19672-01-6

Upstream product

• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 67827-55-8 1-ethyl-2,4,6-trimethoxybenzene 
• 106800-22-0 2-(2,4,6-trimethoxyphenyl)ethyl bromide 
• 621-23-8 1,2,3-trimethoxybenzene 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 830-79-5 2,4,6-trimethoxybenzaldehyde 
• 708-76-9 2-hydroxy-4,6-dimethoxybenzaldehyde 
• 1026183-20-9 2-(1-hydroxyethyl)-3,5-dimethoxyphenol 
• 832-87-1 2-(2,4,6-trimethoxyphenyl)ethan-1-ol 

Downstream Products

• 80986-08-9 8-ethyl-5,7-dimethoxy-4-phenylcoumarin 
• 144688-18-6 (4-ethyl-3,5-dimethoxyphenyl) crotonate 
• 19786-68-6 3-(3,5-Dimethoxy-2-ethyl-phenoxy)-butanon-⁽²⁾ 
• 531502-60-0 1-(3-ethyl-2-hydroxy-4,6-dimethoxy-phenyl)-ethanone 
• 870681-73-5 (+/-)-8-ethyl-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin 
• 144688-19-7 1-(3-ethyl-2-hydroxy-4,6-dimethoxyphenyl)but-2-en-1-one 

Relevant academic research and scientific papers

3-site piperazinylchalcone derivative, and pharmaceutical composition and applications thereof

The present invention relates to a 3-site piperazinylchalcone derivative, which has a structure formula represented by a general formula (I) defined in the specification, wherein R is one selected from a substituted or unsubstituted phenyl group, a fused ring group and substituted or a unsubstituted heterocyclic group. The present invention further provides a pharmaceutical composition of the3-site piperazinylchalcone derivative, and applications thereof. According to the present invention, the results of the activity test based on P-gp target show that the 3-site piperazinylchalcone derivative and the pharmaceutical composition have good activity, can provide practical value in the treatment of the multidrug resistance of tumors, can solve the technical problems of difficult synthesis and high cost in the synthesis of the reversing agent used in the prior art, and is meaningful.

Design, synthesis and biological evaluation of chalcones as reversers of P-glycoprotein-mediated multidrug resistance

Overexpression of P-glycoprotein (P-gp) is one of the major causes for multidrug resistance (MDR), which has become a major obstacle in cancer therapy. One hopeful approach to reverse the MDR is to develop inhibitors of P-gp in expression and/or function. Here, we designed and synthesized a series of chalcone derivatives as P-gp inhibitors and evaluated their potential reversal activities against MDR. Among them, the most active compound MY3 had little intrinsic cytotoxicity and showed the highest activity (RF = 50.19) in reversing DOX resistance in MCF-7/DOX cells. Further studies demonstrated that MY3 could increase intracellular accumulation of DOX and inhibit expression of P-gp at mRNA and protein levels. More importantly, MY3 significantly enhanced the efficacy of DOX against the tumor xenografts bearing MCF-7/DOX cells with the precondition of unchanged body weight. Therefore, MY3 might represent a promising lead to develop MDR reversal agents for cancer chemotherapy.

Deoxygenation of α,β-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction

An efficient protocol for deoxygenation of α,β-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction is described. The reaction shows very good selectivity and tolerates a wide range of functionalities on α,β-unsaturated acylphenols, giving corresponding 2-allylphenols in good to excellent yields.

Regioselective synthesis and estrogenicity of (±)-8-alkyl-5,7- dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins

Nine new (±)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4- dihydrocoumarins have been synthesized from 2,4,6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (±)-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarin. The compounds were tested for estrogenic activity using a yeast-based estrogen screen. Weak estrogenicity was determined for seven members of the series.

Synthesis of novel flavonoid derivatives as potential HIV-integrase inhibitors

Eighteen novel flavonoid derivatives - substituted chalcones and flavones were synthesized and characterized by using NMR, IR, UV/Vis spectroscopy and elemental analysis. The target compounds were achieved by using a sequence of simple and effective reactions starting from phloroglucinol. The initial hydroxyl groups were protected by methylation and in the final flavones the 5-OH group was selectively demethylated by means of AlBr3. 5-methoxy flavones exhibit a strong fluorescence, which was quenched after the removal of the methyl group.

Antispasmodic activity of xanthoxyline derivatives: Structure-activity relationships

The antispasmodic activity of several xanthoxyline derivatives against acetylcholine-induced contraction of the guinea pig ileum was evaluated in vitro. The acetophenones with two methoxyl groups, mainly in the 3,4 positions, exhibited potent antispasmodic activity. Modification of the hydroxyl group in xanthoxyline by the introduction of benzoyl, acetyl, or tosyl groups produced inactive compounds, whereas the introduction of benzyl or p-methoxybenzyl groups furnished compounds that were four- to eight-fold more potent than xanthoxyline. In marked contrast, the introduction of a methyl group gave a compound that caused contractant activity. Modification of the carbonyl group of xanthoxyline lead to inactive compounds, whereas the condensation of xanthoxyline with benzaldehydes gave chalkones that were about fivefold more potent than xanthoxyline. The introduction of benzyl and styrene groups, on the basis of the similarity with papaverine, improves the antispasmodic action of the xanthoxyline derivatives. Our results suggest that the methoxyl and carbonyl groups are critical structural points for the antispasmodic activity of xanthoxyline derivatives. The hydroxyl group improves antispasmodic activity, but is not fundamental to its manifestation.

Structural Revision and Synthesis of LL-D253α and Related Chromanone Fungal Metabolites

The structure of LL-D253α, a chromanone metabolite of Phoma pigmentivora has been revised by analysis of the 1H-coupled 13C NMR to 7-hydroxy-8-(2'-hydroxyethyl)-5-methoxy-2-methyl-chroman-4-one.This has been further established by the synthesis of the revised and previously proposed structures of LL-D253α.

Hydroxyl-Directed Regioselective Monodemethylation of Polymethoxyarenes

Methoxyl groups ortho to β-hydroxyethyl or γ-hydroxypropyl substituents in polymethoxybenzene derivatives were regioselectively demethylated with sodium thioethoxide in N,N-dimethylformamide.Methoxydihydrobenzofurans or methoxychromans were produced by cyclization of the monodemethylated β-hydroxyethyl or γ-hydroxypropyl derivatives, respectively.