1087-26-9Relevant academic research and scientific papers
Synthesis and evaluation of gallocyanine dyes as potential agents for the treatment of Alzheimer's disease and related neurodegenerative tauopathies
Mpousis, Spyros,Thysiadis, Savvas,Avramidis, Nicolaos,Katsamakas, Sotirios,Efthimiopoulos, Spiros,Sarli, Vasiliki
, p. 28 - 38 (2016)
In search of safe and effective anti-Alzheimer disease agents a series of gallocyanine dyes have been synthesized and evaluated for their ability to inhibit LRPs/DKK1 interactions. Modulation of the interactions between LRPS and DKK1, regulate
Synthesis and cytotoxic activities of hexyl-esters derivatives of gallic acid against MCF-7 cell line
Paramita, Rafika Indah,Arsianti, Ade,Radji, Maksum
, p. 295 - 300 (2018)
Gallic acid is found in many plants, fruits, and foods where the anti-cancer activity is found. However, gallic acid has a problem on the high polarity and low bio availability. So, it takes molecular modifications in order to increase its lipophilicity, which is expected to increase bio availability and cytotoxic activity of gallic acid. Hexyl esters derivatives of gallic acid were synthesized and characterized by spectrometer 1H-NMR, 13C-NMR, mass spectrometry and infrared spectrophotometer (FTIR). All compounds were then evaluated for cytotoxic activity on MCF-7 cell line using MTT method. Compound cis-2′-hexenyl-3,4,5-trimethoxygallate (19) had the lowest IC50 value compared with gallic acid and other derivatives hexyl esters. IC50 value of cis-2′-hexenyl-3,4,5-trimethoxygallate (19) is 14.48 μg/ml. Compound (19) also has approached with IC50 values of gossypol as a positive control. Compound (19) is a potential compound to inhibit growth of MCF-7 cell line.
Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum
Arsianti, Ade,Astuty, Hendri,Fadilah,Simadibrata, Daniel Martin,Adyasa, Zoya Marie,Amartya, Daniel,Bahtiar, Anton,Tanimoto, Hiroki,Kakiuchi, Kiyomi
, p. 655 - 662 (2018/05/28)
This study is aimed to synthesize alkyl esters gallate and determine its in vitro antimalarial activity against parasite Plasmodium falciparum. Fourteen compounds of alkyl esters gallate were synthesized by esterification of the carboxyl group of gallic acid with a series of alkyl alcohols, as well as methoxylation of the hydroxy groups on the aromatic ring of gallic acid. Antimalarial activity of the synthesized alkyl esters gallate were expressed by IC50 value, with gallic acid as an original compound and artemisin as a positive control. Compared to gallic acid, eleven synthesized compounds of alkyl esters gallate, have a greater antimalarial activity against Plasmodium falciparum. On the other hand, three compounds, that are propyl gallate, butyl gallate and trimethoxy methyl gallate, showed a lower antimalarial activity. Moreover, compared to gallic acid (IC50: 194.86 mM) and artemisin (IC50: 0.5 mM), two synthesized compounds of alkyl gallates, namely methyl gallate and hexyl gallate exhibited the stronger antimalarial activity against Plasmodium falciparum, with IC50 value of 0.03 mM and 0.11 mM, respectively. Our result clearly demonstrated that methyl gallate and hexyl gallate as a promising candidate for the new antimalarial agents.
Synthetic method of gallic acid lower alkanol ester
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Paragraph 0033, (2017/01/12)
A synthetic method of gallic acid lower alkanol ester comprises the following steps of: (1) placing gallic acid and lower alkanol in a reactor, adding a sulfonic acid resin catalyst subjected to hydrophobic modification, carrying out stirring, heating to a temperature of 65 to 120 DEG C, performing the reaction for 4 to 10h and filtering to obtain filtrate; (2) removing excessive alcohol in the filtrate by evaporation so as to obtain a crude product, then carrying out recrystallization by deionized water, and carrying out suction filtration and drying to obtain the gallic acid lower alkanol ester. The synthetic method disclosed by the invention is simple, is safe to operate; yield of the gallic acid lower alkanol ester is greater than or equal to 92 percent; product purity is more than or equal to 99.5 percent; moreover, the catalyst has excellent performance; the water distribution link in a conventional method is reduced; a reaction apparatus is simplified; the synthetic method has good repeatability.
Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors
Rivero-Buceta, Eva,Carrero, Paula,Doyagüez, Elisa G.,Madrona, Andrés,Quesada, Ernesto,Camarasa, María José,Peréz-Pérez, María Jesús,Leyssen, Pieter,Paeshuyse, Jan,Balzarini, Jan,Neyts, Johan,San-Félix, Ana
, p. 656 - 671 (2015/01/30)
Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used.
Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum
Bertoldo, Jean Borges,Chiaradia-Delatorre, Louise Domeneghini,Mascarello, Alessandra,Leal, Paulo César,Cordeiro, Marlon Norberto Sechini,Nunes, Ricardo José,Sarduy, Emir Salas,Rosenthal, Philip Jon,Terenzi, Hernán
, p. 299 - 307 (2015/04/14)
Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkyl-esters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5±0.8μM, 9.5±0.2μM and 4.9±1.3μM, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.
COMBINATION OF COMPOUNDS DERIVED FROM GALLIC ACID FOR THE TREATMENT OF CANCER
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, (2015/11/27)
The invention relates to a combination of compounds derived from gallic acid, with an antitumoral and antimetastatic activity via a mechanism that involves the induction of apoptosis and the immunogenic death of the tumour cells and the subsequent activation of the specific immune response. The invention also relates to a composition containing a combination of derivatives of gallic acid and pharmaceutically acceptable excipients for the production of useful medicaments in the treatment of cancer. The invention further relates to the use of said composition in a coadjuvant in conventional chemotherapy, reducing the doses of chemptherapeutic agents used in the treatment of cancer.
Antifungal activity of alkyl gallates against plant pathogenic fungi
Ito, Shinsaku,Nakagawa, Yasutaka,Yazawa, Satoru,Sasaki, Yasuyuki,Yajima, Shunsuke
, p. 1812 - 1814 (2014/04/17)
The antifungal activity of alkyl gallates against plant pathogenic fungi was evaluated. All of the fungi tested in this study were susceptible to some alkyl gallates, and the effect of linear alkyl gallates against plant pathogenic fungi was similar to the previously reported effects against Gram-negative and Gram-positive bacteria. We found that branched alkyl gallates showed stronger activity than did linear alkyl gallates with similar log P values. In addition, the antifungal activity of alkyl gallates was correlated with gallate-induced inhibition of the activity of mitochondrial complex II. The antifungal activity of alkyl gallates likely originates, at least in part, from their ability to inhibit the membrane respiratory chain.
ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX
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Page/Page column 26, (2014/02/16)
Provided are compounds, compositions and methods for treating Toll-like receptor 1/2 complex (TLRI/2) related inflammatory disorders. Small molecules, based on the benzotropolone scaffold, capable of influencing downstream signaling are dislcosed as well as methods of making and modifying these molecules. Also provided are methods for treating a subject for a clinical condition associated with Toll? like receptor complex 1/2 activation, comprising administering to the subject an effective amount of a benzotropolone compound.
Discovery of small-molecule inhibitors of the TLR1/TLR2 complex
Cheng, Kui,Wang, Xiaohui,Zhang, Shuting,Yin, Hang
supporting information, p. 12246 - 12249 (2013/02/23)
An important regulator of innate immunity, the protein complex of Toll-like receptors 1 and 2 (TLR1/TLR2) provides an attractive target for the treatment of various immune disorders. The novel compound CU-CPT22 can compete with the binding of the specific lipoprotein ligand to TLR1/TLR2 (see picture) with high inhibitory activity and specificity. Repression of downstream signaling from TNF-α and IL-1β was also observed. Copyright
