20146-10-5

Upstream product

• 1857-57-4 3-(3-bromo-4-methoxyphenyl)propionic acid 
• 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 

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 
• 60553-38-0 methyl 3-(3-bromo-4-hydroxy-phenyl)propionate 
• 196597-78-1 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one 
• 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 academic research and scientific papers

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.

Indanol-Based Chiral Organoiodine Catalysts for Enantioselective Hydrative Dearomatization

Rapid development in the last decade has rendered chiral organoiodine(I/III) catalysis a reliable methodology in asymmetric catalysis. However, due to the severely limited numbers of effective organoiodine catalysts, many reactions still give low to modes

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.

Defining the mechanism of action and enzymatic selectivity of psammaplin A against its epigenetic targets

Psammaplin A (11c) is a marine metabolite previously reported to be a potent inhibitor of two classes of epigenetic enzymes: histone deacetylases and DNA methyltransferases. The design and synthesis of a focused library based on the psammaplin A core has been carried out to probe the molecular features of this molecule responsible for its activity. By direct in vitro assay of the free thiol generated upon reduction of the dimeric psammaplin scaffold, we have unambiguously demonstrated that 11c functions as a natural prodrug, with the reduced form being highly potent against HDAC1 in vitro (IC50 0.9 nM). Furthermore, we have shown it to have high isoform selectivity, being 360-fold selective for HDAC1 over HDAC6 and more than 1000-fold less potent against HDAC7 and HDAC8. SAR around our focused library revealed a number of features, most notably the oxime functionality to be important to this selectivity. Many of the compounds show significant cytotoxicity in A549, MCF7, and W138 cells, with the SAR of cytotoxicity correlating to HDAC inhibition. Furthermore, compound treatment causes upregulation of histone acetylation but little effect on tubulin acetylation. Finally, we have found no evidence for 11c functioning as a DNMT inhibitor.

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.

Substituted phenylalkanoic acid derivatives and use thereof

A compound represented by the formula (I) or a salt thereof: wherein n represents an integer of 1 to 3, R represents an alkyl group having 3 to 8 carbon atoms, a group represented by the following formula: R1(CH2)k— (wherein k represents 0 or an integer of 1 to 3; R1 represents a saturated cyclic alkyl group having 3 to 7 carbon atoms or a saturated condensed cyclic alkyl group having 6 to 8 carbon atoms, and the group R1 may be substituted with a lower alkyl group having 1 to 4 carbon atoms) and the like, and Ar represents a condensed bicyclic group such as naphthalen-1-yl group, which has suppressing action on prostaglandin and leukotriene production and is useful for prophylactic and/or therapeutic treatment of various inflammatory diseases and the like caused by these lipid mediators.