55667-12-4

Usage

Uses

Used in Organic Synthesis:
2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene is used as a versatile building block in organic synthesis for the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable reagent for the modification and functionalization of organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene is used as a key intermediate in the development of drugs. Its potential applications include the synthesis of new drug candidates and the modification of existing drugs to improve their efficacy and safety.
Used in Agrochemicals:
2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene is also used in the development of agrochemicals, where it serves as a building block for the synthesis of various agrochemical compounds. Its unique properties make it suitable for the development of new pesticides, herbicides, and other agricultural chemicals.
Used in Materials Science:
In the field of materials science, 2-(Benzyloxy)-4-(bromomethyl)-1-methoxybenzene is used for the synthesis of new materials with specific properties. Its unique structure and reactivity make it a valuable component in the development of advanced materials for various applications, such as polymers, coatings, and adhesives.

InChI:InChI=1/C15H15BrO2/c1-17-14-8-7-13(10-16)9-15(14)18-11-12-5-3-2-4-6-12/h2-9H,10-11H2,1H3

Upstream product

• 1860-60-2 3-benzyloxy-4-methoxy-benzyl alcohol 
• 148235-40-9 3-benzyloxy-4-methoxybenzoic acid benzyl ester 
• 100-39-0 benzyl bromide 
• 4383-06-6 3-hydroxy-4-methoxybenzyl alcohol 
• 621-59-0 isovanillin 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 

Downstream Products

• 909203-44-7 arctigenin 
• 89018-71-3 2-(3-Benzyloxy-4-methoxy-benzyl)-2-(3,4,5-trimethoxy-phenyl)-[1,3]dithiane 
• 93376-04-6 (+/-)-Prestegane B 
• 111959-15-0 (3R^*,4R^*)-3-(3-benzoxy-4-methoxybenzyl)-4-(3-benzoxy-4-methoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 105485-74-3 2-[4-methoxy-3-(phenylmethoxy)phenyl]-1-(3,4,5-trimethoxyphenyl)-ethanone 
• 696664-22-9 2-(3'-benzyloxy-4'-methoxyphenethyl)quinoline 
• 536974-74-0 4-((3-(benzyloxy)-4-methoxybenzyl)(4H-1,2,4-triazol-4-yl)amino)benzonitrile 
• 1256961-73-5 10-(3-benzyloxy-4-methoxybenzyl)-4,5-dichloro-10H-anthracen-9-one 
• 116518-95-7 <3-(benzyloxy)-4-methoxybenzyl>triphenylphosphonium bromide 

Relevant academic research and scientific papers

A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction

The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields.

Repurposing human PDE4 inhibitors for neglected tropical diseases: Design, synthesis and evaluation of cilomilast analogues as Trypanosoma brucei PDEB1 inhibitors

A medicinal chemistry exploration of the human phosphodiesterase 4 (hPDE4) inhibitor cilomilast (1) was undertaken in order to identify inhibitors of phosphodiesterase B1 of Trypanosoma brucei (TbrPDEB1). T. brucei is the parasite which causes African sleeping sickness, a neglected tropical disease that affects thousands each year, and TbrPDEB1 has been shown to be an essential target of therapeutic relevance. Noting that 1 is a weak inhibitor of TbrPDEB1, we report the design and synthesis of analogs of this compound, culminating in 12b, a sub-micromolar inhibitor of TbrPDEB1 that shows modest inhibition of T. brucei proliferation.

Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction

An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.

Design and synthesis of carbon-11-labeled dual aromatase-steroid sulfatase inhibitors as new potential PET agents for imaging of aromatase and steroid sulfatase expression in breast cancer

Aromatase and steroid sulfatase (STS) are particularly attractive targets in the treatment of estrogen-receptor-positive breast cancer and the development of enzyme-based cancer imaging agents for the biomedical imaging technique positron emission tomography (PET). New carbon-11-labeled sulfamate derivatives were first designed and synthesized as potential PET dual aromatase-steroid sulfatase inhibitor (DASSI) radiotracers for imaging of aromatase and STS expression in breast cancer. The target tracers 5-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-[11C]methoxyphenyl sulfamate ([11C]8a) and 4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-[11C]methoxyphenyl sulfamate ([11C]8b) were prepared from their corresponding precursors 5-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-hydroxyphenyl sulfamate (16) and 4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-hydroxyphenyl sulfamate (21) with [11C]CH3OTf under basic conditions through the O-[11C]methylation and isolated by the reversed-phase high pressure liquid chromatography (HPLC) method in 30-45% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The specific activity at end of synthesis (EOS) was 111-185 GBq/μmol.

Dual aromatase-steroid sulfatase inhibitors

By introducting the steroid sulfatase inhibitory pharmacophore into aromatase inhibitor 1 (YM511), two series of single agent dual aromatase-sulfatase inhibitors (DASIs) were generated. The best DASIs in'vitro (JEG-3 cells) are 5, (IC50(aromatase) = 0.82 nM; IC 50(sulfatase) = 39 nM), and 14, (IC50(aromatase) = 0.77 nM; IC50(sulfatase) = 590 nM). X-ray crystallography of 5, and docking studies of selected compounds into an aromatase homology model and the steroid sulfatase crystal structure are presented. Both 5 and 14 inhibit aromatase and sulfatase in PMSG pretreated adult female Wistar rats potently 3 h after a single oral 10 mg/kg dose. Almost complete dual inhibition is observed for 5 but the levels were reduced to 85% (aromatase) and 72% (sulfatase) after 24 h. DASI 5 did not inhibit aldosterone synthesis. The development of a potent and selective DASI should allow the therapeutic potential of dual aromatase-sulfatase inhibition in hormone-dependent breast cancer to be assessed.

Novel 2,7-dialkyl-substituted 5(S)-amino-4(S)-hydroxy-8-phenyl- octanecarboxamide transition state peptidomimetics are potent and orally active inhibitors of human renin

The action of renin is the rate-limiting step of the renin-angiotensin system (RAS), a key regulator of blood pressure. Effective renin inhibitors directly block the RAS entirely at source and, thus, may provide a vital weapon for hypertension therapy. Our efforts toward identifying novel small-molecule peptidomimetic renin inhibitors have resulted in the design of transition-state isosteres such as 1 bearing an all-carbon 8-phenyl-octanecarboxamide framework. Optimization of the extended P3 portion of 1 and extensive P2′ modifications provided analogues with improved in vitro potencies in the presence of plasma. X-ray resolution of rh-renin/38a in the course of SAR work surprisingly unveiled the exploitation of a previously unexplored pocket (S3sp) important for strong binding affinities. Several inhibitors demonstrated oral efficacy in sodium-depleted marmosets. The most potent, 38a, induced dose-dependently a pronounced reduction in mean arterial blood pressure, paralleled by complete blockade of active plasma renin, up to 8 h post-dose. Oral bioavailability of 38a was 16% in marmosets.

The enantioselective total synthesis of alkaloid (-)-galipeine

The first total synthesis of (-)-galipeine was accomplished in seven steps with 54% overall yield from isovanillin based on Ir-catalyzed asymmetric hydrogenation of a quinoline derivative as a key step, with its absolute stereochemistry being established.

Substituted γ-phenyl-Δ-lactams and uses related thereto

γ-Phenyl-substituted Δ-lactams are disclosed. They may be formulated into pharmaceutical compositions, and/or used in the treatment or prevention of inflammation or other conditions or disease states.

Substituted gamma-phenyl-delta-lactams and uses related thereto

gamma-Phenyl-substituted Delta-lactams are disclosed. They may be formulated into pharmaceutical compositions, and/or used in the treatment or prevention of inflammation or other conditions or disease states.