947675-12-9

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 

Downstream Products

• 1061544-95-3 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(biphenyl-4-yl)prop-2-en-1-one 
• 1374855-19-2 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4'-fluoro-3'-methylbiphenyl-4-yl)prop-2-en-1-one 
• 1374855-18-1 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3'-fluoro-4'-methoxybiphenyl-4-yl)prop-2-en-1-one 
• 1374855-17-0 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3'-nitrobiphenyl-4-yl)prop-2-en-1-one 
• 1374855-16-9 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4'-methoxybiphenyl-4-yl)prop-2-en-1-one 

Relevant academic research and scientific papers

Organocatalytic asymmetric vinylogous 1,4-addition of α,α-Dicyanoolefins to chalcones under a bio-based reaction media: Discovery of new Michael adducts with antiplasmodial activity

The organocatalysed asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydes and ketones have been reported in the last decade, however, chalcones have been poorly explored. Moreover, a considerable part of the publications in this theme still employs undesirable solvents, such as toluene and THF, with concerns related to health and environmental safety. We report herein the use of a bifunctional catalyst derived from a Cinchona alkaloid to perform the enantio- and diastereoselective Michael addition of α,α-dicyanoolefins to chalcones using 2-MeTHF as solvent. The Michael adducts were obtained in moderate to good yields and were evaluated for their antiplasmodial and cytotoxic activity.

Design, synthesis and biological evaluation of oxygenated chalcones as potent and selective MAO-B inhibitors

The present study documents the synthesis of oxygenated chalcone (O1–O26) derivatives and their abilities to inhibit monoamine oxidases. All 26 derivatives examined showed potent inhibitory activity against MAO-B. Compound O23 showed the greatest inhibitory activity against MAO-B with an IC50 value of 0.0021 μM, followed by compounds O10 and O17 (IC50 = 0.0030 and 0.0034 μM, respectively). In addition, most of the derivatives potently inhibited MAO-A and O6 was the most potent inhibitor with an IC50 value of 0.029 μM, followed by O3, O4, O9, and O2 (IC50 = 0.035, 0.053, 0.072, and 0.082 μM, respectively). O23 had a high selectivity index (SI) value for MAO-B of 138.1, and O20 (IC50 value for MAO-B = 0.010 μM) had an extremely high SI of >4000. In dialysis experiments, inhibitions of MAO-A and MAO-B by O6 and O23, respectively, were recovered to their respective reversible reference levels, demonstrating both are reversible inhibitors. Kinetic studies revealed that O6 and O23 competitively inhibited MAO-A and MAO-B, respectively, with respective Ki values of 0.016 ± 0.0007 and 0.00050 ± 0.00003 μM. Lead compound are also non-toxic at 200 μg/mL in normal rat spleen cells. Molecular docking simulations and subsequent Molecular Mechanics/Generalized Born Surface Area calculations provided a rationale that explained experimental data.

SAR and molecular mechanism studies of monoamine oxidase inhibition by selected chalcone analogs

The present study describes the synthesis of a series of 22 chalcone analogs. These compounds were evaluated as potential human MAO-A and MAO-B inhibitors. The compounds showed varied selectivity against the two isoforms. The IC50 values were f

Selective Horner-Wittig/Nazarov vsKnoevenagel/Nazarov Reactions in the Synthesis of Biologically Active 3-Aryl-Substituted 1-Indanones

3-Aryl-1-indanones and a previously unknown group of 3-aryl-2-phosphoryl-1-indanones have been synthesized from β-ketophosphonates and aromatic aldehydes via corresponding chalcones, in a selective Horner-Wittig or Knoevenagel olefination, followed by a Nazarov cyclization. In preliminary tests, the final compounds and the intermediate chalcones revealed anticancer activity against HeLa and K562 at the μM level.

Asymmetric synthesis of new γ-butenolides: Via organocatalyzed epoxidation of chalcones

γ-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched γ-butenolides in moderate overall yield and good enantiomeric excess.

Green synthesis of novel chalcone and coumarin derivatives via Suzuki coupling reaction

Chalcones and coumarins are important naturally occurring plant constituents and display a wide range of pharmacological and biological activities. In an environmentally benign approach, synthesis of biphenyl chalcone and coumarin derivatives was successfully accomplished via Suzuki coupling by using PEG-400 as a solvent under microwave irradiation. Salient feature of this methodology includes: short reaction time, good to excellent yields, and prominent tolerance of different functional groups.

Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from trypanosoma cruzi

Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 μM), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.

Solution phase synthesis of a spiro[pyrrolidine-2,3'-oxindole] library via a three component 1,3-dipolar cycloaddition reaction

A combinatorial library of 26,500 spiro[pyrrolidine,-2,3-oxindoles] was prepared in a single-compound format by a facile intermolecular 1,3-dipolar cycloaddition. An azomethine ylide, generated by the decarboxylative condensation of an isatin 1 with an α-amino acid 2, was trapped by a transchalcone 3 to afford heterocycles of the general structure 4. The regio- and stereochemistry of a representative product was determined by single crystal X-ray structure.