- PH-dependent optical properties of synthetic fluorescent imidazoles
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An imidazole moiety is often found as an integral part of fluorophores in a variety of fluorescent proteins and many such proteins display pH-dependent light emission. In contrast, synthetic fluorescent compounds with incorporated imidazoles are rare and
- Berezin, Mikhail Y.,Kao, Jeff,Achilefu, Samuel
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- (+)-Echinobetaine B: Isolation, structure elucidation, synthesis and preliminary SAR studies on a new nematocidal betaine from a southern Australian marine sponge, Echinodictyum sp
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The principle nematocidal agent present in a southern Australian marine sponge of the genus Echinodictyum has been isolated and identified as the novel betaine (+)-echinobetaine B (6), and the structure assigned by spectroscopic analysis has been confirmed by total synthesis. Preliminary SAR conclusions are drawn from analysis of synthetic intermediates and the known marine metabolites zooanemonin (12) and norzooanemonin (13), and the new sponge metabolite norzooanemonin methyl ester (14). The latter compound is reported for the first time from a selection of Australian sponges, including an Axinyssa sp., a Niphates sp., an Axinella sp. and a Ptilocaulis sp.
- Capon, Robert J.,Vuong, Dat,McNally, Michelle,Peterle, Torsten,Trotter, Nicholas,Lacey, Ernest,Gill, Jennifer H.
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- Mass Spectrometry of Imidazole-4(5)-carboxaldehyde and Some 1-Methyl and Nitro Derivatives
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The mass spectra of imidazole-4(5)-carboxaldehyde, its two 1-methyl derivatives, 4(5)-nitroimidazole, 5(4)-nitroimidazole-4(5)-carboxaldehyde and 1-methyl-5-nitroimidazole-4-carboxaldehyde are presented and discussed in comparison with those of other imidazole-carboxaldehydes and nitroimidazoles earlier reported.The imidazole-carboxaldehydes and their 1-methyl derivatives exhibit the characteristic fragmentation of aromatic aldehydes, and differences between the isomers can be observed.The nitroimidazoles show the fragmentation typical of aromatic nitrocompounds.In the o-nitroimidazole-carboxaldehydes, the typical losses of aldehydes do not occur, but primary ortho effects between the formyl and nitro groups give rise to important fragmentation routes.In their 1-methyl derivatives, the presence of the methyl group adjacent to the nitro group originates additional double and secondary ortho effects.For some of these transformations, fragmentation mechanisms are proposed.
- Cert, Arturo,Delgado-Cobos, Pedro,Perez-Lanzac, Mariana Trujillo
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- BICYCLIC COMPOUNDS
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Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.
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Paragraph 00599
(2020/06/01)
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- MATRIX METALLOPROTEINASE (MMP) INHIBITORS AND METHODS OF USE THEREOF
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Hydantoin based compounds useful as inhibitors of matrix metalloproteinases (MMPs), particularly macrophage elastase (MMP-12) are described. Also described are related compositions and methods of using the compounds to inhibit MMP-12 and treat diseases mediated by MMP-12, such as asthma, chronic obstructive pulmonary disease (COPD), emphysema, acute lung injury, idiopathic pulmonary fibrosis (IPF), sarcoidosis, systemic sclerosis, liver fibrosis, nonalcoholic steatohepatitis (NASH), arthritis, cancer, heart disease, inflammatory bowel disease (IBD), acute kidney injury (AKI), chronic kidney disease (CKD), Alport syndrome, and nephritis.
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Paragraph 0684-0685
(2019/12/02)
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- BIARYL PYRAZOLES AS NRF2 REGULATORS
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The present invention relates to biaryl pyrazole compounds, methods of making them, pharmaceutical compositions containing them and their use as NRF2 regulators.
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- Concise Synthesis of Anserine: Efficient Solvent Tuning in Asymmetric Hydrogenation Reaction
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A concise synthesis of anserine and related compounds was accomplished by Et-DuPhos-Rh-catalyzed asymmetric hydrogenation of dehydrohistidine derivatives in 2,2,2-trifluoroethanol, which played a key role in improving the yield and selectivity.
- Yamashita, Megumi,Shimizu, Keita,Koizumi, Yasuaki,Wakimoto, Toshiyuki,Hamashima, Yoshitaka,Asakawa, Tomohiro,Inai, Makoto,Kan, Toshiyuki
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supporting information
p. 2734 - 2736
(2016/11/30)
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- HAT INHIBITORS AND METHODS FOR THEIR USE
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Compounds having a structure of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R3c, R4a, R4b, R5, R6, Z and X are as defined herein are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.
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Page/Page column 61
(2016/04/10)
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- Design of coordination interaction of Zn(II) complex with oligo-aspartate peptide to afford a high-affinity tag-probe pair
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A complementary recognition pair consisting of a genetically encodable peptide tag and a small molecular probe isa powerful tool to specifically label and manipulate a protein ofinterest under biological conditions. In this study, we report the redesign of a tag-probe pair comprising an oligo-aspartate peptide tag (such as DDDD) and a binuclear zinc complex. Isothermal-titration calorimetry screening of binding between the series of peptides and zinc complexes revealed that the binding affinity was largely influenced by subtle changes of the ligand structure of the probe. However, the binding was tolerant to differences of the tag peptide sequence. Of those tested, a pair containing a peptide tag (DDAADD) and a binuclear zinc complex possessing 4-chloropyridines (3-2Zn(II)) showed the strongest binding affinity (Ka = 3.88 × 105 M-1), which was about 10-fold larger than the conventional pair of D4-peptide tag (DDDD) and 1-2Zn(II) containing nonsubstituted pyridines (Ka = 3.73 × 104 M-1). The strong binding of this new complementary recognition pair enabled the rapid covalent labeling of a tag-fused maltose binding protein with a fluorescent zinc complex, demonstrating its potential utility in protein analysis.
- Fuchida, Hirokazu,Tabata, Shigekazu,Shindo, Naoya,Takashima, Ippei,Leng, Qiao,Hatsuyama, Yuji,Hamachi, Itaru,Ojida, Akio
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supporting information
p. 784 - 791
(2015/06/25)
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- Supported TBD-assisted solution phase diversification of formyl-aza-heterocycles through alkylation-knoevenagel one pot sequences
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An efficient solution-phase parallel procedure to perform the structural diversification of some formyl-nitrogen heterocycles (A) using the reusable TBD supported base is described. The library synthesis is based in a consecutive Alkylation-Knoevenagel functionalisation that uses alkyl halides (B), Michael acceptors (C) and activated methylene compounds (D) as diversity elements.
- Maatougui, Abdelaziz El,Crespo, Abel,Silva, Artur M.S.,Coelho, Alberto
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experimental part
p. 570 - 582
(2012/07/31)
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- Regiochemistry of N-substitution of some 4(5)-substituted imidazoles under solvent-free conditions
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(Chemical Equation Presented) Imidazole-4(5)-carboxaldehyde and 4(5)-cyanoimidazole were N-benzylated and N-methylated using benzyl chloride and methyl iodide on zinc oxide (ZnO), alumina, and KF/alumina under basic conditions without solvent. Triethylamine (Et3N) or potassium carbonate was added as base in the reactions on ZnO and alumina. Imidazole-4(5)-carboxaldehyde was also benzylated on silica and carbon nanotubes. The effect of bases and solids on the product distribution of 1,4- and 1,5-substituted compounds was investigated. In some cases, the product ratios were different for imidazole-4(5)-carboxaldehyde and 4(5)-cyanoimidazole. In the reactions on KF/alumina the 1,4-product was favored for both compounds. The combination of Et3N and ZnO favored the 1,5-product, however for the nitrile effect was not so pronounced. When N-benzylation and methylation of the aldehyde were performed in the presence of catalytic amount of zinc chloride with Et3N as base, the product distributions were the same as in the reactions on ZnO. Nitrile gave different product ratios on ZnO and in the presence of ZnCl2. In addition, a mixture of N-benzylimidazole and 1,3-dibenzylimidazolium was produced when imidazole was benzylated on KF/alumina. Only the latter product was afforded when two equivalents of benzyl chloride were used.
- Oresmaa, Larisa,Taberman, Helena,Haukka, Matti,Vainiotalo, Pirjo,Aulaskari, Paula
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p. 1445 - 1451
(2008/09/18)
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- Inhibitors of tumor progression loci-2 (Tpl2) kinase and tumor necrosis factor α (TNF-α) production: Selectivity and in vivo antiinflammatory activity of novel 8-substituted-4-anilino-6-aminoquinoline-3- carbonitriles
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Tumor progression loci-2 (Tpl2) (Cot/MAP3K8) is a serine/threonine kinase in the MAP3K family directly upstream of MEK. Recent studies using Tpl2 knockout mice have indicated an important role for Tpl2 in the lipopolysaccharide (LPS) induced production of
- Green, Neal,Hu, Yonghan,Janz, Kristin,Li, Huan-Qiu,Kaila, Neelu,Guler, Satenig,Thomason, Jennifer,Joseph-McCarthy, Diane,Tam, Steve Y.,Hotchandani, Rajeev,Wu, Junjun,Huang, Adrian,Wang, Qin,Leung, Louis,Pelker, Jefferey,Marusic, Suzana,Hsu, Sang,Telliez, Jean-Baptiste,Hall, J. Perry,Cuozzo, John W.,Lin, Lih-Ling
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p. 4728 - 4745
(2008/03/11)
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- NOVEL COMPOUNDS
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Compounds of formula (I): are inhibitors of the enzyme Lp-PLA2 and are of use in therapy, in particular for treating atherosclerosis. In Formula (I) R1, R2, R3, R4, R5, R6, X and Y are as d
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(2010/02/07)
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- REGIOSPECIFIC SYNTHESIS OF N-ALKYL-4- AND 5-SUBSTITUTED IMIDAZOLES
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A facile regiospecific synthesis of 4- and 5-substituted N-alkyl imidazoles has been developed from N-trimethylsilyloxyethylimidazole(s).The method combines directed metallation with alkyl triflate mediated imidazole quaternization and SEM group cleavage.
- Shapiro, Gideon,Gomez-Lor, Berta
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p. 215 - 218
(2007/10/02)
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- Carboxylate protection for the synthesis of 4,5-disubstituted 1-methylimidazoles
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Using the carboxylate function as a readily removed blocking group for the 2-position, a regioselective synthesis of diverse 4,5-disubstituted 1-methylimidazoles has been developed starting from 1-methyltribromoimidazole, 5.
- Shapiro,Gomez-Lor
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p. 5524 - 5526
(2007/10/02)
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