2153-11-9

Usage

Uses

Used in Pharmaceutical Industry:
2'-CHLORO-4-HYDROXYACETANILIDE is used as a building block for the synthesis of novel thiazolidinedione derivatives, which act as irreversible allosteric IKK-β modulators. These modulators play a crucial role in the development of new drugs targeting inflammatory and autoimmune diseases, as well as certain types of cancer.
Used in Chemical Synthesis:
2'-CHLORO-4-HYDROXYACETANILIDE is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for further functionalization and modification, making it a versatile starting material for the development of new molecules with potential applications in various industries.

InChI:InChI=1/C8H8ClNO2/c9-5-8(12)10-6-1-3-7(11)4-2-6/h1-4,11H,5H2,(H,10,12)

Upstream product

• 123-30-8 4-amino-phenol 
• 79-04-9 chloroacetyl chloride 
• 541-88-8 Chloroacetic anhydride 

Downstream Products

• 70453-52-0 mercapto-acetic acid-(4-hydroxy-anilide) 
• 106653-50-3 1-(2-chloro-acetylamino)-4-(3-nitro-benzoyloxy)-benzene 
• 84327-82-2 2-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-N-(4-hydroxy-phenyl)-acetamide 
• 87439-65-4 N-(4-Hydroxy-phenyl)-2-{5-[3-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-propyl]-4-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl}-acetamide 
• 511283-88-8 2-(1H-Benzoimidazol-2-ylsulfanyl)-N-(4-hydroxy-phenyl)-acetamide 
• 87439-75-6 N-(4-Hydroxy-phenyl)-2-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetamide 
• 182502-68-7 SCP-1 
• 53527-05-2 N-(4-hydroxyphenyl)-2-iodoacetamide 
• 1214879-92-1 6-amino-7-cyano-N-(4-hydroxyphenyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamide 
• 1552322-94-7 methyl 3-(3-(4-(2-chloroacetamido)phenoxy)propylthio)propanoate 
• 1552323-05-3 2-chloro-N-(4-(3-(2,3-dihydroxypropylthio)propoxy)phenyl)acetamide 
• 1552323-06-4 C₄₉H₅₆N₄O₈S₄ 
• 1552322-93-6 N-(4-allyloxyphenyl)-2-(4-bromophenylthio)acetamide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel thiazolidinedione derivatives as irreversible allosteric IKK-β modulators

The kinase known as IKK-β activates NF-κB signaling pathway leading to expression of several genes contributing to inflammation, immune response, and cell proliferation. Modulation of IKK-β kinase activity could be useful for treatment and management of such diseases. Starting from a discovered weakly active hit compound, twenty four thiazolidinedione-scaffold based chemical entities belonging to five series have been designed, synthesized and evaluated as potential IKK-β modulators. Among them, compounds 6q, 6r and 6u showed low micromolar IC50 values while compounds 6v, 6w, and 6x elicited submicromolar IC50 values equal to 0.4, 0.7 and 0.9 μM respectively. These submicromolar IC50 values are 243, 139 and 105 folds the value of the reported IC50 of the starting hit compound. Kinetic study of compounds 6v and 6w confirmed this class of modulators as irreversible inhibitors. LPS-treated RAW 264.7 macrophages proved the anti-inflammatory activity of compounds 6q and 6v. Assay of hERG inhibition demonstrated a safe profile of compound 6q suggesting it as a lead for further development of IKK-β modulators.

Optimization study towards more potent thiazolidine-2,4-dione IKK-β modulator: Synthesis, biological evaluation and in silico docking simulation

Inhibition of IKK-β (inhibitor of nuclear factor kappa-B kinase subunit beta) has been broadly documented as a promising approach for treatment of acute and chronic inflammatory diseases, cancer, and autoimmune diseases. Recently, we have identified a novel class of thiazolidine-2,4-diones as structurally novel modulators for IKK-β. Herein, we report a hit optimization study via analog synthesis strategy aiming to acquire more potent derivative(s), probe the structure activity relationship (SAR), and get reasonable explanations for the elicited IKK-β inhibitory activities though an in silico docking simulation study. Accordingly, a new series of eighteen thiazolidine-2,4-dione derivatives was rationally designed, synthesized, identified with different spectroscopic techniques and biologically evaluated as noteworthy IKK-β potential modulators. Successfully, new IKK-β potent modulators were obtained, including the most potent analog up-to-date 7m with IC50 value of 260 nM. A detailed structure activity relationship (SAR) was discussed and a mechanistic study for 7m was carried out indicating its irreversible inhibition mode with IKK-β (Kinact value = 0.01 (min?1). Furthermore, the conducted in silico simulation study provided new insights for the binding modes of this novel class of modulators with IKK-β.

Substituted-3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and Stimulator for Interferon Genes (STING) modulators as cancer immunotherapeutics

Substituted -3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and related compounds, which are useful as inhibitors of ENPP1; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the ENPP1.

Thiazolidine-2,4-dione-based irreversible allosteric IKK-β kinase inhibitors: Optimization into in vivo active anti-inflammatory agents

Selective kinase inhibitors development is a cumbersome task because of ATP binding sites similarities across kinases. On contrast, irreversible allosteric covalent inhibition offers opportunity to develop novel selective kinase inhibitors. Previously, we

Antidiabetic compounds

Compounds for the treatment of hyperglycemia and/or diabetes are provided. The compounds, which inhibit the enzyme dipeptidyl peptidase (DPP-4), are based on the structure where X may be present or absent an may be OH, Ar is an aryl group; and n ranges from 0 to 5.

Substituted-3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and Stimulator for Interferon Genes (STING) modulators as cancer immunotherapeutics

Substituted-3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and related compounds, which are useful as inhibitors of ENPP1; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the ENPP1.

COMPOSITIONS AND METHODS FOR AMELIORATING PAIN

This invention is directed to compositions, methods and kits that can be used for the treatment or amelioration of pain.

Glycosylated lanthanide cyclen complexes as luminescent probes for monitoring glycosidase enzyme activity

The development of synthetic chemical probes for the detection of enzymes is extremely important for biological, medicinal, and industrial applications. Here we report the synthesis of an array of novel glycosylated Tb(iii) complexes, their photophysical properties in solution, and their ability to function as luminescent probes for observing glycosidase enzyme activity in real time. Our initial studies into the application of these complexes for the detection of the Concanavalin A (ConA) lectin is also reported, highlighting the broad scope of these novel chemical probes.

Sulfonamide-1,3,5-triazine-thiazoles: Discovery of a novel class of antidiabetic agents: Via inhibition of DPP-4

Dipeptidyl peptidase-4 (DPP-4) inhibitors are a novel class of antidiabetic drugs used for treating type 2 diabetes mellitus. In the present study, a novel hybrid sulphonamide-1,3,5-triazine-thiazole derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, FT-IR, mass spectroscopy and elemental analysis. The result showed that among the tested compounds, 8c was found to be a more potent inhibitor of DPP-4 (2.32 nM) than the alogliptin standard. Moreover, molecular docking results showed that ligand 8c was efficiently docked into the active site of the catalytic triad of Ser630, Asp708 and His740, encompassing both the S1 and S2 pocket with a CDOCKER interaction energy of 57.80. The in vitro results were further substantiated by in vivo blood glucose lowering effects in experimental subjects. The results of the investigation showed that compound 8c exhibited concentration-dependent improvement of glucose tolerance in ICR after oral administration. It has been also found that compound 8c (30 mg kg-1) showed a reduction in the area under the curve from 0 to 120 min [(AUC) 0-120 min] to 37.46%, which was found to be approximately similar to the hypoglycemic profile of alogliptin (standard). The activity of compound 8c was also investigated in STZ-induced diabetic rats where it showed a dose-dependent decrease in blood glucose levels together with an improvement in insulin levels probably via inhibition of DPP-4. The effect of compound 8c was also investigated on the lipid profile and antioxidant enzyme system.

Discovery of novel AHLs as potent antiproliferative agents

Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog 11e induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner.