- A Quantitative Assay of Sodium Triacetoxyborohydride
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Sodium triacetoxyborohydride (STAB) is a common reducing agent with potency that degrades over time and is not uniformly assigned. A simple assay based on an aldehyde reduction has been developed to determine the active borohydride content of this reagent. The HPLC assay yield of a salicylaldehyde reduction has been shown to accurately determine this potency and has been validated against the H2 evolution method as well as yields obtained from a reductive amination. The use of these assay data to adjust the STAB charge as well to optimize a reductive amination has been demonstrated.
- Zacuto, Michael J.,Perona, Joseph,Dunn, Robert
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- Porous Ge@C materials via twin polymerization of germanium(II) salicyl alcoholates for Li-ion batteries
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The germylenes, germanium(ii) 2-(oxidomethyl)phenolate (1), germanium(ii) 4-methyl-2-(oxidomethyl)phenolate (2) and germanium(ii) 4-bromo-2-(oxidomethyl)phenolate (3) were synthesized and their thermally induced twin polymerization to give organic-inorganic hybrid materials was studied. The compounds 1-3 form oligomers including dimers, trimers and tetramers as a result of intermolecular coordination of the benzylic oxygen atom to germanium. The structural motifs were studied by single crystal X-ray diffraction analysis and DFT-D calculations. Thermally induced twin polymerization of these germylenes gave hybrid materials based on germanium-containing phenolic resins. Carbonization of these resins under reductive conditions resulted in porous materials that are composed of germanium and carbon (Ge@C materials), while oxidation with air provided non-porous germanium dioxide. The porous Ge@C materials were tested as potential anode materials for rechargeable Li-ion batteries. Reversible capacities of 540 mA h g-1 were obtained at a current density of 346 mA g-1 without apparent fading for 100 cycles, which demonstrates that germanium is well accessible in the hybrid material.
- Kitschke, Philipp,Walter, Marc,Rüffer, Tobias,Seifert, Andreas,Speck, Florian,Seyller, Thomas,Spange, Stefan,Lang, Heinrich,Auer, Alexander A.,Kovalenko, Maksym V.,Mehring, Michael
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- Synthesis, characterization and Twin Polymerization of a novel dioxagermine
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The synthesis of 6-bromo-2,2-di-tert-butyl-4H-1,3,2-benzo[d]dioxagermine (1) via an alcohol/alkoxide exchange starting from di-tert-butyl-di-ethoxy germane is reported. Characterization of the title compound including single crystal X-ray diffraction and TGA/DSC analysis, mass spectrometry, 1H NMR, 13C{1H} NMR and IR spectroscopy is reported. DFT-D calculations have been carried out to assign the absorption band maxima of the IR spectrum to the corresponding vibrational modes. The suitability for Twin Polymerization of the novel dioxagermine 1 has been studied by TGA/DSC analysis and mass spectrometry. Proton-assisted Twin Polymerization of 1 results in an organic-inorganic hybrid material composed of a phenolic resin and [ tBu2GeO]n.
- Kitschke, Philipp,Auer, Alexander A.,Seifert, Andreas,Rüffer, Tobias,Lang, Heinrich,Mehring, Michael
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- 5-Diacetoxymethyl-cycloSal-d4TMP - A prototype of enzymatically activated cyclosal-pronucleotides
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A new class of "lock-in"-modified cycloSal-pronucleotides has been synthesized. On the example of 5-diacetoxymethyl-cycloSal-d4T-monophosphate (5-di-AM-cycloSal-d4TMP), the concept of enzymatically activated cycloSal-pronucleotides is elucidated. Synthesis, hydrolysis studies, and antiviral activities against HIV are presented. Copyright Taylor & Francis Group, LLC.
- Gisch,Balzarini,Meier
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- Diels-Alder reaction of 4-bromo-6-spiroepoxycyclohexa-2,4-dienone with electron-rich and neutral dienophiles
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Spirodienone 1, prepared by Adler-Becker oxidation of 4-bromo-2- hydroxymethylphenol, undergoes [4+2] cycloaddition with various dienophiles (enol ethers, enol esters, styrenes, N-methylvinylacetamide) under thermal conditions (20-160°C). Three sets of experiments have been carried out, either with CH2Cl2 as solvent or neat with 1, or under tandem oxidation- cycloaddition conditions with phase-transfer catalysis. Complete regio- and syn diastereofacial selectivities were obtained but a switch in endo/exo selectivity has been observed between enol ethers and styrenes (endo addition), enol esters (low selectivity) and an enamide (exo addition). The FMO analysis confirms that theses reactions are under LUMO(diene) control and that the observed regioselectivity is in agreement with orbital coefficients. Except for vinyl acetate, the formation of the major isomer is qualitatively confirmed at the AM1 level.
- Bonnarme, Vincent,Bachmann, Christian,Cousson, Alain,Mondon, Martine,Gesson, Jean-Pierre
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- Asymmetric Retro-Claisen Reaction by Synergistic Chiral Primary Amine/Palladium Catalysis
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We described herein a chiral primary amine/palladium catalyzed asymmetric retro-Claisen reaction of β-diketones with salicylic carbonates. A series of chiral α-alkylated ketones and macrolides were obtained with good yields and excellent enantioselectivities upon a sequence of decarboxylative benzylation, retro-Claisen cleavage, and enamine protonation. This strategy features broad substrate scope, mild conditions, as well as high atom economy with salicylic carbonates as the o-quinone methide precursors.
- Han, Yanfang,Zhang, Long,Luo, Sanzhong
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- Enthalpies, Free Energies, and Entropies of Transfer of Phenols from Nonpolar Solvents to Water
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The enthalpies of transfer of seven phenols from 1-octanol to water and from toluene to water were determined by calorimetry.In the case of two phenols, whose rate of solution in water was found to be too slow for measurement by the usual heat of solution method, a new two-phase titration method was employed.The free energies of transfer between these solvents were determined by measuring the appropriate partition coefficients.The nature of the nonpolar solvent (toluene or 1-octanol) was found to cause large changes in the average values of the thermodynamic parameters of transfer into water, as well as changes in the ordering of the phenols in the series with respect to these transfer parameters.A curious correlation was observed between the octanol-water partition coefficients and the toluene -> water entropies of transfer.
- Haberfield, Paul,Kivuls, Juris,Haddad, Michael,Rizzo, Thomas
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- Preparation method of racemic salbutamol
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The invention discloses a preparation method of racemic salbutamol. The method comprises the following steps: taking 5-bromosalicylaldehyde as a raw material, carrying out reduction reaction on the 5-bromosalicylaldehyde and sodium borohydride to obtain an intermediate I; carrying out alkylation reaction on the intermediate I, sodium hydride and benzyl halide to obtain an intermediate II; carryingout cross-coupling reaction on the intermediate II and vinyl potassium trifluoroborate to obtain an intermediate III; carrying out addition reaction on the intermediate III and N-bromo succinimide toobtain an intermediate IV; carrying out alkylation reaction on the intermediate IV and tert-butylamine to obtain an intermediate V; and carrying out deprotection reaction on the intermediate V in a hydrogen atmosphere to obtain the racemic salbutamol. The 5-bromosalicylaldehyde is used as a reaction raw material for the first time to reduce the production cost, and bromine atoms are introduced, so that functional groups can be directionally introduced to the 5th site by the reaction, and the selectivity and yield of the reaction are improved; no high-risk highly toxic reagent is involved; andthe Suzuki-Miyaura cross-coupling reaction is applied to synthesis of salbutamol for the first time, and a catalytic amount of palladium catalyst is used, so that efficient introduction of double bonds on an aromatic ring can be realized, and the cost is reduced while the reaction yield is increased.
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Paragraph 0074-0077; 0099-0100; 0106-0107; 0113-0114
(2021/04/03)
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- A synthetic approach to chrysophaentin F
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The chrysophaentins are a newly discovered natural product family displaying promising anti-infective activity. Herein we describe an approach to chrysophaentin F that uses an array of metal catalysed coupling reactions (Cu, Ni, Pd, W, Mo) to form key bonds.
- Vendeville, Jean-Baptiste,Matters, Rebecca F.,Chen, Anqi,Light, Mark E.,Tizzard, Graham J.,Chai, Christina L. L.,Harrowven, David C.
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supporting information
p. 4837 - 4840
(2019/05/02)
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- New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis
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Cdc2-like kinase 1 (CLK1) and dual specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) are involved in the regulation of alternative pre-mRNA splicing. Dysregulation of this process has been linked to cancer progression and neurodegenerative diseases, making CLK1 and DYRK1A important therapeutic targets. Here we describe the synthesis of new pyrido[3,4-g]quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward CDK5, CK1, GSK3, CLK1 and DYRK1A. Introduction of aminoalkylamino groups at the 2-position resulted in several compounds with low nanomolar affinity and selective inhibition of CLK1 and/or DYRK1A. Their evaluation on several immortalized or cancerous cell lines showed varying degree of cell viability reduction. Co-crystal structures of CLK1 with two of the most potent compounds revealed two alternative binding modes of the pyrido[3,4-g]quinazoline scaffold that can be exploited for future inhibitor design.
- Tazarki, Helmi,Zeinyeh, Wael,Esvan, Yannick J.,Knapp, Stefan,Chatterjee, Deep,Schr?der, Martin,Joerger, Andreas C.,Khiari, Jameleddine,Josselin, Béatrice,Baratte, Blandine,Bach, Stéphane,Ruchaud, Sandrine,Anizon, Fabrice,Giraud, Francis,Moreau, Pascale
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p. 304 - 317
(2019/02/07)
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- Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol-Derived Chlorohydrosilane
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A newly developed stable chlorohydrosilane derived from pinacol is herein described. This was successfully used in the reduction of salicylaldehydes in reasonable to excellent yields (51–97 %). The ability of the hydrosilane to react as a reducing agent is increased upon the in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by density functional theory studies. 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was identified to be a suitable catalyst for this metal-free reduction, promoting the regio- and chemoselective reduction of aldehydes in ortho-position to phenols, despite the presence of vicinal ketones. The performance of pinacol-derived chlorohydrosilane in the reduction of salicylaldehydes was further observed to be superior to that of well-established commercially available chlorohydrosilanes.
- Assoah, Benedicta,Vale, Jo?o R.,Kalenius, Elina,Veiros, Luis F.,Candeias, Nuno R.
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supporting information
p. 2910 - 2917
(2018/06/27)
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- Rhodium-Catalyzed Annulations of 1,3-Dienes and Salicylaldehydes/2-Hydroxybenzyl Alcohols Promoted by 2-Ethylacrolein
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A rhodium-catalyzed 2-ethylacrolein-promoted protocol enables the annulation reactions of 1,3-dienes with either salicylaldehydes or 2-hydroxybenzyl alcohols leading to 2-alkylchroman-4-ones with high regioselectivity. This research highlights the use of 2-ethylacrolein which probably serves as a tool of bidentate coordination to rhodium intermediates. Mechanistic studies reveal that the transformation proceeds through the 1,4-hydroacylation pathway to access unsaturated linear ketones with subsequent oxo-Michael addition. (Figure presented.).
- Li, Hong-Shuang,Xiong, Yang,Zhang, Guozhu
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supporting information
p. 4246 - 4251
(2018/10/02)
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- NITROGEN-CONTAINING COMPOUNDS SUITABLE FOR USE IN THE PRODUCTION OF POLYURETHANES
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The present invention provides for the use of nitrogen compounds of formula (I) and/or of corresponding quaternized and/or protonated compounds for production of polyurethanes, compositions containing these compounds and polyurethane systems, especially polyurethane foams, which have been obtained using the compounds.
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Paragraph 0275; 0276
(2018/07/31)
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- Phenylethanolamine derivative and its preparation method and application
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The invention relates to a phenylethanolamine derivative represented in the following formula 1. The phenylethanolamine derivative can serve as a beta 2 receptor agonist. The formula can be seen from the description.
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Paragraph 0054; 0065-0066
(2017/10/07)
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- 2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling
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A series of 2-phenylbenzofurans compounds was designed, synthesized and evaluated as cholinesterase inhibitors. The biological assay experiments showed that most of the compounds displayed a clearly selective inhibition for butyrylcholinesterase (BChE), while a weak or no effect towards acetylcholinesterase (AChE) was detected. Among these benzofuran derivatives, compound 16 exhibited the highest BChE inhibition with an IC50 value of 30.3 μM. This compound was found to be a mixed-type inhibitor as determined by kinetic analysis. Moreover, molecular dynamics simulations revealed that compound 16 binds to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of BChE and it displayed the best interaction energy value, in agreement with our experimental data.
- Delogu, Giovanna L.,Matos, Maria J.,Fanti, Maura,Era, Benedetta,Medda, Rosaria,Pieroni, Enrico,Fais, Antonella,Kumar, Amit,Pintus, Francesca
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p. 2308 - 2313
(2016/04/20)
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- Extended Naphthalene Diimides with Donor/Acceptor Hydrogen-Bonding Properties Targeting G-Quadruplex Nucleic Acids
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Naphthalene diimides with one or two centrosymmetric arylethynyl moieties capable of synergic donor and acceptor hydrogen bonding exhibit promising binding properties and selectivity towards parallel G-quadruplex (G4) nucleic acids (c-myc, bcl-2 and parallel hTel22). The hydrogen-bonding network involving the phosphate backbone and outside rim of the G-quartet represents an opportunity to exploit G4 selectivity for extended aromatics.
- Doria, Filippo,Nadai, Matteo,Costa, Giosuè,Sattin, Giovanna,Gallati, Caroline,Bergamaschi, Greta,Moraca, Federica,Alcaro, Stefano,Freccero, Mauro,Richter, Sara N.
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p. 4824 - 4833
(2016/10/13)
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- Identification and Structure–Activity Relationship Studies of Small-Molecule Inhibitors of the Methyllysine Reader Protein Spindlin1
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The methyllysine reader protein Spindlin1 has been implicated in the tumorigenesis of several types of cancer and may be an attractive novel therapeutic target. Small-molecule inhibitors of Spindlin1 should be valuable as chemical probes as well as potential new therapeutics. We applied an iterative virtual screening campaign, encompassing structure- and ligand-based approaches, to identify potential Spindlin1 inhibitors from databases of commercially available compounds. Our in silico studies coupled with in vitro testing were successful in identifying novel Spindlin1 inhibitors. Several 4-aminoquinazoline and quinazolinethione derivatives were among the active hit compounds, which indicated that these scaffolds represent promising lead structures for the development of Spindlin1 inhibitors. Subsequent lead optimization studies were hence carried out, and numerous derivatives of both lead scaffolds were synthesized. This resulted in the discovery of novel inhibitors of Spindlin1 and helped explore the structure–activity relationships of these inhibitor series.
- Robaa, Dina,Wagner, Tobias,Luise, Chiara,Carlino, Luca,McMillan, Joel,Flaig, Ralf,Schüle, Roland,Jung, Manfred,Sippl, Wolfgang
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supporting information
p. 2327 - 2338
(2016/10/24)
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- Design, synthesis and evaluation of 4-dimethylamine flavonoid derivatives as potential multifunctional anti-Alzheimer agents
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A new series of 4-dimethylamine flavonoid derivatives were designed and synthesized as potential multifunctional anti-Alzheimer agents. The inhibition of cholinesterase activity, self-induced β-amyloid (Aβ) aggregation, and antioxidant activity by these derivatives was investigated. Most of the compounds exhibited potent acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity. A Lineweaver-Burk plot and molecular modeling study showed that these compounds targeted both the catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. The derivatives showed potent self-induced Aβ aggregation inhibition and peroxyl radical absorbance activity. Moreover, compound 6d significantly protected PC12 neurons against H2O2-induced cell death at low concentrations. Thus, these compounds could become multifunctional agents for further development for the treatment of AD.
- Luo, Wen,Wang, Ting,Hong, Chen,Yang, Ya-Chen,Chen, Ying,Cen, Juan,Xie, Song-Qiang,Wang, Chao-Jie
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supporting information
p. 17 - 26
(2016/07/06)
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- Synthesis and antitumor activity of 5-bromo-7-azaindolin-2-one derivatives containing a 2,4-dimethyl-1H-pyrrole-3-carboxamide moiety
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We report herein the design and synthesis of a series of novel 5-bromo-7-azaindolin-2-one derivatives containing a 2,4-dimethyl-1H-pyrrole-3-carboxamide moiety. These newly synthesized derivatives were evaluated for in vitro activity against selected cancer cell lines by MTT assay. Results revealed that some compounds exhibit broad-spectrum antitumor potency, and the most active compound 23p (IC50: 2.357-3.012 μM) was found more potent than Sunitinib (IC50: 31.594-49.036 μM) against HepG2, A549 and Skov-3, respectively.
- Zhang, Jun,Shen, Weiyi,Li, Xiaoning,Chai, Yun,Li, Senjun,Lv, Kai,Guo, Huiyuan,Liu, Mingliang
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- Ruthenium Catalyzed Selective Hydroboration of Carbonyl Compounds
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Using the [Ru(p-cymene)Cl2]2 (1) complex, catalytic hydroboration of aldehydes and ketones with pinacolborane under neat and mild conditions is reported. At rt, chemoselective hydroboration of aldehydes over the ketones is also attained. Mechanistic studies confirmed the immediate formation of monohydride bridged dinuclear complex [{(μ6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1b) from the reaction of 1 with pinacolborane, which catalyzed the highly efficient hydroboration reactions. The catalytic cycle containing mononuclear Ru-H species and intramolecular 1,3-hydride transfer is postulated.
- Kaithal, Akash,Chatterjee, Basujit,Gunanathan, Chidambaram
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p. 4790 - 4793
(2015/10/12)
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- Novel and selective detection of Tabun mimics
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Detection of nerve agent-related molecules based on BODIPY-salicylaldehyde oxime conjugation was studied. Fluorescence intensity of the B-SAL-OXIME species increases in the presence of DECP, whereas it decreases in the presence of DCP and DEMP (limit of detection = 997 nM). Benzonitrile formation in the novel fluorescent B-SAL-OXIME system was elucidated using model substrates. the Partner Organisations 2014.
- Jang, Yoon Jeong,Tsay, Olga G.,Murale, Dhiraj P.,Jeong, Jeong A.,Segev, Aviv,Churchill, David G.
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supporting information
p. 7531 - 7534
(2014/07/07)
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- ANTIDIABETIC BICYCLIC COMPOUNDS
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Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.
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Page/Page column 102
(2014/09/03)
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- Water-promoted ortho-selective monohydroxymethylation of phenols in the NaBO2 system
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Water-promoted ortho-selective monohydroxymethylation of phenols in the NaBO2 system generates salicyl alcohols in 65-97% yields. A remarkable rate-enhancement by water was observed, and NaBO2 appeared to serve the dual role of a suitable base and an efficient chelating reagent. This protocol possesses many advantages such as short reaction times, expanded substrate scope, and high mono- and regio-selectivities. The experimental results were explained by the calculations based on local ionisation energy minima, leading to a possible reaction mechanism.
- Li, Hui-Jing,Wu, Ying-Ying,Wu, Qin-Xi,Wang, Rui,Dai, Chun-Yang,Shen, Zhi-Lun,Xie, Cheng-Long,Wu, Yan-Chao
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p. 3100 - 3107
(2014/05/06)
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- MAO Inhibitory Activity of 2-Arylbenzofurans versus 3-Arylcoumarins: Synthesis, invitro Study, and Docking Calculations
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Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Several 3-arylcoumarin derivatives were previously described as interesting selective MAO-B inhibitors. Preserving the trans-stilbene structure, a series of 2-arylbenzofuran and corresponding 3-arylcoumarin derivatives were synthesized and evaluated as inhibitors of both MAO isoforms, MAO-A and MAO-B. In general, both types of derivatives were found to be selective MAO-B inhibitors, with IC50 values in the nano- to micromolar range. 5-Nitro-2-(4-methoxyphenyl)benzofuran (8) is the most active compound of the benzofuran series, presenting MAO-B selectivity and reversible inhibition (IC50=140nM). 3-(4′-Methoxyphenyl)-6-nitrocoumarin (15), with the same substitution pattern as that of compound 8, was found to be the most active MAO-B inhibitor of the coumarin series (IC50=3nM). However, 3-phenylcoumarin 14 showed activity in the same range (IC50=6nM), is reversible, and also severalfold more selective than compound 15. Docking experiments for the most active compounds into the MAO-B and MAO-A binding pockets highlighted different interactions between the derivative classes (2-arylbenzofurans and 3-arylcoumarins), and provided new information about the enzyme-inhibitor interaction and the potential therapeutic application of these scaffolds.
- Ferino, Giulio,Cadoni, Enzo,Matos, Maria Joao,Quezada, Elias,Uriarte, Eugenio,Santana, Lourdes,Vilar, Santiago,Tatonetti, Nicholas P.,Yanez, Matilde,Vina, Dolores,Picciau, Carmen,Serra, Silvia,Delogu, Giovanna
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p. 956 - 966
(2013/07/27)
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- Hydrosoluble and solvatochromic naphthalene diimides with NIR absorption
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Mimicking biochromophore anions containing phenolate moieties, eight conjugated naphthalene diimides (NDIs) have been synthesized in order to develop probes, displaying charge-transfer transitions affected by the nearby environment. NIR absorption of the resulting phenolates and their solvatochromic properties in both organic solvents and water are described.
- Doria, Filippo,Gallati, Caroline Marie,Freccero, Mauro
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p. 7838 - 7842
(2013/11/19)
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- Enantioselective synthesis of (R)-salmeterol employing an asymmetric Henry reaction as the key step
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A practical synthesis of (R)-salmeterol has been accomplished from 3-bromo salicylaldehyde, which involved a Cu(II)-sparteine complex catalyzed asymmetric Henry reaction as the key step. (R)-Salmeterol can be obtained in 39% overall yield and 95% ee.
- Guo, Zong-Liang,Deng, Yan-Qiu,Zhong, Shi,Lu, Gui
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scheme or table
p. 1395 - 1399
(2011/11/06)
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- Reduction of aldehydes and ketones with NaBH4/Al 2O3 under solvent-free conditions
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Aldehydes and ketones are efficiently reduced to the corresponding alcohol using NaBH4 supported onto alumina under solvent free conditions. It was found that the presence of small amount of methanol in reaction media is essential. Chemoselective 1,2-reduction of α, β- unsaturated carbonyl compounds to the corresponding allylic alcohols are also observed.
- Shalbaf
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experimental part
p. 6761 - 6764
(2012/06/18)
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- SUBSTITUTED ETHANOLAMINES
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The present invention relates to new substituted ethanolamine adrenergic receptor modulators, pharmaceutical compositions thereof, and methods of use thereof.
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Page/Page column 20
(2010/02/17)
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- Enzymatically activated cycloSal-d4T-monophosphates: The third generation of cycloSal-pronucleotides
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The third generation of cycloSal-pronucleotides, 5-diacetoxymethyl- cycloSal-d4T-monophosphates (5-di-AM-cycloSal-d4TMPs), is reported as a new class of "lock-in"-modified cycloSal-pronucleotides. These compounds bear an esterase-cleavable geminal dicarboxylate (acylal) attached to the aromatic ring of the saligenyl unit. The conversion into a strong acceptor group (aldehyde) leads to a strong decrease in hydrolytic stability. As a consequence, a fast release of a nucleoside monophosphate (i.e., d4TMP) follows. The concept of this enzymatic activation is proven by hydrolysis studies in phosphate buffer, cell extracts, and human serum. These investigations showed the conversion of the acylal group into a polar aldehyde by enzymatic cleavage. Besides, antiviral activities against HIV are presented.
- Gisch, Nicolas,Balzarini, Jan,Meier, Chris
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p. 1658 - 1667
(2008/01/27)
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- New developments of the "lock-in" modified cycloSal-d4TMPs
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New developments of the "lock-in" modified cycloSal-d4TMP are reported. Novel prodrugs with variations in the linker chain were introduced. The synthesis, hydrolysis properties in different media (PBS, CEM/0- and liver extracts) and the antiviral activities against HIV are shown. Copyright Taylor & Francis Group, LLC.
- Vukadinovic-Tenter, Dalibor,Balzarini, Jan,Meier, Chris
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p. 1325 - 1328
(2008/09/18)
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- Efficient and selective reduction protocols of the 2,2-dimethyl-1,3- benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols
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Two complementary procedures have been developed that selectively allow for the synthesis of either substituted salicylaldehydes or the corresponding 2-hydroxylbenzyl alcohols upon treatment of the 2,2-dimethyl-1,3-benzodioxan-4- one functional group with DIBAL-H or LAH, respectively.
- Bajwa, Naval,Jennings, Michael P.
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p. 3646 - 3649
(2007/10/03)
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- ALYKYLENE DERIVATIVE HAVING EDG RECEPTOR ANTAGONISM
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PROBLEM TO BE SOLVED: To provide novel compounds having EDG (endothelial differentiation gene) receptor antagonism which are useful as active components of drugs for preventing and/or treating inflammatory diseases or the like. SOLUTION: The compounds are represented by formula (I) (wherein R1 is hydrogen or an alkyl group; R2 is hydrogen present at any substitutable position on ring C or a substituent such as a hydroxy group, a carboxy group, and a nitro group; R3 is hydrogen present at any substitutable position on ring D or a substitutent such as a hydroxy group and an aralkyloxy group; X is an alkylamino group, an amino group or the like; Y is a carboxy group, a sulfo group or a phosphono group; Z is oxygen, sulfur or the like; a ring represented by A is a 5- or 6-membered saturated or unsaturated hydrocarbon ring; and a ring represented by B is a 4- or 7-membered saturated or unsaturated hydrocarbon ring containing one -C=C- as a partial structure shown in the above formula) and include their salts and their esters.
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Page/Page column 91
(2010/02/12)
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- Wet THF as a suitable solvent for a mild and convenient reduction of carbonyl compounds with NaBH4
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NaBH4 in wet THF can readily reduce varieties of carbonyl compounds such as aldehydes, ketones, conjugated enones, acyloins, and α-diketones to their corresponding alcohols in good to excellent yields. Reduction reactions were performed at room temperature or under reflux condition. In addition, the chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system.
- Zeynizadeh, Behzad,Behyar, Tarifeh
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p. 307 - 315
(2007/10/03)
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- NaBH4/NaHSO4·H2O a heterogeneous acidic system for a mild and convenient reduction of carbonyl compounds under protic condition
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NaBH4 in the presence of sodium bisulfate (NaHSO 4·H2O), a weakly acidic reagent, efficiently reduces a variety of carbonyl compounds such as aldehydes, ketones, α, β-unsaturated aldehydes and ketones, α-diketones and acyloins to their corresponding alcohols in acetonitrile under heterogeneous condition. Reduction reactions were accomplished at room temperature or under reflux condition.
- Zeynizadeh, Behzad,Behyar, Tarifen
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p. 453 - 457
(2007/10/03)
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- Vitamin D analogues
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The invention concerns novel bi-aromatic compounds having the formula: which are analogs of vitamin D, the process of preparing them, as well as their use in pharmaceutical compositions in human or veterinary medicine, particularly in dermatology, cancer treatment, treatment of auto-immune diseases, and in organ or tissue transplants. Cosmetic compositions and methods of use are also included.
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Page column 27
(2010/02/05)
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- Reduction of carbonyl compounds with NaBH4 under ultrasound irradiation and aprotic condition
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A variety of carbonyl compounds are reduced to their corresponding alcohols with sodium borohydride under ultrasound irradiation and aprotic condition. Reduction reactions are performed in THF at room temperature or under reflux condition. The product alcohols were obtained in good to excellent yields. The chemoselective reduction of aldehydes over ketones was achieved successfully with this system.
- Zeynizadeh, Behzad,Yahyaei, Saiedeh
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p. 704 - 710
(2007/10/03)
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- Novel n(phenylsulphonyl)glycine derivatives and their therapeutic use
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The present invention relates to novel N-(phenylsulphonyl)glycyl-glycine compounds, which are defined by formula I and the description, as well as their method of preparation and their use in therapeutics
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- Mild and efficient method for reduction of aldehydes and ketones with NaBH4 in the presence of Dowex1-x8
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Various aldehydes and ketones are reduced efficiently to alcohols with NaBH4/Dowex1-x8.
- Zeynizadeh, Behzad,Shirini, Farhad
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p. 335 - 339
(2007/10/03)
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- Titanyl Acetylacetonate as an Efficient Catalyst for a Mild and Convenient Reduction of Carbonyl Compounds with NaBH4 under Aprotic Condition
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Titanyl acetylacetonate, TiO(acac)2, is used as an efficient catalyst for the reduction of carbonyl compounds with sodium borohydride under aprotic condition. Reduction reactions are performed in CH3CN and THF. The corresponding alcohols are obtained in high to excellent yields and the chemoselective reduction of aldehydes over ketones is achieved successfully.
- Zeynizadeh, Behzad
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p. 1220 - 1226
(2007/10/03)
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- Modified hydroborate agent: (2,2′-bipyridyl)(tetrahydroborato)zinc complex, [Zn(BH4)2(bpy)], as a new, stable, efficient ligand-metal hydroborate and chemoselective reducing agent
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(2,2′-Bipyridyl)(tetrahydroborato)zinc complex, [Zn(BH4)2(bpy)], is a new white stable compound which has been used for efficient reduction of variety of carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α, β-unsaturated carbonyl compounds (1,2-reduction) to their corresponding alcohols in acetonitrile at room temperature. Excellent chemoselectivity was also observed for the reduction of aldehydes over ketones with this reducing agent.
- Zeynizadeh, Behzad
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p. 317 - 326
(2007/10/03)
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- A new class of histamine H3-receptor antagonists: Synthesis and structure - Activity relationships of 7,8,9,10-Tetrahydro-6H-cyclohepta[b]quinolines
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The synthesis and biological evaluation of novel cycloheptaquinoline antagonists of the human H3 receptor are described. Two series of compounds, bearing either an amino substituent or an alkyne linker at the 11-position, were investigated. Modifications of the amino substituents, optimization of chain length and the effect of conformational restraints are described. Several compounds with high affinity and selectivity for the H3 receptor were discovered.
- Turner, Sean C.,Esbenshade, Timothy A.,Bennani, Youssef L.,Hancock, Arthur A.
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p. 2131 - 2135
(2007/10/03)
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- 2-aminobenzoxazole derivatives and combinatorial libraries thereof
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The present invention relates to novel 2-aminobenzoxazole derivative compounds of the following formula: wherein R1 to R4 and Z have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminobenzoxazole derivative compounds.
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- N-SUBSTITUTED-N'-SUBSTITUTED UREA DERIVATIVE AND USE THEREOF AS TNF-γ(a) PRODUCTION INHIBITOR
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N-Substituted-N'-substituted urea derivatives represented by the following formula, analogs thereof or pharmaceutically acceptable salts thereof are herein provided. These compounds show a TNF- α production inhibitory activity.
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- Azolyl methyl phenyl derivatives having aromatase inhibitory activity
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Compounds exerting excellent aromatase inhibitory activity in vivo and in vitro with higher specificity and greater safety are provided together with the salts thereof. Using the same, there are also provided, prophylactic agents and/or therapeutical agents of estrogen-dependent diseases, contraceptive agents for females, and aromatase inhibitory agents for use in the form of reagents for human or animals. The compounds are of the formula (I), wherein R2 is represented by the formula (II) or (III). (I) (II) or
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- Pancreatic imaging agents
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A novel group of radiolabelled diamines are provided, effective for pancreatic imaging and represented by the formula STR1 wherein n is 1 to 10; R1 and R2 are the same or different and are hydrogen, hydroxyl or lower alkyl having 1 to 6 carbon atoms; R3 is lower alkyl having 1 to 6 carbon atoms; and N' is a nitrogen atom forming part of a 4- to 8-membered heterocyclic ring containing one or two hetero atoms, one of which is said nitrogen, said heterocyclic ring being unsubstituted or substituted with one or more lower alkyl groups and pharmaceutically acceptable acid addition salts thereof.
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- Substituted 1H-imidazoles
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New substituted 1H-imidazoles and their salts, processes for the preparation thereof and pharmaceutical compositions. These compounds have the formula STR1 wherein R1, R2, R3 and R5 =hydrogen or C1 -C4 -alkyl; R4 =hydrogen, C1 -C4 -alkyl or C1 -C4 -alkoxy; Y1 =hydrogen and Y2 =OZ2 or the reverse; Z1 =Z2 =hydrogen or C1 -C4 -alkyl or Z1 and Z2 =--CH2 -- or --C(CH3)2 --. These compounds are prepared either by reducing a corresponding imidazole compound having a hydroxyl or alkoxy group on the methyl bridge between the imidazole and phenyl rings, or by hydrolyzing a 4-[[2,2-dimethyl-4H-1,3-benzodioxin-6(or 8)-yl]methyl]-1H-imidazole, or yet by reducing an alkyl 3-[(1H-imidazol-4-yl)methyl]-2-hydroxybenzoate. These compounds have cardiac, cerebral and tissular anti-ischemic activities.
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- POTENTIAL ANTIDEPRESSANTS: 10-AMINO-2-CHLORO-10,11-DIHYDRODIBENZOTHIEPINS
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Reduction of N-(2-chloro-10,11-dihydrodibenzothiepin-10-yl)formamide with lithium aluminium hydride resulted in the methylamino compound IV.The dimethylamino compound V was obtained by methylation of 10-amino-2-chloro-10,11-dihydrodibenzothiepin with formic acid and aqueous formaldehyde.Substitution reactions of 2,10-dichloro-10,11-dihydrodibenzothiepin with a series of primary and secondary amines afforded the title compounds VI to XXVIII.The bases were transformed to salts and pharmacologically tested.Only the pyrrolidino compound IX (hydrogen succinate VUFB-15551) showed a clear pharmacological profile of a potential antidepressant.
- Valenta, Vladimir,Vlkova, Marie,Holubek, Jiri,Metysova, Jirina,Protiva, Miroslav
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p. 1979 - 1994
(2007/10/02)
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- Studies of Pendant-arm Macrocyclic Ligands. Part 5. Synthesis of Two Pyridine-containing Penta-aza Macrocycles with Single Pyrrolidinyl Pendant Arms and Characterisation of their Nickel(II) and Copper(II) Complexes. Crystal Structure of Perchlorato-3,7,...
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Two new pyridine-containing penta-aza macrocyclic ligands, 7-- and 7--3,7,11,17-tetra-azabicycloheptadeca-1(17),13,15-triene (L1 and L2 respectively) have been prepared, and their nickel(II) and copper(II) complexes of formulae 1)(OClO3)> and 3 (M = Ni or Cu, L = L1 or L2) have been isolated and characterised.In the octahedral complex 1)(OClO3)> the presence of a co-ordinated perchlorate group has been established by X-ray crystallography, and the macrocyclic ligand found to co-ordinate close to the corners of a square pyramid with the pendant pyrrolidinyl group at the apical position.
- Alcock, Nathaniel W.,Balakrishnan, Karappulli P.,Moore, Peter,Omar, Hadi A. A.
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p. 545 - 550
(2007/10/02)
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