57017-95-5

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-chloro-4-hydroxyphenylacetate is used as a reagent for the preparation of benzenesulfonamide derivatives, which are important in the development of ATP citrate lyase inhibitors. These inhibitors play a crucial role in targeting metabolic pathways in cancer cells, making them potential candidates for cancer treatment and therapy.

InChI:InChI=1/C9H9ClO3/c1-13-9(12)5-6-2-3-8(11)7(10)4-6/h2-4,11H,5H2,1H3

Upstream product

• 67-56-1 methanol 
• 33697-81-3 (3-chloro-4-hydroxy-phenyl)-acetic acid 
• 13719-57-8 3-chloro-4-methoxybenzyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 766-51-8 2-Chloroanisole 
• 141805-68-7 N-(3-Chloro-4-hydroxyphenylacetyl)fumarate 
• 7569-58-6 2-(3-chloro-4-methoxyphenyl)acetonitrile 

Downstream Products

• 60736-66-5 3-chloro-4-(3'-chloro-4'-methoxybenzyloxy)-phenylacetic acid 
• 194793-04-9 methyl 3-chloro-4-(3-bromopropyloxy)-phenylacetate 
• 927178-35-6 3-(2-chloro-4-methoxycarbonylmethyl-phenoxymethyl)-5-phenylisoxazole-4-carboxylic acid tert-butyl ester 
• 870289-04-6 [3-chloro-4-(3,5-dibromobenzyloxy)phenyl]acetic acid methyl ester 
• 905991-54-0 methyl (4-{2-[(tert-butoxycarbonyl)(methyl)amino]ethoxy}-3-chlorophenyl)acetate 
• 905991-57-3 methyl (4-{3-[(tert-butoxycarbonyl)(methyl)amino]propoxy}-3-chlorophenyl)acetate 
• 194793-09-4 methyl 3-chloro-4-(4-bromobutyloxy)-phenylacetate 
• 228577-81-9 methyl 4-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-3-chlorophenylacetate 
• 496856-44-1 methyl 2-(3-chloro-4-(triuoromethylsulfonyloxy)phenyl)acetate 
• 58120-90-4 methyl 2-(3-chloro-4-methoxyphenyl)acetate 
• 863119-29-3 methyl [3-chloro-4-({3-[3-methyl-6-(trifluoromethyl)-1-benzothien-2-yl]heptyl}oxy)phenyl]acetate 
• 709028-30-8 {3-Chloro-4-[3-(3-hydroxy-2-propyl-4-{2,2,2-trifluoro-1-[(Z)-hydroxyimino]-ethyl}-phenoxy)-propylsulfanyl]-phenyl}-acetic acid methyl ester 
• 709028-29-5 (3-Chloro-4-{3-[3-hydroxy-2-propyl-4-(2,2,2-trifluoro-acetyl)-phenoxy]-propylsulfanyl}-phenyl)-acetic acid methyl ester 
• 194608-89-4 {3-chloro-4-[3-(7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propylsulfanyl]-phenyl}-acetic acid methyl ester 

Relevant academic research and scientific papers

Design and synthesis of a screening library using the natural product scaffold 3-chloro-4-hydroxyphenylacetic acid

The fungal metabolite 3-chloro-4-hydroxyphenylacetic acid (1) was utilized in the generation of a unique drug-like screening library using parallel solution-phase synthesis. A 20-membered amide library (3-22) was generated by first converting 1 to methyl (3-chloro-4-hydroxyphenyl)acetate (2), then reacting this scaffold with a diverse series of primary amines via a solvent-free aminolysis procedure. The structures of the synthetic analogues (3-22) were elucidated by spectroscopic data analysis. The structures of compounds 8, 12, and 22 were confirmed by single X-ray crystallographic analysis. All compounds were evaluated for cytotoxicity against a human prostate cancer cell line (LNCaP) and for antiparasitic activity toward Trypanosoma brucei brucei and Plasmodium falciparum and showed no significant activity at 10 μM. The library was also tested for effects on the lipid content of LNCaP and PC-3 prostate cancer cells, and it was demonstrated that the fluorobenzyl analogues (12-14) significantly reduced cellular phospholipid and neutral lipid levels.

CHEMOSELECTIVE METHYLENE HYDROXYLATION IN AROMATIC MOLECULES

A chemoselective and reactive Mn(CF3-PDP) catalyst system that enables for the first time the strategic advantages of late-stage aliphatic C—H hydroxylation to be leveraged in aromatic compounds. This discovery will benefit small molecule therapeutics by enabling the rapid diversification of aromatic drugs and natural products and identification of their metabolites.

Aryl or N-heteroaryl Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands

The invention relates to aryl or N-heteroaryl substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

ARYL OR N-HETEROARYL SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to aryl or N-heteroaryl substituted methanesulfonamide derivatives of Formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

Amine Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands

The invention relates to amine substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

AMINE SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to amine substituted methanesulfonamide derivatives of formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN N-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives of formula (R) bearing a phenyl moiety substituted with an N-containing group as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

NOVEL 3-PHENYL ACRYLIC ACID COMPOUND ACTIVATORS OF TYPE PPAR RECEPTORS AND PHARMACEUTICAL/COSMETIC COMPOSITIONS COMPRISED THEREOF

Novel 3-phenyl acrylic acid compounds have the following general formula (I): and are formulated into pharmaceutical compositions for administration in human or veterinary medicine (in dermatology, as well as in the field of cardiovascular diseases, immune diseases and/or diseases associated with lipid metabolism), or into cosmetic compositions.

CHEMICAL COMPOUNDS 785

DGAT-1 inhibitor compounds of formula (I), pharmaceutically-acceptable salts and pro-drugs thereof are described, together with pharmaceutical compositions, processes for making them and their use in treating, for example, obesity wherein, for example, r is 0 or 1 and X1 is linear (1-3C)alkyl; q is 0 or 1 and X2 is fluoro, chloro or (1-3C)alkyl; Y1 is selected from fluoro, chloro, bromo, cyano, (1-3C)alkyl and (1-2C)alkoxy; n is 0, 1 or 2 and Y2 is fluoro, chloro or (1-3C)alkyl; p is 0, 1 or 2 and Y3 is (1-3C)alkyl or forms a (3-5C)cycloalkyl ring; Z is carboxy or —CONHSO2Me or —CONRbRc wherein Rb and Rc are independently selected, for example, from hydrogen and (1-4C)alkyl or Rb and Rc are linked so as to form a morpholine ring or a (4-6C)heterocyclic ring and when Z is —CONRbRc the Rb and Rc groups may be optionally substituted by carboxy.

Highly twisted adamantyl arotinoids: Synthesis, antiproliferative effects and RXR transactivation profiles

Retinoid-related molecules with an adamantyl group (adamantyl arotinoids) have been described with selective activities towards the retinoid receptors as agonists for NR1B2 and NR1B3 (RARβ,γ) (CD437, MX3350-1) or RAR antagonists (MX781) that induce growth arrest and apoptosis in cancer cells. Since these molecules induce apoptosis independently of RAR transactivation, we set up to synthesize novel analogs with impaired RAR binding. Here we describe adamantyl arotinoids with 2,2′-disubstituted biaryl rings prepared using the Suzuki coupling of the corresponding fragments. Those with cinnamic and naphthoic acid end groups showed significant antiproliferative activity in several cancer cell lines, and this effect correlated with the induction of apoptosis as measured by caspase activity. Strikingly, some of these compounds, whereas devoid of RAR binding capacity, were able to activate RXR.