43192-31-0

Usage

Chemical Properties

White solid

InChI:InChI=1S/C8H7BrO2/c1-11-7-3-2-6(5-10)8(9)4-7/h2-5H,1H3

Upstream product

• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 2398-37-0 3-methoxyphenyl bromide 
• 4885-02-3 Dichloromethyl methyl ether 
• 99177-37-4 1-(2-bromo-4-methoxyphenyl)-N,N-dimethylmethanamine 
• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 124-41-4 sodium methylate 
• 75-36-5 acetyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 36942-56-0 3-bromo-4-methylanisole 

Downstream Products

• 74317-85-4 2-bromo-4-methoxybenzoic acid 
• 100516-31-2 9-(2-bromo-4-methoxybenzylidene)fluorene 
• 139527-73-4 methyl 3-<2'-(2-carbomethoxyethyl)-4'-methoxyphenyl>-2-propenoate 
• 557056-02-7 7-(2-bromo-4-methoxyphenyl)hept-6-enenitrile 
• 163190-79-2 (2-bromo-4-methoxyphenyl)methanol 
• 557056-03-8 7-(2-bromo-4-methoxyphenyl)heptanenitrile 
• 557056-04-9 4-[2-(6-cyanohexyl)-5-methoxyphenyl]piperazine-1-carboxylic acid tert-butyl ester 
• 557056-05-0 4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester 
• 1141467-28-8 (E)-methyl 3-(2-bromo-4-methoxyphenyl)-2-formamidoacrylate 
• 1141467-30-2 (Z)-methyl 3-(2-bromo-4-methoxyphenyl)-2-formamidoacrylate 
• 1242167-47-0 2-(2-bromo-4-methoxyphenyl)-2-methyl-1,3-dioxolane 
• 1431656-03-9 2-bromo-4-methoxybenzyl 4-chlorobenzoate 
• 1398743-09-3 7-methoxy-2-phenylquinoline-3-carbonitrile 

Relevant academic research and scientific papers

Visible-Light-Mediated α-Oxygenation of 3-(N,N-Dimethylaminomethyl)-Indoles to Aldehydes

The visible-light-mediated oxygenation of 3-N,N-(dimethylaminomethyl)-indoles bearing various substituents afforded a series of 3-carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)-vincorine is described as well.

Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs

The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors.

Cyclotrimerization of unsymmetrically bromo-substituted diynes: Toward the synthesis of potential selective inhibitors of tyrosine kinase 2

A study on transition metal catalyzed alkyne cyclotrimerization of unsymmetrically bromo-substituted diynes with ethynyltrimethylsilane was carried out to prepare bicyclic bromobenzene key intermediates for the total synthesis of five potential tyrosine k

NOVEL ACYL GUANIDINE DERIVATIVES

The present invention provides a pharmaceutical which possesses an excellent inhibitory effect on NHE3 (Na+/H+ exchanger type 3) and effectively improves diseases or conditions of organs in which NHE3 is expressed.

Asymmetric total syntheses of (-)-variabilin and (-)-glycinol

Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "interrupted" Feist-Benary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products in over 90% ee in both cases. Other key steps include an intramolecular Buchwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.

Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1, 1-diester

Total synthesis of natural product (±)-bruguierol A was accomplished in 10-steps and with an overall 16.8% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)3-catalyzed intramolecular [3+2] cycloaddition of cyclopropane which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products.

QUINOLINONE DERIVATIVES

HIV inhibitory compounds of formula (I) including the stereoisomeric forms thereof, the pharmaceutically acceptable salts, and pharmaceutically acceptable solvates thereof; wherein R1 is cyano; R2 is H, C1-6alkyl, trifluoromethyl, amino, mono- or di-C1-6alkylamino, C1-6alkylamino wherein the C1-6alkyl group can be substituted; X1 is CH or N; R3 is phenyl or pyridyl, each unsubstituted or substituted; R4 is H, C1-6alkyl, (C1-6alkylcarbonyla mino)C1-6alkyl-, Ar, potionally substituted thienyl, furanyl, pyridyl, pyrimidyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazo lyl, oxazolyl, thiazolyl, halo, trifluoromethyl, hydroxy, C1-6alkyloxy, -OPO(OH)2, amino, aminocarbonyl, cyano, -Y1-R6, -Y1-Alk-R6, or -Y1-Alk-Y2-R7; R5 is H, halo, hydroxy or C1-6alkyloxy; or R4 and R5 form -O-CH2-O-; Y1 is O or NR8; Y2 is O or NR9; Alk is bivalent C1-6alkyl; R6 is pyrrolidinyl, piperidinyl, morpho linyl, piperazinyl, 4-C1 -6alkylpiperazinyl, 4-(C1-6alkylcarbonyl)piperazinyl, pyridyl, or imidazolyl; R7 is H, C1-6alkyl, hydroxyC1 -6alkyl, C1-6alkylcarbonyl; R8 and R9 are H or C1-6alkyl; Ar is optionally substituted phenyl; pharmaceut ical compositions comprising the above compounds (I) as active ingredient.

Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (-)-aphanorphine

A full account of studies which led to the efficient asymmetric synthesis of (-)-aphanorphine 1 is reported. Two routes to the key cyclic sulfamidate intermediate 5 are described, the first was based on a chiral auxiliary approach and the second utilised

Photoinduced C-Br homolysis of 2-bromobenzophenones and Pschorr ring closure of 2-aroylaryl radicals to fluorenones

(Chemical Equation Presented) A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl σ-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl π-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.

An efficient synthesis of a lycobetaine-tortuosine analogue: A potent topoisomerase inhibitor

An efficient gram-scale synthesis that uses a Suzuki cross-coupling reaction to yield 5-methyl-2,9-dimethoxyphenanthridinium chloride, a lycobetaine-tortuosine analogue and potent topoisomerase inhibitor, is presented. Georg Thieme Verlag Stuttgart.