130820-59-6

Upstream product

• 551-93-9 2-aminoacetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 19115-30-1 1-(4-methoxyphenyl)-2-propyn-1-ol 
• 577-59-3 2-acetylnitrobenzene 
• 127844-65-9 N-{2-[2-Bromo-3-methoxy-3-(4-methoxy-phenyl)-propionyl]-phenyl}-benzenesulfonamide 
• 127844-63-7 N-{2-[2,3-Dibromo-3-(4-methoxy-phenyl)-propionyl]-phenyl}-benzenesulfonamide 
• 148564-94-7 2-[3-hydroxy-3-(p-methoxyphenyl)prop-1-ynyl]trifluoroacetanilide 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 197730-11-3 [E]-3-(p-methoxyphenyl)-1-(2-trifluoroacetamidophenyl)prop-2-en-1-one 

Downstream Products

• 144709-08-0 2-(4-methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one 
• 127844-72-8 2'-amino-4-methoxychalcone epoxide 
• 127844-72-8 (2-Amino-phenyl)-[(2S,3R)-3-(4-methoxy-phenyl)-oxiranyl]-methanone 
• 136490-89-6 (E)-N-[2-[3-(4-methoxyphenyl)-1-oxo-2-propenyl]phenyl]acetamide 
• 144221-12-5 (E)-3-(4-methoxyphenyl)-1-(2-(phenylsulfonylamine)phenyl)prop-2-en-1-one 
• 136490-91-0 N-{2-[(E)-3-(4-Methoxy-phenyl)-acryloyl]-phenyl}-4-methyl-benzenesulfonamide 
• 190901-33-8 (E)-3-(4-methoxystyryl)benzo[c]isoxazole 
• 144709-03-5 2-(4'-methoxyphenyl)-4-methoxyquinoline 

Relevant academic research and scientific papers

Design, synthesis and antibacterial activity of chalcones against MSSA and MRSA planktonic cells and biofilms

Staphylococcus aureus is the one of the most successful modern pathogens. The same bacterium that lives as a skin and mucosal commensal can be transmitted in health-care and community-settings and causes severe infections. Thus, there is a great challenge for a discovery of novel anti-Staphylococcus aureus compounds, which should act against resistant strains. Herein, we designed and synthesized a series of 17 chalcones, substituted by amino group on ring A, which were evaluated against methicillin-susceptible S. aureus (MSSA) and methicillin-resistant S. aureus MRSA planktonic cells. The antibacterial potency was improved by substituents on ring B, which were designed according to Topliss’ manual method. 4-bromo-3′-aminochalcone (5f) was the most active, demonstrating minimum inhibitory concentration (MIC) values of 1.9 μg mL?1 and 7.8 μg mL?1 against MSSA and MRSA, respectively. The association of 5f with vancomycin demonstrated synergistic effect against MSSA and MRSA, with Fractional Inhibitory Concentration Index (FICI) values of 0.4 and 0.3, respectively. Subinhibitory concentration of 5f inhibited the MSSA and MRSA adhesion to human keratinocytes. Chalcone 5f was able to reduce MSSA and MRSA biofilm formation, as well as acts on preformed biofilm in concentration-dependent mode. Scanning electron microscopy analyses confirmed severe perturbations caused by 5f on MSSA and MRSA biofilm architecture. The acute toxicity assay, using Galleria mellonella larvae, indicated a low toxic effect of 5f after 72 h, displaying lethality of 20% and 30% at 7.8 μg mL?1 and 78.0 μg mL?1, respectively. In addition, the antibacterial activity spectrum of 5f indicated action against planktonic cells of Enterococcus faecalis (MIC = 7.8 μg mL?1), Acinetobacter baumannii (MIC = 15.6 μg mL?1) and Mycobacterium tuberculosis (MIC = 5.7 μg mL?1). Altogether, these results open new avenues for 5f as an anti-Staphylococcus aureus agent, with potential applications as antibacterial drug, adjunct of antibiotics and medical devices coating.

Synthesis of [1,4]Thiazino[4,3- a]indol-10-one Derivatives through Radical Anti Aza-Michael Addition of 2′-Aminochalcones

An efficient method for the synthesis of [1,4]thiazino[4,3-a]indole derivatives using sodium chlorodifluoroacetate (ClCF2CO2Na) and elemental sulfur as the difluoromethylthiolating reagent system has been developed. Three-component reactions of 2′-aminochalcones, sulfur, and ClCF2CO2Na under basic conditions using TEMPO as the oxidant afforded [1,4]thiazino[4,3-a]indol-10-ones containing a difluoromethyl thioether moiety in good yields. Four bonds including one C-N, two C-S, and one C-C bonds are selectively formed in the sequential transformation process.

Synthesis of 2-(1h-indol-2-yl)acetamides via br?nsted acid-assisted cyclization cascade

An efficient and straightforward Br?nsted-acid mediated cascade process was developed, involving cyclization of readily available β-ketonitriles into 2-aminofurans, and their subsequent recyclization into 2-(1H-indol-2-yl)acetamides is developed. This synthetic route opens a new avenue for an expeditious assembly of various isotryptamine derivatives for medicinal chemistry.

Br?nsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines

A highly efficient synthetic method to prepare 1,2-dihydroquinolines that relies on trifluoromethanesulfonic acid (TfOH)-catalysed allylic amination of 1-(2-aminoaryl)prop-2-en-1-ols is described. Achieved at a catalyst loading of 0.01 mol-% under mild conditions at room temperature, the reaction was found to be robust, with a wide range of substitution patterns tolerated. The corresponding N-heterocyclic adducts were obtained in good to excellent yields of 45-93 %.

Nazarov cyclization of 1,4-pentadien-3-ols: Preparation of cyclopenta[b]indoles and spiro[indene-1,4′-quinoline]s

The first Lewis acid-catalyzed intramolecular interrupted Nazarov cyclization of 1,4-pentadien-3-ols is described. Using FeBr3 as the catalyst, a series of new substituted cyclopenta[b]indoles was prepared - through a sequence of Nazarov cyclization, nucleophilic amination, and isomerization - with good yields and high diastereo- and regioselectivities. A similar catalytic process was also developed for the synthesis of structurally interesting spiro[indene-1,4′-quinoline]s.

Process Intensification with Bifunctional Heterogeneous Catalysts: Selective One-Pot Synthesis of 2′-Aminochalcones

(Chemical Equation Presented) 2′-Aminochalcones of pharmaceutical and commercial interest have been obtained in high yields and selectivities through a one-pot process using a bifunctional heterogeneous catalyst bearing base and metal active sites. This is a physical mixture material formed by a high-surface-area MgO and Pt on TiO2. The process involves as the first step the Claisen-Schmidt condensation between o-nitroacetophenone and benzaldehyde derivatives on the basic catalytic function. This is followed by a chemoselective hydrogenation of the nitro group in the presence of the carbonyl and double-bond carbon-carbon groups within the molecule. Using the bifunctional catalyst and the reaction system proposed here, it is possible to produce, under mild reaction conditions and short reaction times, 2′-aminochalcones with higher yields and selectivities than those obtained by conventional multistep methods.

Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure-activity relationship analysis and regulation of apoptotic proteins

In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-lymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, Bcl-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, sTNF-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated.

Synthesis of azaisoflavones and their inhibitory activities of NO production in activated microglia

A series of azaisoflavones were synthesized and their biological activities were evaluated for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in BV-2 microglia cell lines. Among these compounds, compound 8d was the most potent with IC50 7.83 μM for inhibition of NO production. Also, compound 8d inhibited expression of iNOS in LPS-induced BV2 cells. This result suggests that compound 8d inhibited the production of NO by suppressing the expression of iNOS.

Incvestigation of the possible role of arylamine formation in the ortho-substituted nitroarenes reductive cyclization reactions to afford heterocycles

Reductive carbonylation of nitroarenes with an unsaturated group in the ortho position generally affords high yields of heterocyclic compounds, including indoles, chalcones, quinolines, benzimidazoles, benzotriazoles, and indazoles. There is, however, no direct information on the organic intermediates formed during the reaction. In this paper, we have examined the possible formation of anilines as intermediates in the synthesis of indoles, acylindoles, quinolines, and quinolones with several catalytic systems based on palladium, ruthenium and rhodium. It transpired that, independent of the metal complex used as a catalyst, the formation of aniline as an intermediate is essential in the intra-molecular condensation reactions of nitroarenes involving an aldehydic or a keto group (including Michael addition reactions), but plays at best a very limited role in the addition reactions involving a C=C double bond.

Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2',3',4'-substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents

A novel series of 6,7,2',3',4'-substituted-1,2,3,4-tetrahydro-2-phenyl- 4-quinolones were synthesized and evaluated for interactions with tubulin and for cytotoxic activity against a panel of human tumor cell lines, including ileocecal carcinoma (HCT-8), breast cancer (MCF-7), lung carcinoma (A-549), epidermoid carcinoma of the nasopharynx (KB), renal cancer (CAKI-1), and melanoma cancer (SKMEL-2). Most compounds (18, 20, 22-27) showed potent cytotoxic and antitubulin effects. The most active compounds (23, 26, 27) demonstrated strong cytotoxic effects with ED50 values in the nanomolar or subnanomolar range in almost all tumor cell lines. Three active racemates (20, 22, 25) were separated into the enantiomers, and generally, the optically pure (-)-isomers (20a, 22a, 25a) exhibited greater biological activity than the racemates or (+)-isomers. Cytotoxicity and antitubulin activity were closely correlated, with the most active compounds (23, 26, 27) having effects comparable to those of colchicine, podophyllotoxin, and combretastatin A-4.