1035266-33-1

Basic information

• Product Name: 3-Cyano-5-methoxyphenylboronic acid,pinacol ester
• Synonyms: 3-Cyano-5-methoxyphenylboronic acid,pinacol ester;3-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
• CAS NO: 1035266-33-1
• Molecular Formula: C₁₄H₁₈BNO₃
• Molecular Weight: 259.11
• Mol File: 1035266-33-1.mol

Chemical Properties

• Boiling Point: 375.7±37.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3-Cyano-5-methoxyphenylboronic acid,pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyano-5-methoxyphenylboronic acid,pinacol ester(1035266-33-1)
• EPA Substance Registry System: 3-Cyano-5-methoxyphenylboronic acid,pinacol ester(1035266-33-1)

Safety Data

• Hazardous Substances Data: 1035266-33-1(Hazardous Substances Data)

Usage

Uses

3-Methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile can be used to treat diseases.

Upstream product

• 473923-96-5 3-chloro-5-methoxybenzonitrile 
• 73183-34-3 bis(pinacol)diborane 
• 1527-89-5 3-methoxybenzonitrile 
• 867366-91-4 3-bromo-5-methoxybenzonitrile 

Downstream Products

• 1268263-05-3 C₂₀H₂₅N₅OS 
• 960589-15-5 (3-cyano-5-methoxyphenyl)boronic acid 
• 33224-19-0 3-methoxy-5-nitrobenzonitrile 

Relevant articles and documents

Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance

Microtubule targeting agents (MTAs) are among the most successful chemotherapeutic drugs, but their efficacy is often limited by the development of multidrug resistance (MDR). Therefore, the development of novel MTAs with the ability to overcome MDR is urgently needed. In this contribution, through modification of the unsymmetric biaryl compounds, we discovered a novel compound dxy-1-175 with potent anti-proliferative activity against cancer cells. Mechanistic study revealed that dxy-1-175 inhibited tubulin polymerization by interacting with the colchicine-binding site of tubulin, which caused cell cycle arrest at G2/M phase. Based on the predicted binding model of dxy-1-175 with tubulin, a series of new 4-benzoylbiphenyl analogues were designed and synthesized. Among them, the hydrochloride compound 12e with improved solubility and good stability in human liver microsome, exhibited the most potent anti-proliferative activity with IC50 value in the low nanomolar range, and markedly inhibited the growth of breast cancer 4T1 xenograft in vivo. Notably, 12e effectively overcame P-gp-mediated MDR and our preliminary data suggested that 12e may not be a substrate of P-glycoprotein (P-gp). Taken together, our study reveals a novel MTA 12e targeting the colchicine-binding site with potent anticancer activity and the ability to circumvent MDR.

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.

(HETERO)ARYL CYCLOPROPYLAMINE COMPOUNDS AS LSD1 INHIBITORS

The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula (I) as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection.

Microwave-assisted, Ir-catalyzed aromatic C-H borylation

One-step conversions of 1,3-disubstituted benzenes to aryl boronates and 2,6-disubstituted pyridines to heteroaryl boronates are described. Microwave heating was used for all reactions. [(COD)Ir(μ-OMe)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine w

Discovery of a series of potent arylthiadiazole H3 antagonists

A series of 2-piperidinopiperidine-5-arylthiadiazoles was synthesized and subjected to a structure-activity relationship (SAR) investigation. The potency of this series was improved to the single digit nanomolar range. The key analogs were shown to be free of P450 issues, and they also maintained good ex vivo activity and brain penetration.

NOVEL 2-AMINO-5, 5-DIARYL-IMIDAZOL-4-ONES

This invention relates to novel compounds having the structural formula (I) below: and to their pharmaceutically acceptable salt, compositions and methods of use. These novel compounds provide a treatment or prophylaxis of cognitive impairment, Alzheimer Disease, neurodegeneration and dementia.