1700-31-8

Usage

Uses

Used in Organic Synthesis:
3-Benzyloxybenzyl bromide is used as a key intermediate for the synthesis of a wide range of organic compounds. Its reactivity in nucleophilic substitution and Grignard reactions allows for the efficient construction of complex molecular structures, facilitating the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Benzyloxybenzyl bromide is utilized as a building block for the development of new drugs. Its ability to undergo various chemical transformations makes it a valuable component in the synthesis of bioactive molecules with potential therapeutic applications.
Used in Agrochemical Industry:
3-Benzyloxybenzyl bromide is employed as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its versatility in organic reactions enables the creation of novel compounds with improved efficacy and selectivity in controlling pests and weeds.
Used in Laboratory Research and Development:
3-Benzyloxybenzyl bromide is a popular substrate in laboratory research and development due to its potential applications in the production of aromatic compounds. Researchers leverage its reactivity in various chemical reactions to explore new synthetic routes and develop innovative methodologies in organic chemistry.

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

Upstream product

• 1700-30-7 (3-(benzyloxy)phenyl)methanol 
• 100-83-4 meta-hydroxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 620-24-6 3-Hydroxybenzyl alcohol 

Downstream Products

• 69944-62-3 2-Amino-2-(3-benzyloxy-benzyl)-but-3-enoic acid methyl ester 
• 122488-18-0 [9-(3-Benzyloxy-benzyl)-2-trifluoromethyl-9H-purin-6-yl]-dimethyl-amine 
• 96995-01-6 (+/-)-trans-2-(3-benzyloxybenzyl)-3-<3-benzyloxy-α,α-bis(phenylthio)benzyl>butyrolactone 
• 135203-60-0 diethyl <(3-benzyloxyphenyl)methyl>phosphonate 
• 158665-01-1 (3R,4R,5R)-3-<(3-(3-Benzyloxy)phenyl)methyl>-4-<(3-(benzyloxy)phenyl)bis(phenylthio)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone 
• 57099-27-1 3-Benzyloxyphenylnitromethan 
• 1860-58-8 3-benzyloxyphenylacetic acid 
• 216491-37-1 (2R,4S)-3-Benzoyl-4-(3-benzyloxy-benzyl)-4-methyl-2-phenyl-oxazolidin-5-one 
• 247186-19-2 (2S,5R)-2-(3-benzyloxybenzyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine 
• 814920-59-7 4-(3-benzyloxybenzyloxy)benzoic acid methyl ester 
• 286459-64-1 (1R,3S)-1-(m-benzyloxybenzyl)-2-pivaloyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 

Relevant academic research and scientific papers

Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

Fused pyrimidine derivatives substituted with a nitrogen-containing heterocyclic ring and their pharmaceutical use

The present application relates to fused pyrimidine derivatives substituted with heterocycles containing nitrogen and to their medicinal use. Provided are a compound represented by chemical formula I, a solvate, a stereoisomer thereof, a pharmaceutically

Discovery and optimization of novel N-benzyl-3,6-dimethylbenzo[d]isoxazol-5-amine derivatives as potent and selective TRIM24 bromodomain inhibitors with potential anti-cancer activities

Tripartite motif-containing protein 24 (TRIM24), recognized as an epigenetic reader for acetylated H3K23 (H3K23ac) via its bromodomain, has been closely involved in tumorigenesis or tumor progression of several cancers. Developing inhibitors of TRIM24 is significant for functional studies and drug discovery. Herein, we report the identification, optimization and evaluation of N-benzyl-3,6-dimethylbenzo[d]isoxazol-5-amines as TRIM24 bromodomain inhibitors starting from an in house library screening. Structure-based optimization leads to two potent and selective compounds 11d and 11h in an Alphascreen assay with IC50 values of 1.88 μM and 2.53 μM, respectively. The viability assay demonstrates the great potential of this series of compounds as inhibitors of proliferation of prostate cancer (PC) cells LNCaP, C4-2B. A colony formation assay further supports this inhibitory activity. Compounds 11d and 11h inhibit cell proliferation of other cancer types such as non-small cell lung cancer (NSCLC) cells A549 with IC50 values of 1.08 μM and 0.75 μM, respectively. These data suggests that compounds 11d and 11h are promising lead compounds for further research.

Naturally occurring Batatasins and their derivatives as α-glucosidase inhibitors

Batatasins are endogenous plant hormones found in yams and other related plant species. These plants are widely consumed as botanical dietary supplements in many parts of the world. This study investigated the inhibitory effects and mechanisms of Batatasin I, III, IV, V against α-glucosidase regarding their antidiabetic activities. The results revealed that Batatasin I, III, IV inhibited α-glucosidase in a reversible and noncompetitive manner, with IC50 values of 2.55, 1.89 and 2.52 mM respectively, while Batatasin V completely abolished its inhibitory activity even at the highest concentrations tested. Furthermore, a class of Batatasin-derived compounds with different substitution patterns was synthesized and subjected to the assay to clarify the structure-activity relationships, which suggested that the hydroxyl at the C-2′ position may play a significant role in improving the inhibitory activities. Their probable binding modes and the specificity of the binding sites were studied using molecule docking simulation. It was concluded that Batatasins, especially Batatasin III and IV, are promising α-glucosidase inhibitors, which therefore could be used as functional food to alleviate postprandial hyperglycemia and as potential candidates for the development of antidiabetic agents.

Chemical synthesis and evaluation of 17α-alkylated derivatives of estradiol as inhibitors of steroid sulfatase

Steroid sulfatase (STS) controls the levels of 3-hydroxysteroids available from circulating steroid sulfates in several normal and malignant tissues. This and the known involvement of active estrogens and androgens in diseases such as breast and prostate cancers thus make STS an interesting therapeutic target. Here we describe the chemical synthesis and characterization of an extended series of 17α-derivatives of estradiol (E2) using different strategies. A variant of the samarium-Barbier reaction with stoichiometric samarium metal and catalytic Kagan reagent formation was used for introducing low reactive benzyl substrates in position 17 of estrone (E1) whereas heterocyclic substrates were metalated and reacted with either the carbonyl or the 17-oxirane of E1. In vitro evaluation of the inhibitory potency of the new compounds against STS identified new inhibitors and allowed a more complete structure-activity relationship study of this family of 17α-derivatives of E2.

Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids

A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C-C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 4-8 linear steps using either a Bischler-Napieralski cyclization or a C1-Cα alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 5-9 linear steps.

Synthesis, in silico docking experiments of new 2-pyrrolidinone derivatives and study of their anti-inflammatory activity

A new class of 2-pyrrolidinone derivatives was designed, synthesized, and tested for their antioxidant and anti-inflammatory activities. The compounds were evaluated for their inhibitory activity against LOX. The most potent among them, 14d [IC50 0.08 (±0.005) mM], and 14e [IC50 0.0705 (±0.003) mM], were also tested in vivo. The compound 14d induced equipotent inhibition against rat paw edema, which is very close to the effect produced by the commonly used standard, namely indomethacin (47%). The LOX inhibitory activity of the compound 14e proceeds in parallel to the % inhibitory value of lipid peroxidation meaning that this LOX inhibitory activity is supported by the lipid peroxidation inhibition. The molecular features that govern their bioactivity were explored through in silico docking experiments. The results showed that acidic moieties must be placed in certain distance and orientation in the active site of LOX enzyme in order to productively exhibit inhibitory activity. In addition, the 2-pyrrolidinone template significantly contributes in the inhibitory properties of the new compounds.

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.

Microwave-assisted cleavage of phosphate, phosphonate and phosphoramide esters

A mild and rapid protocol for cleavage of phosphate, phosphonate and phosphoramide esters. The scope and limitations of this microwave-assisted reaction is explored here.

MACROCYCLIC TERTIARY AMINE BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE

The present invention is directed to macrocyclic tertiary amine compounds represented by general formula (I), which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.