27727-37-3

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Camostat metabolites.

InChI:InChI=1/C15H14O3/c16-14-8-6-12(7-9-14)10-15(17)18-11-13-4-2-1-3-5-13/h1-9,16H,10-11H2

Upstream product

• 156-38-7 4-hydroxyphenylacetate 
• 100-51-6 benzyl alcohol 
• 99-96-7 4-hydroxy-benzoic acid 
• 28141-24-4 4-hydroxybenzoyl chloride 
• 100-39-0 benzyl bromide 
• 18982-18-8 allyl 4-hydroxybenzoate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 100-44-7 benzyl chloride 

Downstream Products

• 42973-19-3 (4-Benzyloxycarbonylmethyl-phenoxy)-acetic acid 
• 38688-58-3 4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid 4-benzyloxycarbonylmethyl-phenyl ester 
• 335200-36-7 benzyl 2-(4-((tert-butyldimethylsilyl)oxy)phenyl)acetate 
• 476330-47-9 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid benzyl ester 
• 335200-40-3 (4-acetylamino-phenyl)-acetic acid 4-benzyloxycarbonylmethyl-phenyl ester 
• 335200-44-7 [4-(2-{4-[2-(4-Acetylamino-phenyl)-acetoxy]-phenyl}-acetoxy)-phenyl]-acetic acid 4-[4-(4-benzyloxycarbonylmethyl-phenoxycarbonylmethyl)-phenoxycarbonylmethyl]-phenyl ester 
• 335200-41-4 {4-[2-(4-Acetylamino-phenyl)-acetoxy]-phenyl}-acetic acid 4-benzyloxycarbonylmethyl-phenyl ester 
• 335200-42-5 {4-[2-(4-Acetylamino-phenyl)-acetoxy]-phenyl}-acetic acid 4-(4-benzyloxycarbonylmethyl-phenoxycarbonylmethyl)-phenyl ester 
• 335200-37-8 [4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acetic acid 4-benzyloxycarbonylmethyl-phenyl ester 
• 476330-52-6 triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate 
• 476330-54-8 [4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acetic acid 
• 476330-51-5 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetic acid 2-cyanoethyl ester 
• 476330-48-0 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester 
• 476330-49-1 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-bromoacetic acid 2-cyanoethyl ester 

Relevant academic research and scientific papers

Targeting enteropeptidase with reversible covalent inhibitors to achieve metabolic benefits

Inhibition of the serine protease enteropeptidase (EP) opens a new avenue to the discovery of chemotherapeutics for the treatment of metabolic diseases. Camostat has been used clinically for treating chronic pancreatitis in Japan; however, the mechanistic basis of the observed clinical efficacy has not been fully elucidated. We demonstrate that camostat is a potent reversible covalent inhibitor of EP, with an inhibition potency (kinact/KI) of 1.5 × 104M-1s-1. High-resolution liquid chromatography-mass spectrometry (LC-MS) showed addition of 161.6 Da to EP after the reaction with camostat, consistent with insertion of the carboxyphenylguanidine moiety of camostat. Covalent inhibition of EP by camostat is reversible, with an enzyme reactivation half-life of 14.3 hours. Formation of a covalent adduct was further supported by a crystal structure resolved to 2.19 ?, showing modification of the catalytic serine of EP by a close analog of camostat, leading to formation of the carboxyphenylguanidine acyl enzyme identical to that expected for the reaction with camostat. Of particular note, minor structural modifications of camostat led to changes in the mechanism of inhibition. We observed from other studies that sustained inhibition of EP is required to effect a reduction in cumulative food intake and body weight, with concomitant improved blood glucose levels in obese and diabetic leptindeficient mice. Thus, the structure-activity relationship needs to be driven by not only the inhibition potency but also the mechanistic and kinetic characterization. Our findings support EP as a target for the treatment of metabolic diseases and demonstrate that reversible covalent EP inhibitors show clinically relevant efficacy. SIGNIFICANCE STATEMENT Interest in targeted covalent drugs has expanded in recent years, particularly so for kinase targets, but also more broadly. This study demonstrates that reversible covalent inhibition of the serine protease enteropeptidase is a therapeutically viable approach to the treatment of metabolic diseases and that mechanistic details of inhibition are relevant to clinical efficacy. Our mechanistic and kinetic studies outline a framework for detailed inhibitor characterization that is proving essential in guiding discovery efforts in this area.

SUPPRESSION AND REGENERATION PROMOTING EFFECT OF LOW MOLECULAR WEIGHT COMPOUND ON CANCER AND FIBROSIS

To obtain a novel therapeutic drug for a malignant tumor or fibrosis. Used is a compound represented by formula (1), a salt thereof, or a solvate thereof. Also used is a therapeutic drug for a malignant tumor or a therapeutic drug for fibrosis, comprising

INHIBITORY EFFECT OF LOW MOLECULAR WEIGHT COMPOUND ON CANCER AND FIBROSIS

A novel therapeutic drug for malignant tumors, cancer stem cells, or fibrosis is obtained. A therapeutic drug for malignant tumors or cancer stem cells is used that includes at least one compound selected from the group consisting of compounds represented

AMINO-BENZOISOTHIAZOLE AND AMINO-BENZOISOTHIADIAZOLE AMIDE COMPOUNDS

Provided herein are amino-benzoisothiazole and benzoisothiadiazole amide compounds. In particular, provided herein are compounds that affect the function of kinases in a cell and that are useful as therapeutic agents or with therapeutic agents. The compounds provided herein are useful in the treatment of a variety of diseases and conditions including eye diseases such as glaucoma, retinal diseases such as acute macular degeneration (AMD) and diabetic macular edema (DME), diseases and conditions characterized by inflammatory processes, cardiovascular diseases, and diseases characterized by abnormal growth, such as cancers. Also provided are compositions (e.g., pharmaceutical compositions) comprising the compounds provided herein.

Phosphonate-based irreversible inhibitors of human γ-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity

γ-Glutamyl transpeptidase (GGT, EC 2.3.2.2) that catalyzes the hydrolysis and transpeptidation of glutathione and its S-conjugates is involved in a number of physiological and pathological processes through glutathione metabolism and is an attractive phar

COMPOUNDS AND METHODS

The present invention relates to novel retinoid-reiated orphan receptor gamma (RORy) modulators and their use in the treatment of diseases mediated by RORy.

PROSTAGLANDIN-BISPHOSPHONATE CONJUGATE COMPOUNDS, METHODS OF MAKING SAME, AND USES THEREOF

The invention provides, in part, amino-bisphosphonate-prostaglandin conjugate compounds as well as methods for their synthesis. Said compounds may be used as EP4 agonist compounds in the prevention or treatment of conditions associated with abnormal or excessive bone loss, with abnormal or reduced bone resorption, or with abnormal calcium metabolism.

DUAL-ACTION INHIBITORS AND METHODS OF USING SAME

Provided are compounds, compositions, and methods for treating diseases and conditions wherein an inhibitor of a kinase, such as rho kinase (ROCK), and an inhibitor of one or more of the monoamine transporters, such as NET or SERT, act in concert to improve the condition.

CCR5 ANTAGONISTS AS THERAPEUTIC AGENTS

The present invention relates to compounds useful in the treatment of CCR5-related diseases and disorders, for example, useful in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acq

Substituted compounds derived from N-(benzyl)phenylacetamide, preparation and uses

This invention relates to poly-substituted derivatives of the N-(benzyl)phenylacetamide type, pharmaceutical compositions comprising same, therapeutic uses thereof, more particularly in the fields of human and animal health. This invention also relates to a process for the preparation of such derivatives.