60992-98-5

Usage

Uses

Used in Pharmaceutical Industry:
4'-Fluorobiphenyl-4-carbaldehyde is used as an intermediate for the synthesis of Paroxetine, a selective serotonin reuptake inhibitor (SSRI) commonly prescribed for the treatment of depression, anxiety, and other mood disorders. Its unique structure allows for the development of Paroxetine-related compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, 4'-Fluorobiphenyl-4-carbaldehyde serves as a valuable building block for the creation of more complex molecules. Its reactivity and functional groups make it a versatile compound for use in the synthesis of various organic compounds, including those with potential applications in materials science, pharmaceuticals, and other industries.
Chemical Properties:
The chemical properties of 4'-Fluorobiphenyl-4-carbaldehyde are not provided in the materials. However, based on its structure, it can be inferred that the compound may exhibit reactivity typical of aromatic compounds, such as electrophilic substitution and nucleophilic addition reactions. The presence of the fluorine atom and the formyl group may also influence its reactivity and the types of reactions it can undergo.

Upstream product

• 176913-70-5 bis(4-fluorophenyl)(hydroxy)borane 
• 1122-91-4 4-bromo-benzaldehyde 
• 398-21-0 4-bromo-4'-fluorobiphenyl 
• 598-30-1 sec.-butyllithium 
• 1765-93-1 4-fluoroboronic acid 
• 42030-76-2 4-((4,6-dimethoxy-1,3,5-triazin-2-yl)oxy)benzaldehyde 
• 87199-17-5 4-formylphenylboronic acid, 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1643-96-5 7-(4-fluorophenyl)cyclohepta-1,3,5-triene 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 128376-64-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 189254-48-6 (C₆H₄F)2BOCH(CH₃)2 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 776291-03-3 (4'-fluoro-[1,1'-biphenyl]-4-yl)methanamine 
• 1149337-48-3 (Z)-3-cyclohexyl-5-[(4'-fluorobiphenyl-4-yl)methylene]-2-thioxothiazolidin-4-one 
• 1401624-51-8 N'-((4'-fluorobiphenyl-4-yl)methyl)sulfonyl hydrazide 
• 1401624-52-9 C₂₂H₂₄FNO₄ 
• 1401624-53-0 (1R,2R)-methyl 1-amino-2-(4-fluorobipheny-4-yl)cyclopropanecarboxylate 
• 1401624-54-1 (1R,2R)-methyl 1-((S)-2-(tert-butoxycarbonylamino)butanamido)-2-(4'-fluorobiphenyl-4-yl)cyclopropanecarboxylate 
• 1401624-55-2 tert-butyl (S)-1-((1R,2R)-1-carbamoyl-2-(4'-fluorobiphenyl-4-yl)cyclopropylamino)-1-oxobutan-2-ylcarbamate 
• 1401624-57-4 tert-butyl (S)-1-((1R,2R)-1-cyano-2-(4'-fluorobiphenyl-4-yl)cyclopropylamino)-1-oxobutan-2-ylcarbamate 
• 1401624-20-1 (S)-2-amino-N-((1R,2R)-1-cyano-2-(4'-fluorobiphenyl-4-yl)cyclopropyl)butanamide 
• 1201662-24-9 N-(3-((3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxyphenylsulfonamido)methyl)benzyl)-N-isobutyl-6-(piperidin-1-yl)nicotinamide 
• 1201662-34-1 N-(3-((3-(biphenyl-2-yl)-1-isobutylureido)methyl)benzyl)-3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxybenzenesulfonamide 
• 1201662-23-8 N-(3-((3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxyphenylsulfonamido)methyl)benzyl)-N-isobutyl-2-phenoxybenzamide 
• 1201662-33-0 3,5-dichloro-N-(3-((3-(2,3-dichlorophenyl)-1-isobutylureido)methyl)benzyl)-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxybenzenesulfonamide 
• 1201663-74-2 tert-butyl 3-((3,5-dichloro-N-((4'-fluorobiphenyl-4-yl)methyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate 

Relevant academic research and scientific papers

Desleucyl-Oritavancin with a Damaged d -Ala- d -Ala Binding Site Inhibits the Transpeptidation Step of Cell-Wall Biosynthesis in Whole Cells of Staphylococcus aureus

We have used solid-state nuclear magnetic resonance to characterize the exact nature of the dual mode of action of oritavancin in preventing cell-wall assembly in Staphylococcus aureus. Measurements performed on whole cells labeled selectively in vivo have established that des-N-methylleucyl-N-4-(4-fluorophenyl)benzyl-chloroeremomycin, an Edman degradation product of [19F]oritavancin, which has a damaged d-Ala-d-Ala binding aglycon, is a potent inhibitor of the transpeptidase activity of cell-wall biosynthesis. The desleucyl drug binds to partially cross-linked peptidoglycan by a cleft formed between the drug aglycon and its biphenyl hydrophobic side chain. This type of binding site is present in other oritavancin-like glycopeptides, which suggests that for these drugs a similar transpeptidase inhibition occurs.

A novel one-pot synthesis of biaryl derivatives by sequential strategies via Suzuki coupling/Knoevenagel condensation in aqueous medium at room temperature

A novel one-pot synthesis of biaryl derivatives has been developed starting from bromobenzaldehyde and phenylboronic acid in the presence of activated methylene compounds via sequential Suzuki coupling/Knoevenagel condensation in aqueous isopropanol medium at room temperature. Significantly, this strategy afforded a straightforward and efficient approach to construct original biaryls in which a new carbon double bond bound to activated moieties such as nitrile, ester and amide is formed from three simple substrates in a one-pot procedure. Moreover, a wide scope of substrates could effectively participate in the process affording the target products in moderate to excellent yields. Copyright

Pd(II)-Mediated C?H Activation for Cysteine Bioconjugation

Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition-metal mediated bioconjugation chemistry involves the use of Pd(II) complexes prepared via an oxidative addition process. Herein, the preparation of Pd(II) complexes for cysteine bioconjugation via a facile C?H activation process is reported. These complexes show bioconjugation efficiency competitive with what is seen in the current literature, with a user-friendly synthesis, common Pd(II) sources, and a more cost-effective ligand. Furthermore, these complexes need not be isolated, and still achieve high conversion efficiency and selectivity of a model peptide. These complexes also demonstrate the ability to selectively arylate a single surface cysteine residue on a model protein substrate, further demonstrating their utility.

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo

The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiology approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, A23 was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury.

KDS2010, a Newly Developed Reversible MAO-B Inhibitor, as an Effective Therapeutic Candidate for Parkinson’s Disease

Monoamine oxidase-B (MAO-B) is a well-established therapeutic target for Parkinson’s disease (PD); however, previous clinical studies on currently available irreversible MAO-B inhibitors have yielded disappointing neuroprotective effects. Here, we tested the therapeutic potential of KDS2010, a recently synthesized potent, selective, and reversible MAO-B inhibitor in multiple animal models of PD. We designed and synthesized a series of α-aminoamide derivatives and found that derivative KDS2010 exhibited the highest potency, specificity, reversibility, and bioavailability (> 100%). In addition, KDS2010 demonstrated significant neuroprotective and anti-neuroinflammatory efficacy against nigrostriatal pathway destruction in the mouse MPTP model of parkinsonism. Treatment with KDS2010 also alleviated parkinsonian motor dysfunction in 6-hydroxydopamine-induced and A53T mutant α-synuclein overexpression rat models of PD. Moreover, KDS2010 showed virtually no toxicity or side effects in non-human primates. KDS2010 could be a next-generation therapeutic candidate for PD.

COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF TUMORS

The present invention relates to compounds of Formula (Ia) or pharmaceutically acceptable salts, hydrates, solvates, clathrates, polymorphs, stereoisomers thereof. It further discloses a pharmaceutical composition comprising compounds of Formula (Ia) and the use of compounds of Formula (Ib), in particular for the use in the treatment of diseases or disorders wherein disrupting Rad51-BRCA2 interaction is beneficial.

Method for synthesizing biphenyl compound by taking suaeda salsa extract liquor as solvent

The invention discloses a method for synthesizing a biphenyl compound by using suaeda salsa extract as a solvent in the technical field of organic chemical synthesis, which comprises the following steps: roasting suaeda salsa in a muffle furnace to obtain ash, dissolving the ash in distilled water, refluxing, cooling the solution, and filtering to obtain a faint yellow solution which is the suaedasalsa extract liquor; sequentially adding 1mmol of aryl halide, 1.1mmol of arylboronic acid, 0.001mmol to 0.01mmol of a catalyst and 4ml of the suaeda salsa extract liquor into a round-bottom flask,stirring at 100 DEG C to react for 2 hours, cooling the reactant to room temperature, filtering, mixing the obtained filter residue with a palladium catalyst to obtain a mixture; and dissolving the mixture in ethyl acetate, filtering to remove the palladium catalyst, and drying the filtrate by distillation to obtain the biphenyl compound. According to the scheme, a phosphine ligand, alkali and anadditive do not need to be added, a Suzuki reaction system with biomass extract as a reaction medium is adopted, and a green, simple, convenient and efficient method is provided for synthesizing biphenyl compounds.

Method for synthesizing biphenyl compound by taking phenol as raw material

The invention discloses a method for synthesizing a biphenyl compound by using phenol as a raw material in the technical field of organic chemical synthesis, which comprises the following steps: carrying out a mixed reaction process on phenol or substituted phenol, alkali and 50-90% ethanol aqueous solution, slowly introducing sulfonyl fluoride gas, and carrying out magnetic stirring reaction at normal temperature for 4-12 hours, adding arylboronic acid, alkali and a palladium catalyst into a round-bottom flask, continuing to react for 6-12 hours at normal temperature, after the reaction is finished, adding a saturated edible salt solution into the round-bottom flask, carrying out a water quenching reaction process to obtain a reaction mixture, extracting a reaction product from the reaction mixture by using ethyl acetate, combining organic phases, concentrating filtrate, and separating the concentrated filtrate by using column chromatography to obtain analytically pure biphenyl or terphenyl compounds. By using the method, on one hand, the production cost of the biphenyl compound is reduced, and on the other hand, the method also has a wide application prospect in the aspects of synthesis of natural products, medicines, pesticides, herbicides, polymer conduction materials, liquid crystal materials and the like.

Synthetic Lethality in Pancreatic Cancer: Discovery of a New RAD51-BRCA2 Small Molecule Disruptor That Inhibits Homologous Recombination and Synergizes with Olaparib

Synthetic lethality is an innovative framework for discovering novel anticancer drug candidates. One example is the use of PARP inhibitors (PARPi) in oncology patients with BRCA mutations. Here, we exploit a new paradigm based on the possibility of triggering synthetic lethality using only small organic molecules (dubbed "fully small-molecule-induced synthetic lethality"). We exploited this paradigm to target pancreatic cancer, one of the major unmet needs in oncology. We discovered a dihydroquinolone pyrazoline-based molecule (35d) that disrupts the RAD51-BRCA2 protein-protein interaction, thus mimicking the effect of BRCA2 mutation. 35d inhibits the homologous recombination in a human pancreatic adenocarcinoma cell line. In addition, it synergizes with olaparib (a PARPi) to trigger synthetic lethality. This strategy aims to widen the use of PARPi in BRCA-competent and olaparib-resistant cancers, making fully small-molecule-induced synthetic lethality an innovative approach toward unmet oncological needs.