85604-06-4

Usage

Uses

Used in Pharmaceutical Industry:
5-Benzyloxy-2-bromobenzaldehyde is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex organic molecules that can possess therapeutic effects.
Used in Dye Industry:
In the dye industry, 5-Benzyloxy-2-bromobenzaldehyde is utilized as a precursor in the production of dyes, where its aromatic properties are leveraged to create a range of colorants for different applications.
Used in Organic Synthesis:
5-Benzyloxy-2-bromobenzaldehyde is used as a versatile building block in organic synthesis for the creation of more complex organic molecules, given its aldehyde and aromatic functional groups that facilitate various chemical reactions.
Used in Drug Development:
5-Benzyloxy-2-bromobenzaldehyde is used in drug development as a potential candidate for the development of new drugs and therapies, due to its studied biological and pharmacological properties that may offer novel treatment options.
Used in Research Applications:
In research settings, 5-Benzyloxy-2-bromobenzaldehyde is used as a subject of study to explore its potential applications in various fields, including medicinal chemistry, material science, and the development of new synthetic methodologies.

Upstream product

• 2973-80-0 2-bromo-5-hydroxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 158584-99-7 3-(benzyloxy)-2-bromobenzaldehyde 
• 1084897-39-1 2-bromo-5-benzyloxybenzyl alcohol 

Downstream Products

• 139962-96-2 5-Benzyloxy-2-bromobenzaldehyde diethyl acetal 
• 173427-53-7 2-(5'-benzyloxy-2'-bromophenyl)-1,3-dioxolan 
• 540483-91-8 (E)-3-(5-Benzyloxy-2-bromo-phenyl)-acrylic acid methyl ester 
• 262450-98-6 2-(5-benzyloxy-2-bromophenyl)ethylamine 
• 262451-00-3 N-(5-benzyloxy-2-bromophenethyl)-2-bromo-5-methoxyphenylacetamide 
• 877271-17-5 4-(benzyloxy)-1-bromo-2-vinylbenzene 
• 1135489-96-1 3-(5-(benzyloxy)-2-bromophenyl)-2-cyanoacrylic acid 
• 1084897-39-1 2-bromo-5-benzyloxybenzyl alcohol 
• 1334296-03-5 ethyl N-benzyl-N-[5-(benzyloxy)-2-bromobenzyl]-β-alaninate 
• 1334296-09-1 ethyl 2-benzyl-7-(benzyloxy)-1,2,3,4-tetrahydroisoquinolidine-4-carboxylate 
• 1334295-97-4 N-benzyl-N-[5-(benzyloxy)-2-bromobenzyl]amine 
• 1354364-65-0 1-[5-(benzyloxy)-2-bromophenyl]propan-1-ol 
• 1393462-36-6 (Z)-4-(benzyloxy)-1-bromo-2-(2-bromovinyl)benzene 
• 1393462-37-7 (E)-4-(benzyloxy)-1-bromo-2-(2-bromovinyl)benzene 

Relevant academic research and scientific papers

Access to 6a-Alkyl Aporphines: Synthesis of (±)-N-Methylguattescidine

(-)-N-Methylguattescidine (3) is an alkaloid recently isolated from Fissistigma latifolium and assigned as a rare example of a 6a-alkyl aporphine. Herein, we report the synthesis of (±)-3 and the des-hydroxyl derivative 4 using our previously reported ortho-phenol arylation methodology mediated by the XPhos precatalyst as a key synthetic step. In addition, substituents on the aryl halide portion of the ortho-phenol arylation substrates significantly influenced the formation of an oxidized side product.

High-Throughput Crystallography Reveals Boron-Containing Inhibitors of a Penicillin-Binding Protein with Di- And Tricovalent Binding Modes

The effectiveness of β-lactam antibiotics is increasingly compromised by β-lactamases. Boron-containing inhibitors are potent serine-β-lactamase inhibitors, but the interactions of boron-based compounds with the penicillin-binding protein (PBP) β-lactam targets have not been extensively studied. We used high-throughput X-ray crystallography to explore reactions of a boron-containing fragment set with the Pseudomonas aeruginosa PBP3 (PaPBP3). Multiple crystal structures reveal that boronic acids react with PBPs to give tricovalently linked complexes bonded to Ser294, Ser349, and Lys484 of PaPBP3; benzoxaboroles react with PaPBP3 via reaction with two nucleophilic serines (Ser294 and Ser349) to give dicovalently linked complexes; and vaborbactam reacts to give a monocovalently linked complex. Modifications of the benzoxaborole scaffold resulted in a moderately potent inhibition of PaPBP3, though no antibacterial activity was observed. Overall, the results further evidence the potential for the development of new classes of boron-based antibiotics, which are not compromised by β-lactamase-driven resistance.

Design and synthesis of π-extended resveratrol analogues and in vitro antioxidant and anti-inflammatory activity evaluation

The research on resveratrol (1) has been conducted intensively over a long time due to its proven antioxidant activity and disease-fighting capabilities. Many efforts have also been made to increase these biological effects. In the present study, six new extended aromatic resveratrol analogues containing naphthalene (2) and its bioisosteres quinoline (3 and 4), isoquinoline (5) quinoxaline (6) and quinazoline (7) scaffolds were designed and synthesized using an annulation strategy. The antioxidant and anti-inflammatory activities of these compounds were investigated. All compounds showed better antioxidant activity than resveratrol in ABTS assay. As for the anti-inflammatory test, 5 and 7 exhibited better activity than resveratrol. It is worth noting that nitrogen substitution on the extended aromatic resveratrol analogues has a significant impact on cell viability. Taking the antioxidant activities and NO inhibition activities into consideration, we conclude that isoquinoline analogue 5 may qualify for the further investigation of antioxidant and anti-inflammatory therapy. Furthermore, our study results suggest that in order to improve the biological activity of polyphenolic compounds, extended aromaticity and nitrogen substitution strategy could be a viable method for the design of future drug candidates.

Preparation method of aporphine alkaloid

The invention discloses a preparation method of aporphine alkaloid as shown in a formula III. The method comprises the following steps: taking a benzaldehyde compound as shown in a formula III-0 as a raw material, and sequentially carrying out Wittig reaction, Pictet-Spengler reaction, Heck reaction and palladium carbon hydrogen deprotection. A bromine-containing benzaldehyde derivative is selected as a raw material, the carbon-carbon coupling co-production rate and the reaction rate are increased through bromine atoms, and the reaction activity is improved; benzyl chloroformate is adopted for NH protection, and an electron withdrawing group is introduced, so that the reaction yield can be improved; and a styrene methyl ether derivative directly reacts with an acylated phenylethylamine derivative in an acid catalysis system by adopting a one-pot method so as to obtain benzyl tetrahydroisoquinoline. The preparation method has the advantages of mild reaction conditions, low toxicity of used reagents, easily available raw materials, convenient post-treatment and simpler reaction route compared with previous reports, and can be suitable for various reaction substrates.

1,4-Palladium Shift/C(sp3)-H Activation Strategy for the Remote Construction of Five-Membered Rings

1,n-Metal shift is an elegant alternative approach enabling the functionalization of remote C-H bonds from simple precursors. In this work, we report a novel and simple Pd0-catalyzed domino reaction involving 1,4-palladium shift and C(sp3)-H activation and leading to (fused) five-membered rings. This method allowed access to a broad range of valuable arylidene γ-lactams and indanones and was applied to the formal synthesis of (-)-pyrrolam.

Preparation method for creboro intermediate

The invention discloses a preparation method for a creboro intermediate. The preparation method for the creboro intermediate comprises the following steps that 1, 2-bromo-5-hydroxybenzaldehyde reactswith benzyl chloride or benzyl bromide in an organic solvent (i) under the existence of alkali to obtain a compound shown in a formula II; 2, the compound shown in the formula II reacts with triethylorthoformate or trimethyl orthoformate or glycol in an organic solvent (ii) under the effect of an acid catalyst to obtain a compound shown in a formula III; 3, 2-methoxyl-4, 4, 5, 5-tetramethyl-1, 3,2-boron dioxane or 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-boron dioxane or trimethyl borate or triisopropyl borate reacts with a standby solution in an organic solvent (iii) under the condition thatthe reaction temperature is 10-30 DEG C, after the reaction is completed, hydrochloric acid is added for regulating the pH value to be not larger than 3, and after a quenching reaction is performed, acompound shown in a formula IV is obtained through the reaction under the temperature of 20-100 DEG C.

Preparation method of Crisaborole intermediate

The invention discloses a preparation method of a Crisaborole intermediate. The Crisaborole intermediate has a structure shown as the formula VI. The preparation method comprises the following steps:performing a contact reaction on a compound shown as the formula I and benzyl halide, so as to form a compound shown as the formula II; performing a contact reaction on the compound shown as the formula II and alkali metal borohydride, so as to obtain a compound shown as the formula III; performing a contact reaction on the compound shown as the formula III and a compound a, or performing a contact reaction on the compound shown as the formula III and dihydropyran, so as to obtain a compound shown as the formula IV, wherein the compound a is trimethylchlorosilane, tert-butyldimethylsilyl chloride and chloromethyl methyl ether; performing a contact reaction on the compound shown as the formula IV and an isopropylmagnesium chloride solution; adding an obtained solution into a compound b, performing a contact reaction on the mixture and fourth organic solvent mixed liquor and adding hydrochloric acid into the mixture for contact reaction, so as to obtain a compound shown as the formula V,wherein the compound b is 2-alkoxy-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane, triisopropyl borate or trimethyl borate; performing a hydrogenation reaction on the compound shown as the formula V toobtain a compound shown as the formula VI.

Second Generation Grp94-Selective Inhibitors Provide Opportunities for the Inhibition of Metastatic Cancer

Glucose regulated protein 94 (Grp94) is the endoplasmic reticulum (ER) resident isoform of the 90 kDa heat shock protein (Hsp90) family and its inhibition represents a promising therapeutic target for the treatment of many diseases. Modification of the first generation cis-amide bioisostere imidazole to alter the angle between the resorcinol ring and the benzyl side chain via cis-amide replacements produced compounds with improved Grp94 affinity and selectivity. Structure–activity relationship studies led to the discovery of compound 30, which exhibits 540 nm affinity and 73-fold selectivity towards Grp94. Grp94 is responsible for the maturation and trafficking of proteins associated with cell signaling and motility, including select integrins. The Grp94-selective inhibitor 30 was shown to exhibit potent anti-migratory effects against multiple aggressive and metastatic cancers.

Simple, copper(I)-catalyzed oxidation of benzylic/allylic alcohols to carbonyl compounds: Synthesis of functionalized cinnamates in one pot

An environmentally benign [Cu(I)]-catalyzed oxidation of activated (benzylic/allylic) alcohols to the corresponding carbonyl compounds is presented. Interestingly, the reaction was also compatible with benzylic alcohols containing ortho-bromo substituents on the aromatic ring without competing with the expected intermolecular Buchwald coupling. Significantly, the catalytic system enables the synthesis of cinnamate-esters in a sequential domino one-pot fashion via oxidation followed by Wittig-Horner protocol. Copyright

GPBP-1 INHIBITION AND ITS THERAPEUTIC USE

The present invention provides compositions including anti-tumor agents and inhibitors of Goodpasture antigen binding protein, p21, and ABCC7, and their use in treating cancer.