invention are useful for the prevention and

NOVEL SPIRO COMPOUNDS USEFUL AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE

Heteroaromatic compounds of structural formula I are selective inhibitors of stearoyl- coenzyme. A delta-9 desaturase (SCDl) relative to other known stearoyl-coenzyme. A desaturases. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, such as atherosclerosis; obesity; diabetes; neurological disease; metabolic syndrome; insulin resistance; and liver steatosis. Formula (I).

INHIBITORS OF FATTY ACID BINDING PROTEIN (FABP)

The present invention relates to novel heterocyclic compounds as Fatty Acid Binding Protein ("FABP") inhibitors, pharmaceutical compositions comprising the heterocyclic compounds and the use of the compounds for treating or preventing a cardiovascular disease, a metabolic disorder, obesity or an obesity-related disorder, diabetes, dyslipidemia, a diabetic complication, impaired glucose tolerance or impaired fasting glucose. An illustrative compound of the present invention is shown below: (I)

Novel spiropiperidine-based stearoyl-CoA desaturase-1 inhibitors: Identification of 1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-5-(trifluoromethyl)-3,4-dihydrospiro[chromene-2,4′-piperidine]

Cyclization of the benzoylpiperidine in lead compound 2 generated a series of novel and highly potent spiropiperidine-based stearoyl-CoA desaturase (SCD)-1 inhibitors. Among them, 1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-5-(trifluoromethyl)-3,4-dihydrospiro[chromene-2,4′-piperidine] (19) demonstrated the most powerful inhibitory activity against SCD-1, not only in vitro but also in vivo (C57BL/6 J mice). With regard to the pharmacological evaluation, 19 showed powerful reduction of the desaturation index in the plasma of C57BL/6 J mice on a non-fat diet after a 7-day oral administration (q.d.) without causing notable abnormalities in the eyes or skin up to the highest dose (3 mg/kg) in our preliminary analysis.

Synthesis and evaluation of novel stearoyl-CoA desaturase 1 inhibitors: 1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-3, 4-dihydrospiro[chromene-2,4′-piperidine] analogs

In continuation of our investigation on novel stearoyl-CoA desaturase (SCD) 1 inhibitors, we have already reported on the structural modification of the benzoylpiperidines that led to a series of novel and highly potent spiropiperidine-based SCD1 inhibitors. In this report, we would like to extend the scope of our previous investigation and disclose details of the synthesis, SAR, ADME, PK, and pharmacological evaluation of the spiropiperidines with high potency for SCD1 inhibition. Our current efforts have culminated in the identification of 5-fluoro-1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol- 2-yl]pyridazin-3-yl}-3,4-dihydrospiro[chromene-2,4′-piperidine] (10e), which demonstrated a very strong potency for liver SCD1 inhibition (ID 50 = 0.6 mg/kg). This highly efficacious inhibition is presumed to be the result of a combination of strong enzymatic inhibitory activity (IC 50 (mouse) = 2 nM) and good oral bioavailability (F >95%). Pharmacological evaluation of 10e has demonstrated potent, dose-dependent reduction of the plasma desaturation index in C57BL/6J mice on a high carbohydrate diet after a 7-day oral administration (q.d.). In addition, it did not cause any noticeable skin abnormalities up to the highest dose (10 mg/kg).