87199-15-3

Usage

Uses

Used in Suzuki Reaction:
3-(Hydroxymethyl)phenylboronic acid is used as a reactant in the Suzuki reaction for the formation of carbon-carbon bonds. This reaction is a widely employed cross-coupling process in organic chemistry, allowing the synthesis of biaryl compounds, which are prevalent in pharmaceuticals, agrochemicals, and materials science.
Used in Copper-Mediated Trifluoromethylation:
In the field of organic synthesis, 3-(Hydroxymethyl)phenylboronic acid serves as a reactant for copper-mediated trifluoromethylation. This reaction is crucial for the introduction of the trifluoromethyl group, which is a valuable moiety in medicinal chemistry and has significant effects on the biological activity of molecules.
Used in Copper-Catalyzed Transformations from Arylboronic Acids in Water:
3-(Hydroxymethyl)phenylboronic acid is utilized as a reactant in copper-catalyzed transformations from arylboronic acids in water. These reactions contribute to the development of green chemistry approaches, as they take place in an aqueous medium, reducing the environmental impact of organic synthesis.
Used in Mitsunobu and Amidation Reactions:
3-(Hydroxymethyl)phenylboronic acid is also employed as a reactant in Mitsunobu and amidation reactions with hydroxyphenylamino bromopyrazinecarboxylate. These reactions are essential for the synthesis of complex organic molecules and have applications in the preparation of pharmaceuticals and bioactive compounds.
Used in the Synthesis of Biologically Active Molecules:
3-(Hydroxymethyl)phenylboronic acid is involved in the synthesis of biologically active molecules, such as Mycobacterium tuberculosis H37Rv chorismate mutase inhibitors via Suzuki coupling reactions. These inhibitors are crucial for the development of new antibiotics to combat drug-resistant tuberculosis.
Used in the Synthesis of HIV Protease Inhibitors:
3-(Hydroxymethyl)phenylboronic acid is also used in the synthesis of HIV protease inhibitors with antiviral activity against drug-resistant viruses. The development of such inhibitors is vital for the treatment of HIV/AIDS and addressing the growing issue of drug resistance.
Used in the Synthesis of Pyrrole Derivatives for PDE4B Inhibition:
3-(Hydroxymethyl)phenylboronic acid is employed in the synthesis of pyrrole derivatives, which are used as phosphodiesterase 4B (PDE4B) inhibitors. These inhibitors have potential applications in the treatment of various inflammatory and autoimmune diseases, as well as central nervous system disorders.

InChI:InChI=1/C7H9BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,9-11H,5H2

Upstream product

• 109-72-8 n-butyllithium 
• 121-43-7 Trimethyl borate 
• 15852-73-0 (3-Bromophenyl)methanol 
• 5419-55-6 Triisopropyl borate 
• 103978-12-7 [(3-bromobenzyl)oxy](tert-butyl)dimethylsilane 

Downstream Products

• 939-57-1 (E)-3-(2-methylphenyl)acrylic acid 
• 691407-89-3 [2'-(tert-butyl-diphenyl-silanyloxymethyl)-biphenyl-3-yl]-methanol 
• 346629-86-5 [3-(6-isopropyl-quinolin-8-yl)-phenyl]-methanol 
• 1013099-23-4 8-cyclopentyl-6-(3-(hydroxymethyl)phenyl)-4-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 918309-15-6 tert-butyl (2E)-3-(8-{[(4-tert-butyl-1,3-thiazol-2-yl)amino]carbonyl}-2-[3-(hydroxymethyl)phenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)acrylate 
• 954221-11-5 C₁₁H₉ClN₂O 
• 851229-55-5 7-(3-(hydroxymethyl) phenyl)-1-phenyl-5-trifluoromethylbenzimidazole 

Relevant academic research and scientific papers

Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis

Flow chemistry processes for boronic acid syntheses utilizing lithiation-borylation have been developed. The side reactions in the lithiation step that occur in batch were suppressed, and unstable lithium intermediates were handled safely. Flow technology was applied to several kinds of boronic acid syntheses, and scale-up was successfully conducted to allow kilogram-scale production. Some of the key benefits of flow flash chemistry were utilized, both to avoid side reactions and to enable dianion chemistry that is difficult to perform successfully in batch reactions. The examples showed further perspectives on the utility of flow technologies for process development.

Design and synthesis of novel meta-linked phenylglycine macrocyclic FVIIa inhibitors

Two novel series of meta-linked phenylglycine-based macrocyclic FVIIa inhibitors have been designed to improve the rodent metabolic stability and PK observed with the precursor para-linked phenylglycine macrocycles. Through iterative structure-based design and optimization, the TF/ FVIIa Ki was improved to subnanomolar levels with good clotting activity, metabolic stability, and permeability.

MACROCYCLIC FACTOR VIIA INHIBITORS

The present invention provides compounds of Formula (I) as defined in the specification and compositions comprising any of such novel compounds. These compounds are Factor VIIa inhibitors which may be used as medicaments.

Binding of E-selectin or P-selectin to sialyl Lewisx or sialyl-Lewisa

This invention relates to compounds that inhibit the binding of E-selectin and/or P-selectin to sialyl-Lewisx or sialyl-Lewisa presented on a cell surface having the general structure STR1 wherein X is selected from the group consisting of --(CH2)n CO2 H, --O(CH2)m CO2 H, --(CH2)n O(CH2)m CO2 H, --CONH(CH2)m CO2 H, --CH(OZ)(CO2 H), --CH(Z)(CO2 H), --(CH2)n SO3 H, --(CH2)n PO3 D1 D2, --NH(CH2)m CO2 H, --CONH(CHR6)CO2 H, (1-H-tetrazolyl-5-alkyl-), and --OH; R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, halogen, --OZ, --NO2, --NH2 and --NHZ; R3 is selected from the group consisting of hydrogen, halogen, alkyl, --OZ and --NHZ; R4 is selected from the group consisting of hydrogen, halogen, alkyl, hydroxyl, hydroxyl-O-sulfate and --OZ; R5 is selected from the group consisting of hydroxyl, --CN, --N3, --NH2, --NHNH2, --NE1 E2, --NHE1, --NHCO(CH2)n CO2 H, --S(CH2)m CO2 H and --NHCHNHNH2 ; R6 is selected from the group consisting of hydrogen, alkyl, aralkyl, hydroxyalkyl, aminoalkyl, alkyl carboxylic acid and alkyl carboxamide; wherein n is 0 to 6, m is 1 to 6, p is 0 to 6, b is 0 to 2, Z is alkyl, aryl or aralkyl, D1 and D2 are independantly hydrogen or alkyl, E1 is alkyl or --(CH2)8 CO2 H, and E2 is alkyl, and the pharmaceutically acceptable salts, esters, amides, and prodrugs thereof. This invention also relates to methods of inhibiting the binding of E-selectin and/or P-selectin to sialyl-Lewisx or sialyl-Lewisa presented on a cell surface using said compounds and to pharmaceutically active compositions comprising compounds that inhibit the binding of E-selectin to sialyl-Lewisx and to methods of treatment of septic shock, ARDS, Crohn's disease, chronic inflammatory diseases, such as psoriasis and rheumatoid arthritis, and reperfusion injuries that occur following heart attacks, strokes and organ transplants.