- Salicylaldimine-aluminum complexes for the facile and efficient ring-opening polymerization of ε-caprolactone
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A facile and efficient catalytic system of salicylaldimine-aluminum complexes for the ring-opening polymerization (ROP) of ε-caprolactone (CL) was investigated. The polymerization of Cl was examined at 25 °C in the presence of 1 mol % of benzyl alcohol (B
- Nomura, Nobuyoshi,Aoyama, Takuji,Ishii, Ryohei,Kondo, Tadao
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Read Online
- Photophysical property vs. medium: Mononuclear, dinuclear and trinuclear Zn(II) complexes
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Three complexes [Zn2(L)2(μ1,2-OAc)(μ1,1-OAc)]·C9H8N21·C9H8N2, [Zn3(L)4]·(ClO4)22 and [Zn(L)2/su
- Hens, Amar,Rajak, Kajal Krishna
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Read Online
- Comparative evaluation of antioxidant activity of 2-alkyl-4-methylphenols and their 6-n-octylaminomethyl derivatives
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A series of 2-alkyl-4-methyl-6-n-octylaminomethylphenols (where alkyl is methyl or tert-butyl group, or terpene substituent) was synthesized. A comparative evaluation of the antioxidant properties of the starting alkyl- and terpenylphenols and their Mannich bases was carried out using in vitro assays. Structural features providing high antioxidant activity of these compounds were revealed.
- Buravlev,Fedorova,Shevchenko
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p. 985 - 992
(2019/06/17)
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- NOVEL SMALL MOLECULE DRUG CONJUGATES OF GEMCITABINE DERIVATIVES
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Disclosed are compounds having formula (I) or a pharmaceutically acceptable salt, ester, amide, solvate, or stereoisomer thereof, wherein L, Y1, Y2, Y3, Y4, Y5, Z1, Z2, Z3, Z4, Z5, Z6, and Effector are each as defined in the specification; compositions thereof; uses thereof; and methods of use thereof.
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Page/Page column 63
(2019/08/26)
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- SMALL MOLECULE DRUG CONJUGATES OF GEMCITABINE MONOPHOSPHATE
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Disclosed are compounds having formula (I): or a pharmaceutically acceptable salt, ester, amide, solvate, or stereoisomer thereof, wherein L, Y1, Y2, Y3, Y4, Y5, Z1, Z2, Z3, Z4, Z5, Z6 are each as defined in the specification; compositions thereof; uses thereof; and methods of use thereof.
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Page/Page column 59
(2019/08/26)
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- A designed protein binding-pocket to control excited-state intramolecular proton transfer fluorescence
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Excited-state intramolecular proton transfer involves a photochemical isomerization and creates the opportunity for the emission of two distinct wavelengths of light from a single fluorophore. The selectivity between these two wavelengths of emission is d
- Lampkin, Bryan J.,Monteiro, Cecilia,Powers, Evan T.,Bouc, Paige M.,Kelly, Jeffery W.,Vanveller, Brett
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supporting information
p. 1076 - 1080
(2019/02/07)
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- Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions
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In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.
- Naeimi, Hossein,Zakerzadeh, Elham
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p. 4590 - 4595
(2018/03/21)
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- Solvent dependent disproportionation of Cu(II) complexes of N2O2-type ligands: Direct evidence of formation of phenoxyl radical: An experimental and computational study
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Four Cu(II) complexes (1, 2, 3 and 4) with N2O2-type ligand, H2L1, H2L2, H2L3 and H2L4, respectively have been synthesized as the functional model for galactose oxidase. In presence of acetonitrile the Cu(II) centres in the complexes, undergo reduction with simultaneous oxidation of the ligands. The ligand oxidized products are isolated and characterized. Spectroscopic studies indicate that this disproportionation goes through the formation of a Cu(II)-phenoxyl intermediate. The complexes also undergoes the same reaction with pyridine, which indicates the involvement of the exergonic N-donor ligand for the formation of Cu(II)-phenoxyl complex. The Cu(II)-phenoxyl complexes are found to be stable in methanol in presence of a strong base. The paramagnetic centers in the Cu(II)-phenoxyl complexes were found to be weakly ferromagnetically coupled. The complexes, in acetonitrile solvent, have been found to oxidize primary alcohols to corresponding aldehydes. In absence of single crystal structures of the complexes, we optimized the structures using density functional theory (DFT). The UV-visible peaks of complexes as found from time dependent density functional theory (TDDFT) calculations match well with the observed experimental results.
- Debnath, Rajib Kumar,Kalita, Apurba,Sinha, Sourab,Bhattacharyya, Pradip Kr.,Mondal, Biplab,Ganguli, Jatindra Nath
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p. 4490 - 4500
(2015/11/27)
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- Synthesis and characterisation of aluminium(III) imine bis(phenolate) complexes with application for the polymerisation of rac-LA
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A series of tridentate imine bis(phenolate) ligands have been synthesised and complexed to aluminium. Solid-state analysis identified two structural motifs of an aluminium dimer [Al2(Me)2(X)2]; one consisting of two five-c
- Forder, Thomas R.,Jones, Matthew D.
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supporting information
p. 1974 - 1978
(2015/03/18)
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- Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Catalyzed by Rare-Earth Amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 with Phenoxy-Functionalized Chiral Prolinols
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A simple and efficient catalytic enantioselective epoxidation of α,β-unsaturated ketones has been successfully developed, which was catalyzed by rare-earth metal amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 (RE = Yb (1), La (2), Sm (3), Y (4), Lu (5)) in the presence of phenoxy-functionalized chiral prolinols at room temperature using tert-butylhydroperoxide (TBHP) as the oxidant. The combination of an Yb-based amide 1 and a chiral proligand (S)-2,4-di-tert-butyl-6-((2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)phenol) performed very well, and both the yields and the enantiomeric excess of the chiral epoxides reached up to 99% and 99% ee. (Figure Presented).
- Zeng, Chao,Yuan, Dan,Zhao, Bei,Yao, Yingming
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supporting information
p. 2242 - 2245
(2015/05/13)
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- A convenient synthesis of tri- and tetramethylbenzaldehydes from readily available phenols
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This letter describes a convenient synthesis of the six isomeric tri- and tetramethylbenzaldehydes, which are not readily available from major chemical suppliers. Formylation of readily available phenols via electrophilic aromatic substitution provides compounds containing the correct aromatic substitution pattern. ?Suzuki cross-coupling of the corresponding trifluoromethanesulfonates with methylboronic acid then provides the benzaldehydes as single isomers. Georg Thieme Verlag Stuttgart. New York.
- Dhankher, Persis,Sheppard, Tom D.
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supporting information
p. 381 - 384
(2014/03/21)
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- Synthesis of deuterated benzopyran derivatives as selective COX-2 inhibitors with improved pharmacokinetic properties
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We designed a series of specifically deuterated benzopyran analogues as new COX-2 inhibitors with the aim of improving their pharmacokinetic properties. As expected, the deuterated compounds retained potency and selectivity for COX-2. The new molecules possess improved pharmacokinetic profiles in rats compared to their nondeuterated congeners. Most importantly, the new compounds showed pharmacodynamic efficacy in several murine models of inflammation and pain. The benzopyran derivatives were separated into their enantiomers, and the activity was found to reside with the S-isomers. To streamline the synthesis of the desired S-isomers, an organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction was developed for their preparation.
- Zhang, Yanmei,Tortorella, Micky D.,Wang, Yican,Liu, Jianqi,Tu, Zhengchao,Liu, Xiaorong,Bai, Yang,Wen, Dingsheng,Lu, Xin,Lu, Yongzhi,Talley, John J.
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p. 1162 - 1166
(2014/12/10)
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- Facile one-pot transformation of phenols into o-cyanophenols
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The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.
- Nakai, Yuhta,Moriyama, Katsuhiko,Togo, Hideo
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p. 6077 - 6083
(2015/03/30)
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- Cu(OAc)2·H2O-promoted tandem β-alkynyl elimination of α-or β-hydroxy propargylic alcohols and homocoupling of the resulting alkynyl species
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α or β-hydroxy propargylic alcohols undergo tandem C(sp)-C(sp3) bond cleavage via β-alkynyl elimination and homocoupling of the resulted alkynyl species in the presence of Cu(OAc)2·H2O to produce the corresponding hydroxycarbonyl com
- Xu, Xiangsheng,Huang, Zhenyong,Lu, Yanfeng
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p. 546 - 549
(2013/10/22)
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- The one pot synthesis salicylaldehyde prepared by reactive grinding with derivative phenol and paraformaldehyde in absence magnesium methoxide
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The formylation phenols are mono-formylated using a mixture of paraformaldehyde, Mg(OMe)2, by reactive grinding. In all cases but one, only one regioisomer of the salicylaldehyde is obtained in good to high yield.
- Balali, Ebrahim,Shameli, Abolghasem,Naeimi, Hoseein,MehdiGhanbari, Mohammad
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p. 1611 - 1614
(2014/05/06)
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- Photocycloaddition of arenes and allenes
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In this work, we report on a new intramolecular para cycloaddition of arenes with allenes, yielding attractive rigid scaffolds bearing several reactive functionalities to build in further diversity. Bicyclo[2.2.2]octadiene- type products and benzoxepine acetals are formed in this reaction, in ratios and yields depending on the substitution pattern on the aromatic ring, the nature of the chromophore, and the tether. This unprecedented reaction has remarkable features that distinguish it from many other photochemical transformations: it is particularly robust with respect to substituents, it can be scaled up without a notable loss of efficiency, and it can lead to structures with a high degree of complexity in low to good yields. All photochemical precursors could be synthesized readily in three steps. We confirmed the compatibility of the nitrogen atom in the photocycloaddition step, which gives access to a bicyclo[2.2.2]octadiene scaffold with two points that allow further diversification. This reaction was scaled up to multigram quantities without erosion of the typically high yields in photocycloadducts. Sequential deprotection of the N- or C-terminus of bicyclic amino acids gave access to two conformationally constrained unnatural amino acids with different dispositions of the two anchor points.
- Streit, Ursula,Birbaum, Frederic,Quattropani, Anna,Bochet, Christian G.
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p. 6890 - 6910
(2013/08/23)
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- Cationic ring-opening polymerization of 1,3-benzoxazines: Mechanistic study using model compounds
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The benzoxazine monomer is used to simplify the study of the benzoxazine initiation mechanism. The HPLC retention time and the 1H NMR spectra of crude products from the benzoxazine reaction are compared with the results from a vast number of pure model compounds, which are synthesized based on the hypothesized mechanisms. Products involved in the process are identified, with species having benzoxazine structures, Mannich base and other components (acetal, nonacetal phenoxy structures, and methylene bridge structure). Initiation mechanisms of benzoxazine, e.g., the oxygen protonation and the nitrogen protonation, are proposed.
- Chutayothin, Papinporn,Ishida, Hatsuo
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experimental part
p. 4562 - 4572
(2011/10/18)
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- The novel benzopyran class of selective cyclooxygenase-2 inhibitors. Part III: The three microdose candidates
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In this manuscript, we report the discovery of the substituted 2-trifluoromethyl-2H-benzopyran-3-carboxylic acids as a novel series of potent and selective cyclooxygenase-2 (COX-2) inhibitors. We provide the structure-activity relationships, optimization of design, testing criteria, and human half-life data. The challenge of a surprisingly long half-life (t 1/2 = 360 h) of the first clinical candidate 1 and human t 1/2 had been difficult to predict based on allometric scaling for this class of highly ppb compounds. We used a microdose strategy which led to the discovery of clinical agents 18c-(S), 29b-(S), and 34b-(S) with human half-life of 57, 13, and 11 h.
- Wang, Jane L.,Aston, Karl,Limburg, David,Ludwig, Cindy,Hallinan, Ann E.,Koszyk, Francis,Hamper, Bruce,Brown, David,Graneto, Matthew,Talley, John,Maziasz, Timothy,Masferrer, Jaime,Carter, Jeffery
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scheme or table
p. 7164 - 7168
(2011/01/03)
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- R-Isomers of Arg-Gly-Asp (RGD) mimics as potent αvβ3 inhibitors
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The integrin αvβ3, vitronectin receptor, is expressed in a number of cell types and has been shown to mediate adhesion of osteoclasts to bone matrix, vascular smooth muscle cell migration, and angiogenesis. We recently disclosed the
- Nagarajan, Srinivasan R.,Devadas, Balekudru,Malecha, James W.,Lu, Hwang-Fun,Ruminski, Peter G.,Rico, Joseph G.,Rogers, Thomas E.,Marrufo, Laura D.,Collins, Joe T.,Kleine, H. Peter,Lantz, Melissa K.,Zhu, Jun,Green, Nawasa F.,Russell, Mark A.,Landis, Bryan H.,Miller, Lawrence M.,Meyer, Debra M.,Duffin, Tiffany D.,Engleman, V. Wayne,Finn, Mary B.,Freeman, Sandra K.,Griggs, David W.,Williams, Melanie L.,Nickols, Maureen A.,Pegg, Jodi A.,Shannon, Kristen E.,Steininger, Christina,Westlin, Marisa M.,Nickols, G. Alan,Keene, Jeffery L.
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p. 3783 - 3800
(2008/02/11)
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- SUBSTITUTED CYCLOPROPYL CHROMENE COMPOUNDS FOR USE IN THE TREATMENT AND PREVENTION OF INFLAMMATION RELATED CONDITIONS
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The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (1) Wherein Z
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Page/Page column 44
(2010/11/08)
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- Discovery of a potent phenolic N1-benzylidene- pyridinecarboxamidrazone selective against Gram-positive bacteria
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As part of a study into antimycobacterial compounds a set of phenolic N1-benzylidene-pyridinecarboxamidrazones was prepared and evaluated. This report describes the unexpected discovery of a potent compound with a pronounced selectivity for Gram-positive bacteria over Gram-negative micro-organisms. In addition, this compound is active against various drug-resistant Gram-positive bacteria.
- Rathbone, Daniel L.,Parker, Katy J.,Coleman, Michael D.,Lambert, Peter A.,Billington, David C.
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p. 879 - 883
(2007/10/03)
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- ANTI-BACTERIAL COMPOUNDS
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Compounds of formula (I), or salts or solvates thereof, in vitro as inhibitors of growth of Gram-positive bacteria, where A is selected from formula (a).
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(2008/06/13)
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- THE R-ISOMER OF BETA AMINO ACID COMPOUNDS AS INTEGRIN RECEPTOR ANTAGONISTS DERIVATIVES
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The present invention relates to a class of compounds represented by the Formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula (I), and methods of selectively inhibiting or antagonizing the αVβ3 and/or the αV β5 integrin without significantly inhibiting the αV β6 integrin
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Page/Page column 165-166
(2010/02/07)
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- Non-metallocene compounds, method for the production thereof and use of the same for the polymerisation of olefins
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The invention relates to a method for producing special transition metal compounds, to novel transition metal compounds and to the use of the same for the polymerisation of olefins.
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- BENZOPYRAN COMPOUNDS USEFUL FOR TREATING INFLAMMATORY CONDITIONS
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The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (1). Wherein Z, X, R1, R2, R3, and R4 are as described in specification.
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- CHROMENE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS
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The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (I). Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.
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- Biaryl-bridged Schiff base complexes of zirconium alkyls: Synthesis structure and stability
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Three substituted salicylaldimine derivatives H2 L1-3 of 2,2′-diamino-6,6′-dimethylbiphenyl give, under appropriate conditions, isolable alkyls of zirconium [ZrL1-3R2] (R=CH2Ph, CH2 But). Two molecular structures confirm their cis-α geometry (C2-symmetric with cis alkyl ligands). They decompose via 1,2-migratory insertion of an alkyl group to imine, followed in some instances by a second similar reaction. The dimeric molecular structure of one such doubly-inserted product is presented. The kinetics of decomposition by this process are studied briefly, and it is noted that the rate increases with increased steric demand of the salicylaldimine unit.
- Knight, Paul D.,O'Shaughnessy, Paul N.,Munslow, Ian J.,Kimberley, Brian S.,Scott, Peter
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p. 103 - 113
(2007/10/03)
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- Cyclo-saligenyl-2',3'-dideoxy-2',3' didehydroythymidinemonophosphate (cyclosal-d4TMP) - A new pro-nucleotide approach
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The synthesis of cycloSal-d4TMP 3a-g as new pro-nucleotide approach for d4TMP 2 is described. Phosphotriesters 3 release the d4TMP 2 selectively by a controlled, chemically induced tandem reaction. CycloSa1-phosphotriesters 3 exhibited high biological activity against HIV-1/HIV-2 in CEM cells which was completely retained in CEM TK- cells.
- Meier, Chris,Lorey, Martina,De Clercq, Eric,Balzarini, Jan
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p. 1303 - 1306
(2007/10/03)
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- New chromene compounds having a triene side chain
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A compound selected from those of formula (I): STR1 in which the groups R1 to R8 are as defined the description. Medicaments.
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- A modified synthesis of O-hydroxyaryl aldehydes
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A modified method for the synthesis of o-hydroxyaryl aldehydes in moderate yields has been developed by treating aryloxymagnesium bromides with formaldehyde using triethylamine in place of hexamethylphosphoric triamide (HMPA).
- Wang,You,Meng,Mintz,Bu
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p. 1757 - 1760
(2007/10/02)
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New oxygen-activating systems for dehydrogenation of 2-hydroxymethyl phenols 1 (a: R = tBu ; b: R = CH3; c : R = H) to the corresponding salicylaldehydes 3 are described. These systems are composed of a transition metal (M0 = Fe0 or Cu0), a transition metal ion (MnCln=Fe11Cl2 or Cu1Cl) in catalytic amount and molecular oxygen. The most active systems are Fe0FeCl2O2CH3OH and Cu0CuCl + FeCl2O2CH3OH. Based on all the results so far obtained a mechanistic hypothesis is proposed.
- Sparfel, Daniel,Baranne-Lafont, Joele,Cuong, Nguyen Kim,Capdevielle, Patrice,Maumy, Michel
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p. 793 - 802
(2007/10/02)
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- Selective Reactions between Phenols and Formaldehyde. A Novel Route to Salicylaldehydes
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Treatment of phenols (1) with 2 mol equiv. of paraformaldehyde in aprotic and poorly electron-donating solvents in the presence of selected metal halides coupled with suitable bases produces salicylaldehydes (3) in high yields.The route is highly selective for ortho-formylation and also specific towards monoformylation.The crucial role of added bases is emphasized.
- Casiraghi, Giovanni,Casnati, Giuseppe,Puglia, Giuseppe,Sartori, Giovanni,Terenghi, Giuliana
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p. 1862 - 1865
(2007/10/02)
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