- PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS
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Photoactive probes and probe systems for detecting biological interactions are described. The photoactive probes include probes that combine both photocleavable and photoreactive moieties. The photoactive probe systems can include a first probe comprising a photocatalytic group and a second probe comprising a group that can act as a substrate for the reaction catalyzed by the photocatalytic group. The probes and probe systems can also include groups that can specifically bind to a binding partner on a biological entity of interest and a detectable group or a precursor thereof. The probes and probe systems can detect spatiotemporal interactions of proteins or cells. In some embodiments, the interactions can be detected in live cells. Also described are methods of detecting the biological interactions.
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- Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions
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Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.
- Lanzi, Matteo,Ali Abdine, Racha Abed,De Abreu, Maxime,Wencel-Delord, Joanna
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p. 9047 - 9052
(2021/12/06)
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- PROBE FOR DETECTING CARBAPENEM-RESISTANT BACTERIA AND USE THEREOF
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The present disclosure relates to a compound represented by Chemical Formula 1, a probe for detecting antibiotic-resistant bacteria, which includes the compound, a composition containing the compound, a kit including the compound and a method for detectin
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Paragraph 0085; 0120-0122
(2021/09/10)
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- Synthesis and Biological Evaluation of Hapten-Clicked Analogues of The Antigenic Peptide Melan-A/MART-126(27L)-35
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A click-chemistry-based approach was implemented to prepare peptidomimetics designed in silico and made from aromatic azides and a propargylated GIGI-mimicking platform derived from the altered Melan-A/MART-126(27L)-35 antigenic peptide ELAGIGILTV. The CuI-catalyzed Huisgen cycloaddition was carried out on solid support to generate rapidly a first series of peptidomimetics, which were evaluated for their capacity to dock at the interface between the major histocompatibility complex class-I (MHC-I) human leucocyte antigen (HLA)-A2 and T-cell receptors (TCRs). Despite being a weak HLA-A2 ligand, one of these 11 first synthetic compounds bearing a p-nitrobenzyl-triazole side chain was recognized by the receptor proteins of Melan-A/MART-1-specific T-cells. After modification of the N and C termini of this agonist, which was intended to enhance HLA-A2 binding, one of the resulting seven additional compounds triggered significant T-cell responses. Thus, these results highlight the capacity of naturally circulating human TCRs that are specific for the native Melan-A/MART-126-35 peptide to cross-react with peptidomimetics bearing organic motifs structurally different from the native central amino acids.
- Tarbe, Marion,Miles, John J.,Edwards, Emily S. J.,Miles, Kim M.,Sewell, Andrew K.,Baker, Brian M.,Quideau, Stéphane
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p. 799 - 807
(2020/04/20)
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- Inhibition of Mycobacterium tuberculosis InhA: Design, synthesis and evaluation of new di-triclosan derivatives
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Multi-drug resistant tuberculosis (MDR-TB) represents a growing problem for global healthcare systems. In addition to 1.3 million deaths in 2018, the World Health Organisation reported 484,000 new cases of MDR-TB. Isoniazid is a key anti-TB drug that inhibits InhA, a crucial enzyme in the cell wall biosynthesis pathway and identical in Mycobacterium tuberculosis and M. bovis. Isoniazid is a pro-drug which requires activation by the enzyme KatG, mutations in KatG prevent activation and confer INH-resistance. ‘Direct inhibitors’ of InhA are attractive as they would circumvent the main clinically observed resistance mechanisms. A library of new 1,5-triazoles, designed to mimic the structures of both triclosan molecules uniquely bound to InhA have been synthesised. The inhibitory activity of these compounds was evaluated using isolated enzyme assays with 2 (5-chloro-2-(4-(5-(((4-(4-chloro-2-hydroxyphenoxy)benzyl)oxy)methyl)-1H-1,2,3-triazol-1-yl)phenoxy)phenol) exhibiting an IC50 of 5.6 μM. Whole-cell evaluation was also performed, with 11 (5-chloro-2-(4-(5-(((4-(cyclopropylmethoxy)benzyl)oxy)methyl)-1H-1,2,3-triazol-1-yl)phenoxy)phenol) showing the greatest potency, with an MIC99 of 12.9 μM against M. bovis.
- Alderwick, Luke J.,Armstrong, Tom,Lamont, Malcolm,Lanne, Alice,Thomas, Neil R.
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-
- Development of carbapenem-based fluorogenic probes for the clinical screening of carbapenemase-producing bacteria
-
This report describes the synthesis of a library of fluorogenic carbapenemase substrates consisting of carbapenem derivatives, fluorescence dyes, and active cleavable linkers and their evaluation for specifically detecting carbapenemase-producing organism
- Kim, Juhyeon,Kim, Yihoon,Abdelazem, Ahmed Z.,Kim, Hak Joong,Choo, Hyunah,Kim, Hoon Seok,Kim, Jung Ok,Park, Yeon-Joon,Min, Sun-Joon
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- Reinvestigation of the synthesis of “covalent-assembly” type probes for fluoride ion detection. Identification of novel 7-(diethylamino)coumarins with aggregation-induced emission properties
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An unprecedented C-3 functionalization of 4-(diethylamino)salicylaldehyde through a Friedel-Crafts type alkylation reaction has been discovered during the synthesis of “covalent-assembly”-based fluorescent probes for detection of fluoride ions. The resulting Friedel-Crafts adduct was successfully used for the preparation of two novel 8-substituted 7-(diethylamino)coumarin dyes. The photophysical study of these fluorophores has enabled us to highlight their remarkable aggregation-induced emission (AIE) properties characterized by a yellow-orange emission of aggregates in water. Therefore, 4-(tert-butyldimethylsilyloxy)benzyl substituent was identified as a novel AIE-active moiety which could be seen as a possible alternative to popular tetraphenylethylene (TPE).
- Quesneau, Valentin,Roubinet, Beno?t,Renard, Pierre-Yves,Romieu, Anthony
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supporting information
(2019/11/05)
-
- Fluorescent probe for detecting fluoride ions
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The invention discloses a fluorescent probe for detecting fluoride ions in an organism, and belongs to the technical field of analytical chemistry. The fluorescent probe uses a cyanine dye QCy7 as a parent body, a silicon-oxygen bond as a switch and hydroxybenzyl as a linker, and the chemical structure general formula of the fluorescent probe is as shown in a formula (I). The fluorescent probe hassimple synthesis and is convenient to use, can specifically react with the fluoride ions, breaks the silicon-oxygen bond, and releases fluorescence of fluorogen QCy7 through electron transfer. The fluorescent probe is not interfered with other ions in the process of detecting the fluoride ions, has good selectivity to the fluoride ions, and can accurately detect the fluoride ions in the organism.
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-
- FLUORIDE FLUORESCENCE PROBE
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Methylene blue (MB) derivatives selectively detect F? by desilylation reaction to act as a fluorescent probe.
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Paragraph 0096-0099; 0102-0103
(2019/01/09)
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- Novel methinic functionalized and dendritic C-scorpionates
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The study of chelating ligands is undoubtedly one of the most significant fields of research in chemistry. The present work is directed to the synthesis of new functionalized derivatives of tripodal C-scorpionate compounds. Tris-2,2,2-(1-pyrazolyl)ethanol, HOCH2C(pz)3 (1), one of the most important derivatives of hydrotris(pyrazolyl)methane, was used as a building block for the synthesis of new functionalized C-scorpionates, aiming to expand the scope of this unexplored class of compounds. The first dendritic C-scorpionate was successfully prepared and used in the important industrial catalytic reactions, Sonogashira and Heck C-C cross-couplings.
- Martins, Luísa M.D.R.S.,Wanke, Riccardo,Silva, Telma F.S.,Pombeiro, Armando J.L.,Servin, Paul,Laurent, Régis,Caminade, Anne-Marie
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- Method for identifying fluorine-containing toothpaste by naked eyes through probe S-F
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The invention relates to a method for identifying fluorine-containing toothpaste by naked eyes through a probe S-F. The structure of the probe is as follows: the formula is shown in the description. After the probe is added into a toothpaste sample, wheth
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- A fluoride activated methylene blue releasing platform for imaging and antimicrobial photodynamic therapy of human dental plaque
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We report a F- activated methylene blue (MB) releasing platform for imaging and antimicrobial photodynamic therapy (aPDT). By utilizing this platform, one of the selected probes, FD-F3, displays a remarkable near-infrared fluorescence and absor
- Wei, Peng,Xue, Fengfeng,Shi, Yunming,Strand, Ross,Chen, Hui,Yi, Tao
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p. 13115 - 13118
(2018/11/30)
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- Highly sulphated cellulose: a versatile, reusable and selective desilylating agent for deprotection of alcoholic TBDMS ethers
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A mild, efficient and rapid protocol was developed for the deprotection of alcoholic TBDMS ethers using a recyclable, eco-friendly highly sulphated cellulose sulphate acid catalyst in methanol. This acid catalyst selectively cleaves alcoholic TBDMS ethers in bis-TBDMS ethers containing both alcoholic and phenolic TBDMS ether moieties.
- Dachavaram, Soma Shekar,Penthala, Narsimha R.,Calahan, Julie L.,Munson, Eric J.,Crooks, Peter A.
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p. 6057 - 6062
(2018/09/06)
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- Low-Valent Titanium-Mediated Radical Conjugate Addition Using Benzyl Alcohols as Benzyl Radical Sources
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A concise method to directly generate benzyl radicals from benzyl alcohol derivatives has been developed. The simple and inexpensive combination of TiCl4(collidine) (collidine = 2,4,6-collidine) and manganese powder afforded a low-valent titanium reagent, which facilitated homolytic cleavage of benzylic C-OH bonds. The application to radical conjugate addition reactions demonstrated the broad scope of this method. The reaction of various benzyl alcohol derivatives with electron-deficient alkenes furnished the corresponding radical adducts.
- Suga, Takuya,Shimazu, Shoma,Ukaji, Yutaka
-
supporting information
p. 5389 - 5392
(2018/09/12)
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- Total Synthesis of Two Glycosylated Stilbenes, Oxyresveratrol 2-O-β- d -Glucopyranoside and 2,3,5,4′-Tetrahydroxystilbene 2-O-β- d -Glucopyranoside
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Glycosylated stilbenes are biologically active secondary metabolites of plants and have the potential to alleviate a broad range of human diseases. However, some of these compounds are not naturally abundant, and thus the synthesis of such molecules is de
- Kumar, Sunil,Lee, Hsueh-Yun,Liou, Jing-Ping
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p. 1294 - 1301
(2017/05/31)
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- Resveratrol derivative containing fluorine group, and preparation method and application
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The invention belongs to the technical field of medicines and discloses a resveratrol derivative containing a fluorine group, and a preparation method and an application. The resveratrol derivative has the structural characteristics as shown in a general
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- AZASULFURYLPEPTIDE-BASED CD36 MODULATORS AND USES THEREOF
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Novel azasulfuryl-containing peptidomimetics capable of inhibiting CD36 activity are disclosed. Use of these azasulfuryl-containing peptidomimetics for the treatment of CD36-related diseases, disorders or conditions, including TLR2-mediated inflammatory disease, disorder or condition, and methods of obtaining such azasulfuryl-containing peptidomimetics, are also disclosed.
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- Decarboxylative Csp3-Csp3 coupling for benzylation of unstable ketone enolates: Synthesis of: P -(acylethyl)phenols
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A new decarboxylative Csp3-Csp3 coupling approach for the benzylation of ketone enolates has been developed. A variety of raspberry ketone derivatives were conveniently synthesized in good to excellent yields under mild conditions. A crossover reaction shed light on the mechanism of this tandem reaction.
- Wang, Sasa,Chen, Xinzheng,Ao, Qiaoqiao,Wang, Huifei,Zhai, Hongbin
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p. 9454 - 9457
(2016/07/29)
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- FLUOROCHROME-COUPLED COELENTERAZINE
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PROBLEM TO BE SOLVED: To provide techniques of making the light emission wavelength of a Renilla luciferase (Rluc)-coelenterazine light-emitting system longer by modifying coelenterazine. SOLUTION: A fluorochrome-coupled coelenterazine is represented by t
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- Coelenterazine analog and preparing method and application thereof
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The invention discloses a coelenterazine analog and a preparing method and application thereof. The coelenterazine analog has the general structure formula (I) shown in the description, wherein R1, R2 and R3 in the formula are different substituents. According to application of the compound as a bioluminescence substrate, the existence and quantity (including the enzyme level, the cell level and the animal level) of coelenterazine luciferase can be detected with bioluminescence, and the in vitro, cell and in vivo distribution imaging of luciferase can be detected; the compound can serve as a report signal to detect the pharmacologic action and the toxic effect of medicine on the enzyme level, the cell level and the animal level under the existence of luciferase.
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-
Paragraph 0209-0213
(2018/02/04)
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- Bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution
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Three novel coelenterazine (CTZ) derivatives with extension at the C-6 position of the imidazopyrazinone structure show significant bioluminescence emission with known renilla luciferase variants, indicating a promising method to develop CTZ derivatives w
- Nishihara, Ryo,Suzuki, Hideyuki,Hoshino, Emi,Suganuma, Sakura,Sato, Moritoshi,Saitoh, Tsuyoshi,Nishiyama, Shigeru,Iwasawa, Naoko,Citterio, Daniel,Suzuki, Koji
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p. 391 - 394
(2015/02/19)
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- Mild and selective deprotection of tert -butyl(dimethyl)silyl ethers with catalytic amounts of sodium tetrachloroaurate(III) dihydrate
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A simple and mild method for the removal of tert-butyl(dimethyl)silyl (TBS) protecting groups with catalytic amounts of sodium tetrachloroaurate(III) dihydrate is described. The procedure permits selective deprotection of aliphatic TBS ethers in good to excellent yields in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into 4-methoxybenzyl ethers or methyl ethers in one pot by using larger quantities of the catalyst and a higher reaction temperature.
- Zhang, Qi,Kang, Xiuqin,Long, Lei,Zhu, Lijuan,Chai, Yonghai
-
-
- A fluorescent off-on NBD-probe for F- sensing: Theoretical validation and experimental studies
-
The design, synthesis and fluoride sensing ability of a 7-nitro-2,1,3-benzoxadiazole (NBD) based chemodosimeter is reported. Theoretical calculations were used to design a more applicable off-on response, by choosing NBD as the accurate fluorophore. React
- Roy, Arundhati,Datar, Avdhoot,Kand, Dnyaneshwar,Saha, Tanmoy,Talukdar, Pinaki
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p. 2143 - 2149
(2014/03/21)
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- Strategies for large-scale synthesis of coelenterazine for in vivo applications
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A new application of two Negishi-type coupling reactions for the synthesis of coelenterazine is reported. The synthesis of coelenterazine in high purity on a gram scale will enable numerous approaches to bioluminescence imaging and possibly photodynamic therapy of deep-seated tumors. Coelenterazine is the substrate for several luciferases, among them Gaussia luciferase (gLuc). This synthesis starts with pyrazin-2-amine and uses inexpensive starting materials and catalysts. Georg Thieme Verlag Stuttgart New York.
- Shrestha, Tej B.,Troyer, Deryl L.,Bossmann, Stefan H.
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p. 646 - 652
(2014/03/21)
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- COELENTERAZINE ANALOGUES AND COELENTERAMIDE ANALOGUES
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Coelenterazine analogs with different luminescence properties from conventional ones and coelenteramide analogs with different fluorescence properties from conventional ones have been desired. The invention provides coelenterazine analogs modified at the
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- Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction
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A series of monophenols and diphenols containing the ferrocene-C triazolyl and ferrocene-Ntriazolyl bond were prepared in a cycloaddition reaction of ethynylferrocene with aryl and benzyl azides and in a reaction of azidoferrocene with phenylacetylenes, respectively. The anticancer activity of the prepared compounds against hormone-dependent (MCF-7) and hormone-independent (HCC38) breast cancer cell lines was studied. The investigated compounds exhibited moderate anticancer activity against hormone-independent (IC50 ~ 15-48 μM) cancer cell line and low activity against hormone-dependent cancer cell line (IC50 ~ 84-98 μM).
- Plazuk, Damian,Rychlik, B?azej,B?auz, Andrzej,Domaga?a, S?awomir
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p. 102 - 112
(2012/09/07)
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- A mild, efficient, and selective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using dicationic ionic liquid as a catalyst
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Selective deprotection of alkyl TBDMS ether in the presence of phenolic TBDMS ether using dicationic ionic liquid [tetraEG(mim)2][OMs] 2 as a homogeneous catalyst showed significant catalytic activity in methanol at ambient temperature to produce respective alcohol in excellent yield. The present environmentally benign catalytic system is found to be very convenient, fast, high yielding, and clean method for selective desilylation of alkyl silyl ethers even in the existence of other sensitive organic functional groups such as aldehyde, methoxy, and acetate were also achieved.
- Jadhav, Arvind H.,Kim, Hern
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p. 5338 - 5342
(2012/11/07)
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- A novel oxidative transformation of alcohols to nitriles: An efficient utility of azides as a nitrogen source
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An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN3 as a source of nitrogen in the presence of a catalytic amount of Cu(ClO4)2·6H 2O.
- Rokade, Balaji V.,Malekar, Sanjeev K.,Prabhu, Kandikere Ramaiah
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supporting information; body text
p. 5506 - 5508
(2012/07/03)
-
- COELENTERAZINE ANALOGUES AND COELENTERAMIDE ANALOGUES
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Coelenterazine analogues with different luminescence properties from conventional ones and coelenteramide analogues with different fluorescence properties from conventional ones have been desired. The invention provides coelenterazine analogues modified at the 8-position of coelenterazine and coelenteramide analogues modified at the 2- or 3-position of coelenteramide.
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- A structurally simple self-immolative reagent that provides three distinct, simultaneous responses per detection event
-
A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the pKa of the pendant alcohol decreases (Figure presented).
- Nunez, Sean A.,Yeung, Kimy,Fox, Nicole S.,Phillips, Scott T.
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p. 10099 - 10113
(2012/02/05)
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- Total synthesis of naturally occurring furan compounds 5-{[(4- hydroxybenzyl)oxy]methyl}-2-furaldehyde and pichiafuran C
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The synthesis of the natural furan derivatives 5-{[(4-hydroxybenzyl)oxy] methyl}-2-furaldehyde and pichiafuran C is described. Diverse alternative synthetic approaches were developed for the preparation of these natural products. They were prepared through an etherification reaction of the key furan precursor 5-(hydroxymethyl)-2-furaldehyde (HMF), which can be readily obtained from d-fructose, d-glucose, or sucrose, with the corresponding alcohols. 5-{[(4-Hydroxybenzyl)oxy]methyl}-2-furaldehyde was not only obtained in a two-step methodology but also by a biomimetic single-step synthesis. Similarly, pichiafuran C was prepared by three different syntheses, each one by a two-step procedure, also including a biomimetic approach. Georg Thieme Verlag Stuttgart.
- Quiroz-Florentino, Hector,Hernandez-Benitez, R. Israel,Avina, Judit A.,Burgueno-Tapia, Eleuterio,Tamariz, Joaquin
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p. 1106 - 1112
(2011/06/20)
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- Use of Dendrimers to Stimulate Cell Growth
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The present invention relates to the use of dendrimers with monophosphonic or bisphosphonic terminations in order to stimulate the growth of cell cultures or to activate cells in culture.
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Page/Page column 86
(2009/06/27)
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- Facile and highly selective deprotection of tert-butyldimethyl silyl ethers using sulfated SnO2 as a solid catalyst
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Highly selective deprotection of tert-butyldimethylsilyl ethers at room temperature has been described using sulfated SnO2 as an efficient solid catalyst. Copyright Taylor & Francis Group, LLC.
- Bhure, Mahesh H.,Kumar, Indresh,Natu, Arun D.,Rode, Chandrashekhar V.
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p. 346 - 353
(2008/09/16)
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- A facile and catalytic method for selective deprotection of tert-butyldimethylsilyl ethers with copper(II) bromide
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Copper(II) bromide is found to be a simple and efficient catalyst for selective deprotection of tert-butyldimethylsilyl ethers of alcohols/phenols at ambient temperature. Various labile functional groups such as ketal, alkene, ketone, OTBDPS, OTHP and allyl and benzyl ethers are found to be compatible under the reaction conditions.
- Bhatt, Suchitra,Nayak, Sandip K.
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p. 8395 - 8399
(2007/10/03)
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- A simple, efficient and highly selective deprotection of t-butyldimethylsilyl (TBDMS) ethers using silica supported sodium hydrogen sulfate as a heterogeneous catalyst
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t-Butyldimethylsilyl (TBDMS) ethers have been efficiently and selectively deprotected using silica supported sodium hydrogen sulfate (NaHSO4·SiO2) as a heterogeneous catalyst at room temperature to regenerate the parent alcohols in high yields.
- Das, Biswanath,Reddy, K. Ravinder,Thirupathi
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p. 5855 - 5857
(2007/10/03)
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- A mild and efficient desilylation of O-tert-butyldimethylsilyl ethers mediated by chlorotrimethylsilane and potassium fluoride dihydrate in acetonitrile
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Desilylation of O-tert-butyldimethylsilyl ethers was achieved by a reagent system consisting of chlorotrimethylsilane and potassium fluoride dihydrate in acetonitrile. This alternative desilylation procedure is chemoselective, generally effective and operationally simple, and should find practical applications in organic synthesis. Georg Thieme Verlag Stuttgart.
- Peng, Yu,Li, Wei-Dong Z.
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p. 1165 - 1168
(2007/10/03)
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- 5-Pyrrolidinylsulfonyl isatins as a potential tool for the molecular imaging of caspases in apoptosis
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Caspases are the unique enzymes responsible for the execution of the cell death program and may represent an exclusive target for the specific molecular imaging of apoptosis in vivo. 5-Pyrrolidinylsulfonyl isatins represent potent nonpeptidyl caspase inhibitors that may be suitable for the development of caspase binding radioligands (CBRs). (S)-5-[1-(2-Methoxymethylpyrrolidinyl) sulfonyl]isatin (7) served as a lead compound for modification of its N-1-position. Corresponding pairs of N-1-substituted 2-methoxymethyl- and 2-phenoxymethylpyrrolidinyl derivatives were examined in vitro by biochemical caspase inhibition assays. All target compounds possess high in vitro caspase inhibition potencies in the nanomolar to subnanomolar range for caspase-3 (Ki = 0.2-56.1 nM). As shown for compound (S)-1-(4-(2-fluoroethoxy) benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin (35), the class of N-1-substituted 5-pyrrolidinylsulfonyl isatins competitively inhibits caspase-3. All caspase inhibitors show selectivity for the effector caspases-3 and -7 in vitro. The 2-methoxymethylpyrrolidinyl versions of the isatins appear to possess superior caspase inhibition potencies in cellular apoptosis inhibition assays compared with the 2-phenoxymethylpyrrolidinyl inhibitors.
- Kopka, Klaus,Faust, Andreas,Keul, Petra,Wagner, Stefan,Breyholz, Hans-J?rg,H?ltke, Carsten,Schober, Otmar,Sch?fers, Michael,Levkau, Bodo
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p. 6704 - 6715
(2007/10/03)
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- Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol
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Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time.
- Yeom, Chang-Eun,Kim, Young Jong,Lee, So Young,Shin, Yong Je,Kim, B. Moon
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p. 12227 - 12237
(2007/10/03)
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- A high loading sulfonic acid-functionalized ordered nanoporous silica as an efficient and recyclable catalyst for chemoselective deprotection of tert-butyldimethylsilyl ethers
-
A high loading sulfonic acid-functionalized ordered nanoporous silica efficiently catalyzes the deprotection of a variety of alcoholic TBDMS (tert-butyldimethylsilyl)ethers in methanol. The catalyst shows high thermal stability (up to 240°C) and can be recovered and reused for at least seven reaction cycles without loss of reactivity. This method can be used to deprotect TBDMS ethers of alcohols in the presence of TBDMS ethers of phenols.
- Karimi, Babak,Zareyee, Daryoush
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p. 4661 - 4665
(2007/10/03)
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- A catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol is a good combination for the cleavage of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers
-
Various THP and TBS ethers can be unmasked easily to the corresponding hydroxyl compounds in good yields by using a combination of a catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol at room temperature. In addition, alkyl TBS ethers can be hydrolyzed chemoselectively in the presence of aryl TBS ethers. Moreover, alkyl TBS ethers can be cleaved easily in the presence of alkyl or aryl THP ethers using the same conditions.
- Khan, Abu T.,Islam, Samimul,Choudhury, Lokman H.,Ghosh, Subrata
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p. 9617 - 9621
(2007/10/03)
-
- N-Iodosuccinimide (NIS) as a mild and highly chemoselective catalyst for deprotection of tert-butyldimethylsilyl ethers
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A variety of alcoholic TBDMS (t-butyldimethylsilyl) ethers are easily removed in excellent yields by treatment with a catalytic amount of N-iodosuccinimide (NIS, 5 mol %) in methanol. This method is able to deprotect TBDMS ethers of alcohols in the presence of TBDMS ethers of phenols.
- Karimi, Babak,Zamani, Asghar,Zareyee, Daryoush
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p. 9139 - 9141
(2007/10/03)
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- A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers
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A wide variety of tert-butyldimethylsilyl ethers 1 can be easily cleaved to the corresponding parent hydroxyl compound 2 in the presence of 5 mol % of acetonyltriphenylphosphonium bromide (ATPB) at room temperature. In addition, tert-butyldiphenylsilyl ethers can also be cleaved by using 20 mol % of the same catalyst. Alkyl tert-butyldimethylsilyl ethers can be deprotected to the hydroxyl compounds chemoselectively in the presence of aryl tert- butyldimethylsilyl ethers. Some of the major advantages are mild reaction conditions, no aqueous workup, high efficiency and chemoselectivity and compatibility with other protecting groups; no brominations occur in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Khan, Abu T.,Ghosh, Subrata,Choudhury, Lokman H.
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p. 2198 - 2204
(2007/10/03)
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- A mild, efficient, and inexpensive protocol for the selective deprotection of TBDMS ethers using KHSO4
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Potassium hydrogensulfate in 30% aq. methanol deprotects a variety of tert-butyldimethylsilyl ethers at room temperature in excellent yields.
- Arumugam, Pandurangan,Karthikeyan, Ganesan,Perumal, Paramasivan T.
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p. 1146 - 1147
(2007/10/03)
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- Studies on non-thiazolidinedione antidiabetic Agents. 2. Novel oxyiminoalkanoic acid derivatives as potent glucose and lipid lowering agents
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We previously reported that (Z)-2-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl) methoxy]benzyloxyimino}-2-(4-phenoxyphenyl)acetic acid (3) showed potent glucose and lipid lowering effects in genetically obese and diabetic mice, KKA y. This compound a
- Imoto, Hiroshi,Sugiyama, Yasuo,Kimura, Hiroyuki,Momose, Yu
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p. 138 - 151
(2007/10/03)
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- A highly efficient and useful synthetic protocol for the cleavage of tert-butyldimethylsilyl (TBS) ethers using a catalytic amount of acetyl chloride in dry methanol
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A wide variety of tert-butyldimethylsilyl (TBS) ethers as well as tert-butyldiphenylsilyl (TBDPS) ethers 1 can be easily deprotected to the corresponding parent hydroxyl compounds 2 by employing catalytic amounts of acetyl chloride in dry MeOH at 0°C to room temperature in good yields. Some of the major advantages are mild conditions, high efficiency, high selectivity, high yields, easy operation, and also compatibility with other protecting groups. Furthermore, no acetylation nor chlorination takes place under the experimental conditions.
- Khan, Abu T.,Mondal, Ejabul
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p. 694 - 698
(2007/10/03)
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- Selective Deprotection of tert-Butyldimethylsilyl Ethers Using Nafion-H/Sodium Iodide (or Bromodimethylsulfonium Bromide) in Methanol
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Catalytic amounts of bromodimethyl sulfonium bromide, or Nafion-H along with NaI (1 equiv.), in methanol cleave a variety of TBDMS ethers readily in high yields. Alkyl TBDMS ethers react more readily and selectively compared to phenolic TBDMS ethers, benzyl, and methyl ethers.
- Rani, Shikha,Babu, J. Lokesh,Vankar, Yashwant D.
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p. 4043 - 4052
(2007/10/03)
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- Efficient and chemoselective cleavage of TBS ethers by a sub-stoichiometric amount of decaborane
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TBS ethers od aliphatic alcohols in THF-MeOH (or methanol) were deprotected chemoselectively to the corresponding alcohols using a sub-stoichiometric amount of decaborane at rt under nitrogen in high yields.
- Jeong, Yeon Joo,Lee, Ji Hee,Park, Eun Soo,Yoon, Cheol Min
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p. 1223 - 1225
(2007/10/03)
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- Oxyiminoalkanoic acid derivatives with hypoglycemic and hypolipidemic activity
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This invention provides a novel oxyiminoalkanoic acid derivative which has excellent hypoglycemic and hypolipidemic actions and which is used for the treatment of diabetes mellitus, hyperlipemia, insulin insensitivity, insulin resistance and impaired glucose tolerance.
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- An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide: Synthesis and preliminary biological studies
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The synthesis of a nonhydrolyzable, carbon-linked analogue (4-HBR) of the retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) using Umpolung methods is described. Preliminary studies of biological activity show 4-HBR is similar to 4-HPR in its actions although a potentially relevant and desirable difference is its reduced suppression of plasma vitamin A levels. These results show that 4-HPR does not have to be hydrolyzed to retinoic acid to produce its chemotherapeutic effects. Elsevier Science Ltd. All rights reserved.
- Weiss, Kevin L.,Alshafie, Galal,Chapman, Jason S.,Mershon, Serena M.,Abou-Issa, Hussein,Clagett-Dame, Margaret,Curley Jr., Robert W.
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p. 1583 - 1586
(2007/10/03)
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