111038-89-2

Upstream product

• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 100-52-7 benzaldehyde 
• 274-09-9 Methylenedioxybenzene 
• 102-92-1 cinnamoyl chloride 
• 120-57-0 piperonal 
• 98-86-2 acetophenone 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 141075-48-1 7,7-dimethyl-5-oxo-2-(3',4'-methylenedioxy)-4-phenyl-5,6,7,8-tetrahydro-4H-1-benzopyran 
• 205048-80-2 2-Benzo[1,3]dioxol-5-yl-4-phenyl-5,7-dihydro-1,7-diaza-dibenzo[a,c]cyclohepten-6-one 
• 1204141-62-7 1-acetyl-3-(benzo[d][1,3]dioxol-5-yl)-5-phenyl-4,5-dihydro-1H-pyrazole 
• 126266-78-2 1-(benzo[d][1,3]dioxol-5-yl)-3-phenylpropan-1-one 

Relevant academic research and scientific papers

Synthesis, Molecular Structure, Spectral, Thermal, and DFT Studies of an Organic Crystal: 1-(benzo[d][1,3]dioxol-5-yl)-3-phenylprop-2-en-1-One

The synthesis, characterization, thermal stability, optical spectroscopic, FT-IR, and theoretical studies of a novel 1-(benzo[d][1,3]dioxol-5-yl)-3-phenylprop-2-en-1-one (BDP) is reported. Structure is elucidated by single-crystal X-ray diffraction analysis. The crystal belongs to monoclinic system with centrosymmetric space group P21/c with four molecules in the unit cell. The various mode of vibration present in the molecule are confirmed by FT-IR analysis and the experimental pattern is compared with theoretical one. The crystal is transparent in the entire visible region having a lower optical cut-off ～390 nm and the observed values are compared with theoretical values. The surface morphology of the specimen was analyzed by scanning electron microscopy (SEM). The TG/DTA study reveals the purity of the materials and no decomposition is observed up to the melting point. Theoretical calculations were performed to derive the optimized geometry, average polarizability (α), dipole moment (μ), first-order molecular hyperpolarizability (β), HOMO-LUMO, chemical hardness (η), softness (S), and electronegativity (χ) by using B3LYP/6-31G(d,p) level of theory. The atomic charge distributions of the various atoms present in BDP are obtained by Mulliken charge population analysis.

N-Heterocyclic Carbene Catalyzed Synthesis of Trisubstituted Epoxides via Tandem Amidation/Epoxidation Sequence

A tandem amidation/epoxidation sequence between various substituted chalcones and N,N-dimethylformamide (DMF) for the synthesis of trisubstituted epoxides employing N-heterocyclic carbene catalysis was developed. This reaction was performed under metal-free conditions in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant. Trisubstituted epoxides bearing a ketone and an amide functionality (N,N-dimethyl formyl group) were synthesized starting from a wide range of chalcones in moderate to good yields with excellent diastereoselectivity.

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.

Electrochemical 1,4-reduction of α,β-unsaturated ketones with methanol and ammonium chloride as hydrogen sources

A sustainable, chemoselective 1,4-reduction of α,β-unsaturated ketones by means of an electrochemical method is presented, wherein the extremely inexpensive ammonium chloride (NH4Cl) is applied as the only additive. The reaction proceeds smoothly in the air at ambient temperature. Mechanistic studies reveal that both NH4Cl and solvent methanol work as hydrogen donors.

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.

Synthesis and biological evaluation of novel aryl-2H-pyrazole derivatives as potent non-purine xanthine oxidase inhibitors

A series of aryl-2H-pyrazole derivatives were synthesized and evaluated for inhibitory activity against xanthine oxidase in vitro as potent xanthine oxidase inhibitors. Among them, 2 aryl-2H-pyrazole derivatives showed significant inhibitory activities against xanthine oxidase. Compound 19 emerged as the most potent xanthine oxidase inhibitor (IC50=9.8 μM) in comparison with allopurinol (IC50=9.5 μM). The docking study revealed that compound 19 might have strong interactions with the active site of xanthine oxidase. This compound is thus a new candidate for further development for the treatment of gout.

Synthesis and characterization of novel benzo[d][1,3]dioxole gathered pyrazole derivatives and their antimicrobial evaluation

Benzo[d][1,3]dioxole gathered pyrazole derivatives (4a-i) were synthesized by the reaction of chalcones with phenyl hydrazine in presence of absolute alcohol as a solvent. Chalcones were prepared by the Claisen-Schmidt reaction between 1-(benzo[d][1,3]dioxol-5-yl)ethanone (2) and substituted aromatic aldehydes. The synthesized compounds were characterized by spectral and elemental analysis data. Furthermore, Benzo[ d][1,3]dioxole gathered pyrazole derivatives (4a-i) were evaluated for their in vitro antimicrobial activity. Among the newly synthesized compounds 4a, 4c, 4 g and 4 h showed the excellent antifungal activity and as well as 4a and 4d showed the excellent antibacterial activity when compared to other compounds. Springer Science+Business Media 2014.

NEW DRUG FOR INHIBITING AGGREGATION OF PROTEINS INVOLVED IN DISEASES LINKED TO PROTEIN AGGREGATION AND/OR NEURODEGENERATIVE DISEASES

The present invention relates to a compound represented by formula (E). The present invention also relates to a compound represented by the formula (E) for use in the treatment or prevention of diseases linked to protein aggregation and/or neurodegenerative diseases. Moreover, the present invention relates to pharmaceutical and diagnostic compositions comprising the compound of the invention as well as to a kit. Furthermore, the present invention relates to a method of imaging deposits of aggregated protein. A kit for preparing a detectably labelled compound of the present invention is also disclosed.

Efficient chemoselective biohydrogenation of 1,3-diaryl-2-propen-1-ones catalyzed by Saccharomyces cerevisiae yeasts in biphasic system

A series of chalcones (1-9) was synthesized by base catalyzed aldol condensation with 50-94% yields. These α,β-unsaturated carbonyl compounds were used as substrates in biotransformation reactions mediated by three industrial Saccharomyces cerevisiae strains in biphasic systems. Several reaction parameters were evaluated, such as yeast concentration, temperature, pH, substrate concentration, organic solvent, volume of aqueous and organic phases and the influence of substituent groups on chalcones 1-9. The biotransformation was chemoselective and formed only the corresponding saturated ketones. The highest conversion (>99%) to the dihydrochalcone was obtained at 30-45°C and pH above 5.5, while the cellular and substrate concentrations also showed a strong influence on the biohydrogenation reaction. Organic solvents with log. P >3.2 (hexane or heptane) were the most appropriate, and 40-80% of aqueous phase allowed the highest conversions probably by maintaining the yeast enzymes catalytically active. The influence of substituents on rings A and B of chalcones 1-9 was low and no correlation between the donor or withdrawing electron groups was observed.

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.