130768-85-3

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 

Downstream Products

• 4087-64-3 1,3-bis-(3,4-dimethoxyphenyl)-1-butanone 
• 94577-55-6 2,4-bis-(3,4-dimethoxy-phenyl)-4-oxo-butyric acid amide 
• 94757-88-7 2,4-bis-(3,4-dimethoxy-phenyl)-4-oxo-butyric acid 
• 19611-19-9 2,4-bis-(3,4-dimethoxy-phenyl)-butyric acid 
• 19611-21-3 6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-1-tetralone 
• 858798-43-3 N-[2-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-[1]naphthyl]-formamide 
• 54785-17-0 2,3,8,9-tetramethoxy-4b,10b,11,12-tetrahydro-benzo[c]phenanthridine 
• 106593-04-8 (E)-1,3-bis(3,4-dihydroxyphenyl)prop-2-en-1-one 
• 1537880-19-5 (R,E)-3-(1,3-bis(3,4-dimethoxyphenyl)allyl)pentane-2,4-dione 
• 1537879-94-9 (E)-1,3-bis(3,4-dimethoxyphenyl)prop-2-en-1-ol 
• 688743-12-6 C₂₆H₂₄N₂O₄ 
• 100976-54-3 1,3-Bis(3',4'-dihydroxyphenyl)-propane 
• 104151-29-3 cis-3-(3,4-dimethoxyphenyl)-1-methyl-5,6-dimethoxyindane 
• 111222-54-9 3-(3,4-Dimethoxy-phenyl)-5,6-dimethoxy-1-methyl-1H-indene 

Relevant academic research and scientific papers

Design and synthesis of quinoline-pyrimidine inspired hybrids as potential plasmodial inhibitors

Presently, artemisinin-based combination therapy (ACT) is the first-line therapy of Plasmodium falciparum malaria. With the emergence of malaria parasites that are resistant to ACT, alternative antimalarial therapies are urgently needed. In line with this

Structural optimization of natural product nordihydroguaretic acid to discover novel analogues as AcrB inhibitors

Drug efflux pumps confer multidrug resistance to dangerous bacterial pathogens which makes these proteins promising drug targets. Herein, we present initial chemical optimization and structure-activity relationship (SAR) data around a previously described efflux pump inhibitor, nordihydroguaretic acid (NDGA). Four series of novel NDGA analogues that target Escherichia coli AcrB were designed, synthesized and evaluated for their ability to potentiate the activity of antibiotics, to inhibit AcrB-mediated substrate efflux and reduce off-target activity. Nine novel structures were identified that increased the efficacy of a panel of antibiotics, inhibited drug efflux and reduced permeabilization of the bacterial outer and inner membranes. Among them, WA7, WB11 and WD6 possessing broad-spectrum antimicrobial sensitization activity were identified as NDGA analogues with favorable properties as potential AcrB inhibitors, demonstrating moderate improvement in potency as compared to NDGA. In particular, WD6 was the most broadly active analogue improving the activity of all four classes of antibacterials tested.

Chalcone derivatives targeting mitosis: synthesis, evaluation of antitumor activity and lipophilicity

This study describes the synthesis of a series of chalcones, including pyrazole and α,β-epoxide derivatives, and evaluation of their cell growth inhibitory activity in three human tumor cell lines, as well as their lipophilicity using liposomes as a biomi

The synthesis of chalcones as anticancer prodrugs and their bioactivation in CYP1 expressing breast cancer cells

Background: Although the expression levels of many P450s differ between tumour and corresponding normal tissue, CYP1B1 is one of the few CYP subfamilies which is significantly and consistently overexpressed in tumours. CYP1B1 has been shown to be active within tumours and is capable of metabolising a structurally diverse range of anticancer drugs. Because of this, and its role in the activation of procarcinogens, CYP1B1 is seen as an important target for anticancer drug development. Objective: To synthesise a series of chalcone derivatives based on the chemopreventative agent DMU-135 and investigate their antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1. Method: A series of chalcones were synthesised in yields of 43-94% using the Claisen-Schmidt condensation reaction. These were screened using a MTT assay against a panel of breast cancer cell lines which have been characterised for CYP1 expression. Result: A number of derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing significantly lower toxicity towards a non-tumour breast cell line with no CYP expression. Experiments using the CYP1 inhibitors acacetin and α-naphthoflavone provided supporting evidence for the involvement of CYP1 enzymes in the bioactivation of these compounds. Conclusion: Chalcones show promise as anticancer agents with evidence suggesting that CYP1 activation of these compounds may be involved.

Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents

Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in L

Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as α-glucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards α-glucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good α-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 μM concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line).

Aerobic Oxidative Intramolecular Aromatic Coupling via Heterogeneous Metal Catalysts

An aerobic, heterogeneously catalyzed oxidative intramolecular coupling reaction of aromatic compounds is reported here. Using commercially available, recyclable heterogeneous metal catalysts, the coupling reactions of o-terphenyls and 1,ω-biarylalkanes proceeded quickly under mild conditions, i.e., at room temperature under oxygen as a co-oxidant almost all within 1 h, to provide the corresponding coupled products like triphenylenes and phenanthrenes in good to excellent yields. This reaction is an easily handled, practical, and atom-economical coupling method, which is of great importance in modern organic syntheses. (Figure presented.).

Carbon-carbon bond formation in acid deep eutectic solvent: Chalcones synthesis: Via Claisen-Schmidt reaction

One of the most studied properties of novel organic solvents is represented by their use as media for many chemical reactions. In this field Ionic Liquids (ILs) and more recently Deep Eutectic Solvents (DESs) have been playing significant roles for their smart properties. DESs are increasing their relevance thanks to their low toxicity, and because of their simple and cheap preparation that can be carried out by simply mixing two compounds. In this work we present the studies of the use of an acid DES obtained from 3-(cyclohexyldimethylammonio)propane-1-sulfonate and (1S)-(+)-10-camphorsulfonic acid (SB3-Cy/CSA) as reaction media and catalyst for carbon-carbon bond formation reaction via Claisen-Schmidt condensation. This powerful and widely used aldol condensation was performed without the use of any catalysts that are usually needed in this reaction, because of the presence of acid CSA in the DES components. We synthesised fourteen substituted chalcones from benzaldehydes and substituted benzaldehydes in combination with acetophenone and substituted acetophenones as probe reactions. The advantages of the use of this DES in this relevant reaction are represented by: the green properties of the media and its low toxicity; the absence of harmful acids to catalyse the aldol condensation because of the camphorsulfonic acid composing the DES mixture; the recycling and the re-use of the DES in subsequent reaction cycles; the mild conditions and the excellent conversions and yields observed.

An organocatalytic asymmetric allylic alkylation allows enantioselective total synthesis of hydroxymetasequirin-a and metasequirin-b tetramethyl ether diacetates

The first highly stereoselective organocatalytic intermolecular allylic alkylation of allylic alcohols with 1,3-dicarbonyls has been developed to allow the first enantioselective total synthesis of hydroxymetasequirin-A and metasequirin-B tetramethyl ethe

Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein

Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 2′ and 4′ on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition.