149507-26-6

Usage

Uses

1. Used in Pharmaceutical Industry:
3-Fluoro-4-methoxybenzeneboronic acid is used as a reactant for the preparation of hydroxyphenylnaphthols, which serve as 17β-hydroxysteroid dehydrogenase Type 2 inhibitors. These inhibitors play a crucial role in the development of drugs targeting hormonal imbalances and related conditions.
2. Used in Organic Synthesis:
3-Fluoro-4-methoxybenzeneboronic acid is used as a reagent in regioselective Suzuki coupling reactions. This type of reaction is essential in the formation of carbon-carbon bonds, which are vital in the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals.
3. Used in Catalyst Industry:
3-Fluoro-4-methoxybenzeneboronic acid is also used in ruthenium-catalyzed arylation reactions, which are significant in the synthesis of various organic compounds, including those with potential applications in the pharmaceutical and chemical industries.
4. Used in Anticancer Research:
3-Fluoro-4-methoxybenzeneboronic acid is utilized in the synthesis of amino-trimethoxyphenyl-aryl thiazoles, which have been identified as microtubule inhibitors and potential antitumor agents. These compounds are being investigated for their potential use in the development of novel anticancer drugs.
5. Used in Cyanation Reactions:
3-Fluoro-4-methoxybenzeneboronic acid is employed in rhodium-catalyzed cyanation reactions, which are essential in the synthesis of various organic compounds, including those with potential applications in the pharmaceutical and chemical industries.
6. Used in Petasis Reaction:
3-Fluoro-4-methoxybenzeneboronic acid is also used in the Petasis reaction, a type of chemical reaction that involves the formation of boronic esters from aldehydes and boronic acids. This reaction is crucial in the synthesis of various organic compounds, including those with potential applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C13H10F3NO2/c1-2-19-12(18)10(8-17)7-9-3-5-11(6-4-9)13(14,15)16/h3-7H,2H2,1H3/b10-7+

Upstream product

• 2357-52-0 3-fluoro-4-methoxyphenyl bromide 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 169902-73-2 1-[2-(3-fluoro-4-methoxyphenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene 
• 550998-36-2 3-(3-fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile 
• 858946-64-2 8-fluoro-3-(3-fluoro-4-methoxyphenyl)-7-methoxy-1-naphthonitrile 
• 550998-51-1 8-chloro-3-(3-fluoro-4-methoxyphenyl)-7-hydroxy-1-naphthonitrile 
• 858946-75-5 7-(3-fluoro-4-methoxyphenyl)-3-methoxy-1-naphthonitrile 
• 934690-58-1 4-(3-fluoro-4-methoxy-phenoxy)-benzoic acid ethyl ester 
• 1003298-33-6 3-(3-fluoro-4-methoxy-phenyl)-1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine 
• 934690-70-7 4-(3-fluoro-4-methoxy-phenoxy)-benzoic acid 
• 799765-96-1 4-(3-fluoro-4-methoxyphenyl)-naphthalene-1-carbaldehyde 
• 99452-78-5 3-chloro-6-(3-fluoro-4-methoxy-phenyl)-pyridazine 
• 890021-36-0 5-bromo-2-(3-fluoro-4-methoxyphenyl)pyrimidine 
• 890021-30-4 5-(3-fluoro-4-methoxyphenyl)-3-methyl-2-(methylthio)pyrimidin-4(3H)-one 
• 890021-28-0 2-benzyl-5-(3-fluoro-4-methoxyphenyl)-3-methyl-3H-pyrimidin-4-one 

Relevant academic research and scientific papers

Ligand-Based Design of Nondimethylphenyl-Diarylpyrimidines with Improved Metabolic Stability, Safety, and Oral Pharmacokinetic Profiles

A series of nondimethylphenyl-diarylpyrimidines with much lower cytotoxicities than their dimethyl analogues were developed. Compound B13 with a difluorobiphenyl moiety showed the highest antiviral activity against WT, mutant strains, and RT. The hydrochloride form of B13 exhibited an improved water solubility of 5.6 μg/mL compared with ETR (?1 μg/mL), better stability in human and rat liver microsomes, and a great oral bioavailability of 44%, making it promising as a drug candidate. In addition, no apparent toxicity was observed in the acute toxicity assay (2 g/kg) and HE staining.

Conformational restriction design of thiophene-biphenyl-DAPY HIV-1 non-nucleoside reverse transcriptase inhibitors

Conformational restriction is a promising strategy in the development of DAPY-type non-nucleoside reverse transcriptase inhibitors (NNRTIs). Herein, eighteen thiophene-biphenyl-DAPY derivatives were designed and synthesized as potent HIV-1 NNRTIs in which halogen and methyl groups were introduced to explore the conformationally constrained effects. Molecular docking and dynamic simulation analysis indicated that substituents on different positions of the biphenyl ring induced different dihedral angles and binding conformations, further explaining their anti-viral activities. The 2′-fluoro and 3′-chloro substitutions could form electrostatic or halogen-bonding interactions with adjacent residues of the RT enzyme. The 2′-methyl group contributed to enlarge the dihedral angle of biphenyl ring and was positioned to a space-filling hydrophobic pocket. Notably, compounds 22 and 23 with two methyl groups exhibited potent biological activity against WT HIV-1-infected MT-4 cells (EC50 = 14 and 17 nM, respectively) and RT enzyme (EC50 = 27 and 42 nM, respectively). In particular, 23 exhibited much lower cytotoxicity (CC50 = 264.19 μM) and higher selectivity index (SI = 18,564) than etravirine. Taken together, a rational conformational model for further design of DAPYs is proposed, providing a new guidance for the development of NNRTIs.

HYDROXY-BIPHENYL-CARBALDEHYDE OXIME DERIVATIVES AND THEIR USE AS ESTROGENIC AGENTS

This invention provides estrogen receptor modulators having the structure formula (I): wherein R1 to R6 and R8 are as defined in the specification; or a pharmaceutically acceptable salt thereof.

ERβ ligands. Part 2: Synthesis and structure-activity relationships of a series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives

A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have significant selectivity for the estrogen receptor-β (ERβ). The exploitation of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring of genistein makes these compounds unique. Molecular modeling studies showed the oxime moiety hydrogen bonding to the histidine residue, which was supported by the structure-activity relationships. The most potent compounds in this study had IC50 values in a radioligand binding assay of between 8-35nM. Among the most selective compounds were 6i and 6s (49- and 31-fold ERβ selective, respectively).

ERbeta ligands. Part 1: the discovery of ERbeta selective ligands which embrace the 4-hydroxy-biphenyl template.

The synthesis and structure-activity relationships of a series of simple biphenyls is described. Optimization of the 4-hydroxy-biphenyl template led to compounds with ERbeta selectivity on the order of 20-70-fold.

Substituted phenyl naphthalenes as estrogenic agents

This invention provides estrogen receptor modulators of formula I, having the structure 1wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10, are as defined in the specification, or a pharmaceutically acceptable salt thereof.

Substituted terphenyl compounds for the treatment of inflammation

A class of terphenyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: STR1 wherein each of R2 and R3 is independently selected from hydrido and halo; or wherein R2 and R3 together form --OCH2 O--; wherein each of R6 through R8 is independently selected from hydrido, lower alkyl, halo, lower alkoxy, lower haloalkyl, and lower dialkylamino; or wherein R6 and R7 together form --OCH2 O; and wherein R12 is selected from lower alkylsulfonyl and aminosulfonyl; or a pharmaceutically-acceptable salt thereof.