20146-10-5

Basic information

• Product Name: 3-(3-bromo-4-hydroxyphenyl)propanoic acid
• Synonyms: 3-(3-bromo-4-hydroxyphenyl)propanoic acid
• CAS NO: 20146-10-5
• Molecular Weight: 245.073
• Mol File: 20146-10-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 78-79 °C
• Boiling Point: 371.7±27.0 °C(Predicted)
• Density: 1.655±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3-(3-bromo-4-hydroxyphenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-bromo-4-hydroxyphenyl)propanoic acid(20146-10-5)
• EPA Substance Registry System: 3-(3-bromo-4-hydroxyphenyl)propanoic acid(20146-10-5)

Safety Data

• Hazardous Substances Data: 20146-10-5(Hazardous Substances Data)

Upstream product

• 501-97-3 4-hydroxyphenylpropionic acid 
• 60553-38-0 methyl 3-(3-bromo-4-hydroxy-phenyl)propionate 
• 5597-50-2 3-(4-hydroxyphenyl)propionic acid methyl ester 
• 1857-57-4 3-(3-bromo-4-methoxyphenyl)propionic acid 

Downstream Products

• 1314789-15-5 N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)propanamide] 
• 1356929-98-0 C₁₁H₁₄BrNO₂S 
• 196597-78-1 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one 
• 60553-38-0 methyl 3-(3-bromo-4-hydroxy-phenyl)propionate 
• 1428317-39-8 2-(tert-butyldimethylsilyl)-4-(3-hydroxypropyl)phenol 
• 29277-74-5 3-[3-Bromo-4-(2-hydroxy-3-isopropylamino-propoxy)-phenyl]-propionamide 

Relevant articles and documents

Preparation method 1, 2, 6, 7 - tetrahydro - 8H - indeno [5, 4 - b] furan -8 - ketone

The invention provides a preparation method of 1, 2, 6, 7 - tetrahydro - 8H - indeno [5, 4 - b] furan -8 - ketone, which comprises the following steps of (1) taking compound II as a raw material, adding a halogenating agent and hydrogen peroxide to halogenate to obtain compound III: 3 - X - 4 - hydroxybenzoic acid. (2) The compound III was mixed with 1 - bromo -2 - chloroethane and an alkali metal hydroxide to give compound IV: 3 - X - 4 - (2 - chloroethoxy) phenylpropionic acid. (3) Compound IV was added to nitrobenzene, and an acylation reagent was added to react to give compound V: 3 - X - 4 - (2 - chloroethoxy) phenylpropionyl chloride. (4) To the reaction system, aluminum trichloride was added to react to give compound VI: 4 - X - 1, 2, 6, 7 - tetrahydro - 8H - indeno [5, 4 - b] furan -8 - ketone. (5) Compound VI was added to toluene, and a palladium carbon and sodium acetate aqueous solution were added to catalyze hydrogenation to give compound I: 1, 2, 6, 7 - tetrahydro - 8H - indeno [5, 4 - b] furan -8 - ketone.

Total Synthesis of (-)-Melanthioidine by Copper-Mediated Cyclodimerization

An efficient asymmetric total synthesis of the dimeric macrocyclic diaryl ether phenethyltetrahydroisoquinoline alkaloid (-)-melanthiodine is reported. Key steps of the synthesis include an efficient Noyori asymmetric transfer hydrogenation to access the enantioenriched phenethyltetrahydroisoquinoline monomeric subunit and a copper-mediated cyclodimerization to form the two diaryl ether linkages with concomitant macrocyclization.

Epigenetic profiling of the antitumor natural product psammaplin A and its analogues

A collection of analogues of the dimeric natural product psammaplin A that differ in the substitution on the (halo)tyrosine aryl ring, the oxime and the diamine connection has been synthesized. The effects on cell cycle, induction of differentiation and apoptosis of the natural-product inspired series were measured on the human leukaemia U937 cell line. Epigenetic profiling included induction of p21WAF1, effects on global H3 histone and tubulin acetylation levels as well as in vitro enzymatic assays using HDAC1, DNMT1, DNMT3A, SIRT1 and a peptide domain with p300/CBP HAT activity. Whereas the derivatives of psammaplin A with modifications in the length of the connecting chain, the oxime bond and the disulfide unit showed lower potency, the analogues with changes on the bromotyrosine ring exhibited activities comparable to those of the parent compound in the inhibition of HDAC1 and in the induction of apoptosis. The lack of HDAC1 activity of analogues modified on the disulfide bond suggests that its cleavage must occur in cells to produce the monomeric Zn2+-chelating thiol. This assumption is consistent with the molecular modelling of the complex of psammaplin A thiol with h-HDAC8. Only a weak inhibition of DNMT1, DNMT3A and residual activities with SIRT1 and a p300/CBP HAT peptide were measured for these compounds.