1002925-69-0Relevant articles and documents
Catalytic Efficient Nazarov Reaction of Unactivated Aryl Vinyl Ketones via a Bidentate Diiron Lewis Acid Activation Strategy
Zhou, Xin,Zhao, Yukun,Cao, Yang,He, Lirong
, p. 3325 - 3331 (2017)
A catalytic highly efficient Nazarov reaction of unactivated aryl vinyl ketones has been accomplished by employing aryl boric acid/Fe(OTf)3. Significant progress was obtained in utilizing an extremely broad substrate scope, giving indanones in high yields with high regioselectivities and diastereoselectivities. The mechanistic investigation supports a bidentate diiron Lewis acid catalysis, and the strong double electrophilic activation of aryl vinyl ketones via simultaneous coordination plays a key role in achieving a high reaction efficiency. (Figure presented.).
Design, synthesis and biological evaluation of oxygenated chalcones as potent and selective MAO-B inhibitors
Parambi, Della Grace Thomas,Oh, Jong Min,Baek, Seung Cheol,Lee, Jae Pil,Tondo, Anna Rita,Nicolotti, Orazio,Kim, Hoon,Mathew, Bijo
, (2019/10/14)
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.
Synthesis and characterization of novel benzo[d][1,3]dioxole gathered pyrazole derivatives and their antimicrobial evaluation
Umesha, Basavaiah,Basavaraju, Yeriyur Basavaiah
, p. 3744 - 3751 (2014/08/05)
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.
Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from trypanosoma cruzi
Borchhardt, Deise M.,Mascarello, Alessandra,Chiaradia, Louise Domeneghini,Nunes, Ricardo J.,Oliva, Glaucius,Yunes, Rosendo A.,Andricopulo, Adriano D.
experimental part, p. 142 - 150 (2010/08/22)
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
Fokas, Demosthenes,Ryan, William J.,Casebier, David S.,Coffen, David L.
, p. 2235 - 2238 (2007/10/03)
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.
