- Anti-tyrosinase, antioxidant and antibacterial activities of gallic acid-benzylidenehydrazine hybrids and their application in preservation of fresh-cut apples and shrimps
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A series of gallic acid-benzylidenehydrazine hybrids were synthesized and evaluated for their tyrosinase inhibitory activity. Thereinto, compounds 5d and 5f potently inhibited tyrosinase with IC50 of 15.3 and 3.3 μM, compared to kojic acid (44.4 μM). The inhibition mechanism suggested that 5d and 5f not only chelated with Cu2+, but also reduced Cu2+ to Cu1+ in the tyrosinase active site. Additionally, 5d and 5f exhibited strong DPPH scavenging and antibacterial activities against Vibrio parahaemolyticu and Staphylococcus aureus, which can be attributed to the function of gallic acid and hydrazone moiety. These compounds also exhibited capacity to preserve fresh-cut apples and shrimps. Finally, 5d and 5f exhibited low cytotoxic activity in a human cell line (HEK293). Therefore, these compounds possess anti-tyrosinase, antioxidant, and antibacterial activities, and can be used in the development of novel food preservatives.
- Chen, Lu,Li, Yufeng,Liu, Haiquan,Peng, Zhiyun,Shi, Qiandai,Tan, Lijun,Wang, Jing Jing,Zeng, Qiao-Hui,Zhao, Yong
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- Synthesis and Antioxidant Activity of New N-Containing Hybrid Derivatives of Gallic and Ursolic Acids
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New hybrid derivatives of ursolic and gallic acids linked through an ethylene linker and containing hydrazide and 1,3,4-oxadiazol-2-thione as terminal substituents were synthesized. Hydrazinolysis of methyl 3-(3β-acetoxyurs-12-en-28-oyloxy)-4,5-dihydroxyb
- Popov,Wang,Qi,Shul’ts,Turks
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p. 1042 - 1046
(2021/11/26)
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- One-Component Multifunctional Sequence-Defined Ionizable Amphiphilic Janus Dendrimer Delivery Systems for mRNA
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Efficient viral or nonviral delivery of nucleic acids is the key step of genetic nanomedicine. Both viral and synthetic vectors have been successfully employed for genetic delivery with recent examples being DNA, adenoviral, and mRNA-based Covid-19 vaccines. Viral vectors can be target specific and very efficient but can also mediate severe immune response, cell toxicity, and mutations. Four-component lipid nanoparticles (LNPs) containing ionizable lipids, phospholipids, cholesterol for mechanical properties, and PEG-conjugated lipid for stability represent the current leading nonviral vectors for mRNA. However, the segregation of the neutral ionizable lipid as droplets in the core of the LNP, the "PEG dilemma", and the stability at only very low temperatures limit their efficiency. Here, we report the development of a one-component multifunctional ionizable amphiphilic Janus dendrimer (IAJD) delivery system for mRNA that exhibits high activity at a low concentration of ionizable amines organized in a sequence-defined arrangement. Six libraries containing 54 sequence-defined IAJDs were synthesized by an accelerated modular-orthogonal methodology and coassembled with mRNA into dendrimersome nanoparticles (DNPs) by a simple injection method rather than by the complex microfluidic technology often used for LNPs. Forty four (81%) showed activity in vitro and 31 (57%) in vivo. Some, exhibiting organ specificity, are stable at 5 °C and demonstrated higher transfection efficiency than positive control experiments in vitro and in vivo. Aside from practical applications, this proof of concept will help elucidate the mechanisms of packaging and release of mRNA from DNPs as a function of ionizable amine concentration, their sequence, and constitutional isomerism of IAJDs.
- Atochina-Vasserman, Elena N.,Billingsley, Margaret M.,Huang, Ning,Kim, Kyunghee,Liu, Matthew,Maurya, Devendra S.,Mitchell, Michael J.,Ni, Houping,Ona, Nathan,Percec, Virgil,Pochan, Darrin J.,Shahnawaz, Hamna,Weissman, Drew,Xiao, Qi,Zhang, Dapeng
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supporting information
p. 12315 - 12327
(2021/08/20)
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- Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo
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A series of alkyl gallates was synthesized by reacting gallic acid with the corresponding alcohols. Their structures were determined on the basis of spectroscopic data, including NMR and MS. The antifungal activities of these compounds against plant pathogenic fungi in vitro and in vivo were assessed.
- Zhao, Xiao-Long,Li, Chun-Qing,Song, Xiao-Mei,Yan, Shuang-Mei,Luo, Du-Qiang
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- A novel colorimetric and ratiometric fluoride ion sensor derived from gallic acid
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A novel colorimetric and ratiometric probe (SH-GA) for the fluoride ion detection was designed and synthesized from gallic acid. SH-GA exhibited a selective color change from colorless to yellow in the presence of F- among the eight anions (F-, Cl-, Br-, I-, H2PO4-, HSO4-, CH3COO-, and ClO4-), either in THF or DMF solutions. The binding stoichiometry between SH-GA and fluoride ions was determined to be 1?:?1, and the complexation constant was 1.5 × 103 M-1 in THF. The detection limit of the SH-GA probe reached as low as around 1 μM in THF. 1H NMR titration results and DFT calculations suggested a deprotonation process via hydrogen bonding interactions between the fluoride ion and amino group of SH-GA.
- Shi, Heng,Li, Xiangguo,Chen, Hongjin,Xing, Jieni,Zhang, Rui,Liu, Jian
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p. 597 - 602
(2021/01/25)
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- Polyhydroxybenzoic acid derivatives as potential new antimalarial agents
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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).
- Degotte, Gilles,Francotte, Pierre,Pirotte, Bernard,Frédérich, Michel
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- Highly luminescent liquid crystals by connecting 1,3,4-oxadiazole with thiazolo[5,4-d]thiazole units
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The direct bonding between a thiazolo[5,4-d]thiazole and two 1,3,4-oxadiazole units allowed us to create a new and versatile rigid core for luminescent liquid crystal, which showed interesting and variable mesomorphic and photophysical properties. From the 5-bis(5-phenyl-1,3,4-oxadiazol-2-yl)thiazolo[5,4-d]thiazole new core, three molecules with different number of alkoxy chains were synthesized and had their properties correlated with the molecular structure. The molecule with two chains showed a smectic C mesophase, while the mesogens with four and six chains presented hexagonal columnar mesomorphism, which was confirmed by POM and XRD measurements. In addition, the molecule with six chains presented liquid crystalline behavior close to room temperature. In solution, the molecules presented strong photoluminescence ranging from blue to yellow, with quantum yields higher than 0.6. Excited state lifetimes allowed to correlate the fluorescence component associated to the different emitting species to the molecular organization in spin coated films. The molecular energy levels, together with thermal stability and possible charge carrier transport due to molecular packing, suggest that these molecules are promising for optoelectronic applications. Overall, this work contributes to the development of the use of thiazolo[5,4-d]thiazole in liquid crystals, demonstrating its great efficiency and versatility.
- Bechtold, Ivan H.,Cazati, Thiago,Curcio, Sergio F.,Eccher, Juliana,Falc?o, Eduardo H. L.,Farias, Giliandro,Gallardo, Hugo,Girotto, Edivandro,Malvestiti, Ivani,Manfredi, Alex M.,Salla, Cristian A. M.,Santos, Arthur B. S.,Westphal, Eduard
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- α-D-Mannoside ligands with a valency ranging from one to three: Synthesis and hemagglutination inhibitory properties
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Six mono-, di-, and trivalent α-D-mannopyranosyl conjugates built on aromatic scaffolds were synthesized in excellent yields by Cu(I) catalyzed azide-alkyne cycloaddition reaction (CuAAC). These conjugates were designed to have unique, flexible tails that combine a mid-tail triazole ring, to interact with the tyrosine gate, with a terminal phenyl group armed with benzylic hydroxyl groups to avoid solubility problems as well as to provide options to connect to other supports. Biological evaluation of the prepared conjugates in hemagglutination inhibition (HAI) assay revealed that potency increases with valency and the trivalent ligand 6d (HAI = 0.005 mM) is approximately sevenfold better than the best meta-oriented monovalent analogues 2d and 4d (HAI ≈ 0.033 mM) and so may serve as a good starting point to find new lead ligands.
- Al-Mughaid, Hussein,Khazaaleh, Maha
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- Cannabidiol derivative, preparation method and application thereof
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The invention discloses a cannabidiol derivative, a preparation method and application thereof, and belongs to the technical field of medicinal chemistry, wherein the cannabidiol derivative is obtained by taking cannabidiol as a main body through a synthesis means, and an anti-tumor activity determination result shows that the cannabidiol derivative prepared by the invention has an inhibition effect on lung cancer cell strains, human breast cancer cell strains, nasopharynx cancer and drug-resistant strains thereof.
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Paragraph 0027; 0035-0037; 0051-0053
(2021/07/28)
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- CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation
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Glycodendrimers are receiving considerable attention to mimic a number of imperative features of cell surface glycoconjugate and acquired excellent relevance to a wide domain of investigations including medicine, pharmaceutics, catalysis, nanotechnology, carbohydrate-protein interaction, and moreover in drug delivery systems. Toward this end, an expeditious, modular, and regioselective triazole-forming CuAAC click approach along with double stage convergent synthetic method was chosen to develop a variety of novel chlorine-containing cyclen cored glycodendrimers of high sugar tethers at low generation of promising therapeutic potential. We developed a novel chlorine-containing hypercore unit with 12 alkynyl functionality originated from cyclen scaffold which was confirmed by its single crystal X-ray data analysis. Further, the modular CuAAC technique was utilized to produce a variety of novel 12–sugar coated (G0) glycodendrimers 12-15 adorn with β-Glc-, β-Man-, β-Gal-, β-Lac, along with 36-galactose coated (G1) glycodendrimer 18 in good-to-high yield. The structures of the developed glycodendrimer architectures have been well elucidated by extensive spectral analysis including NMR (1H & 13CNMR), HRMS, MALDI-TOF MS, UV–Vis, IR, and SEC (Size Exclusion Chromatogram) data.
- Agrahari, Anand K.,Jaiswal, Manoj K.,Yadav, Mangal S.,Tiwari, Vinod K.
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- Dinuclear Copper(I) Thiodiacetate Complex-Mediated Expeditious Synthesis of the Chlorine-Containing Cyclen-Cored 36-Glucose-Coated Glycodendrimer
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High-sugar-tethered glycodendrimers are a remarkable tool in glycobiology for the investigation of carbohydrate-protein interaction using its multivalency property. An enthralling double-stage convergent synthetic approach was selected to build a novel class of chlorine-containing glucose-coated dendrimers using an efficient click catalyst 'dinuclear copper(I) thiodiacetate complex.' In this context, cyclen core was developed through a divergent approach, while the glucodendron was developed via a convergent approach independently. Both azide-alkyne partners were coupled through a modular copper azide-alkyne cycloaddition (CuAAC) strategy to afford a high yield of the desired 36-glucose-coated glycodendrimer. The synthesized glycodendrimer has been elucidated by NMR, gel permeation chromatography (GPC), and IR spectral analysis.
- Agrahari, Anand K.,Kumar, Sunil,Sharma, Anindra,Tiwari, Vinod K.
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- An expeditious click approach towards the synthesis of galactose coated novel glyco-dendrimers and dentromers utilizing a double stage convergent method
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The primary motive behind this article is to bring to the forefront a unique kind of dendrimer which has remained a dark horse since its discovery, namely dentromer. We herein report the synthesis of glycodendrimers and glycodentromers crowned with galactose units by harnessing an expeditious synthesis of dendrimer core 18 and dentromer core 19, divergently with branching directionality (1 → 2) and (1 → 3), respectively. A competent, double stage convergent synthetic path was chosen to facilitate ease of refining and spectroscopic elucidations. By exploiting a Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction strategy, we successfully developed a new series of galactosylated dendrimers 20, 21, 22, and 24 containing 6, 12, 18, and 18 peripheral galactose units, respectively. We are first to report the practical synthesis of 9-peripheral galactose coated glycodentromer 23 (0th generation) and 27-peripheral galactose coated glycodentromer 25 (1st generation). These synthesized scaffolds were characterized by spectral studies such as 1H, 13C NMR, FT-IR, MALDI-TOF MS, HRMS and SEC analysis. Additionally, gel permeation chromatography depicted the regular progression in size from 6 to 27-peripheral galactose coated glycodendrimers along with glycodentromers, with their high monodispersity. Also, the glyco-dendrimers and dentromers synthesized from two different hypercore units i.e. dendrimers core (18) and dentromer core (19), have been supported by their UV-visible absorbance and emission spectroscopy. This journal is
- Agrahari, Anand K.,Mukherjee, Rishav,Singh., Anoop S.,Tiwari, Vinod K.
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p. 31553 - 31562
(2020/09/21)
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- Development and structure-activity relationship study of SHP2 inhibitor containing 3,4,6-trihydroxy-5-oxo-5H-benzo[7]annulene
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SHP2, a non-receptor protein tyrosine phosphatase encoded by PTPN11 gene, plays an important role in the cell growth and proliferation. Activating mutations of SHP2 have been reported as a cause of various human diseases such as solid tumors, leukemia, and Noonan syndrome. The discovery of SHP2 inhibitor can be a potent candidate for the treatment of cancers and SHP2 related human diseases. Several reports on a small molecule targeting SHP2 have published, however, there are limitations on the discovery of SHP2 phosphatase inhibitors due to the polar catalytic site environment. Allosteric inhibitor can be an alternative to catalytic site inhibitors. 3,4,6-Trihydroxy-5-oxo-5H-benzo[7]annulene 1 was obtained as an initial hit with a 0.097 μM of IC50 from high-throughput screening (HTS) study. After the structure-activity relationship (SAR) study, compound 1 still showed the most potent activity against SHP2. Moreover, compound 1 exerted good potency against SHP2 expressing 2D and 3D MDA-MB-468.
- Kim, Bohee,Jo, Seungjin,Park, Sung Bum,Chae, Chong Hak,Lee, Kwangho,Koh, Byumseok,Shin, Inji
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supporting information
(2019/11/29)
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- The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization
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The application of oxidative dimerization for the biomimetic synthesis of balsaminone A and ellagic acid is described. Balsaminone A is synthesized via the oxidative dimerization of 1,2,4-trimethoxynaphthalene under anhydrous conditions using CAN, PIDA in BF3·OEt2 or PIFA in BF3·OEt2 in 7–8% yields over 3 steps. Ellagic acid is synthesized from its biosynthetic precursor gallic acid, in 83% yield over 2 steps.
- Daley, Sharna-Kay,Downer-Riley, Nadale
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supporting information
p. 2026 - 2031
(2020/10/02)
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- INHIBITORS OF D-AMINO ACID OXIDASE (DAAO) AND USES THEREOF
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Provided herein are compounds of Formula (I) and uses thereof for inhibiting the activity of D-amino acid oxidase (DAAO) or treating diseases or disorders associated with DAAO, such as a central nervous system (CNS) disorder, obesity, diabetes, or hyperlipidemia. Also provided in the present disclosure are methods of synthesizing the Formula (I) compounds described herein.
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- DIARYL TREHALOSE COMPOUNDS AND USES THEREOF
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Disclosed herein are diaryl trehalose compounds and methods of use thereof, for example as vaccine adjuvants.
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Paragraph 00262
(2019/09/12)
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- A preparation method of electronic grade gallic octyl ester
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The present invention provides a kind of electronic grade gallic octyl ester of preparation method, which belongs to the technical field of organic synthesis. The gallic acid dissolved in alcohol, then drop adds the chlorination [...], then adding aromatic hydrocarbon solvent, a catalytic amount of B (C6F5) 3 and octanol, moiety will be distillation after the exchange, getting the gallic octyl ester. This method avoids the use of heavy metal catalyst, high yield, low cost, and is suitable for industrial scale production, the ester exchange after the end of the added metal ion adsorbent after the metal ion adsorption, distillation electronic level of gallic octyl ester.
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Paragraph 0027; 0053; 0054; 0055; 0056
(2019/03/31)
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- Novel coumarin-based containing denrons selective fluorescent chemosesor for sequential recognition of Cu2+ and PPi
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In this study, we have successfully synthesized a novel coumarin-based dendrons derivative CD and its chemical structure was characterized by 1H NMR, 13C NMR and ESI-HR-MS. The sensor CD showed an obvious “on-off” fluorescence quenching response toward Cu2+ with a maximum quenching efficiency of 99.8%. The CD-Cu2+ complex showed an “off-on” fluorescence enhancement response toward PPi over many competitive anions. The detection limit of the sensor CD was 0.29 × 10?6 M to Cu2+ and 2.39 × 10?9 M to PPi. In addition, the sensor CD showed a 1:1 binding stoichiometry to Cu2+ and the sensor CD-Cu2+ showed a 2:1 binding stoichiometry to PPi in CH3CN/HEPES buffer medium (9:1 v/v, pH = 7.2). The stable pH range of sensor CD to Cu2+ and CD-Cu2+ to PPi was from 3 to 8.
- Zhao, Chongyang,Chen, Jian,Cao, Duanlin,Wang, Jianlong,Ma, Wenbing
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p. 1997 - 2003
(2019/02/24)
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- Design and synthesis of novel parabanic acid derivatives as anticonvulsants
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In this work a set of novel derivatives of parabanic acid 9a-d, 12a-d and 13a-d was synthesized and their anticonvulsant potential was evaluated. All the compounds under investigation exhibited anticonvulsant activity in both scPTZ and MES tests. In phase II anticonvulsant study, the trimethoxy phenyl derivative 9a evoked the highest potency among the tested compounds in scPTZ test. It displayed 1.72- and 17.05-folds activity more than the standard drugs phenobarbital and ethosuximide, respectively. In addition, the margin of safety for compound 9a is better than that of the reference antiepileptic drug ethosuximide. Also, compound 9a was devoid of hepatotoxicity indicated by measurements of serum level of ALT, AST, ALP, albumin and total protein. Furthermore, treatment with compound 9a significantly increased the GABA brain level by 2.56-folds compared to the control value. Additionally, molecular docking was performed on the active site of GABA-AT to clarify the interactions of the most potent compound 9a with the enzyme. In MES test, compound 12a exhibited the most potent activity against electric stimuli-induced seizures with the lowest ED50 = 13.7 mg/kg and protective index >36.5. Both candidates 9a and 12a could be a good starting point to develop new molecules as novel antiepileptic drugs.
- Aboutabl, Mona Elsayed,Hassan, Rasha Mohamed,El-Azzouny, Aida Abdel-Sattar,Aboul-Enein, Mohamed Nabil,Abd-Allah, Walaa Hamada
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supporting information
(2019/12/24)
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- Design, synthesis and anticancer evaluation of novel 1,3-benzodioxoles and 1,4-benzodioxines
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A new set of 1,3-benzodioxoles and 1,4-benzodioxines was designed and synthesized starting from gallic acid as anticancer agents. The antiproliferative effect of the target compounds was evaluated against a panel of cancer cell lines (HepG2, PC-3, MCF-7 and A549) using MTT assay. The 1,4-benzodioxine derivative 11a manifested broad spectrum effect towards the four tested cancer cell lines (IC50 50 = 6.37 μM. Also, flow cytometeric analysis revealed that compound 11a could induce both early and late stage apoptosis in MCF-7 cell line. Moreover, the ability of this compound to stimulate apoptosis in the latter cell line was further confirmed by: increment of Bax/Bcl-2 ratio, increase the expression of tumor suppressor gene p53, boosting the levels of initiator and executioner caspases as well as raise in the amount of cytochrome C. In addition molecular docking study was accomplished on the colchicine binding site of tubulin (pdb: 1SA0) to illustrate the interactions of the most potent compound 11a to the receptor.
- Abd-Allah, Walaa Hamada,Aboul-Enein, Mohamed Nabil,El-Azzouny, Aida Abdel-Sattar,Hassan, Rasha Mohamed,Salman, Asmaa Mohamed
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- Synthesis, structure activity relationship and in vitro anti-influenza virus activity of novel polyphenol-pentacyclic triterpene conjugates
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It is urgently necessary to develop more effective anti-influenza agents due to the continuous emergence of drug-resistant strains of influenza virus. Our earlier studies have identified that certain pentacyclic triterpene derivatives are effective inhibitors of influenza virus infection. In the present study, a series of C-28 modified pentacyclic triterpene derivatives via conjugation with a series of polyphenols were synthesized, and their antiviral activities against influenza A/WSN/33 (H1N1) virus in MDCK (Madin-Darby canine kidney) cells were evaluated. Four compounds 23m, 23o, 23q and 23s displayed robust anti-influenza potency with averaged IC50 values at the low-micromole level, surpassing the potency of oseltamivir. In addition, the in vitro cytotoxic activity of the four conjugates against MDCK cells showed no toxicity at 100 μM. Further mechanism studies of compound 23s, one of the best representative conjugates with IC50 value of 5.80 μM and a selective index (SI) value of over 17.2, by hemagglutination inhibition (HI), surface plasmon resonance and molecular modeling indicated that this conjugate bound tightly to the viral envelope hemagglutinin (KD = 15.6 μM), thus blocking the invasion of influenza viruses into host cells.
- Li, Haiwei,Li, Man,Xu, Renyang,Wang, Shouxin,Zhang, Yongmin,Zhang, Lihe,Zhou, Demin,Xiao, Sulong
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p. 560 - 568
(2019/01/03)
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- Gallate-induced nanoparticle uptake by tumor cells: Structure-activity relationships
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How nanoparticles interact with biological systems determines whether they can be used in theranostic applications. It has been demonstrated that tea catechins, may enhance interactions of magnetic nanoparticles (MNPs) with tumor cells and the subsequent cellular internalization of MNPs. As part of the chemical structure of the major tea catechins, gallates are found in a variety of plants and thus food components. We asked whether the structure of gallate might act as a pharmacophore in the enhancement of the effects of MNP-cell interactions. Uptake of dextran-coated MNPs by glioma cells and cell-associated MNPs (MNPcell) were respectively analyzed by confocal microscopy and a colorimetric iron assay. Co-incubation of MNPs and gallates, such as gallic acid and methyl gallate, induced a concentration-dependent increase in MNPcell, which was associated with co-localization of internalized MNPs and lysosomes. An analysis of the structure-activity relationship (SAR) revealed that the galloyl moiety exerted the most prominent enhancement effects on MNPcell which was further potentiated by the application of magnetic force; catechol coupled with a conjugated carboxylic acid side chain displayed comparable effects to gallate. Blockade or reduction in the number of hydroxyl groups rendered these compounds less effective, but without inducing cytotoxicity. The SAR results suggest that neighboring hydroxyl groups on the aromatic ring form an essential scaffold for the uptake effects; a similar SAR on antioxidant activities was also observed using a free radical-scavenging method. The results provide pivotal information for theranostic applications of gallates by facilitating nanoparticle-cell interactions and nanoparticle internalization by tumor cells.
- Cheng, Min-Chi,Lu, Yi-Ching,Wu, Jender,Ma, Yunn-Hwa
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- METHOD FOR ENHANCING DELIVERY OF THERAPEUTIC DRUGS TO TREATMENT SITES
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Disclosed herein is a method for enhancing uptake of magnetic nanoparticles (MNPs) having a therapeutic agent associated therein to a target site (e.g., a tumor), thereby resulting in elevated level of therapeutic agents being accumulated in the target site. The method comprises concurrently administering a sufficient amount of a polyphenolic compound and MNPs to the target site. Also disclosed herein is a method for treating a cancer in a subject. The method comprises concurrently administering an effective amount of the polyphenolic compound and MNPs to the subject, so as to ameliorate or alleviate symptoms associated with the cancer.
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Paragraph 0129-0131
(2019/05/18)
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- PHYTOCHEMICAL ANTIBIOTIC CONJUGATES AS INHIBITORS OF LACTOBACILLALES BACTERIA
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The present application relates to treatments for bacterial infections. For example, the application relates to the use a gallic acid-sulfamethoxazole conjugate for treatment of a Lactobacillales bacterial infection or a disease, disorder or condition arising from a Lactobacillales bacterial infection.
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Paragraph 0098
(2019/11/21)
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- Mimic catechins to develop selective MMP-2 inhibitors
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Abstract: Matrix metalloproteinase 2 (MMP-2) is a well-known anticancer target belonging to the MMP family. Because of the bilateral role of MMPs in cancer, developing highly selective MMP-2 inhibitors is a current challenge. In this paper, we investigated the binding modes of green tea polyphenols epigallocatechin gallate and epicatechin into the active site of the MMP-2 enzyme. The structure-based analysis allowed the optimization of these hits and hence led to a better lead candidate. Moreover, using a pharmacophore model, we screened FooDB compounds and selected food components as potential MMP-2 inhibitors. The search for food-derived compounds that target this enzyme may represent a strategy to identify new lead molecules with improved safety profiles and provide indications about possible functional foods. Graphical abstract: [Figure not available: see fulltext.].
- Di Pizio, Antonella,Agamennone, Mariangela,Laghezza, Antonio,Loiodice, Fulvio,Tortorella, Paolo
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p. 1293 - 1300
(2018/06/14)
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- Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum
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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.
- Arsianti, Ade,Astuty, Hendri,Fadilah,Simadibrata, Daniel Martin,Adyasa, Zoya Marie,Amartya, Daniel,Bahtiar, Anton,Tanimoto, Hiroki,Kakiuchi, Kiyomi
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p. 655 - 662
(2018/05/28)
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- The Synthesized Plant Metabolite 3,4,5-Tri-O-Galloylquinic Acid Methyl Ester Inhibits Calcium Oxalate Crystal Growth in a Drosophila Model, Downregulates Renal Cell Surface Annexin A1 Expression, and Decreases Crystal Adhesion to Cells
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The plant metabolite 3,4,5-tri-O-galloylquinic acid methyl ester (TGAME, compound 6) was synthesized, and its potential effect on calcium oxalate monohydrate (COM) crystal binding to the surface of Madin-Darby canine kidney cells type I (MDCKI) and crystal growth in a Drosophila melanogaster Malpighian tubule (MT) model were investigated. Membrane, cytosolic, and total annexin A1 (AxA1), α-enolase, and heat shock protein 90 (HSP90) amounts were examined by Western blot analysis after subcellular fractionation, then confirmed by immunofluorescence staining of cultured cells. Pretreatment of MDCKI cells with TGAME for up to 6 h significantly diminished COM crystal binding in a concentration-dependent manner. TGAME significantly inhibited AxA1 surface expression by immunofluorescence microscopy, whereas intracellular AxA1 increased. Western blot analysis confirmed AxA1 expression changes in the membrane and cytosolic fractions of compound-treated cells, whereas whole cell AxA1 remained unchanged. TGAME also significantly decreased the size, number, and growth of calcium oxalate (CaOx) crystals induced in a Drosophila melanogaster MT model and possessed a potent antioxidant activity in a DPPH assay.
- Abd El-Salam, Mohamed,Bastos, Jairo Kenupp,Han, Jing Jing,Previdi, Daniel,Coelho, Eduardo B.,Donate, Paulo M.,Romero, Michael F.,Lieske, John
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p. 1609 - 1621
(2018/03/08)
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- Antifungal activity of cinnamic acid and benzoic acid esters against Candida albicans strains
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Candida albicans is an important opportunistic fungal pathogen capable of provoking infection in humans. In the present study, we evaluated the antifungal effect of 23 ester derivatives of the cinnamic and benzoic acids against 3 C. albicans strains (ATCC-76645, LM-106 and LM-23), as well as discuss their Structure–Activity Relationship (SAR). The antifungal assay results revealed that the screened compounds exhibited different levels of activity depending on structural variation. Among the ester analogues, methyl caffeate (5) and methyl 2-nitrocinnamate (10) were the analogues that presented the best antifungal effect against all C. albicans strains, presenting the same MIC values (MIC?=?128?μg/mL), followed by methyl biphenyl-2-carboxylate (21) (MIC?=?128, 128 and 256?μg/mL for C. albicans LM-106, LM-23, and ATCC-76645, respectively). Our results suggest that certain molecular characteristics are important for the antifungal action.
- Lima, Tamires C.,Ferreira, Alana R.,Silva, Daniele F.,Lima, Edeltrudes O.,de Sousa, Dami?o P.
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p. 572 - 575
(2017/09/30)
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- Interfacial bioconjugation on emulsion droplet for biosensors
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Interfacial bioconjugation methods are developed for intact liquid emulsion droplets. Complex emulsion droplets having internal hydrocarbon and fluorocarbon immiscible structured phases maintain a dynamic interface for controlled interfacial reactivity. The internal morphological change after binding to biomolecules is readily visualized and detected by light transmission, which provides a platform for the formation of inexpensive and portable bio-sensing assays for enzymes, antibodies, nucleic acids and carbohydrates.
- Zhang, Qifan,Scigliano, Anita,Biver, Tarita,Pucci, Andrea,Swager, Timothy M.
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supporting information
p. 5307 - 5313
(2018/05/05)
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- A rapid, solvent-free deprotection of methoxymethyl (MOM) ethers by pTSA; An eco-friendly approach
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Background: Ease of preparation and alkaline stability of methoxymethyl (MOM) makes it an important hydroxyl protecting group. A number of methods are available for the deprotection of MOM. Though the methods are good in general, they use solvents, require prolonged reaction time and tedious work up. A solvent free, solid phase, fast deprotection of MOM has been developed and is the major theme of this paper. Methods: A mixture of MOM protected compounds and pTSA is triturated in a mortar (5 min) and left at room temperature for 30 min. On addition of water (4°C), pTSA, methanol and formaldehyde dissolved leaving the products as precipitates. Results: A series of different MOM ethers were deprotected by this method in good to excellent yield (85-98%). The compatibility of MOM in the presence of other protections such as methoxyl, benzyl, ester, amide, allyl and lactone was also established. Acetate protection is not stable under these conditions. Conclusion: An efficient, selective and high yielding deprotection MOM groups by pTSA under solvent free condition is described. The process is environment friendly since no solvent was used in the deprotection process. The reaction conditions are mild and should be useful for the deprotection of MOM derivatives of complex and labile molecules.
- Pandurangan, Nanjan
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p. 231 - 235
(2017/07/15)
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- ANTHOCYANIN SYNTHESIS PROMOTER AND CHLOROPHYLL DEGRADATION PROMOTER
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PROBLEM TO BE SOLVED: To provide an anthocyanin synthesis promoter and a chlorophyll degradation promoter that are safe and practicable. SOLUTION: The present invention provides an anthocyanin synthesis promoter and a chlorophyll degradation promoter comprising extract of plant belonging to Hydrocharitaceae Egeria or Elodea. The extract preferably comprises at least one of a compound of formula (I) and a compound of formula (II) as an active compound. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0058; 0059
(2017/06/24)
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- Synthesis and self-assembly of shape amphiphiles based on POSS-dendron conjugates
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Shape has been increasingly recognized as an important factor for self-assembly. In this paper, a series of shape amphiphiles have been built by linking polyhedral oligomeric silsesquioxane (POSS) and a dendron via linkers of different lengths. Three conjugates of octahedral silsesquioxanes (T8-POSS) and dendron are designed and synthesized and are referred to as isobutyl T8-POSS gallic acid derivatives (BPOSS-GAD-1, BPOSS-GAD-2, BPOSS-GAD-3). These samples have been fully characterized by 1H-NMR, 13C-NMR, Fourier transform infrared (FT-IR) spectroscopy and matrix-assisted laser desorption/ionization time of flight (MALDI-TOF) mass spectrometry to establish their chemical identity and purity. Driven by different interactions between POSS and dendron, ordered superstructure can be found upon self-assembly. The stabilities and structures of these samples are further studied by using differential scanning calorimetry (DSC), small-angle X-ray scattering (SAXS), wide-angle X-ray diffraction (WAXD), and molecular simulations. The results show that their melting points range from 74°C to 143°C and the molecular packing schemes in the assemblies can form lamellar structure of BPOSS-GAD-3 as determined by the different linkers.
- Shao, Yu,Ding, Minyuan,Xu, Yujie,Zhao, Fangjia,Dai, Hui,Miao, Xia-Ran,Yang, Shuguang,Li, Hui
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- Synthetic method of gallic acid lower alkanol ester
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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.
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Paragraph 0023
(2017/01/12)
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- Synthesis of tyrosyl-DNA phosphodiesterase i inhibitors
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The first report for the synthesis of tyrosyl-DNA phosphodiesterase I inhibitors 3,4-dimethoxyphenol-1-β-d-(6′-O-galloyl)glucopyranoside 3 and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol 2-β-d-(6′-O-galloyl) glucopyranoside 5 has been accomplished starting from readily available d-glucose as a starting material. An efficient and general approach has been reported for the synthesis of compounds 3 and 5 with an overall yield of 26% and 27%, respectively.
- Nale, Sagar D.,Jadhav, Vrushali H.
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supporting information
p. 2652 - 2654
(2016/06/01)
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- Aryl ethers coupled pyridoxal as supramolecular gelator for selective sensing of F?
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Aryl ethers coupled pyridoxal Schiff base 1 has been synthesized and its gelation properties have been examined. The gelator 1 forms colorless gels from various solvents such as DMSO, DMF, DMSO/H2O and DMF/H2O. The gel matrix obtained from DMSO shows ribbon-like fibrous morphology and has been utilized for efficient ‘naked eye’ detection of fluoride ion through a reversible gel-sol transition, which is associated with color change from almost colorless to yellow. In DMSO, the Schiff base 1 has also been observed to sense F?ion more efficiently over the basic ions AcO?and CN?. Though few examples of anion sensing in solution with pyridoxal-based Schiff bases are known, anion recognition utilizing pyridoxal-based gelators is unexplored in the literature.
- Ghosh, Kumaresh,Pati, Chiranjit
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supporting information
p. 5469 - 5474
(2016/11/19)
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- Preparation and preliminary application of 5-HMF@SiO2 micro-particles
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A new approach for the surficial-modification of silica with 5-HMF as a functional molecule was first designed. The infrared spectrum, X-ray photoelectron spectroscopy and elemental analysis showed that the modified-SiO2 particles were successfully established. Full dispersion of SiO2 and the introduction of gallic acid were confirmed to be favorable for the 5-HMF content. The retention behavior of bovine serum albumin on the modified-SiO2 particle suggested that the novel particles could serve as a promising stationary phase on the identification of the particular proteins.
- Wang, Cheng,He, Huaizhen,Lin, Yuanyuan,Huang, Limin,Sun, Meng,Zhang, Tao,He, Langchong
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p. 70586 - 70591
(2016/08/06)
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- The effect of solvent composition on grafting gallic acid onto chitosan via carbodiimide
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The primary antioxidant (AOX) activity of chitosan can be introduced by grafting of phenolic compound - gallic acid (GA) to its amino and/or hydroxyl groups. The objective of this study was to investigate the effect of ethanol (EtOH) concentration (0%, 25%, 50%, and 75% in water) on efficiency of grafting GA onto chitosan in the presence of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC)/N-hydroxysuccinimide (NHS). The grafting was confirmed by FTIR and the efficiency was quantified as Folin's total phenolics. When pure deionized water was used as a sole solvent (0% EtOH), GA was grafted to chitosan at the largest extent (285.9 mg GA/g chitosan). As the concentration of EtOH increased, the grafting efficiency proportionally decreased. NMR studies showed that EtOH inhibited grafting of GA by prohibiting the production of the intermediate - NHS ester. The results confirm that the concentration of EtOH in grafting solution significantly affects grafting efficiency of GA on chitosan.
- Guo, Ping,Anderson, John D.,Bozell, Joseph J.,Zivanovic, Svetlana
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p. 171 - 180
(2016/01/15)
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- COMBINATION OF COMPOUNDS DERIVED FROM GALLIC ACID FOR THE TREATMENT OF CANCER
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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.
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- Microwave-assisted esterification of gallic acid
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An efficient synthesis of alkyl gallates under microwave irradiation was described. The reaction took place in 6-10 mins, which was much shorter than the traditional synthetic methods, with almost quantitative yields.
- Shi, Zhi-Hao,Li, Nian-Guang,Tang, Yu-Ping,Shi, Qian-Ping,Zhang, Wei,Zhang, Peng-Xuan,Li, Wei,Dong, Ze-Xi,Duan, Jin-Ao
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p. 1351 - 1354
(2016/06/13)
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- Lower critical solution temperature behaviors of aromatic compounds with oligo(ethylene glycol) chains
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Amphiphilic small molecules comprising aromatic units and amphiphilic oligo(ethylene glycol) side chains were synthesized. These compounds exhibit lower critical solution temperatures (LCST) in aqueous solutions. Control of the LCST has been achieved by changing the solute concentration and adding salts or organic solvents.
- Arai, Masato,Ito, Kazuaki
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supporting information
p. 1416 - 1418
(2015/11/24)
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- Synthesis, antiproliferative activity and molecular properties predictions of galloyl derivatives
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The present study was designed to investigate the in vitro antiproliferative activity against ten human cancer cell lines of a series of galloyl derivatives bearing substituted-1,3,4-oxadiazole and carbohydrazide moieties. The compounds were also assessed in an in silico study of the absorption, distribution, metabolism and excretion (ADME) in the human body using Lipinski's parameters, the topological polar surface area (TPSA) and percentage of absorption (%ABS). In general, the introduction of N'-(substituted)-arylidene galloyl hydrazides 4-8 showed a moderate antitumor activity, while the 2-methylthio- and 2-thioxo-1,3,4-oxadiazol-5-yl derivatives 9 and 10 led to increased inhibition of cancer cell proliferation. The precursor compound methyl gallate 2 and the intermediary galloyl hydrazide 3 showed greater antiproliferative activity with GI50 values 50 = 0.05-5.98 μM) was also shown, with compounds 2, 3, 9 and 10 with GI50 ≤ 0.89 μM standing out in this respect. The in silico study revealed that the compounds showed good intestinal absorption.
- Da Silva, Marciane Maximo,Comin, Marina,Duarte, Thiago Santos,Foglio, Mary Ann,De Carvalho, Jo?o Ernesto,Do Carmo Vieira, Maria,Formagio, Anelise Samara Nazari
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p. 5360 - 5373
(2015/05/13)
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- Taxiphyllin 6′-O-gallate, actinidioionoside 6′-O-gallate and myricetrin 2′-O-sulfate from the leaves of Syzygium samarangense and their biological activities
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Three new compounds were isolated from a MeOH extract of the leaves of Syzygium samarangense, one new cyanogenic glucoside, taxiphyllin 6′-O-gallate (1), one new megastigmane glucoside, actinidioionoside 6′-O-gallate (2), and one new sulfated flavonoid rhamnoside, myricetrin 2″-O-sulfate (3), together with 14 known compounds, lupeol (4), demethoxymatteucinol (5), cryptostrobin (6), betulinic acid (7), β-sitosterol glucoside (8), 2R-prunasin (9), myrciaphenone A (10), 1-feruloyl-β-D-glucopyranoside (11), (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene (12), guaijaverin (13), myricetin 4′-methyl ether 3-O-α-L-rhamno-pyranoside (14), myricetrin (15), gallic acid (16) and actinidioionoside (17). The structures of the new compounds were determined through a combination of spectroscopic, HPLC and chemical analyses.
- Mamdouh, Nabil Samy,Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki,Kamel, Mohamed Salah
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p. 1013 - 1018
(2015/02/19)
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- Design, synthesis, and characterization of 1,3,5-Tri(1 H-benzo[d]imidazol-2-yl)benzene-based fluorescent supramolecular columnar liquid crystals with a broad mesomorphic range
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A new kind of supramolecular columnar liquid crystal T-A with a broad mesomorphic range (up to 164.9 °C), good thermal stability, and strong fluorescence is designed and formed by the H-bonding between 1,3,5-tri(1H-benzo[d]imidazol-2-yl)benzene (T) and serial gallic acid derivatives (A). Two components are easily available because of simple routes, common reactions, high yields, commercial starting materials, and inexpensive catalysts. The introduction of the 1,2,3-triazole structure into component A makes the textures different and is slightly disadvantageous for the T-A complexes.
- Xiong, Jin-Feng,Luo, Shi-He,Huo, Jing-Pei,Liu, Jin-Yan,Chen, Shui-Xia,Wang, Zhao-Yang
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p. 8366 - 8373
(2015/03/18)
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- MULTI-FLUORESCENT SUBSTANCE INCLUDING NOVEL COUMARIN DERIVATIVE, AND LED LIGHT SOURCE-BASED MICROFLUORESCENT QUANTITATIVE BIOSENSOR FOR DIAGNOSIS USING SAME
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The present invention relates to a novel coumarin derivative, to a method for preparing the same, and a multi-fluorescent substance that includes a plurality of the coumarin derivatives and is able to emit light using an LED light source. A novel coumarin derivative multi-fluorescent substance according to the present invention has an optimal emission wavelength band of 512 nm to 590 nm and thereby is effective in improving a signal intensity and stability since light emission using an LED light source is possible. In addition, higher fluorescence reactivity is exhibited compared to coumarin fluorescent substances known in the related arts since one molecule has a plurality of fluorescent substances, and the problem of the coumarin fluorescent substance possibly binding to a binding site of the antigen of the antibody is solved since fluorescence detection is possible even when a minimum number of fluorescent substance molecules bind to an antibody. Moreover, the novel coumarin derivative multi-fluorescent substance according to the present invention is suitably used in a fluorescent-linked immunosorbent assay (FLISA) and a rapid fluorescent immunochromatographic test (FICT) as an LED-based microfluorescent quantitative biosensor for diagnosis, therefore, diseases such as malaria may be rapidly and quantitatively analyzed.
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Page/Page column
(2014/12/09)
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- ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX
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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.
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Page/Page column 23
(2014/02/16)
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- Design, synthesis and characterization of novel inhibitors against mycobacterial β-ketoacyl CoA reductase FabG4
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We report the design and synthesis of triazole-polyphenol hybrid compounds 1 and 2 as inhibitors of the FabG4 (Rv0242c) enzyme of Mycobacterium tuberculosis for the first time. A major advance in this field occurred only a couple of years ago with the X-ray crystal structure of FabG4, which has helped us to design these inhibitors by the computational fragment-based drug design (FBDD) approach. Compound 1 has shown competitive inhibition with an inhibition constant (Ki) value of 3.97 ± 0.02 μM. On the other hand, compound 2 has been found to be a mixed type inhibitor with a Ki value of 0.88 ± 0.01 μM. Thermodynamic analysis using isothermal titration calorimetry (ITC) reveals that both inhibitors bind at the NADH co-factor binding domain. Their MIC values, as determined by resazurin assay against M. smegmatis, indicated their good anti-mycobacterial properties. A preliminary structure-activity relationship (SAR) study supports the design of these inhibitors. These compounds may be possible candidates as lead compounds for alternate anti-tubercular drugs. All of the reductase enzymes of the Mycobacterium family have a similar ketoacyl reductase (KAR) domain. Hence, this work may be extrapolated to find structure-based inhibitors of other reductase enzymes. The Royal Society of Chemistry.
- Banerjee, Deb Ranjan,Dutta, Debajyoti,Saha, Baisakhee,Bhattacharyya, Sudipta,Senapati, Kalyan,Das, Amit K.,Basak, Amit
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- Antifungal activity of alkyl gallates against plant pathogenic fungi
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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.
- Ito, Shinsaku,Nakagawa, Yasutaka,Yazawa, Satoru,Sasaki, Yasuyuki,Yajima, Shunsuke
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p. 1812 - 1814
(2014/04/17)
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- Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides
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Efficient synthetic procedures for the preparation of acid hydrazines and hydrazides were developed by converting the corresponding carboxylic acid into the methyl ester catalyzed by Amberlyst-15, followed by a reaction with hydrazine monohydrate. Sulfohydrazides were prepared from the corresponding sulfonyl chlorides and hydrazine monohydrate. Both of these group of compounds were condensed with substituted salicylaldehydes using gradient concentration methods that generated a large library of hydrazone, hydrazide and sulfohydrazide analogs. Antifungal activity of the prepared analogs showed that salicylaldehyde hydrazones and hydrazides are potent inhibitors of fungal growth with little to no mammalian cell toxicity, making these analogs promising new targets for future therapeutic development.
- Backes, Gregory L.,Neumann, Donna M.,Jursic, Branko S.
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p. 4629 - 4636
(2014/11/08)
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- Synthetic studies of fisetin, myricetin and nobiletin analogs and related probe molecules
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We synthesized a series of analogs of fisetin, myricetin and nobiletin, as well as related fluorescein- and biotin-based flavone-probe molecules, on a suitable scale for biological and structure-activity relationship studies.
- Hiza, Aiki,Tsukaguchi, Yuta,Ogawa, Takahiro,Inai, Makoto,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
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p. 1371 - 1396
(2016/10/12)
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