433969-27-8

Basic information

• Product Name: 2-BOC-AMINOMETHYL-PHENYLBORONIC ACID
• Synonyms: 2-BOC-AMINOMETHYL-PHENYLBORONIC ACID;(2-{[(TERT-BUTOXYCARBONYL)AMINO]METHYL}PHENYL)BORONIC ACID;2-(tert-Butoxycarbonyl)benzylamineboronic acid
• CAS NO: 433969-27-8
• Molecular Formula: C₁₂H₁₈BNO₄
• Molecular Weight: 251.09
• Product Categories: Boronate Ester;Boronic Acid;Potassium Trifluoroborate
• Mol File: 433969-27-8.mol

Chemical Properties

• Melting Point: 190-192 °C
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 8.53±0.53(Predicted)
• CAS DataBase Reference: 2-BOC-AMINOMETHYL-PHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BOC-AMINOMETHYL-PHENYLBORONIC ACID(433969-27-8)
• EPA Substance Registry System: 2-BOC-AMINOMETHYL-PHENYLBORONIC ACID(433969-27-8)

Safety Data

• Hazardous Substances Data: 433969-27-8(Hazardous Substances Data)

Usage

Uses

Used in Materials Science:
2-BOC-AMINOMETHYL-PHENYLBORONIC ACID is used as a building block for the synthesis of new materials, taking advantage of its phenylboronic acid structure and the reactivity of the BOC amino group.
Used in Medicinal Chemistry:
2-BOC-AMINOMETHYL-PHENYLBORONIC ACID is used as a key intermediate in the synthesis of pharmaceutical compounds, where the BOC protecting group can be selectively removed to reveal the desired amine functionality, facilitating the formation of various drug molecules.
Used in Palladium-Catalyzed Processes:
2-BOC-AMINOMETHYL-PHENYLBORONIC ACID is used as a reagent or ligand in palladium-catalyzed cross-coupling reactions, contributing to the formation of carbon-carbon or carbon-heteroatom bonds in the synthesis of complex organic molecules.
Used in Research Procedures:
2-BOC-AMINOMETHYL-PHENYLBORONIC ACID is used as a research tool in the development of new synthetic methods, allowing chemists to explore the potential of the BOC protecting group in various chemical transformations and applications.

Upstream product

• 5465-63-4 2-bromobenzylamine hydrochloride 
• 5419-55-6 Triisopropyl borate 
• 162356-90-3 N-(tert-butoxycarbonyl)-2-bromobenzylamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 248274-03-5 2-(aminomethyl)phenylboronic acid 

Downstream Products

• 437988-04-0 tert-Butyl {2-[2-(3-methylbutylcarbamoyl)thiophen-3-yl]benzyl}carbamate 
• 1034110-41-2 ethyl 1-(benzenesulfonyl)-3-[2-(tert-butyloxycarbonylaminomethyl)phenyl]-1H-indole-2-carboxylate 

Relevant articles and documents

Characterization of a novel multifunctional resveratrol derivative for the treatment of atrial fibrillation

Background and Purpose Atrial fibrillation (AF) is the most common cardiac arrhythmia and is associated with an increased risk for stroke, heart failure and cardiovascular-related mortality. Candidate targets for anti-AF drugs include a potassium channel Kv1.5, and the ionic currents I KACh and late INa, along with increased oxidative stress and activation of NFAT-mediated gene transcription. As pharmacological management of AF is currently suboptimal, we have designed and characterized a multifunctional small molecule, compound 1 (C1), to target these ion channels and pathways. Experimental Approach We made whole-cell patch-clamp recordings of recombinant ion channels, human atrial IKur, rat atrial I KACh, cellular recordings of contractility and calcium transient measurements in tsA201 cells, human atrial samples and rat myocytes. We also used a model of inducible AF in dogs. Key Results C1 inhibited human peak and late Kv1.5 currents, frequency-dependently, with IC50 of 0.36 and 0.11 μmol·L-1 respectively. C1 inhibited I KACh (IC50 of 1.9 μmol·L-1) and the Nav1.5 sodium channel current (IC50s of 3 and 1 μmol·L-1 for peak and late components respectively). C1 (1 μmol·L-1) significantly delayed contractile and calcium dysfunction in rat ventricular myocytes treated with 3 nmol·L -1 sea anemone toxin (ATX-II). C1 weakly inhibited the hERG channel and maintained antioxidant and NFAT-inhibitory properties comparable to the parent molecule, resveratrol. In a model of inducible AF in conscious dogs, C1 (1 mg·kg-1) reduced the average and total AF duration. Conclusion and Implications C1 behaved as a promising multifunctional small molecule targeting a number of key pathways involved in AF.

RESVERATROL ANALOGS AND THERAPEUTIC USES THEREOF

Resveratrol analogs and their use to inhibit Kv1.5 channels are provided. The resveratrol analogs are useful in the treatment of atrial arrhythmias, including atrial fibrillation (AF). Exemplary resveratrol analogs are compounds of general Formula (I):

Efficient preparation of 2-aminomethylbiphenyls via suzuki-miyaura reactions

We prepared four 2-(aminomethyl)arylboronic acids and studied their reactivity in the Suzuki-Miyaura coupling reaction with different aryl halides. We observed significant increases in yields and shorter reaction times when the amine adjacent to the boron

New C5-alkylated indolobenzazepinones acting as inhibitors of tubulin polymerization: Cytotoxic and antitumor activities

A series of 5-alkylindolobenzazepin-7-ones was synthesized by Suzuki coupling between 3-iodoindole-2-carboxylates and the appropriate α-alkylbenzylamino α-boronic acids followed by cyclization to the lactam. Derivatives having a linear alkyl chain at C5 were found to be highly cytotoxic to KB cells with IC50 values in the 30-80 nM range. These compounds also inhibited the polymerization of tubulin with IC50's of 1-2 μM. Compound 4f ((S)-5-ethyl) showed comparable antiproliferative activities (IC50's of 30-70 nM) in a variety of cancer cell lines, cell growth being arrested at the G2/M phase. Compound 4f induced apoptosis in a dose-dependent manner in three different cancer cell lines and was shown to affect cell morphology in a manner consistent with its inhibitory action on tubulin polymerization. Using the experimental model of glioma grafted on the chick chorio-allantoic membrane, local treatment with compound 4f markedly reduced tumor progression.

Small molecule thienopyrimidine-based protein tyrosine kinase inhibitors

Various thienopyrimidine-based analog compounds are able to selectively inhibit the Src family of tyrosine kinases. These compounds are useful in the treatment of various diseases including hyperproliferative diseases, hematologic diseases, osteoporosis, neurological diseases, autoimmune diseases, allergic/immunological diseases, or viral infections.

Identification, synthesis, and activity of novel blockers of the voltage-gated potassium channel Kv1.5

The voltage-gated potassium channel Kv1.5 is regarded as a promising target for the development of new atrial selective drugs with fewer side effects. In the present study the discovery of ortho, ortho-disubstituted bisaryl compounds as blockers of the Kv