872459-87-5

Basic information

• Product Name: 4-Fluoro-3-methoxycarbonylphenylboronic acid pinacol ester
• Synonyms: 4-Fluoro-3-methoxycarbonylphenylboronic acid pinacol ester
• CAS NO: 872459-87-5
• Molecular Formula: C₁₄H₁₈BFO₄
• Molecular Weight: 298.1150032
• Mol File: 872459-87-5.mol

Chemical Properties

• Boiling Point: 368.5±37.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-Fluoro-3-methoxycarbonylphenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-3-methoxycarbonylphenylboronic acid pinacol ester(872459-87-5)
• EPA Substance Registry System: 4-Fluoro-3-methoxycarbonylphenylboronic acid pinacol ester(872459-87-5)

Safety Data

• Hazardous Substances Data: 872459-87-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoro-3-methoxycarbonylphenylboronic acid pinacol ester is used as a synthetic intermediate for the preparation of biphenyl pyridazinone derivatives, which are inhaled PDE4 inhibitors. These inhibitors play a crucial role in structural biology and structure-activity relationship studies, aiding in the development of novel therapeutic agents for the treatment of various diseases, such as chronic obstructive pulmonary disease (COPD) and other inflammatory conditions.
Additionally, this compound may also be utilized in other industries for different applications, such as in the synthesis of advanced materials, agrochemicals, or as a research tool in academic and industrial laboratories. However, the specific uses in these industries are not provided in the given materials.

Upstream product

• 57381-59-6 methyl 2-fluoro-5-bromobenzoate 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Relevant articles and documents

Biphenyl Pyridazinone Derivatives as Inhaled PDE4 Inhibitors: Structural Biology and Structure-Activity Relationships

Cyclic nucleotide cAMP is a ubiquitous secondary messenger involved in a plethora of cellular responses to biological agents involving activation of adenylyl cyclase. Its intracellular levels are tightly controlled by a family of cyclic nucleotide degrading enzymes, the PDEs. In recent years, cyclic nucleotide phosphodiesterase type 4 (PDE4) has aroused scientific attention as a suitable target for anti-inflammatory therapy in respiratory diseases, particularly in the management of asthma and COPD. Here we describe our efforts to discover novel, highly potent inhaled inhibitors of PDE4. Through structure based design, with the inclusion of a variety of functional groups and physicochemical profiles in order to occupy the solvent-filled pocket of the PDE4 enzyme, we modified the structure of our oral PDE4 inhibitors to reach compounds down to picomolar enzymatic potencies while at the same time tackling successfully an uncovered selectivity issue with the adenosine receptors. In vitro potencies were demonstrated in a rat lung neutrophilia model by administration of a suspension with a Penn-Century MicroSprayer Aerosolizer.

Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): New electrophilic coupling partners for room temperature Suzuki-Miyaura cross-coupling reactions

The first cross-coupling reaction between aryl/heteroaryl pentafluorobenzenesulfonates and aryl/heteroaryl boronic acids under mild conditions is described. The successful synthesis of highly ortho substituted biaryls and high chemoselectivity of these bench stable intermediates over tosylates, triflates, mesylates, and chlorides increases its scope as a valuable cross-coupling partner. The generality of this protocol was further extended to other boron containing nucleophiles (boronates, trifluoroborates) and alkyl boronic acids.

(3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors

New (3-oxo)pyridazin-4-ylurea derivatives having the chemcial structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of the phosphodiesterase IV (PDE4).

Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity

The present invention is directed to compounds of the formula I: Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, X, n and the broken lines are as defined herein which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.

SIX-MEMBERED HETEROCYCLES USEFUL AS SERINE PROTEASE INHIBITORS

The present invention provides compounds of Formula (I) or a stereoisomer or pharmaceutically acceptable salt or solvate form thereof, wherein the variables A, L, Z, X1, X2, X3, X4, and X5 are as defined herein. The compounds of Formula (I) are useful as selective inhibitors of serine protease enzymes of the coagulation cascade and/or contact activation system; for example thrombin, factor Xa, factor XIa, factor IXa, factor VIIa and/or plasma kallikrein. In particular, it relates to compounds that are selective factor XIa inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.