- Preparation of 2,4-dihydroxybenzaldehyde by the Vilsmeier-Haack reaction
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An efficient synthesis of 2,4-dihydroxybenzaldehyde (1) from resorcinol via the Vilsmeier-Haack reaction has been developed. Either phosphorous oxychloride/DMF or oxalyl chloride/DMF produces 1 in yields of 65-75%. The intermediate formamidinium salts have been characterized.
- Mendelson, Wilford L.,Hayden, Stuart
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Read Online
- Cytoplasmic Reactive Cationic Amphiphiles for Efficient Intracellular Delivery and Self-Reporting Smart Release
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Nonviral gene delivery vectors need to overcome both extracellular and intracellular obstacles before releasing plasmid DNA in the transcriptionally active form. However, serum and transport stability desired for cationic polymer/pDNA polyplexes contradicts with the eventual plasmid release requirement; chain lengths of cationic polymer vectors render additional compromise between cytotoxicity and transfection efficiency. Although the introduction of stimuli-triggered degradable cationic polymers can partially solve these issues, the quest for novel design criteria and elucidation of elementary cellular transport pathways are highly desirable. Herein we report a supramolecular approach to construct fluorogenic gene delivery vectors via self-assembly of intracellular milieu-reactive cationic amphiphiles. This new type of micellar nanocarriers can effectively bind pDNA to form polyplexes due to multivalent cationic segments at micellar coronas. Upon cellular uptake and endosomal escape, hydrophobic micellar cores are subjected to fluorogenic Michael addition reactions with highly hydrophilic cytoplasmic thiols, leading to micellar disintegration, pDNA release, and emission turn-on for image-guided delivery. (Figure Presented).
- Hu, Jinming,Wang, Xiao,Qian, Yinfeng,Yu, Yongqiang,Jiang, Yanyan,Zhang, Guoying,Liu, Shiyong
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Read Online
- Hydrogen-bonded supramolecular array in the crystal structure of ethyl 7-hydroxy-2-oxo-2h-chromene-3-carboxylate monohydrate
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The crystal structure of ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate monohydrate (1), C12H10O5.H2O, was established by X-ray crystallographic analysis. The molecule of the title compound is essentially planar except for the carboxylate substituent group. The crystal packing supramolecular array arises from hydrogen bonds and intermolecular C-H...O=C contacts of the organic molecules and solvent water molecules, with graph-set descriptor)R24(8), R 21(6), R44(20)and5 (C) motifs. The water molecules are involved as donors and acceptors. The hydrogen bond and intermolecular interaction network is reinforced by stacking of the sheet through π-π interactions.
- Galdamez, Antonio,Garcia-Beltran, Olimpo,Cassels, Bruce K.
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Read Online
- Coumarin-chalcone hybrids as inhibitors of MAO-B: Biological activity and in silico studies
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Fourteen coumarin-derived compounds modified at the C3 carbon of coumarin with an α,β-unsaturated ketone were synthesized. These compounds may be designated as chalcocoumarins (3-cinnamoyl-2H-chromen-2-ones). Both chalcones and coumarins are recognized scaffolds in medicinal chemistry, showing diverse biological and pharmacological properties among which neuro-protective activities and multiple enzyme inhibition, including mitochondrial enzyme systems, stand out. The evaluation of monoamine oxidase B (MAO-B) inhibitors has aroused considerable interest as therapeutic agents for neurodegenerative diseases such as Parkinson’s. Of the fourteen chalcocumarins evaluated here against MAO-B, ChC4 showed the strongest activity in vitro, with IC50 = 0.76 ± 0.08 μM. Computational docking, molecular dynamics and MM/GBSA studies, confirm that ChC4 binds very stably to the active rMAO-B site, explaining the experimental inhibition data.
- Moya-Alvarado, Guillermo,Ya?ez, Osvaldo,Morales, Nicole,González-González, Angélica,Areche, Carlos,Nú?ez, Marco Tulio,Fierro, Angélica,García-Beltrán, Olimpo
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supporting information
(2021/05/28)
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- Three-Component Dynamic Covalent Chemistry: From Janus Small Molecules to Functional Polymers
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A new multicomponent reaction involving 2-hydroxybenzaldehyde, amine, and 2-mercaptobenzaldehyde (HAM reaction) has been developed and applied to multicomponent polymerization and controlled radical polymerization for the construction of random and block copolymers. This chemistry features mild reaction conditions, high yield, simple isolation, and water as the only byproduct. With the advantages of the distinct nucleophilicity of thiol and hydroxyl groups, the chemistry could be used for stepwise labeling and modifications on primary amines. The Janus chemical joint formed from this reaction exhibits degradability in buffers and generates the corresponding starting reagents, allowing amine release. Interestingly, the chemical joint exhibits thermally activated reversibility with water as the catalyst. This multicomponent dynamic covalent feature has been applied to the metamorphosis of random and block copolymers, generating polymers with diverse architectures. This chemistry is expected to be broadly applicable to synthetic polymer chemistry and materials science.
- Liu, Hongxu,Lu, Hung-Hsun,Thayumanavan, S.,Zhuang, Jiaming
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supporting information
p. 20735 - 20746
(2021/12/17)
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- Method for preparing 4-butyl resorcinol
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The invention discloses a method for preparing 4-butyl resorcinol. The method comprises the following steps: (1) preparing 2, 4-dihydroxy benzaldehyde; (2) preparing 2, 4-dihydroxy benzylidene acetone; and (3) preparing the 4-butyl resorcinol. The method has the advantages as follows: firstly, raw materials and reagents used in the method are lower in toxicity, safer, cheaper, easier to obtain andconvenient to store, and the raw material cost and operation cost are greatly reduced; secondly, the method has few reaction steps, is convenient to operate, and is easier for large-scale production;and thirdly, high-toxicity three wastes are not generated, environmental pollution is reduced, and the ecological environment is protected. Meanwhile, the yield of the prepared product is high and can reach 90% or above.
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Paragraph 0015; 0034-0035; 0038-0039
(2020/04/02)
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- Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions
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In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.
- Naeimi, Hossein,Zakerzadeh, Elham
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p. 4590 - 4595
(2018/03/21)
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- Functional group manoeuvring for tuning stability and reactivity: Synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products
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The protecting group manoeuvring as a strategy was applied for tuning the stability and reactivity of 4-(2,2-dibromovinyl)benzene-1,3-diol (12a) and 6-(2,2-dibromovinyl)-2,2-dimethylchroman-7-ol (22) in the domino synthesis of benzofuran-based natural products (1-8). The functional group demands and their impact on the reactivity driven by electronic effects were successfully managed by varying the protecting groups with substituted gem-dibromovinylphenols in domino couplings and triarylbismuth reagents under palladium-catalyzed conditions. This approach paved the way for the synthesis of moracin M (1) and cicerfuran (2), and the first time synthesis of moracin D (3) and moracin E (4) along with chromene-fused benzofuran-based natural products (5-8) in overall good yields.
- Rao, Maddali L. N.,Murty, Venneti N.,Nand, Sachchida
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p. 9415 - 9423
(2017/11/23)
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- Nitric oxide donor type coumarin derivatives, preparation methods therefor and medicinal use of nitric oxide donor type coumarin derivatives
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The invention relates to the fields of pharmacochemistry and pharmacotherapeutics and particularly relates to nitric oxide donor type coumarin derivatives, preparation methods therefor and an application of the nitric oxide donor type coumarin derivatives. The compounds play a role in resisting tumors and can be applied to the preparation of antitumor drugs.
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Paragraph 0491; 0524; 0525; 0526; 0527
(2017/09/01)
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- The first total synthesis of anemarchalconyn and anemarcoumarin A
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Anemarchalconyn (1) and anemarcoumarin A (2), the natural bioactive compounds isolated from the rhizomes of Anemarrhena asphodeloides Bunge (Liliaceae), were first totally synthesized using easily available materials in short, convenient routes with overall yields of 32 and 48%.
- Zhang, Jing-Xia,Li, Zhe-Yu,Wang, Yu-Chi,Ma, Wen-Bo,Hou, Ming,Cao, Sheng-Hua,Tang, Ke-Hui,Dong, Hong-Bo
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p. 903 - 909
(2017/08/22)
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- Method for preparing 2,4-dihydroxy benzaldehyde
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The invention relates to a method for preparing 2,4-dihydroxy benzaldehyde. The method comprises the following steps: by taking m-dihydroxybenzene as a raw material, performing reaction on bis(trichloromethyl) carbonate triphosgene BTC and N,N-dimethylformamide DMF in an organic solvent, and purifying, thereby obtaining a target compound. According to the method, as the triphosgene is adopted to replace a phosphorus-containing or sulfur-containing chlorination agent, the problems of treatment of a great amount of phosphorus-containing or sulfur-containing byproducts, discharging of wastewater and the like in the production process are solved, and the method has the characteristics of being easy in raw material obtaining, gentle in reaction condition, simple in operation step, low in cost, low in energy consumption, small in pollution, possible in clean production and the like and has industrial application prospects.
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Paragraph 0014; 0015; 0016; 0017; 0018; 0019; 0020
(2017/10/07)
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- Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki-Miyaura coupling reactions of aryl chlorides
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A series of N,O-bidentate ligands were synthesized using the Vilsmeier-Haack reaction and oximation. 2,5-Dihydroxyterephthalaldehyde dioxime (L8) as an efficient N,O-symmetrical bidentate ligand was prepared from hydroquinone. It was studied as a high activity ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions. The coupling reactions were performed in the presence of PdCl2 as the catalyst, L8 as the ligand, Na2CO3 as the base, PEG-400 as the PTC and in ethanol/water (1?:?1) as an environmentally benign solvent at 85 °C. Plentiful biaryls were obtained by the optimized reaction with good yields at a low palladium loading of 0.20 mol%.
- Song, Jinyi,Zhao, Hongyan,Liu, Yang,Han, Huatao,Li, Zhuofei,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 372 - 376
(2016/12/30)
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- 1,2,3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents
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A series of novel ethyl-7-((1-(benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2-oxo-2H-chromene-3-carboxylates 8a-h as potential antifungal agents were synthesized via click chemistry. The antifungal activity was evaluated against five human pathogenic fungal strains, such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger and Cryptococcus neoformans. Compound 8c, 8d, 8e and 8h were found to be equipotent against C. albicans when compared with miconazole and compound 8f was found to be two-fold more active compared with miconazole and equipotent to fluconazole against C. albicans. The coumarin-based triazole derivatives were also evaluated for antioxidant activity and compound 8a was found to be potent antioxidant when compared with standard drug. Furthermore, molecular docking study of the newly synthesized compounds was performed and results showed good binding mode in the active site of fungal C. albicans enzyme P450 cytochrome lanosterol 14α-demethylase. Moreover, the synthesized compounds were also analyzed for ADME properties and showed potential to build up as good oral drug candidates.
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.
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p. 295 - 301
(2018/03/22)
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- Cytosol-specific fluorogenic reactions for visualizing intracellular disintegration of responsive polymeric nanocarriers and triggered drug release
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Supramolecular aggregates of stimuli-responsive block copolymers are increasingly utilized as drug nanocarriers. Although in situ tracking their triggered disintegration and drug release processes at the cellular level is highly desirable, it remains a considerable challenge. We report the fabrication of double hydrophilic block copolymers covalently conjugated with ?±,?2-unsaturated ketone-caged coumarin functionalities in the thermoresponsive block. Upon thermo-induced micellization and cellular uptake, Michael addition reaction of unsaturated ketone moieties with thiol compounds (GSH and Cys) in the reductive subcellular compartments leads to micelle-to-unimer transition. This is accompanied by concomitant fluorescence emission turn-on and triggered drug release, allowing for the process visualization.
- Jiang, Yanyan,Liu, Guhuan,Wang, Xiaorui,Hu, Jinming,Zhang, Guoying,Liu, Shiyong
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p. 764 - 774
(2015/03/05)
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- Exploring the synthetic applicability of a new carboxylic acid reductase from Segniliparus rotundus DSM 44985
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A new carboxylic acid reductase (CAR) gene from Segniliparus rotundus DSM 44985 was overexpressed in Escherichia coli. The recombinant enzyme exhibited high activity toward a variety of aromatic and aliphatic carboxylic acids. Especially, it effectively reduced 4-hydroxybenzoic acid (8a) and 4-nitrobenzoic acid (19a), toward which the known Nocardia CAR exhibited no or little activity. The recombinant E. coli cells co-expressing the Segniliparus CAR and Nocardia PPTase genes catalyzed the reductions of vanillic acid (20a) and 3,4-dihydroxyphenylacetic acid (25a) to give vanillyl alcohol (20c) and 3-hydroxytyrosol (25c) with high yield, respectively. The endogenous aldehyde reductases of E. coli should be responsible for the further reduction of the produced aldehydes. These results demonstrated that Segniliparus CAR was a useful addition to the biocatalyst tool-box for the reduction of carboxylic acids and might find applications in the synthesis of valuable bio-based chemicals from renewable resources.
- Duan, Yitao,Yao, Peiyuan,Chen, Xi,Liu, Xiangtao,Zhang, Rui,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming
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- 2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead
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Hsp90 is a molecular chaperone that heals diverse array of biomolecules ranging from multiple oncogenic proteins to the ones responsible for development of resistance to chemotherapeutic agents. Moreover they are over-expressed in cancer cells as a complex with co-chaperones and under-expressed in normal cells as a single free entity. Hence inhibitors of Hsp90 will be more effective and selective in destroying cancer cells with minimum chances of acquiring resistance to them. In continuation of our goal to rationally develop effective small molecule azomethines against Hsp90, we designed few more compounds belonging to the class of 2,4-dihydroxy benzaldehyde derived imines (1-13) with our validated docking protocol. The molecules exhibiting good docking score were synthesized and their structures were confirmed by IR, 1H NMR and mass spectral analysis. Subsequently, they were evaluated for their potential to suppress Hsp90 ATPase activity by Malachite green assay. The antiproliferative effect of the molecules were examined on PC3 prostate cancer cell lines by adopting 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay methodology. Finally, schiff base 13 emerged as the lead molecule for future design and development of Hsp90 inhibitors as anticancer agents.
- Dutta Gupta, Sayan,Revathi,Mazaira, Gisela I.,Galigniana, Mario D.,Subrahmanyam,Gowrishankar,Raghavendra
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- Synthesis and characterization of a novel fluorescent and colorimetric probe for the detection of mercury (II) even in the presence of relevant biothiols
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We present here a novel probe, coumarin 3-azomethine derivative (AGB), which can detect selectively mercuric ions (Hg2+) via a hydrolysis reaction promoted by these ions. Interestingly, the probe can be used to assess the response to Hg2+ even in the presence of the most important biothiols-glutathione and cysteine - and could be used in the Hg2+ - imaging in living cells.
- García-Beltrán, Olimpo,Rodríguez, Alejandra,Trujillo, Ariel,Ca?ete, Alvaro,Aguirre, Pabla,Gallego-Quintero, Sebastián,Nu?ez, Marco T.,Aliaga, Margarita E.
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p. 5761 - 5766
(2015/09/29)
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- Rational design and synthesis of novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazole derivatives as an anti-angiogenesis and anti-cancer agent
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Based on earlier proven pharmacophore analogues of cancer a novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazoles (13-16) were rationally designed and synthesized by the reaction of chromene-3-carboxylic acids (10a-d) with substituted acyl bromides in the presence of TEA followed by refluxing with NH4OAc in toluene. Compounds 13-16 were screened in vitro for the inhibition of KRAS/Wnt and their anti-angiogenesis properties. Compound 16f has been identified as a potent anti-angiogenesis molecule, which can be considered as a new lead structure. The molecular docking analysis displayed the higher binding affinity of 16f with KRAS, Wnt and VEGF.
- Gudipudi, Gopinath,Sagurthi, Someswar R.,Perugu, Shyam,Achaiah,Krupadanam, G. L. David
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p. 56489 - 56501
(2015/02/05)
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- Synthesis of new derivatives of 2,4-dihydroxybenzoic acid and aldehyde and the study of the spectral-luminescent properties of their lanthanide complexes
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4-Acylated derivatives of 2,4-dihydroxybenzoic acid and aldehyde were synthesized. It was found that 2-hydroxy-4-[(4-decyloxy)benzoyloxy]benzaldehyde coordinates to Eu(III) ion, and when the aldehyde group is replaced by the carboxy group, a complex with Tb(III) ions is formed. The photoluminescent properties of the resulting complexes in solution were studied.
- Derkach,Teslyuk,Novikova,Doga,Yarkova,Meshkova
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p. 1293 - 1298
(2014/11/08)
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- Derivatization of coumarins at the benzenoid ring in aqueous medium
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Some 6-disubstituted, 8-disubstituted, and/6,8-disubstituted compounds have been prepared from coumarin, 7-methylcoumarin, and 3,4-benzocoumarin. The Reimer-Tiemann reaction, Lederer-Manasse reaction, bromination using molecular bromine as well as 2,4,4,6-tetrabromocyclohex-2,5-dien-1-one, Elbs reaction, and diazocoupling have been carried under controlled conditions to obtain various derivatives. Further, several reactions of aldehyde derivatives of these coumarins have been carried on to prepare important functional compounds including some heterocycles. It is noteworthy that these aldehydes behave as phenolic aldehydes under alkaline conditions to undergo the Dakin reaction. The reactions are mostly carried in aqueous media involving a dianionic intermediate and hence fulfill one important criterion of green chemistry.
- Bhunia, Sankar C.,Pal, Sutanuka,Patra, Gopal C.,Pal, Sudhir C.
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p. 1679 - 1688
(2015/02/02)
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- Synthesis, characterization, and cytotoxic activity on MCF-7 cell line of some novel metal complexes with substituted benzimidazole ligands
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A series of novel metal complexes with the Schiff base ligands 4-((((1H-benzo[d]imidazol-2-yl)methyl)imino)methyl) benzene-1,3-diol, H 3L1, and (((1H-benzo[d]imidazol-2-yl)methyl) thio)propanenitrile, HL2, have been synthesized and identified by elemental and spectral (UV-vis, IR, 1H NMR, mass) analyses, molar conductivities, as well asmagnetic moment measurements technique. The ligands behave either as neutral tridentate or bidentate ligand. The antitumor activity of the new compounds was tested against breast cancer cell line MCF-7. Ag and Cu complexes 2, 8 and 9 showed a remarkable smaller value of IC50 than that of the Tamoxifen, the standard. This would provide a new potential antitumor drug that deserves more attention. Copyright Taylor & Francis Group, LLC 2013.
- El-Seidy, Ahmed M. A.,El-Zahany, Eman,Barakat, Atiat S.,Youssef, Nabil S.,Galal, Shadia A.,Drweesh, Sayed A.
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- Novel macro metallomesogens derived from simple dihydroxy benzenes
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A series of tetradentate Schiff base metallomesogenic diols and their model compounds were synthesized from two simple dihydroxy benzenes. The metallomesogenic diol was constructed from three ring containing mesogen linked through ester and azomethine with terminal hydroxy group. This upon complexation with copper(II) formed metallomesogenic diol with varing terminal chain length. The related model metallomesogenic compounds were also synthesized with varying chain length with terminal methyl group and compared the properties with metallomesogenic diols. Extensive characterization of all metallomesogenic compounds and intermediates were carried out by FT-IR, 1H & 13C NMR, EPR, VSM, Mass (EI and FAB) and UV-Vis spectroscopy. Hot stage polarizing microscope, Differential scanning calorimetry was used to ensure the phase characteristics such as nature of phase, melting and clearing temperatures and phase range. The appearance of enantiotropic smectic A phases indicated high molecular polarizability of the core due to the metal ion. The role of copper(II) ion on mesogens were discussed.
- Senthilkumar, Natarajan,Raghavan, Aravamudhan,Narasimhaswamy, Tanneru,Kim, Il-Jin
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p. 129 - 139
(2013/06/04)
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- Highly efficient and selective deprotection method for prenyl, geranyl, and phytyl ethers and esters using borontrifluoride-etherate
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An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride-etherate (BF3· OEt2) at room temperature in good to excellent yields for the first time. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Narender,Venkateswarlu,Madhur,Reddy, K. Papi
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- Design and synthesis of a new coumarin-based 'turn-on' fluorescent probe selective for Cu+2
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The novel coumarin-based 'turn-on' fluorescent probe (E)-3-(2,5- dimethoxybenzylideneamino)-7-hydroxy-2H-chromen-2-one (MGM) was designed, synthesized, and characterized. This compound shows high selectivity for Cu +2, combined with a large fluorescence enhancement upon binding to Cu2+. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu2+ complex formed is 2:1. Preliminary studies employing epifluorescence microscopy demonstrated that Cu+2 could be imaged in human neuroblastoma SH-SY5Y cells treated with MGM.
- García-Beltrán, Olimpo,Mena, Natalia,Friedrich, Leidi C.,Netto-Ferreira, José Carlos,Vargas, Víctor,Quina, Frank H.,Nú?ez, Marco T.,Cassels, Bruce K.
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supporting information
p. 5280 - 5283
(2012/11/07)
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- Effect of structure and conformation on fluorescence properties in novel coumarin-based mannich base dyes
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Twelve novel coumarin-based Mannich base dyes have been synthesized via introducing functional aminomethyl group at the 8 position of coumarin ring by Mannich reaction and their chemical structures were confirmed by IR, 1H NMR, MS and elemental analysis. Moreover, the fluorescence intensities and relative quantum yields of all the dyes were measured and studied. The results illustrated that the heavy atom effect was obvious in our designed system and there was a relationship between the structures, the conformations and the fluorescence spectra of the coumarins. Meanwhile, the present β-CD titration experiment illustrated that the aniline nitrogen atom was closely related to the photoinduced electron transfer (PET) course and the PET course was carried out via a conformational control mechanism.
- Ni, Xiaobo,Guo, Yuan,Bu, Huaiyu,An, Jing,En, Da
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p. 1439 - 1445
(2013/03/13)
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- Synthesis and structure-activity relationship studies of cytotoxic cinnamic alcohol derivatives
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Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)- 6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC50 values of 0.4 and 0.5μ M, respectively. The structure-activity relationships of the derivatives are discussed.
- Zou, Hong-Bin,Zhang, Liang,Yang, Lei-Xiang,Yang, Liu-Qing,Zhao, Yu,Yu, Yong-Ping,Stoeckigt, Joachim
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scheme or table
p. 203 - 221
(2011/04/15)
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- Lead identification of β-lactam and related imine inhibitors of the molecular chaperone heat shock protein 90
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Heat shock protein 90 is an emerging target for oncology therapeutics. Inhibitors of this molecular chaperone, which is responsible for the maintenance of a number of oncogenic proteins, have shown promise in clinical trials and represent a new and exciting area in the treatment of cancer. Heat shock protein 90 inhibitors have huge structural diversity, and here we present the lead identification of novel inhibitors based on β-lactam and imine templates. β-Lactam 5 and imines 12 and 18 exhibit binding to heat shock protein 90-α with IC50 values of 5.6 μM, 14.5 μM, and 22.1 μM, respectively. The binding affinity displayed by these compounds positions them as lead compounds for the design of future inhibitors of heat shock protein 90 based on the β-lactam and imine templates.
- O'Boyle, Niamh M.,Knox, Andrew J.S.,Price, Trevor T.,Williams, D. Clive,Zisterer, Daniela M.,Lloyd, David G.,Meegan, Mary J.
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scheme or table
p. 6055 - 6068
(2011/11/06)
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- The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study
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Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells.
- García-Beltrán, Olimpo,Mena, Natalia,Pérez, Edwin G.,Cassels, Bruce K.,Nu?ez, Marco T.,Werlinger, Francisca,Zavala, Daniel,Aliaga, Margarita E.,Pavez, Paulina
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supporting information; scheme or table
p. 6606 - 6609
(2012/01/06)
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- Novel hydroxy- and methyl-terminated triaromatic schiff base compounds: Synthesis and mesogenic properties
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A series of Schiff base hydroxy-mesogens and their model compounds have been synthesized. The mesogen is constructed from three-ring-containing mesogens linked through ester and azomethine groups with a terminal hydroxy group. The related model compounds were also synthesized with varying chain length with a terminal methyl group and their properties were compared with that of hydroxy mesogens. Extensive characterization of all mesogenic compounds was carried out by Fourier-transform IR, 1H and 13C NMR and mass spectroscopy. The phase characteristics such as nature of phase, melting and clearing temperatures and phase range were evaluated using a hot-stage optical polarizing microscope and differential scanning calorimetry. The appearance of enantiotropic smectic phases is due to the high molecular polarizability of the triaromatic core with azomethine and ester linkages. CSIRO 2010.
- Senthilkumar, Natarajan,Narasimhaswamy, Tanneru,Raghavan, Aravamudhan
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scheme or table
p. 276 - 285
(2011/06/19)
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- Microwave assisted one pot synthesis of 7-substituted 2-(2-oxo-2H-chromen-3-yl)acetic acids as precursors of new anti-tumour compounds
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Perkin condensation with subsequent intramolecular lactonisation as one pot syntheses of 2-(2-oxo-2H-chromen-3-yl)acetic acids VIIa-Xa has been studied. The required acids VIIa-Xa were prepared as precursors of recently discovered compounds possessing antineoplastic activities. Syntheses of VIIa-Xa were carried out using para substituted 2-hydroxybenzaldehydes II-VI, succinic acid anhydride, sodium succinate under thermal or microwave conditions. Significant shortening of the reaction time under microwave irradiation was observed (18-50 min instead of 1.5-5 h of heating). Microwave assisted reactions proceeded more smoothly to give higher yield of the required products VIIa-Xa (31-61 %) compared to those under classical thermal conditions e.g. 21.8 % for IXa (Hurenkamp et al., 2007). Seven reaction by-products were isolated and determined as 2H,2′H-3,3′-bichromene-2,2′-diones VIIb-Xb and (E)-3-(2-hydroxystyryl)-2H-chromen-2-ones VIIc-IXc.
- Kovacova, Silvia,Kovacikova, Lucia,Lacova, Margita,Bohac, Andrej,Salisova, Marta
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scheme or table
p. 806 - 811
(2011/11/06)
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- Novel coumarin-based fluorescent probe for selective detection of bisulfite anion in water
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Coumarins and its analogues have been widely used as chromophore in design of fluorescent probe, while less coumarin-based fluorescent probe was reported for detection of anion in water. In this article, coumarin-based fluorescent probes with salicylaldehyde functionality as recognition unit have been developed for selective detection of bisulfite anions in water. Four novel fluorescent probes were synthesized from 4-haloresorcinol in three steps. The chemoprobe exhibited selective response to bisulfite over other anions. Moreover, the detection mechanism was studied. Upon bisulfite added, the fluorescent intensity of the probes was enhanced highly due to the nucleophilic addition reaction of formyl group with bisulfite anion.
- Chen, Kangyu,Guo, Yuan,Lu, Zhenhuan,Yang, Bingqin,Shi, Zhen
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experimental part
p. 55 - 60
(2010/09/07)
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- NaOAc-mediated selective deprotection of aromatic acetates and Its application in the synthesis of natural products
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We have developed an efficient method to deacetylate the aromatic acetates using NaOAc in excellent yields and demonstrated the application of the procedure in the synthesis of natural products.
- Narender,Reddy, K. Papi,Madhur
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experimental part
p. 1949 - 1956
(2009/10/17)
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- Microwave-assisted Vilsmeier-Haack formylation of aromatic substrates
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A microwave-assisted Vilsmeier-Haack formylation reaction has been studied on various amines, phenols and polynuclear hydrocarbons under solvent free condition that rapidly affords higher yield of products compared to traditional thermal condition.
- Ghosh, Kumaresh,Adhikari, Suman
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experimental part
p. 959 - 961
(2009/12/24)
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- Synthesis and electronic absorption and fluorescence of 2-arylbenzothiazole derivatives
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A series of new 2-arylbenzothiazoles have been prepared in high yields by Jacobson's cyclization condensation of 2-aminobenzenethiol with benzoyl chloride or benzaldehyde derivatives under three different routes. These compounds have been fully characterized by EA, IR, NMR and MS. The electronic absorption and fluorescence of these compounds have been systematically investigated for the first time. The relationships between their photophysical properties and structures have been discussed. The alteration of absorption and emission wavelengths can be elucidated by Hammett's substituent constants.
- Chen, Lianqing,Yang, Chuluo,Li, Suyue,Qin, Jingui
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p. 317 - 322
(2008/02/13)
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- Demethylation of aryl methyl ethers using pyridinium p-toluenesulfonate under microwave irradiation
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Aryl methyl ethers are deprotected in high yields using pyridinium p-toluenesulfonate under microwave irradiation and solvent-free conditions.
- Lamba, Mandeep S.,Makrandi, Jagdish K.
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p. 585 - 586
(2008/09/17)
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- One step hair coloring compositions using salts
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A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.
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- Transition metal complexes as dye forming catalysts in hair coloring compositions
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A hair coloring composition comprising a first composition which comprises: (a) a dye forming transition metal salt or complex; which is first applied to the hair; and a second composition which comprises the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an aminophenol, a polyhydric phenol a catechol and mixtures thereof.
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- Vilsmeier reagent for formylation in solvent-free conditions using microwaves
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POCl3-DMF over silica gel has been used for the synthesis of β-chlorovinylaldehydes (1-5), 2-aryl-3-formylindoles (6-8), 2-chloro-3-formylquinolines (9-13) and other aromatic aldehydes (14-20) using solvent-free conditions and microwave irradiation.
- Paul,Gupta,Gupta
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p. 1115 - 1118
(2007/10/03)
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- Enantioselective acylation of 2-hydroxymethyl-2,3-dihydrobenzofurans catalysed by lipase from Pseudomonas cepacia (Amano PS) and total stereoselective synthesis of (-)-(R)-MEM-protected arthrographol
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Lipase Amano PS catalysed acylation of (±)-2-hydroxymethyl-2,3-dihydrobenzofurans using vinyl acetate as the acyl donor in n-hexane gave (-)-(R)-2-acetoxymethyl-2,3-dihydrobenzofurans and (+)-(S)-2-hydroxymethyl-2,3-dihydrobenzofurans in high enantiomeric excess. (-)-(R)-Acetate 18j is converted to (-)-(R)-MEM-protected arthrographol 22. Copyright (C) 2000 Elsevier Science Ltd.
- Ramadas,Krupadanam, G. L. David
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p. 3375 - 3393
(2007/10/03)
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- A convenient total synthesis of isofraxidin, a natural coumarin
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The synthesis of isofraxidin in four steps starting from m-benzendiol, which is one of the important components of adrug in the treatment of insomnia, palpitation, amnesia and sexual deficiency in Chinese traditional medicine, is described.
- Chen, Wan-Mu
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p. 1085 - 1087
(2007/10/03)
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- Photochromism of the synthetic 4′,7-dihydroxyflavylium chloride
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The synthetic compound 4′,7-dihydroxyflavylium chloride shows an interesting photochromic effect at moderately acidic pH values. Pale yellow solutions of this compound, equilibrated in the dark at pH 3.4, become bright yellow upon irradiation with 313-nm light. Switching off the light, gives back the initial pale yellow solution. Photochemical methods, 1H NMR, and molecular orbital calculations were used to elucidate this photochromic behavior. In solutions equilibrated in the dark (pH 5.7), the existence of two main species in equilibrium is demonstrated: the colored flavylium cation and the colorless trans-chalcone. Freshly prepared solutions of this compound at pH 6.2 reveal the existence of another colored form, the quinonoidal base, which reacts thermally to yield trans-chalcone. An analogous reaction takes place in freshly prepared solutions at pH 3.4: the flavylium cation is partially converted into trans-chalcone. The extent of such conversion is pH dependent and nearly complete at pH 6.2. Irradiation of transchalcone at the wavelength of 313 nm partially gives back the initial colored form, with concomitant formation of small amounts of photodegradation products. The turnover of the photochromic reaction is greater at pH 3.4 than at pH 6.2. The photochromism is explained on the basis of a trans-cis photoisomerization. In fact the relative stability of the two chalcone isomers is reversed in the excited state, as predicted from molecular orbital calculations.
- Figueiredo, Paulo,Lima, Jo?o C.,Santos, Helena,Wigand, Marie-Claude,Brouillard, Raymond,Ma?anita, António L.,Pina, Fernando
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p. 1249 - 1254
(2007/10/02)
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- Vilsmeier Formylation and Glyoxylation Reactions of Nucleophilic Aromatic Compounds Using Pyrophosphoryl Chloride
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Reactions of N,N-dimethylformamide and N-methylformanilide with pyrophosphoryl chloride lead to the formation of reagents that undergo reactions with a wide range of nucleophilic aromatic substrates, including indoles, pyrroles, thiophenes, furans, and methoxy-substituted carbocyclic arenes to afford, after hydrolysis of the initial products, good to excellent yields of the expected aldehydes; reactions with methyl oxamates allow the preparation of methyl arylglyoxylates. Key words: pyrophosphoryl chloride, N,N-dimethylformamide, methoxyarene, heterocyle, formylation
- Downie, Ian M.,Earle, Martyn J.,Heaney, Harry,Shuhaibar, Khamis F.
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p. 4015 - 4034
(2007/10/02)
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- THE GENERATION OF C,O,O-TRILITHIATED DERIVATIVES OF DIHYDRIC PHENOLS
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Halogenated dihydric phenols (hydroquinones and resorcinols) undergo halogen metal exchange with nBuLi/TMEDA/THF or ether (inverse addition) under sonication, thereby generating a C,O,O-trilithiated species which can be trapped with electrophiles.
- Saa, Jose M.,Morey, Jeroni,Suner, Guillem,Frontera, Antoni,Costa, Antoni
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p. 7313 - 7316
(2007/10/02)
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- SYNTHESIS OF THREE NATURAL 1,3-DIARYLPROPANES: TWO REVISED STRUCTURES
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1-(2',4'-dihydroxy-3',5'-dimethylphenyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-Propane, isolated from Iryanthera coriacea and I. laevis, 1-(2'-hydroxy-4'-methoxy-5'-methylphenyl)-3-(2"-hydroxy-4",5"-methylene-dioxyphenyl)-propane, isolated from I. laevis, and 1-(2'-hydroxy-4'-methoxyphenyl)-3-(3"-hydroxy-4"-methoxyphenyl)-propane, isolated from Virola multinervia, were synthesized by processes which involved catalityc hydrogenation of the appropriate chalcones and Clemmensen reduction of dihydrochalcones.Only the structures of 1,3-diarylpropanes isolated from V. multinervia and I. laevis were revised. - Keywords: Virola multinervia; Iryanthera coriaceae; I. laevis; Myristicaceae; 1,3-diarylpropanes; synthesis; reduction of chalcones and dihydrochalcones.
- Morais, Anselmo A.,Fo, Raimundo Braz,Fraiz, Silas V. Jr
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p. 239 - 242
(2007/10/02)
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- COUMARINS FROM EDGEWORTHIA CHRYSANTHA
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Two new coumarins, edgeworin and edgeworoside A, were isolated from the root and stem of Edgeworthia chrysantha (E. papyrifera) and their structures determined as 3-(7-coumarinyloxy)-7-hydroxycoumarin and 3-(7-coumarinyloxy)-8-(7-hydroxycoumari-8-yl)-7-α-L-rhamnopyranosyloxycoumarin. - Keywords: Edgeworthia chrysantha; Thymelaeaceae; coumarin; edgeworin; edgeworoside A.
- Baba, Kimiye,Tabata, Yuko,Taniguti, Masahiko,Kozawa, Mitsugi
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p. 221 - 226
(2007/10/02)
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- Ortho Effect in the Fragmentation of 2-Acetoxychalcones under Electron Impact
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2-Acetoxychalcones decompose under electron impact conditions by loss of an acetoxy fragment to form flavylium ions.The effect is restricted to the ortho position and is reduced after hydrogenation of the chalcone double bond.The intense flavylium ion originates as shown by specific labelling with 18O-from two different fragmentation lines: (a) direct loss of an acetoxy radical by cleavage of the phenolic Ar-O bond and (b) sequential elimination of ketene and a hydroxy radical.
- Mentlein, Rolf,Vowinkel, Erich
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p. 330 - 333
(2007/10/02)
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- Selective Syntheses Using Cyclodextrin as Catalyst. 1. Control of Orientation in the Attack of Dichlorocarbene at Phenolates
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4-Hydroxybenzaldehydes, 2,4-dihydroxybenzaldehyde, and 4-(dichloromethyl)-2,5-cyclohexadienones were synthesized in virtually 100percent selectivities and high yields from the corresponding phenols and chloroform in alkaline aqueous solutions by using α- or β-cyclodextrin (α- or β-CD) as catalyst.The regulation of the molar ratio of chloroform to CD below unity throughout the reaction time, by controlling the rate of addition of chloroform, was definitely required to attain high selectivity.Under these conditions, dichlorocarbene, prepared in situ from chloroform and sodium hydroxide, attacked overwhelmingly at the para carbon of phenols with almost perfect suppression of the reaction at the ortho carbon.The structure of the ternary molecular complex composed of β-CD, chloroform, and phenol, formed in the reaction mixture for the selective synthesis of 4-hydroxybenzaldehyde, was determined by NMR spectroscopy.The selective catalysis by CDs was attributed to the regulation of molecular conformation of phenols with respect to chloroform, and thus to dichlorocarbene, in the ternary complex.
- Komiyama, Makoto,Hirai, Hidefumi
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p. 2018 - 2021
(2007/10/02)
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- Process of preparing hexahydropyrimidines
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This invention relates to hexahydropyrimidines (HHP) of the formula STR1 where R' is a substituted group and R is hydrogen or a substituted group; the process of preparing and the uses therefor, particularly as deterioration inhibitors in hydrocarbon fuels.
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- Enzyme-activated oxidative process for coloring hair
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An enzyme-based oxidative process for coloring hair wherein the hair is exposed to a solution having a pH of about 4 to about 10 and containing hydrogen peroxide, soybean peroxidase enzyme and one or more oxidation dye precursors.
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