76243-24-8

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyloxy-2-fluoro-4-nitrobenzene is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its presence in the molecular structure of these compounds contributes to their therapeutic properties, making it an essential component in drug development.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Benzyloxy-2-fluoro-4-nitrobenzene is employed as a precursor in the production of agrochemicals. Its chemical structure allows for the creation of compounds that can be used in pest control and crop protection, thereby enhancing agricultural productivity.
Used in Organic Synthesis:
As a versatile building block, 1-Benzyloxy-2-fluoro-4-nitrobenzene is used in organic synthesis for the creation of a wide range of organic products. Its unique combination of functional groups facilitates various chemical reactions, leading to the formation of complex organic molecules with specific applications in different industries.

Upstream product

• 403-19-0 2-fluoro-4-nitrophenol 
• 100-39-0 benzyl bromide 
• 369-34-6 3,4-difluoronitrobenzene 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 

Downstream Products

• 1256261-50-3 C₁₇H₁₈FN₃O₂S 
• 1256261-51-4 C₁₉H₂₀FN₃O₂S 
• 1256261-52-5 C₁₉H₂₀FN₃O₃S 
• 1256261-41-2 C₁₉H₂₀FN₃OS 
• 1256261-68-3 C₁₄H₁₁FN₂OS 
• 1256261-64-9 C₂₁H₁₇FN₂OS 
• 1256261-60-5 C₂₁H₁₇FN₂O₄S 
• 1256261-56-9 C₂₁H₁₈FNO₂S 
• 790703-40-1 (4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester 
• 790703-49-0 (R)-3-(4-benzyloxy-3-fluoro-phenyl)-5-(hydroxymethyl)-oxazolidin-2-one 

Relevant academic research and scientific papers

Design, synthesis and evaluation of tetrahydrocarbazole derivatives as potential hypoglycemic agents

Two series of tetrahydrocarbazole derivatives have been designed and synthesized based on ZG02, a promising candidate developed in our previous studies. The newly prepared compounds were screened for glucose consumption activity in HepG2 cell lines. Aza-tetrahydrocarbazole compound 12b showed the most potent hypoglycemic activity with a 45% increase in glucose consumption when compared to the solvent control, which had approximately 1.2-fold higher activity than the positive control compounds (metformin and ZG02). An investigation of the potential mechanism indicated that 12b may exhibit hypoglycemic activity via activation of the AMPK pathway. Metabolic stability assays revealed that 12b showed good stability profiles in both artificial gastrointestinal fluids and blood plasma from SD rats. An oral glucose tolerance test (OGTT) was performed and the results further confirmed that 12b was a potent hypoglycemic agent.

Synthesis, antibacterial activities, mode of action and acute toxicity studies of new oxazolidinone-fluoroquinolone hybrids

To combat bacterial resistance, a series of new oxazolidinone-fluoroquinolone hybrids have been synthesized and characterized. All synthetic hybrids were preliminarily evaluated for their in vitro antibacterial activities against 6 standard strains and 3 clinical isolates. The majority of hybrids displayed excellent activities against Gram-positive bacteria, but limited activities against Gram-negative bacteria. Hybrids OBP-4 and OBP-5 were found to be the most promising compounds. Further, in vitro antibacterial activities, mode of action and acute toxicity in mice of hybrids OBP-4 and OBP-5 were investigated. Hybrids OBP-4 and OBP-5 exhibited potent activities against Gram-positive bacteria, including drug-resistant strains. Correspondingly, studies on the mode of action of hybrids OBP-4 and OBP-5 indicated a strong inhibitory activity on protein synthesis by binding the active site of 50S subunit, but a weak inhibitory action on DNA synthesis. In addition, LD50 values of hybrids OBP-4 and OBP-5 in the acute oral toxicity were larger than 2000 mg/kg, suggesting a good safety profile.

Cadazolid key intermediate preparation method

The invention discloses a cadazolid key intermediate preparation method, which comprises: reducing a compound represented by a formula (2) in a solvent in the presence of one or a combination of a metal element-containing compound and a reducing agent to obtain a reaction solution containing a compound represented by a formula (3), and collecting the compound 4-benzyloxy-3-fluoroaniline represented by the formula (3) from the reaction product. According to the present invention, the expensive platinum carbon is replaced with the composition of ferric chloride hexahydrate and hydrazine hydrate,the reducing reaction time is shortened to about 5 h from 48 h, the expensive reducing agent is not required, the reaction time is shortened, and the conversion rate of the raw materials is improved;and the whole route has characteristics of mild reaction, simple operation and low cost, and is suitable for industrial production. The formulas (2) and (3) are defined in the specification.

Exploration of novel pyrrolo[2,1-f][1,2,4]triazine derivatives with improved anticancer efficacy as dual inhibitors of c-Met/VEGFR-2

c-Met and VEGFR-2 have attracted interest as novel targets for treatment of various cancers. Aiming to develop potent dual c-Met and VEGFR-2 inhibitors, a series of pyrrolo[1,2-f][1,2,4]triazine derivatives were designed and synthesized. The majority of target compounds exhibited potent antiproliferative effect against c-Met addictive cancer cell lines with IC50 values ranged from 1.2 to 24.6 nM, especially 27a. In-depth studies demonstrated 27a has great selectivity to c-Met and VEGFR-2, and potent inhibitory activity against them (IC50 of 2.3 ± 0.1 nM and 5.0 ± 0.5 nM). Furthermore, it also showed the highest anticancer activity with IC50 of 0.71 ± 0.16 nM (better than the positive compound) against BaF3-TPR-Met and 37.4 ± 0.311 nM (comparable to the positive compound) against HUVEC-VEGFR2, consistent with that in c-Met sensitive tumor cell lines. Subsequently, physicochemical and pharmacokinetic characterization indicated 27a has favorable druggability and pharmacokinetic properties. Further docking studies suggested a common mode of interaction at the ATP-binding site of c-Met and VEGFR-2, also indicating that 27a was a potential candidate for cancer therapy deserving further study.

Design, synthesis, and biological evaluation of thieno[2,3-d]pyrimidine derivatives as novel dual c-Met and VEGFR-2 kinase inhibitors

Both c-Met and VEGFR-2 are important targets for cancer therapies. Here we report a series of potent dual c-Met and VEGFR-2 inhibitors bearing thieno[2,3-d]pyrimidine scaffold. The cell proliferation assay in vitro demonstrated that most target compounds had inhibition potency both on c-Met and VEGFR-2 with IC50 values in nanomolar range, especially compound 12j and 12m. Based on the further enzyme assay in vitro, compound 12j was considered as the most potent one, the IC50 values of which were 25 nM and 48 nM for c-Met and VEGFR-2, respectively. Following that, we docked the compound 12j with the proteins c-Met and VEGFR-2, and interpreted the SAR of these analogues. All the results indicate that 12j is a dual inhibitors of c-Met and VEGFR-2 that holds promising potential.

Design, synthesis and biological evaluation of 4-aminopyrimidine-5-cabaldehyde oximes as dual inhibitors of c-Met and VEGFR-2

The synergistically collaboration of c-Met/HGF and VEGFR-2/VEGF leads to development of tumor angiogenesis and progression of various human cancers. Therefore, inhibiting both HGF/c-Met and VEGF/VEGFR signaling may provide a novel and effective therapeutic approach for treating patients with abroad spectrum of tumors. Toward this goal, we designed and synthesized a series of derivatives bearing 4-aminopyrimidine-5-cabaldehyde oxime scaffold as potent dual inhibitors of c-Met and VEGFR-2. The cell proliferation assay in vitro demonstrated most target compounds have inhibition potency both on c-Met and VEGFR-2 with IC50values in nanomolar range, especially compound 14i, 18a and 18b. Based on the further enzyme assay in vitro, compound 18a was considered as the most potent one, the IC50s of which were 210?nM and 170?nM for c-Met and VEGFR-2, respectively. Following that, we docked the compound 10 and 18a with the proteins c-Met and VEGFR-2, and interpreted the SAR of these analogs. All the results indicate that 18a is a dual inhibitors of c-Met and VEGFR-2 that holds promising potential.

Synthesis and in vitro anti-hepatitis B virus activity of 1H-benzimidazol-5-ol derivatives

A series of 1H-benzimidazol-5-ol derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in HepG2.2.15 cells. Half of the tested compounds were found to be potent against HBsAg secretion with IC50 values less than 100μmol/L. Compounds 14c, 14d, and 14e showed significant inhibitory activity to the viral antigen HBeAg.

C-MET MODULATORS AND METHODS OF USE

The present invention provides compounds, which have activity for modulating protein kinase enzymatic activity and are potentially useful for modulating cellular activities such as, e.g., proliferation, differentiation, programmed cell death, migration and chemoinvasion. The present invention also provides compositions containing such compounds, and methods for producing and using such compounds and compositions.

Optimization and SAR for dual ErbB-1/ErbB-2 tyrosine kinase inhibition in the 6-furanylquinazoline series

Synthetic modifications on a 6-furanylquinazoline scaffold to optimize the dual ErbB-1/ErbB-2 tyrosine kinase inhibition afforded consistent SAR whereby a 4-(3-fluorobenzyloxy)-3-haloanilino provided the best enzyme potency and cellular selectivity. Changes made to the 6-furanyl group had little impact on the enzyme activity, but appeared to dramatically affect the cellular efficacy. The discovery of lapatinib emerged from this work.

INTERMEDIATE PRODUCTS FOR PRODUCING OXAZOLIDINONE-QUINOLONE HYBRIDS

The invention relates to intermediate products (ZP) for a novel and efficient synthesis of compounds, wherein the pharmacophores of quinolone and oxazolidinone are linked together by means of a chemically stable linker.