2150-43-8Relevant articles and documents
Study of acylhydrazone derivatives with deoxygenated seven-membered rings as potential β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors
Zhou, Yang,Luo, Yin,Yang, Yu-Shun,Lu, Liang,Zhu, Hai-Liang
, p. 1980 - 1987 (2016)
Fatty acid biosynthesis is essential for bacterial survival. FabH, β-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and highly conserved among Gram-positive and Gram-negative bacteria. Following previous studies, a series of acylhydrazone derivatives with deoxygenated rings were synthesized in this work. For all of the 36 analogues synthesized, studies using H NMR, C NMR, MS and elemental analyses were conducted. Their biological activities were also evaluated against two Gram-negative bacterial strains: E. coli and P. aeruginosa, and two Gram-positive bacterial strains: B. subtilis and S. aureus by the MTT method as potential FabH inhibitors. The resulting compound F18 showed the highest antibacterial activity with MIC values of 1.56-3.13 μg mL-1 against the tested bacterial strains and was found to be the most potent E. coli FabH inhibitor with an IC50 value of 2.0 μM. Molecular modeling simulation studies were performed in order to predict the biological activities of compound F18 into the E. coli FabH active site.
Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction
Kawabata, Jun,Okamoto, Yasuko,Kodama, Asuka,Makimoto, Terumasa,Kasai, Takanori
, p. 5468 - 5471 (2002)
DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging reactions of protocatechuic and gallic acids, and their methyl esters, have been investigated by NMR. In acetone, methyl protocatechuate was gradually converted to a Diels-Alder adduct of two molecul
Direct conversion of phenols to o-quinones by copper(I) dioxygen. Questions regarding the monophenolase activity of tyrosinase mimics
Sayre, Lawrence M.,Nadkarni, Durgesh V.
, p. 3157 - 3158 (1994)
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Structure-property-activity relationship of phenolic acids and derivatives. Protocatechuic acid alkyl esters
Reis, Bruno,Martins, Marta,Barreto, Barbara,Milhazes, Nuno,Garrido, E. Manuela,Silva, Paulo,Garrido, Jorge,Borges, Fernanda
, p. 6986 - 6993 (2010)
The esterification of hydrophilic phenolic antioxidants is an efficient approach to enhance their solubility in apolar media. Herein, structurea property studies on the antiradical activity of a series of protocatechuic acid alkyl esters have been accomplished. The increase of the lipophilicity was shown to significantly improve the antioxidant activity of protocatechuic esters. Their efficiency as radical scavengers was evaluated using distinctive analytical methods, namely, 2,2-diphenyl-1-picrylhydrazyl (DPPH) UV/visible method, electrochemistry, and differential scanning calorimetry. All the new alkyl protocatechuate antioxidants studied possessed better radical-scavenging capacity than the natural antioxidant protocatechuic acid. This work has shown that the alkyl ester side chain markedly influences the lipophilicity of this type of phenolic system without disturbing the core of the molecule responsible for antioxidant activity. The data on the antioxidant activity obtained using the different analytical methods correlated well with each other and have revealed the interesting antioxidant potential of alkyl esters of protocatechuic acid.
Ethyl acetate as a co-solvent and sacrificial ester in the aluminum triiodide promoted chemoselective demethylation of methyl vanillate
Tian, Juan,Yi, Cuicui,Fang, Huasheng,Sang, Dayong,He, Zhoujun,Wang, Jiahui,Gan, Yongjiang,An, Qing
, p. 3522 - 3524 (2017)
A synthetic approach towards methyl protocatechuate via chemoselective ether cleavage of methyl vanillate without affecting the carboxylate group is disclosed utilizing a ternary reagent system consisting of aluminum triiodide, 1,3-diisopropylcarbodiimide and ethyl acetate. Ethyl acetate serves as a co-solvent and sacrificial ester. Methyl isovanillate, ethyl vanillate and methyl feruate were analogously demethylated to give methyl protocatechuate, ethyl protocatechuate and methyl caffeate, respectively, in fair to excellent yields.
Kinetic Evaluation of Phenolase Activity of Tyrosinase Using Simplified Catalytic Reaction System
Yamazaki, Shin-Ichi,Itoh, Shinobu
, p. 13034 - 13035 (2003)
A very simple tyrosinase reaction system has been developed using borate anion as a trapping agent of catechols and hydroxylamine as an external reductant to evaluate the phenolase activity without the interference of catecholase activity. Reactivities of variously para-substituted phenols in this system were compared directly to those of the phenols in the model reactions, demonstrating that the enzymatic oxygenation reaction of phenols proceeds via the same mechanism as the model reaction, that is, electrophilic aromatic substitution mechanism. Copyright
Last-Step Enzymatic [18F]-Fluorination of Cysteine-Tethered RGD Peptides Using Modified Barbas Linkers
Zhang, Qingzhi,Dall'Angelo, Sergio,Fleming, Ian N.,Schweiger, Lutz F.,Zanda, Matteo,O'Hagan, David
, p. 10998 - 11004 (2016)
We report a last-step fluorinase-catalyzed [18F]-fluorination of a cysteine-containing RGD peptide. The peptide was attached through sulfur to a modified and more hydrophilic variant of the recently disclosed Barbas linker which was itself link
Synthesis of Protected 3,4- And 2,3-Dimercaptophenylalanines as Building Blocks for Fmoc-Peptide Synthesis and Incorporation of the 3,4-Analogue in a Decapeptide Using Solid-Phase Synthesis
Banerjee, Isita,Ghosh, Keshab Ch.,Oheix, Emmanuel,Jean, Marion,Naubron, Jean-Valère,Réglier, Marius,Iranzo, Olga,Sinha, Surajit
supporting information, p. 2210 - 2223 (2021/02/26)
3,4-Dimercaptophenylalanines and 2,3-dimercaptophenylalanines have been synthesized for the first time by nucleophilic substitution of a protected aminomalonate on 3,4- and 2,3-dimercaptobenzyl bromide derivatives. The dithiol functions were protected as thioketals, and the key precursors, diphenylthioketal-protected dimercaptobenzyl bromides, were synthesized via two distinct routes from either dihydroxy benzoates or toluene-3,4-dithiol. Racemic mixtures of the fully protected amino acids were separated by chiral HPLC into the corresponding enantiomers. The absolute configuration of both 3,4- and 2,3-analogues could be assigned based on X-ray crystallography and VCD/DFT measurements. Thioketal groups were deprotected upon reaction with mercury oxide and aqueous tetrafluoroboric acid followed by treatment with H2S gas under an argon atmosphere to obtain the corresponding dimercapto amino acids. The optically pure l-Fmoc-protected 3,4-analogue (S- enantiomer) was successfully incorporated into a decapeptide using standard solid-phase peptide synthesis. Therefore, dithiolene-functionalized peptides are now accessible from a simple synthetic procedure, and this should afford new molecular tools for research into the catalysis, diagnostic, and nanotechnology fields.
Polyhydroxybenzoic acid derivatives as potential new antimalarial agents
Degotte, Gilles,Francotte, Pierre,Pirotte, Bernard,Frédérich, Michel
, (2021/08/07)
With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).
Metabolite profile of Nectandra oppositifolia Nees & Mart. And assessment of antitrypanosomal activity of bioactive compounds through efficiency analyses
Conserva, Geanne A. Alves,Quiros-Guerrero, Luis M.,Costa-Silva, Thais A.,Marcourt, Laurence,Pinto, Erika G.,Tempone, Andre G.,Fernandes, Jo?o Paulo S.,Wolfender, Jean-Luc,Queiroz, Emerson F.,Lago, Jo?o Henrique G.
, (2021/03/15)
EtOH extracts from the leaves and twigs of Nectandra oppositifolia Nees & Mart. shown activity against amastigote forms of Trypanosoma cruzi. These extracts were subjected to successive liquid-liquid partitioning to afford bioactive CH2Cl2 fractions. UHPL
