1415960-53-0

Basic information

• Product Name: [2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester
• Synonyms: methyl 2-(2-fluoro-4-(4,4 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate;3-Fluoro-4-(methoxycarbonylmethyl)benzeneboronic acid pinacol ester
• CAS NO: 1415960-53-0
• Molecular Formula: C₁₅H₂₀BFO₄
• Molecular Weight: 294.13
• EINECS: -0
• Mol File: 1415960-53-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /Solid
• CAS DataBase Reference: [2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester(1415960-53-0)
• EPA Substance Registry System: [2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester(1415960-53-0)

Safety Data

• Hazardous Substances Data: 1415960-53-0(Hazardous Substances Data)

Usage

Description

[2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester is a complex organic compound that features an ester derivative of acetic acid with a fluorine atom and a boron-containing heterocycle. This unique structure endows the compound with a range of chemical properties that make it valuable in various applications within organic synthesis and medicinal chemistry.

Uses

Used in Organic Synthesis:
[2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester is used as a catalyst or reagent in organic reactions due to the distinctive properties provided by the boron-containing group and the fluorine atom. Its ability to participate in various chemical transformations makes it a versatile tool in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the pharmaceutical industry, [2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester is used as a building block for the synthesis of more complex organic molecules with potential therapeutic applications. Its structural features may contribute to the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Research and Development:
[2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester is also utilized in research settings to explore its chemical reactivity and potential interactions with other molecules. Researchers and chemists are interested in its properties to further understand its behavior in different chemical environments and to discover new applications in both chemical and pharmacological fields.

Upstream product

• 76283-09-5 4-bromo-2-fluorobenzyl bromide 
• 114897-91-5 (4-bromo-2-fluorophenyl)acetonitrile 
• 114897-92-6 2-(4-bromo-2-fluoro-phenyl)acetic acid 
• 193290-19-6 methyl 2-(4-bromo-2-fluoro-phenyl)acetate 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1431546-20-1 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid 
• 1431546-23-4 C₃₁H₄₂BFN₂O₅ 

Relevant articles and documents

Discovery of a First-in-Class Gut-Restricted RET Kinase Inhibitor as a Clinical Candidate for the Treatment of IBS

Abdominal pain and abnormal bowel habits represent major symptoms for irritable bowel syndrome (IBS) patients that are not adequately managed. Although the etiology of IBS is not completely understood, many of the functions of the gastrointestinal (GI) tract are regulated by the enteric nervous system (ENS). Inflammation or stress-induced expression of growth factors or cytokines may lead to hyperinnervation of visceral afferent neurons in GI tract and contribute to the pathophysiology of IBS. Rearranged during transfection (RET) is a neuronal growth factor receptor tyrosine kinase critical for the development of the ENS as exemplified by Hirschsprung patients who carry RET loss-of-function mutations and lack normal colonic innervation leading to colonic obstruction. Similarly, RET signaling in the adult ENS maintains neuronal function by contributing to synaptic formation, signal transmission, and neuronal plasticity. Inhibition of RET in the ENS represents a novel therapeutic strategy for the normalization of neuronal function and the symptoms of IBS patients. Herein, we describe our screening effort and subsequent structure-activity relationships (SARs) in optimizing potency, selectivity, and mutagenicity of the series, which led to the discovery of a first-in-class, gut-restricted RET kinase inhibitor, 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide (15, GSK3179106), as a clinical candidate for the treatment of IBS. GSK3179106 is a potent, selective, and gut-restricted pyridone hinge binder small molecule RET kinase inhibitor with a RET IC50 of 0.3 nM and is efficacious in vivo.

PYRIDONE DERIVATIVES AS REARRANGED DURING TRANSFECTION (RET) KINASE INHIBITORS

This invention relates to novel compounds which are inhibitors of the Rearranged during Transfection (RET) kinase, to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in combination, for the normalization of gastrointestinal sensitivity, motility and/or secretion and/or abdominal disorders or diseases and/or treatment related to diseases related to RET dysfunction or where modulation of RET activity may have therapeutic benefit including but not limited to all classifications of irritable bowel syndrome (IBS) including diarrhea-predominant, constipation-predominant or alternating stool pattern, functional bloating, functional constipation, functional diarrhea, unspecified functional bowel disorder, functional abdominal pain syndrome, chronic idiopathic constipation, functional esophageal disorders, functional gastroduodenal disorders, functional anorectal pain, inflammatory bowel disease, proliferative diseases such as non-small cell lung cancer, hepatocellular carcinoma, colorectal cancer, medullary thyroid cancer, follicular thyroid cancer, anaplastic thyroid cancer, papillary thyroid cancer, brain tumors, peritoneal cavity cancer, solid tumors, other lung cancer, head and neck cancer, gliomas, neuroblastomas, Von Hippel-Lindau Syndrome and kidney tumors, breast cancer, fallopian tube cancer, ovarian cancer, transitional cell cancer, prostate cancer, cancer of the esophagus and gastroesophageal junction, biliary cancer, adenocarcinoma, and any malignancy with increased RET kinase activity.

MONOMERS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME

Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. in vivo) to form a multimer, (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding domains on a protein or on different proteins.