- Metal-organic framework MOF-199 as an efficient heterogeneous catalyst for the aza-Michael reaction
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A highly porous metal-organic framework (MOF-199) was synthesized from the reaction of copper nitrate trihydrate and 1,3,5-benzenetricarboxylic acid by solvothermal method, and used as a recyclable acid catalyst for the aza-Michael reaction. Physical characterizations of the solid catalyst were achieved by using a variety of different techniques, including X-ray powder diffraction (XRD), scanning electron microscope (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), dynamic laser light scattering (DLS), atomic absorption spectrophotometry (AAS), and nitrogen physisorption measurements. Excellent conversions were achieved under mild conditions in the presence of 5 mol% catalyst. The MOF-199 catalyst could be reused several times without a significant degradation in catalytic activity. No contribution from homogeneous catalysis of active species leaching into the liquid phase was detected.
- Nguyen, Lien T.L.,Nguyen, Tung T.,Nguyen, Khoa D.,Phan, Nam T.S.
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Read Online
- Solution chemistry of 1,15-bis(N,N-dimethyl)-5,11-dioxo-8-(N-benzyl)-1,4,8, 12,15-pentaazapentadecane with metal ions of biological interest - Insights toward active metal ion containing therapeutics and diagnostic agents
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The equilibrium constants of Cu(ii), Zn(ii), Ca(ii) and Gd(iii) with 1,15-bis(N,N-dimethyl)-5,11-dioxo-8-(N-benzyl)-1,4,8,12,15-pentaazapentadecane (La) have been studied at 25 °C and an ionic strength of 0.15 mol dm-3. Copper forms more stable complexes with La than the other metal ions investigated. This is probably due to the ease with which Cu(ii) deprotonates the nitrogen donor atoms of the amide groups. UV/Vis spectrophotometric data indicate tetradentate binding of the ligand towards copper in [CuLaH-1] and pentadentate binding in [CuL aH-2]. Octanol-water partition coefficients of Cu(ii)-La complexes indicate that although these species are largely hydrophilic, approximately 5.62% of the [CuLaH-1] complex goes into the organic phase. This percentage may promote dermal absorption of copper with a calculated penetration rate of 3.75 × 10-4 mm h-1. The [CuLaH-1] species which predominates at pH 7.4 is a poor mimic of native copper-zinc superoxide dismutase. Blood-plasma simulation studies predict that La is unable to increase the low molecular mass copper fraction in vivo. This has been confirmed by biodistribution patterns, which are similar to those of 64CuCl 2. The Royal Society of Chemistry 2006.
- Nomkoko, Thembelani E.,Jackson, Graham E.,Nakani, Bandile S.,Hunter, Roger
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Read Online
- EIF4E INHIBITORS AND USES THEREOF
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The present invention provides compounds inhibiting elF4E activity and compositions and methods of using thereof.
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Paragraph 00337; 00363
(2021/09/11)
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- Oxindole spiro-tetrahydrofuran compound as well as preparation method and application thereof
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The invention provides an indole tetrahydrofuran oxide compound or a crystal form thereof, wherein the indole tetrahydrofuran oxide compound is as shown in a formula (I). R1 is selected from benzene rings, naphthalene rings and thiophene rings or cinnamyl, R2 is selected from H, F, Cl, Br and I or C1-3 alkoxy, R3 is selected from H and benzyl or C1-C3 alkyl, and R4 is H, F, Cl, Br, I and C1-3 alkoxy or C1-C3 alkyl. The invention further provides a method for preparing the compound. The compound is simple and convenient in preparation method, moderate in reaction and high in yield and has anti-tumor activity and a wide market application prospect.
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Paragraph 0030; 0034; 0039-0040; 0044; 0045
(2020/04/29)
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- NHC-catalyzed asymmetric α-regioselective [4 + 2] annulation to construct α-alkylidene-δ-lactones
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The unprecedented NHC-catalyzed [4 + 2] annulation of α-bromoenals with dioxopyrrolidines is described. This protocol features broad substrate scope and allows rapid assembly of α-alkylidene-δ-lactones in good to high yields with excellent enantioselectivities. Notably, this process includes α-regioselective activation of azolium dienolate intermediates, which has not yet been reported.
- Liu, Lala,Guo, Donghui,Wang, Jian
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supporting information
p. 7025 - 7029
(2020/09/15)
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- 3-AMINO-2-[2-(ACYLAMINO)PYRIDIN-4-YL]-1,5,6,7-TETRAHYDRO-4H-PYRROLO[3,2-C]PYRIDIN-4-ONE AS CSNK1 INHIBITORS
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Compounds of formula (I), processes for their production and their use as pharmaceuticals. The compounds are inhibitors of Casein kinase 1 alpha and/or delta ( CSNK1α and/or 6) useful for the treatment of proliferative disorders. (l)
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Page/Page column 114
(2020/08/22)
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- Structure-based optimization of 2,3-dioxopyrrolidines as potential inhibitors of flaviviral methyltransferases
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Various studies have shown that NS5 RNA methyltransferase (MTase) is a key enzyme involved in mRNA capping, a step crucial for flaviviral replication. Therefore, it has been identified as a potential target for therapeutic intervention in infections arising due to flaviviruses. In this paper, we report computer-assisted design of 2,3-dioxopyrrolidines, which were synthesised as guided by molecular docking studies on DENV and ZIKA MTase. Their chemical structures and geometric configuration were characterized by FT-IR, NMR (13C and 1H), MS and small molecule X-ray crystallography. Subsequently, their inhibitory potential was evaluated using an enzyme-based assay in DENV MTase (N7 and 2'O-MTase) and Zika virus MTase (N7 and 2'O-MTase). Furthermore, these molecules were also screened against RNMT (human N7 MTase). The most potent lead (compound W07) is seen to inhibit MTase from DENV with IC50 = 24.6±3.8 M and ZIKA with IC50 = 9.0±1.7 M. However, it also inhibits human N7 MTase, indicating plausible toxicity in humans. There is scope to further optimize these molecules to achieve selectivity towards flaviviral MTases.
- Wangikar, Prajakta,Martis, Elvis A.F.,Aouadi, Wahiba,Nandan, Santosh R.,Decroly, Etienne,Coutinho, Evans C.
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p. 1179 - 1189
(2020/12/04)
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- Synthesis of Symmetric and Unsymmetric Secondary Amines from the Ligand-Promoted Ruthenium-Catalyzed Deaminative Coupling Reaction of Primary Amines
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The catalytic system generated in situ from the tetranuclear Ru-H complex with a catechol ligand (1/L1) was found to be effective for the direct deaminative coupling of two primary amines to form secondary amines. The catalyst 1/L1 was highly chemoselective for promoting the coupling of two different primary amines to afford unsymmetric secondary amines. The analogous coupling of aniline with primary amines formed aryl-substituted secondary amines. The treatment of aniline-d7 with 4-methoxybenzylamine led to the coupling product with significant deuterium incorporation on CH2 (18% D). The most pronounced carbon isotope effect was observed on the α-carbon of the product isolated from the coupling reaction of 4-methoxybenzylamine (C(1) = 1.015(2)). A Hammett plot was constructed from measuring the rates of the coupling reaction of 4-methoxyaniline with a series of para-substituted benzylamines 4-X-C6H4CH2NH2 (X = OMe, Me, H, F, CF3) (ρ = -0.79 ± 0.1). A plausible mechanistic scheme has been proposed for the coupling reaction on the basis of these results. The catalytic coupling method provides an operationally simple and chemoselective synthesis of secondary amine products without using any reactive reagents or forming wasteful byproducts.
- Arachchige, Pandula T. Kirinde,Lee, Hanbin,Yi, Chae S.
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p. 4932 - 4947
(2018/05/08)
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- Synthesis and Catalytic Application of Mixed Valence Iron (FeII/FeIII)-Based OMS-MIL-100(Fe) as an Efficient Green Catalyst for the aza-Michael Reaction
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Abstract: In the present study, open metal site iron-based MOF [MIL-100(Fe)], by a solvothermal method with polygonal morphology, are synthesised and then applied as a heterogeneous green catalyst for aza-Michael addition of various amines with α, β-unsaturated compounds. The MIL-100(Fe) was found to be efficient, selective, green and heterogeneous catalyst for the aza-Michael reaction. The proposed catalyst has better recyclability and can be reused six times without apparent loss of activity. Graphical Abstract: [Figure not available: see fulltext.].
- Rostamnia, Sadegh,Alamgholiloo, Hassan
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p. 2918 - 2928
(2018/07/30)
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- METHOD FOR PRODUCING L-CARNOSINE DERIVATIVE AND ITS SALT
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PROBLEM TO BE SOLVED: To provide a method for producing an L-carnosine derivative or its salt by a safe and simple method. SOLUTION: There is provided a method for producing an L-carnosine derivative or its salt from N-substituted benzyl-carboxylic anhydride by performing a desubstitution benzyl reaction and as necessary, a de-esterification reaction, which comprises a step of reacting N-substituted benzyl-carboxylic anhydride and a histidine compound or its salt in the presence of a base, followed performing at least a decarboxylation reaction by converting the inside of the reaction system into an acidic atmosphere to produce an N-substituted benzyl-L-carnosine derivative represented by the formula (3). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0173-0175
(2018/09/08)
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- Halogenated dihydropyran pyrrolidone compound as well as crystal form and preparation method thereof
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The invention provides a compound as shown in a formula (A) as well as a preparation method thereof. The invention also provides a crystal form I of the compound as shown in the formula (A). The crystal form is an orthorhombic system, the space group is P212121 and the unit cell parameters are as shown in the description. The invention also provides a preparation method of the crystal form I. Thehalogenated dihydropyran pyrrolidone compound and the crystal form thereof are prepared successfully. Furthermore, the compound or the crystal form thereof has anti-tumor activity, the hygroscopicityis not improved obviously, the stability is high and great convenience is provided for later-period product transportation, storage or preparation process.
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Paragraph 0032; 0033; 0034
(2018/06/26)
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- Enantioselective Hetero-Diels-Alder Reaction and the Synthesis of Spiropyrrolidone Derivatives
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An efficient enantioselective hetero-Diels-Alder reaction was developed under catalysis of a chiral copper complex. A variety of spiropyrrolidones, which bear a tetra-substituted carbon stereocenter, can be obtained in good yields with excellent enantioselectivities by virtue of this method. Furthermore, a substrate-dependent reaction pathway was proposed on the basis of the isolated intermediates.
- Huang, Yekai,Li, Yanan,Sun, Jianan,Li, Jindong,Zha, Zhenggen,Wang, Zhiyong
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supporting information
p. 8464 - 8472
(2018/07/21)
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- Oxoindole spiral tetrahydrofuran framework and its crystal and preparation method
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The invention discloses an oxoindole spiral tetrahydrofuran framework and its preparation method. The structural formula is shown as Formula I. The invention further discloses a crystal form of the compound shown in Formula I; the crystal form is a monoclinic system, the cell parameter alpha is equal to 90 degrees, beta is equal to 94.278(3) degrees, and gamma is equal to 90 degrees; the space group is P21, Z=2; the cell volume is shown as specification. The invention further discloses a preparation method of the crystal form, and also discloses an application of the compound, or its crystal form, or its solvent compound, or pharmaceutically acceptable salts in preparation of anti-cancer drugs.
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Paragraph 0047; 0051; 0052
(2018/08/04)
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- Halogenated dihydropyran pyrrolidone compound as well as preparation method and application thereof
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The invention provides a halogenated dihydropyran pyrrolidone compound of formula (I) as shown in the description, or a crystal form of the compound, in the formula, X is fluorine, chlorine, bromine and iodine; L1 is vacant or vinyl; ring A is a naphthalene ring, a benzene ring or a thiophene ring; R1 is benzyl, alkyl of C1-C8 or (CH2)n-O-Bn; n is an integer of 1-5; R2 is benzyl, allyl or p-methoxybenzyl; and R3 and R4 are respectively independently selected from hydrogen, fluorine, chlorine, bromine, iodine, alkyl of C1-C3, nitryl or methoxyl. The invention further provides a preparation method of the compound or the crystal form thereof. The compound provided by the invention is simple and convenient in preparation method, gentle in reaction and high in yield, and in addition has certainanti-tumor activity and wide market application prospects.
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Paragraph 0049-0051
(2018/08/04)
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- Cobalt complex, preparation method thereof, and application thereof in selective catalysis of transfer hydrogenation reaction of cyano group
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The invention discloses a cobalt complex, a preparation method thereof, and an application thereof in the selective catalysis of a transfer hydrogenation reaction of a cyano group. The structural formula of the cobalt complex is represented by formula I. The cobalt complex is prepared through a reaction of a cobalt salt and an NNP ligand or a PNP ligand under the protection of an inert atmosphere;and the chemical formula of the cobalt salt is CoX12, wherein X1 represents halogen, a sulfate radical, a perchlorate radical, a hexafluorophosphate radical, a hexafluoroantimonate radical, a tetrafluoroborate radical, a trifluoromethanesulfonate radical or a tetra(pentafluorophenyl)borate radical. The cobalt complex can be used in the selective catalysis of the transfer hydrogenation reaction ofthe cyano group to obtain a primary amine compound, a secondary amine compound and a tertiary amine compound, the primary amine compound, the secondary amine compound and the tertiary amine compoundare important intermediates in a series of subsequent functionalizing reactions, and the cobalt complex has a very high catalysis activity, and has great research values and a great application prospect.
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Paragraph 0173-0175; 0177
(2018/05/07)
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- Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts
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Herein, we report the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon-heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by -COOH functionality could effectively catalyze the formation of synthetically challenging spiro/glycoquinazolinones under the present reaction conditions.
- Majumdar, Biju,Mandani, Sonam,Bhattacharya, Tamalika,Sarma, Daisy,Sarma, Tridib K.
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p. 2097 - 2106
(2017/02/26)
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- Aza-Michael mono-addition using acidic alumina under solventless conditions
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Aza-Michael reactions between primary aliphatic and aromatic amines and various Michael acceptors have been performed under environmentally-friendly solventless conditions using acidic alumina as a heterogeneous catalyst to selectively obtain the corresponding mono-adducts in high yields. Ethyl acrylate was the main acceptor used, although others such as acrylonitrile, methyl acrylate and acrylamide were also utilized successfully. Bi-functional amines also gave the mono-adducts in good to excellent yields. Such compounds can serve as intermediates for the synthesis of anti-cancer and antibiotic drugs.
- Bosica, Giovanna,Abdilla, Roderick
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- Substituted biaryl benzenesulfonamide compound and application thereof
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The invention belongs to the field of agricultural herbicides and relates to a substituted biaryl benzenesulfonamide compound and application thereof. The substituted biaryl benzenesulfonamide compound is shown as the general formula (I), and substituent group definitions can be acquired in descriptions of the invention. The substituted biaryl benzenesulfonamide compound has broad spectrum herbicidal activity, can be used for controlling multiple broadleaf weeds (such as Abutilon theophrasti Medicus and Zinnia elegans Jacq.) and gramineous weeds (such as Echinochloa crusgalli (L.) Beauv. and Setaria viridis (L.) Beauv.), used as a destructive herbicide and used for weeding in transgenic crop fields, and has a certain safety for rice and the like.
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Paragraph 0120; 0121; 0122
(2016/10/08)
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- Mild and Selective Cobalt-Catalyzed Chemodivergent Transfer Hydrogenation of Nitriles
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Herein, we describe a selective cobalt-catalyzed chemodivergent transfer hydrogenation of nitriles to synthesize primary, secondary, and tertiary amines. The solvent effect plays a key role for the selectivity control. The general applicability of this procedure was highlighted by the synthesis of more than 70 amine products bearing various functional groups in high chemoselectivity. Moreover, this mild system achieved >2000 TONs (turnover numbers) for the transfer hydrogenation of nitriles.
- Shao, Zhihui,Fu, Shaomin,Wei, Mufeng,Zhou, Shaolin,Liu, Qiang
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p. 14653 - 14657
(2016/11/23)
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- Selective oxidation of amines to aldehydes or imines using laccase-mediated bio-oxidation
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An efficient and practical chemo-enzymatic aerobic oxidation in water of benzylamines to obtain aldehydes or imines is described. Laccase from Trametes versicolor was chosen as biocatalyst, and TEMPO (radical 2,2,6,6-tetramethylpiperidine 1-oxyl) as mediator. A study on the pH dependence of the aqueous medium allowed us to realise a fine tuning on product selectivity. Under our optimized reaction conditions, the bio-oxidation of a series of primary, secondary and cyclic amines has been achieved.
- Galletti, Paola,Funiciello, Federica,Soldati, Roberto,Giacomini, Daria
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supporting information
p. 1840 - 1848
(2015/06/02)
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- Synthesis of novel dihydropyridothienopyrimidin-4,9-dione derivatives
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A novel molecular scaffold, dihydropyridothienopyrimidin-4,9-dione, was synthesized from benzylamine or p-methoxybenzylamine in six steps involving successive ring closure to form a fused ring system composed of dihydropyridone, thiophene and pyrimidone. The pharmacological versatility of the dihydropyridothenopyrimidin-4,9-dione scaffold was demonstrated by inhibitory activity against metabotropic glutamate receptor subtype 1 (mGluR1), which shows that the title compounds can serve as an interesting scaffold for the discovery of potential bioactive molecules for the treatment of human diseases.
- Kim, Youngjae,Kim, Minjoo,Park, Mooseong,Tae, Jinsung,Baek, Du-Jong,Park, Ki Duk,Choo, Hyunah
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p. 5074 - 5084
(2015/05/27)
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- Reactions of Sulfonium Salts with 2,3-Dioxopyrrolidine Derivatives: A Concise Synthesis of Spirocyclopropane
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An efficient base-promoted spirocyclopropanation of 2,3-dioxopyrrolidine derivatives with sulfonium salts is described. This reaction enables a novel concise access to polysubstituted spirocyclopropane derivatives in good yields and with a trans/cis ratio of up to amp;gt;20:1 under mild conditions. amp;copy; Georg Thieme Verlag Stuttgart.
- Zhang, Shuang,Hu, Xiu-Qin,Wang, Zhu-Yin,Xu, Peng-Fei
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p. 2529 - 2537
(2015/09/01)
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- Room temperature solvent free aza-Michael reactions over nano-cage mesoporous materials
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An efficient highly acidic three dimensional mesoporous aluminosilicate nano-cage material Al-KIT5, exhibited excellent catalytic activity in solvent free room temperature aza-Michael reactions of amines with α,β- unsaturated carbonyl compounds to produce β-amino carbonyl compounds with 100% product selectivity in a short reaction time. The high acidity, 3D pores, and a huge space in the nano-cages materials make them attractive candidate for carrying out important organic reactions. The catalyst provide a simple, easy to handle method, and could be used to solve the problems of corrosion, toxicity, waste production, and a high cost that are being currently encountered by the conventional homogeneous catalysts.
- Kalita, Pranjal,Pegu, Choitayna Dev,Dutta, Prantu,Baruah, Pranjal K.
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p. 145 - 150
(2014/08/18)
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- Titania nanoparticles stabilized HPA in SBA-15 for the intermolecular hydroamination of activated olefins
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A liquid phase hydroamination (HA) of α,β-ethylenic compounds with amines was investigated with TiO2 nanoparticles stabilized 12-tungstophosphoric acid (TPA) in SBA-15. The catalysts were prepared by wet impregnation of TPA/TiO2 nanoparticles into the SBA-15 and calcined at different temperatures. The characterization results reveal that the textural properties and the acidity of the prepared catalysts can be finely controlled with the simple adjustment of the calcination temperature and the structure of the support, decorated with the TiO2 and TPA nanoparticles, was intact even after the modification. The prepared catalysts were investigated for HA of ethyl acrylate with different aromatic and aliphatic amines over a wide range of reaction conditions to optimize the yield and the selectivity of product. It was found that this process is 100% atom efficient and the catalytic performance depended significantly on the loading of TPA over the catalyst and the calcination temperature. Under optimized reaction conditions, the best catalyst, 15 wt%TPA/22.4 wt%TiO2/SBA-15 calcined at 1123 K, offered the highest conversion of p-ethylaniline (70%) with 100% chemo-selectivity to the anti-Markovnikov product, i.e., the mono-addition product. The reaction was heterogeneously catalyzed and no contribution from leached TPA into the reaction was observed.
- Sawant-Dhuri, Dhanashri,Balasubramanian, Veerappan V.,Ariga, Katsuhiko,Park, Dae-Hwan,Choy, Jin-Ho,Cha, Wang Soo,Al-Deyab, Salem S.,Halligudi, Shivappa B.,Vinu, Ajayan
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p. 3347 - 3354
(2015/04/16)
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- Meso-scale microwave-assisted continuous flow reactions utilizing a selective heating matrix
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Convergence of two powerful synthetic tools, microwave heating and flow chemistry, is described herein. Utilizing a selectively heated, microwave absorbing material as part of a packed reactor bed, several chemistries such as N-Boc pyrolysis, Michael additions, and Diels-Alder cycloadditions were performed at elevated temperatures. Scale-up from microwave batch to flow was readily accomplished and results showed that flow greatly increased product output while maintaining high yields. Product quantities of over 150 grams per hour were synthesized in this manner.
- Karney, Michael J.,Porter, Keith A.,Barnhardt, E. Keller,Vanier, Grace S.
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p. 7106 - 7111
(2013/06/04)
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- O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions
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The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and ,-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Brnsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
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p. 758 - 767
(2013/01/15)
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- Lipase-catalyzed aza-michael reaction on acrylate derivatives
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A methodology has been developed for an efficient and selective lipase-catalyzed aza-Michael reaction of various amines (primary and secondary) with a series of acrylates and alkylacrylates. Reaction parameters were tuned, and under the optimal conditions it was found that Pseudomonas stutzeri lipase and Chromobacterium viscosum lipase showed the highest selectivity for the aza-Michael addition to substituted alkyl acrylates. For the first time also, some CLEAs were examined that showed a comparable or higher selectivity and yield than the free enzymes and other formulations.
- Steunenberg, Peter,Sijm, Maarten,Zuilhof, Han,Sanders, Johan P. M.,Scott, Elinor L.,Franssen, Maurice C. R.
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p. 3802 - 3813
(2013/06/05)
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- NOVEL COMPOUNDS
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The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R1, R2, R3 and R4 are defined as in the description, the tautomers, the isomers, the diastereomers, the enantiomers, the hydrates, the mixtures thereof and the salts thereof and the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, medicaments containing these compounds, their use and processes for preparing them.
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Page/Page column 50
(2011/02/18)
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- NOVEL COMPOUNDS
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The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R1, R2, R3 and R4 are defined as mentioned in the description, the tautomers thereof, the isomers thereof, the diastereomers thereof, the enantiomers thereof, the hydrates thereof, the mixtures thereof and the salts thereof as well as the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, medicaments containing these compounds, the use thereof and processes for the preparation thereof.
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Page/Page column 106
(2011/08/22)
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- 7-Oxopyrrolopyridine-derived DPP4 inhibitors - Mitigation of CYP and hERG liabilities via introduction of polar functionalities in the active site
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Design, synthesis, and SAR of 7-oxopyrrolopyridine-derived DPP4 inhibitors are described. The preferred stereochemistry of these atropisomeric biaryl analogs has been identified as Sa. Compound (+)-3t, with a Ki against DPP4, DPP8, and DPP9 of 0.37 nM, 2.2, and 5.7 μM, respectively, showed a significant improvement in insulin response after single doses of 3 and 10 μmol/kg in ob/ob mice.
- Wang, Wei,Devasthale, Pratik,Wang, Aiying,Harrity, Tom,Egan, Don,Morgan, Nathan,Cap, Michael,Fura, Aberra,Klei, Herbert E.,Kish, Kevin,Weigelt, Carolyn,Sun, Lucy,Levesque, Paul,Li, Yi-Xin,Zahler, Robert,Kirby, Mark S.,Hamann, Lawrence G.
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scheme or table
p. 6646 - 6651
(2011/12/21)
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- Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates
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An efficient protocol for the regioselective aza-Michael addition of amines with acrylates using CaL B as a biocatalyst at 60 °C has been developed. The reaction is applicable to a wide variety of primary and secondary amines with different acrylates to synthesize the corresponding β-amino esters with good yields. An alternative route for the synthesis of higher β-amino esters through the additional transesterification step is also studied and was found effective.
- Dhake, Kishor P.,Tambade, Pawan J.,Singhal, Rekha S.,Bhanage, Bhalchandra M.
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experimental part
p. 4455 - 4458
(2010/09/20)
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- WRINKLE-IMPROVING AGENT
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The invention provides a novel wrinkle-improving agent that has an effect of improving wrinkles, that does not entail problems of safety or pain even when applied to the skin, and that contains a very safe substance as an active component. A discovery was made that N-benzoyl-β-alanine, other specific β-alanine derivatives, and salts thereof have a wrinkle-improving effect, whereby a wrinkle-improving agent containing as an active component one, two, or more types of compounds selected from the group composed of these specific β-alanine derivatives and the salts thereof was developed.
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Page/Page column 20
(2008/12/06)
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- Aurora kinase A inhibitors: Identification, SAR exploration and molecular modeling of 6,7-dihydro-4H-pyrazolo-[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-dione scaffold
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Tricyclic 6,7-dihydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-dione was identified as a novel scaffold for Aurora kinase A inhibition through virtual screening. SAR exploration coupled with molecular modeling of 8a reveals the minimum pharmacophore requirements for Aurora kinase A inhibition.
- Coumar, Mohane Selvaraj,Wu, Jian-Sung,Leou, Jiun-Shyang,Tan, Uan-Kang,Chang, Chung-Yu,Chang, Teng-Yuan,Lin, Wen-Hsing,Hsu, John T.-A.,Chao, Yu-Sheng,Wu, Su-Ying,Hsieh, Hsing-Pang
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p. 1623 - 1627
(2008/12/21)
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- Design and synthesis of a pyrido[2,3-d]pyrimidin-5-one class of anti-inflammatory FMS inhibitors
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A series of pyrimidinopyridones has been designed, synthesized and shown to be potent and selective inhibitors of the FMS tyrosine kinase. Introduction of an amide substituent at the 6-position of the pyridone core resulted in a significant potency increase. Compound 24 effectively inhibited in vivo LPS-induced TNF in mice greater than 80%.
- Huang, Hui,Hutta, Daniel A.,Hu, Huaping,DesJarlais, Renee L.,Schubert, Carsten,Petrounia, Ioanna P.,Chaikin, Margery A.,Manthey, Carl L.,Player, Mark R.
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p. 2355 - 2361
(2008/09/20)
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- Samarium(III) triflate catalyzed conjugate addition of amines to electron-deficient alkenes
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Amines undergo smooth nucleophilic addition to α,β-unsaturated compounds in the presence of a catalytic amount of samarium(III) triflate at ambient temperature to produce the corresponding β-amino compounds in excellent yields. This method is simple, convenient, and works efficiently under mild conditions. Georg Thieme Verlag Stuttgart.
- Yadav,Ramesh Reddy,Gopal Rao,Narsaiah,Subba Reddy
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p. 3447 - 3450
(2008/09/19)
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- Natural phosphate modified with lithium nitrate: A new efficient catalyst for the construction of carbon-carbon, carbon-sulfur, and carbon-nitrogen bonds
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The addition of small amounts of lithium nitrate to natural phosphate followed by calcination gives a new catalyst Li/NP (weight ratio LiNO3/NP = 1/15). This material showed catalytic activity in the Michael addition of amines, mercaptans, and active methylene compounds to chalcone derivatives with high yields under mild reaction conditions. Li/NP is used as the catalyst for a facile synthesis of -amino acids, -sulfur acids, and 4 H-chromenes under heterogeneous conditions. The usual, undesirable byproducts from the Michael condensation such as 1,2-addition, bis-addition, and polymerization compounds are not observed with this method. The work-up procedure is simplified by simple filtration with the use of Li/NP.
- Zahouily, Mohamed,Mounir, Bahija,Cherki, Hind,Bahlaouan, Bouchaib,Rayadh, Ahmed,Sebti, Said
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p. 1203 - 1217
(2008/02/02)
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- Cadmium chloride (CdCl2): An efficient catalyst for conjugate addition of amines to electron-poor alkenes
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Electron-deficient olefins undergo rapid Aza-Michael reaction with a wide range of amines catalyzed by cadmium chloride at room temperature. Copyright Taylor & Francis Group, LLC.
- Vijender, Medamoni,Kishore,Satyanarayana
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p. 591 - 594
(2007/10/03)
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- Bromodimethylsulfonium bromide mediated Michael addition of amines to electron deficient alkenes
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Bromodimethylsulfonium bromide has been found to be an efficient catalyst for the Michael addition of a wide variety of amines to electron deficient alkenes at room temperature. The protocol is very simple and chemoselective. Aliphatic and benzylic amines undergo conjugate addition within a very short period under solvent-free conditions and provide excellent yields of products.
- Khan, Abu T.,Parvin, Tasneem,Gazi, Sarifuddin,Choudhury, Lokman H.
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p. 3805 - 3808
(2008/02/06)
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- RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles
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The 1,4-conjugate addition of primary, secondary and aromatic amines, thiols, and carbamate to α,β-unsaturated compounds mediated by a catalytic amount (0.5 mol%) of RuCl3 in poly(ethylene glycol) (PEG) provides the desired β-substituted carbonyls in high yields. In particular, we found that primary aliphatic and aromatic amines produced the single adducts as the sole products in very high yields with RuCl3-PEG. RuCl 3-PEG was readily recycled via solvent precipitation with efficient recyclability as evidenced by high yields. Its properties of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, and efficient recyclability make RuCl3-PEG suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls. Georg Thieme Verlag Stuttgart.
- Zhang, Huaxing,Zhang, Yuhong,Liu, Leifang,Xu, Hailiang,Wang, Yanguang
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p. 2129 - 2136
(2007/10/03)
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- A green, ionic liquid and quaternary ammonium salt-catalyzed aza-Michael reaction of α,β-ethylenic compounds with amines in water
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The first environmentally benign, highly efficient conjugate addition of aliphatic amines to α,β-unsaturated compounds catalysed by simple quaternary ammonium salts and ionic liquids in the green solvent, water, is described.
- Xu, Li-Wen,Li, Jing-Wei,Zhou, Shao-Lin,Xia, Chun-Gu
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p. 183 - 184
(2007/10/03)
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- Natural phosphate and potassium fluoride doped natural phosphate: Efficient catalysts for the construction of a carbon-nitrogen bond
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The application of natural phosphates doped with potassium fluoride as heterogeneous catalysts for the Michael addition of aromatic and aliphatic amines to α,β-unsaturated carbonyl compounds is presented. The natural phosphate catalyst can be regenerated and reused without loss of activity, which makes it an attractive alternative to homogeneous basic reagents. Doping natural phosphate with potassium fluoride significantly enhances the rate and yield of the reaction.
- Zahouily, Mohamed,Bahlaouan, Bouchaib,Rayadh, Ahmed,Sebti, Sa?d
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p. 4135 - 4138
(2007/10/03)
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- Efficient Copper-Catalyzed Chemo Selective Conjugate Addition of Aliphatic Amines to α,β-Unsaturated Compounds in Water
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The first environmentally benign, highly efficient, conjugate addition of aliphatic amines to α,β-unsaturated compounds catalyzed by simple copper salts in the green solvent, water is described.
- Xu, Li-Wen,Li, Jing-Wei,Xia, Chun-Gu,Zhou, Shao-Lin,Hu, Xiao-Xue
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p. 2425 - 2427
(2007/10/03)
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- Pharmaceutically active compounds and methods of use
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New fused thiophene compounds are provided and methods of using those compounds for a variety of therapeutic indications. Compounds of the invention are particularly useful for treatment of neuropathic pain.
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- Process for producing 4a-aryldecahydroisoquinoline derivatives
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The present invention provides a novel process for producing 4a-aryldecahydroisoquinoline compounds. The process is especially useful for preparing 4a-trans-6-oxo-aryldecahydroisoquinoline compounds.
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- Synthesis and reactivity of a 3-vinylidenepiperidine as a model study of α-allenic amines
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4-Acetonyl-1-benzyl-3-vinylidenepiperidine (8), prepared by cyclization of propargylic silane (7), was used as a model to study the usefulness of the allene moiety as a precursor of the two-carbon chain present in the piperidine ring of Strychnos alkaloids.
- Solé, Daniel,García-Rubio, Silvina,Bosch, Joan,Bonjoch, Josep
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p. 2415 - 2424
(2007/10/03)
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- Soft β-adrenergic agonists for the topical treatment of psoriasis
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The soft-drug 1 (R = Me, Et) and pro-soft-drug 3 have been prepared as models of topical anti-psoriatic β-adrenergic agonists. The chemical hydrolysis of 3 proceeded via the acid 18 with a maximum stability at apparent pH ~4.0. In the presence of PLCE, the required metabolism of 3 to the soft-drug 1 (R = Et) was achieved, which slowly degraded to the dihydroxy acid 2. Soft-drug 1 (R = Et) was poorly transported across a silicone membrane, whereas the pro-soft-drug 3 was more efficient and the rate increased over the donor apparent pH range 3-8. Soft-drug 1 (R = Et) was a full β-agonist on the guinea-pig tracheal preparation, whereas the pro-soft-drug 3 produced only slowly developing responses at high concentrations (> 10 μM).
- Gill,Freeman,Irwin,Wilson
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p. 847 - 859
(2007/10/03)
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- 6,7-dihydropyrrol[3,4-c]pyrido[2,3-d]pyrimidine derivatives
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The present invention concerns compounds of the formula: STR1 wherein R is a lower alkyl group, an aryl group or an alkylaryl group and X and Y are the same or different, and each is OH, NH2, or SH. The aryl group or the aryl moiety of the alkylaryl group may be unsubstituted, monosubstituted, disubstituted or trisubstituted. If substituted, each substituent may independently be an alkyl group, an alkyloxy group or a halogen. The present invention also provides methods for synthesizing the compounds described above.
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- Heteroarotinoid compounds as anticancer agents
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Novel heteroarotinoid compositions characterized by the formulae: STR1 where R is H, CH3 or C2 H5 and X is S, S O, O, NCH3, Si(CH3)2, N+ (H)CH3 [Cl- ], N+ (H)CH3 [Br- ] or N+ (alkyl) CH3 [Cl- or Br-) where alkyl is CH3, C2 H5, CH2 =CHCH2 or C6 H5 CH2. Such compositions exhibit activity as anticancer agents.
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- Decarboxylation Reaction. X. Introduction of a Carbon unit at the α-Position of Amines by Reaction of Hexahydro-1,3,5-triazines with Carboxylic Acids
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An efficient method for introducing a carbon unit at the α-position of alicyclic amines is described.The method involves the reaction of monocyclic or tetracyclic hexahydro-1,3,5-triazines with trichloroacetic acid, cyanoacetic acid, malonic acid and their derivatives, which are introduced into the α-position of amines in the decarboxylated form.Keywords --- 1,3,5-trialkylhexahydro-1,3,5-triazine; trimer of alicyclic imine; decarboxylation; β-amino acid; carboxylic acid
- Fukawa, Hidemichi,Terao, Yoshiyasu,Achiwa, Kazuo,Sehiya, Minoru
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