123134-62-3

Upstream product

• 551-93-9 2-aminoacetophenone 
• 555-16-8 4-nitrobenzaldehdye 
• 118-92-3 anthranilic acid 
• 613-89-8 2-Aminoacetophenone 

Downstream Products

• 134271-79-7 4,2'-diaminodihydrochalcone 
• 130820-64-3 2-(4'-nitrophenyl)-2,3-dihydro-4(1H)-quinolinone 
• 918165-53-4 C₁₅H₁₄N₂O₃ 
• 918165-55-6 C₁₆H₁₆N₂O₃ 
• 134271-84-4 di-4,2'-(3-chloropropylamido)-dihydrochalcone 
• 1399086-38-4 (E)-1,1,1-trifluoro-N-(2-(3-(4-nitrophenyl)acryloyl)phenyl)methanesulfonamide 
• 1124190-97-1 C₁₆H₁₁ClN₂O₃ 

Relevant academic research and scientific papers

A novel potential anticancer chalcone: Synthesis, crystal structure and cytotoxic assay

Recently, a wide number of bioactivities has been discovered for chalcones. These applications depend on structural features such as planarity, electronic delocalization paths and substitution pattern on aromatic rings. This work aimed the structural analysis of a novel nitroaminochalcone (C15H12N2O3, NAC) through single crystal X-ray diffraction technique and assessment of its cytotoxicity against tumor cells. NAC is almost completely planar, as evidenced by the low angle formed between its phenyl rings [4.40 (12)°], which enables the π-electron delocalization through whole molecule. A resonance-assisted hydrogen bond (RAHB) is another interesting intramolecular feature of NAC, which is assembled between the amino and carbonyl groups into a cyclic S (6) motif. The crystal packing is featured by the formation of dimers stabilized by a R2 2 (16) motif engaging the carbonyl group and nitrobenzene. These dimers are organized in a 2D layer onto (010) through C–H?O interactions involving the nitro e amine groups in a C1 2(13)[R1 2(4)] motif. Furthermore, Hirshfeld surface analysis showed the crystal packing of NAC is also stabilized by both C–H?π and π?π interactions. The compound showed high cytotoxicity against human tumor cells.

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.

In quest of small-molecules as potent non-competitive inhibitors against influenza

A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.

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 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.

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.

Synthesis and biological evaluation of novel aminochalcones as potential anticancer and antimicrobial agents

A series of 18 aminochalcone derivatives were obtained in yields of 21.5-88.6% by applying the classical Claisen-Schmidt reaction. Compounds 4-9, 14 and 16-18 with 4-ethyl, 4-carboxy-, 4-benzyloxy- and 4-benzyloxy-3-methoxy groups were novel, not previously described in the scientific literature. To determine the biological properties of the synthesized compounds, anticancer and antimicrobial activity assays were performed. Antiproliferative potential was evaluated on four different human colon cancer cell lines-HT-29, LS180, LoVo and LoVo/DX-using the SRB assay and compared with green monkey kidney fibroblasts COS7. Anticancer activity was described as the IC50 value. The best results were observed for 2′-aminochalcone (1), 3′-aminochalcone (2) and 4′-aminochalcone (3) (IC50 = 1.43-1.98 μg·mL-1) against the HT-29 cell line and for amino-nitrochalcones 10-12 (IC50 = 2.77-3.42 μg·mL-1) against the LoVo and LoVo/DX cell lines. Moreover, the antimicrobial activity of all derivatives was evaluated on two strains of bacteria: Escherichia coli ATCC10536 and Staphylococcus aureus DSM799, the yeast strain Candida albicans DSM1386 and three strains of fungi: Alternaria alternata CBS1526, Fusarium linii KB-F1 and Aspergillus Niger DSM1957. In the case of E. coli ATCC10536 almost all derivatives hindered the bacterial growth (ΔOD = 0). Furthermore, the best results were observed in the presence of 4′-aminochalcone (3), that completely limited the growth of all tested strains at the concentration range of 0.25-0.5 mg·mL-1. The strongest bacteriostatic activity was exhibited by novel 3′-amino-4-benzyloxychalcone (14), that prevented the growth of E. coli ATCC10536 with MIC = 0.0625 mg·mL-1

QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase

Thirty three chalcones were synthesized and tested on viral H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure?activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure?activity relationships of these chalcone derivatives. Result from the 2D-quantitative structure?activity relationship model indicates that electrostatic parameter enhanced bioactivity of the chalcones while steric substituents diminished their potency as H1N1 neuraminidase inhibitors. 3D-quantitative structure?activity relationship model showed the importance of the position of the hydroxyl group in chalcone derivatives which can influence on hydrophobicity, hydrogen bond donor and aromatic ring features that enhance the biological activity. Finally, docking studies showed that chalcones MC8 and MC16 with low C docker interaction energies and higher numbers of hydrogen bonding have better inhibitory activity against viral H1N1 neuraminidase.

Synthesis and aromatase inhibitory activity of tetrahydroquinoline derivatives

Aromatase, a cytochrome P450 hemo-protein which is responsible for estrogen biosynthesis, by the conversion of androgens to estrogens, has been an attractive target in the treatment of hormone-dependent breast cancer. As a result, a number of synthetic st