5544-60-5

Usage

Uses

Used in Pharmaceutical Industry:
4-BENZYLOXYBENZYL BROMIDE is used as a reactant in the synthesis of many antibacterial drugs. Its unique structure allows it to participate in various chemical reactions, leading to the formation of new compounds with potent antibacterial properties.
Used in Hypolipidemic Agents:
4-BENZYLOXYBENZYL BROMIDE is also used in the development of Ethyl 4-benzyloxybenzoate analogues, which possess hypolipidemic activity. These analogues can help in managing and reducing high levels of lipids in the blood, thus contributing to the treatment and prevention of cardiovascular diseases.

InChI:InChI=1/C14H13BrO/c15-10-12-6-8-14(9-7-12)16-11-13-4-2-1-3-5-13/h1-9H,10-11H2

Upstream product

• 836-43-1 4-benzyloxybenzyl alcohol 
• 100-39-0 benzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 392717-83-8 1-(benzyloxy)-4-((methoxymethoxy)methyl) benzene 
• 1058648-76-2 1-(benzyloxy)-4-((ethoxymethoxy)methyl) benzene 
• 403986-50-5 (S)-3-{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-pyrrol-1-yl-propionic acid methyl ester 
• 100-44-7 benzyl chloride 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 56441-55-5 ethyl 4-(benzyloxy)benzoate 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 623-05-2 (4-hydroxyphenyl)methanol 

Downstream Products

• 69944-61-2 2-Amino-2-(4-benzyloxy-benzyl)-but-3-enoic acid methyl ester 
• 74649-77-7 methyl 2-methoxy-3-(4-benzyloxy)phenylpropionate 
• 109687-59-4 3-(phenylseleno)-4-<(4-phenylmethoxy)phenyl>butene 
• 124921-30-8 1-(4-(benzyloxy)benzyl)-1-cyano-5-methoxy-1,2,3,4-tetrahydronaphthalene 
• 81625-40-3 1-<4-(benzyloxy)benzyl>-2-(4-tert-butylbenzoyl)-8-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 84293-24-3 N-(3-benzyloxy-4-methoxybenzyl)-N-(2-bromoethyl)-4-benzyloxybenzylamine 
• 187872-31-7 4-(4-Benzyloxy-benzyl)-7-nitro-isochroman-3-one 
• 186612-24-8 diethyl 2,2-bis((4-benzyloxy)benzyl)malonate 
• 217172-40-2 (S)-2-amino-3-(4-benzyloxy-phenyl)-tert-butyl-propionic ester 
• 345269-69-4 2-(4-benzyloxy-benzyl)-2-methyl-malonic acid dimethyl ester 
• 352665-59-9 3-(4-benzyloxy-benzyl)-2-oxo-imidazolidine-1,5-dicarboxylic acid 1-benzyl ester 5-tert-butyl ester 
• 1027921-22-7 2-(benzhydrylidene-amino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester 
• 641611-50-9 1,3-bis-tert-butoxycarbonyl-1-(4'-benzyloxybenzyl)-2-methyl-2-thiopseudourea 

Relevant academic research and scientific papers

Design, Synthesis, and Antimicrobial Evaluation of a Novel Bone-Targeting Bisphosphonate-Ciprofloxacin Conjugate for the Treatment of Osteomyelitis Biofilms

Osteomyelitis is a major problem worldwide and is devastating due to the potential for limb-threatening sequelae and mortality. Osteomyelitis pathogens are bone-attached biofilms, making antibiotic delivery challenging. Here we describe a novel osteoadsorptive bisphosphonate-ciprofloxacin conjugate (BV600022), utilizing a “target and release” chemical strategy, which demonstrated a significantly enhanced therapeutic index versus ciprofloxacin for the treatment of osteomyelitis in vivo. In vitro antimicrobial susceptibility testing of the conjugate against common osteomyelitis pathogens revealed an effective bactericidal profile and sustained release of the parent antibiotic over time. Efficacy and safety were demonstrated in an animal model of periprosthetic osteomyelitis, where a single dose of 10 mg/kg (15.6 μmol/kg) conjugate reduced the bacterial load by 99% and demonstrated nearly an order of magnitude greater activity than the parent antibiotic ciprofloxacin (30 mg/kg, 90.6 μmol/kg) given in multiple doses. Conjugates incorporating a bisphosphonate and an antibiotic for bone-targeted delivery to treat osteomyelitis biofilm pathogens constitute a promising approach to providing high bone-antimicrobial potency while minimizing systemic exposure.

Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors

(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is

Application of gastrodia elata bl derived derivative to preparation of medicine for treating acute or chronic pain

The invention discloses application of gastrodia elata bl derived derivatives to preparation of a medicine for treating the acute or chronic pain, in particular to compounds as shown in general formulas (I), (II) and (III) and application of pharmaceutically acceptable salt thereof to preparation of the medicine for preventing and/or treating the acute or chronic pain, discloses a preparation method of the compounds, and belongs to the technical field of medicine.

Application of gastrodia elata bl derived derivatives to preparation of medicine for treating Inflammatory Bowel disease (IBD)

The invention discloses compounds as shown in general formulas (I) and (II) and application of pharmaceutically acceptable salt thereof to preparation of a medicine for treating the Inflammatory Boweldisease (IBD), and discloses a preparation method of the compounds.

New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents

A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion

The ability to manipulate C-C bonds for selective chemical transformations is challenging and represents a growing area of research. Here, we report a formal insertion of diazo compounds into the "unactivated"C-C bond of benzyl bromide derivatives catalyzed by a simple Lewis acid. The homologation reaction proceeds via the intermediacy of a phenonium ion, and the products contain benzylic quaternary centers and an alkyl bromide amenable to further derivatization. Computational analysis provides critical insight into the reaction mechanism, in particular the key selectivity-determining step.

BONE TARGETED ANTIMICROBIAL OXAZOLIDINONE RELATED COMPOUNDS, FORMULATIONS THEREOF, AND USES THEREOF

Described herein are bisphosphonate oxazolidinone compounds, and conjugates and pharmaceutical formulations thereof, that can include a bisphosphonate and an oxazolidinone (or an oxazolidinone antimicrobial or antibiotic agent, substituent or derivative thereof), where the oxazolidinone can be releasably coupled to the bisphosphonate. Also provided herein are methods of making and methods of using the bisphosphonate oxazolidinone compounds, conjugates and pharmaceutical formulations thereof. Also provided herein are methods of use of the compounds, conjugates and formulations for treating a bone disease or for use in preparing a formulation for the treatment a bone disease.

Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers

A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation.

BISPHOSPHONATE QUINOLONE CONJUGATES AND USES THEREOF

Described herein are bisphosphonate quinolone conjugates and pharmaceutical formulations thereof that can include a bisphosphonate and a quinolone, where the quinolone can be releasably coupled to the bisphosphonate. Also provided herein are methods of making and methods of using the bisphosphonate quinolone conjugates and pharmaceutical formualtions thereof.

Complete synthesis method of natural product Nostosin B

The invention discloses a complete synthesis method of a natural product Nostosin B, and belongs to the technical field of organic synthesis. According to the synthesis method, complete synthesis of the natural product Nostosin B is completed by natural amino acid L-isoleucine, arginine and a non-natural compound 2 which are cheap and easy to obtain through peptide coupling and using of various of functional group protecting groups. The natural product Nostosin B is prepared through the complete synthesis method for the first time. The synthesis method has the advantages of being simple, convenient, feasible, easy to operate and high in yield.