78396-00-6

Upstream product

• 551-93-9 2-aminoacetophenone 
• 100-52-7 benzaldehyde 
• 16619-38-8 2'-nitro-chalcone 
• 577-59-3 2-acetylnitrobenzene 
• 53744-32-4 (2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one 
• 5344-90-1 2-Aminobenzyl alcohol 
• 529-23-7 o-aminobenzaldehyde 
• 536-74-3 phenylacetylene 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 615-43-0 2-iodophenylamine 
• 118-92-3 anthranilic acid 
• 99-03-6 1-(3-aminophenyl)ethanone 
• 148564-90-3 2,2,2-trifluoro-N-(2-(3-hydroxy-3-phenylprop-1-ynyl)phenyl)acetamide 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 

Downstream Products

• 16619-14-0 2-phenyl-2,3-dihydro-1H-quinolin-4-one 
• 107468-41-7 2-Phenyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one 
• 124856-99-1 2'-Aminochalcone Epoxide 
• 124856-99-1 (2-Amino-phenyl)-((2S,3R)-3-phenyl-oxiranyl)-methanone 
• 131423-38-6 [E]-3-phenyl-1-(2-acetamidophenyl)prop-2-en-1-one 
• 16619-52-6 1-(2-acetylaminophenyl)-3-phenyl-2-propen-1-one 
• 144221-11-4 2'-(Benzenesulfonamido)chalcone 
• 217311-72-3 (2-Amino-phenyl)-((2R,3S)-3-phenyl-oxiranyl)-methanone 
• 22680-62-2 4-methoxy-2-phenyl-quinoline 
• 22680-63-3 4-ethoxy-2-phenylquinoline 

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.

Chalcones and their B-aryl analogues as myeloperoxidase inhibitors: In silico, in vitro and ex vivo investigations

In the present study, a series of chalcones and their B-aryl analogues were prepared and evaluate as inhibitors of myeloperoxidase (MPO) chlorinating activity, using in vitro and ex vivo assays. Among these, B-thiophenyl chalcone (analogue 9) demonstrated inhibition of in vitro and ex vivo MPO chlorinating activity, exhibiting IC50 value of 0.53 and 19.2 μM, respectively. Potent ex vivo MPO inhibitors 5, 8 and 9 were not toxic to human neutrophils at 50 μM, as well as displayed weak 2,2-diphenyl-1-pycrylhydrazyl radical (DPPH?) and hypochlorous acid (HOCl) scavenger abilities. Docking simulations indicated binding mode of MPO inhibitors, evidencing hydrogen bonds between the amino group at 4′position (ring A) of chalcones with Gln91, Asp94, and Hys95 MPO residues. In this regard, the efficacy and low toxicity promoted aminochalcones and arylic analogues to the rank of hit compounds in the search for new non-steroidal anti-inflammatory compounds.

Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles

Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).

A Convenient Formal [4+2] Heterocylization Route to Bis(triflyl)tetrahydroquinolines

We report the sustainable and efficient synthesis of a new type of quinoline derivatives bearing one or two SO2CF3 groups. The protocol is metal-, catalyst- and irradiation-free, involves the use of readily available and stable precursors, and avoids the formation of side products. Also, the mild conditions of the process allow the tolerance of a wide range of functional groups.

Synthesis and biological evaluation of 2′-Aminochalcone: A multi-target approach to find drug candidates to treat Alzheimer's disease

Alzheimer's disease (AD) is a neurodegenerative process that compromises cognitive functions. The physiopathology of AD is multifactorial and is mainly supported by the cholinergic and amyloid hypotheses, which allows the identification the fundamental role of some markers, such as the enzymes acetylcholinesterase (AChE) and β-secretase (BACE-1), and the β-amyloid peptide (Aβ). In this work, we prepared a series of chalcones and 2′-aminochalcones, which were tested against AChE and BACE-1 enzymes and on the aggregation of Aβ. All compounds inhibited AChE activity with different potencies. We have found that the majority of chalcones having the amino group are able to inhibit BACE-1, which was not observed for chalcones without this group. The most active compound is the one derived from 2,3-dichlorobenzaldeyde, having an IC50 value of 2.71 μM. A molecular docking study supported this result, showing a good interaction of the amino group with aspartic acid residues of the catalytic diade of BACE-1. Thioflavin-T fluorescence emission is reduced in 30 – 40%, when Aβ42 is incubated in the presence of some chalcones under aggregation conditions. In vitro cytotoxicity and in silico prediction of pharmacokinetic properties were also conducted in this study.

Tandem Access to Acridones and their Fused Derivatives: [1+2+3] Annulation of Isocyanides with Unsaturated Carbonyls

A wide range of acridones and their cyclo[b]-fused derivatives are efficiently constructed by a double annulation of o-enoyl arylisocyanides with α, β-unsaturated carbonyls under simple metal-free condition. This protocol is general, efficient and practical, featuring the successive formation of two rings by a one-pot domino transformation. A tandem process involing an isocyanide-based [1+4] cycloaddition, an aminofuran-based intramolecular [4+2] cycloaddition, ring opening and aromatization is proposed for the transformation. (Figure presented.).

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.

Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds

A copper-catalyzed intramolecular cyclization reaction of 2-isocyanoacetophenone derivatives to afford 4-hydroxyquinolines chemoselectively is described. The transformation proceeds through enol tautomerism and a subsequent C-C bond formation. Compared to previous methods, this study provides a new protocol for the construction of 4-hydroxyquinoline compounds from functionalized isocyanides under mild conditions.

Effect of substituents in the A and B rings of chalcones on antiparasite activity

Chalcones are a group of natural products with many recognized biological activities, including antiparasitic activity. Although a lot of chalcones have been synthetized and assayed against parasites, the number of structural features known to be involved in this biological property is small. Thus, in the present study, 21 chalcones were synthesized to determine the effect of substituents in the A and B rings on the activity against Leishmania braziliensis, Trypanosoma cruzi, and Plasmodium falciparum. The compounds were active against L. braziliensis in a structure-dependent manner. Only one compound was very active against T. cruzi, but none of them had a significant antiplasmodial activity. The electron-donating substituents in ring B and the hydrogen bonds at C-2′ with carbonyl affect the antiparasitic activity.