819058-34-9

Usage

Uses

Used in Pharmaceutical Drug Development:
4-Amino-3-fluorophenylboronic acid, pinacol ester is used as a key intermediate in the synthesis of pharmaceutical compounds. Its boronic acid and amino functional groups facilitate the formation of new bonds and structures, which are essential for creating novel drug molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-Amino-3-fluorophenylboronic acid, pinacol ester is used as a reagent in cross-coupling reactions. These reactions are crucial for constructing complex molecular frameworks that are often found in drug candidates, allowing for the development of new therapeutic agents.
Used in Radiolabeling Techniques:
Due to its fluorinated nature, 4-Amino-3-fluorophenylboronic acid, pinacol ester is used as a precursor for radiolabeling in pharmaceutical research. Radiolabeling is a technique that involves attaching radioactive isotopes to molecules, which can be used to track the distribution and metabolism of drugs in the body, aiding in the understanding of drug pharmacokinetics and pharmacodynamics.
Used in Drug Delivery Systems:
4-Amino-3-fluorophenylboronic acid, pinacol ester can be incorporated into drug delivery systems to improve the bioavailability and metabolic stability of pharmaceutical compounds. Its hydrolyzable pinacol ester group allows for the controlled release of the active pharmaceutical ingredient, potentially enhancing the therapeutic efficacy of the drug.

InChI:InChI=1/C12H17BFNO2/c1-11(2)12(3,4)17-13(16-11)8-5-6-10(15)9(14)7-8/h5-7H,15H2,1-4H3

Upstream product

• 29632-74-4 2-fluro-4-iodoaniline 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 262444-42-8 tert-butyl N-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate 
• 73183-34-3 bis(pinacol)diborane 
• 367-24-8 4-bromo-2-fluoroaniline 
• 2369-13-3 3-fluoro-4-nitroaniline 
• 939968-60-2 2-(3-fluoro-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 209958-42-9 tert-butyl N-(4-bromo-2-fluorophenyl)carbamate 
• 218301-87-2 4-(tert-butoxycarbonylamino)-3-fluorophenylboronic acid 
• 348-54-9 2-Fluoroaniline 

Downstream Products

• 1013403-80-9 4-(4-amino-3-fluorophenyl)-2-(2-difluoromethylbenzimidazol-1-yl)-6-morpholinopyrimidine 
• 1363568-77-7 di(tert-butyl) [5-({[(4-{6-(ethylamino)-5-[(2-hydroxyethyl)carbamoyl]pyridin-2-yl}-2-fluorophenyl)carbamoyl]amino}methyl)pyridin-2-yl]imidodicarbonate 
• 1246494-52-9 6-{4-[3-(6-aminopyridin-3-ylmethyl)ureido]-3-fluorophenyl}-2-ethylamino-N-(2-hydroxyethyl)nicotinamide 
• 1246494-92-7 6-(4-{[({6-[(bis-tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)carbamoyl]amino}-3-fluorophenyl)-2-(ethylamino)nicotinic acid 
• 1246494-87-0 6-(4-amino-3-fluorophenyl)-2-ethylamino-N-[2-(piperidin-1-yl)ethyl]nicotinamide 
• 1408088-31-2 2-fluoro-N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 1565857-77-3 (2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)trimethylstannane 

Relevant academic research and scientific papers

Discovery of pyrrolo[2,3-d]pyrimidine derivatives as potent Axl inhibitors: Design, synthesis and biological evaluation

Axl has emerged as an attractive target for cancer therapy due to its strong correlation with tumor growth, metastasis, poor survival, and drug resistance. Herein, we report the design, synthesis and structure-activity relationship (SAR) investigation of a series of pyrrolo[2,3-d]pyrimidine derivatives as new Axl inhibitors. Among them, the most promising compound 13b showed high enzymatic and cellular Axl potencies. Furthermore, 13b possessed preferable pharmacokinetic properties and displayed promising therapeutic effect in BaF3/TEL-Axl xenograft tumor model. Compound 13b may serve as a lead compound for new antitumor drug discovery.

Para-Selective, Iridium-Catalyzed C-H Borylations of Sulfated Phenols, Benzyl Alcohols, and Anilines Directed by Ion-Pair Electrostatic Interactions

Para C-H borylations (CHB) of tetraalkylammonium sulfates and sulfamates have been achieved using bipyridine-ligated Ir boryl catalysts. Selectivities can be modulated by both the length of the alkyl groups in the tetraalkylammonium cations and the substituents on the bipyridine ligands. Ion pairing, where the alkyl groups of the cation shield the meta C-H bonds in the counteranions, is proposed to account for para selectivity. The 4,4′-dimethoxy-2,2′-bipyridine ligand gave superior selectivities.

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.

NOVEL COMPOUNDS AS REARRANGED DURING TRANSFECTION (RET) 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.

Synthesis of trimethylstannyl arylboronate compounds by sandmeyer-type transformations and their applications in chemoselective cross-coupling reactions

A synthetic method based on Sandmeyer-type reactions to access both tin- and boron-substituted arenes from nitroaniline derivatives is described. This transformation can be applied to the synthesis of a series of functionalized trimethylstannyl arylboronates. In addition, the chemoselective reaction of the Stille and Suzuki-Miyaura cross-coupling reactions is explored, and a series of m- and p-terphenyl derivatives have been synthesized by conducting consecutive one-pot Stille and Suzuki-Miyaura cross-coupling reactions.

ARYLSULFONAMIDE PYRIDINE-PYRIDINONE DERIVATIVES, PREPARATION OF SAME, AND THERAPEUTIC USE THEREOF

The invention relates to pyridine-pyridinone derivatives general formula (I): in which R1, R2, R3, R4, n, n′, V, W, Y, Z, Ar are as defined in the description, and to their methods of preparation and their therapeutic applications.

Substituted sulphoximines as Tie2 inhibitors and salts thereof, pharmaceutical compositions comprising the same, methods of preparing the same and uses of the same

The invention relates to substituted sulphoximines according to the general formula (I): in which A, E, G, X, R1, R2, R3, R4, R5, R6, R7, R8, m, p, q, are given in the

2-BENZIMIDAZOLYL-6-MORPHOLINO-4-PHENYLPYRIMIDINE DERIVATIVES AS PI3K AND MTOR INHIBITORS FOR THE TREATMENT OF PROLIFERATIVE DISORDERS

The invention concerns pyrimidine derivatives of Formula (I), wherein each of p, R1, R2, q, R3, r, R4, X1 and Q1 have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in a method for producing an anti-proliferative effect in a warm blooded animal such as man.

SUBSTITUTED 4-AMINO-PYRROLOTRIAZINE DERIVATIVES USEFUL FOR TREATING HYPER-PROLIFERATIVE DISORDERS AND DISEASES ASSOCIATED WITH ANGIOGENESIS

This invention relates to novel pyrrozolotriazine compounds, pharmaceutical compositions containing such compounds and the use of those compounds and compositions for the prevention and/or treatment of hyper-proliferative disorders and diseases associated with angiogenesis.

SULFONAMIDO-MACROCYCLES AS TIE2 INHIBITORS AND SALTS THEREOF, PHARMACEUTICAL COMPOSITIONS COMPRISING SAME, METHODS OF PREPARING SAME AND USES OF SAME

The invention relates to sulfonamido-macrocycles according to the general formula (I): in which R1, R2, R4, R5, R6, A, B, C, L, X, Y, Z, n, and m are as defined in the claims, and salts, N-oxides, or