- Synthesis,18 F-Radiolabelling and Biological Characterization of Novel Fluoroalkylated Triazine Derivatives for in Vivo Imaging of Phosphodiesterase 2A in Brain via Positron Emission Tomography
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Phosphodiesterase 2A (PDE2A) is highly and specifically expressed in particular brain regions that are affected by neurological disorders and in certain tumors. Development of a specific PDE2A radioligand would enable molecular imaging of the PDE2A protei
- Schr?der, Susann,Wenzel, Barbara,Deuther-Conrad, Winnie,Teodoro, Rodrigo,Egerland, Ute,Kranz, Mathias,Scheunemann, Matthias,H?fgen, Norbert,Steinbach, J?rg,Brust, Peter
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Read Online
- New atropisomeric N-N ligands for CO/vinyl arene copolymerization reaction
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New atropisomeric bidentate bipyridine-based ligands (3,3′- (ethylenedioxy)-2,2′-bipyridine 3; 3,3′-(propylenedioxy)-2,2′- bipyridine 4; 3,3′-(butylenedioxy)-2,2′-bipyridine 5) containing a bridge between the 3,3′ positions of the aromatic rings have been prepared. Together with the previously reported analogous ligands ((R)-3,3′-(1-methylethylenedioxy)-2,2′-bipyridine) 1 and ((S,S)-3,3′-(1,2-dimethylethylenedioxy)-2,2′-bipyridine) 2, they were used to synthesize the corresponding bis-chelated dicationic complexes [Pd(N-N)2][PF6]2. Crystal structures and comparison of the data obtained by X-ray analysis on four of these complexes is reported. These palladium compounds were used as precatalysts in the CO/styrene and CO/4-Me-styrene copolymerization reactions, where they showed that small variations in the ligand backbone remarkably affects the productivity of the catalytic system. The Royal Society of Chemistry 2008.
- Durand, Jerome,Zangrando, Ennio,Carfagna, Carla,Milani, Barbara
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Read Online
- Macrocyclic compound, and preparation method and application thereof
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The invention discloses a macrocyclic kinase inhibitor, and a compound, or a stereoisomer or a pharmaceutically acceptable salt thereof as shown in a formula (I). Experiments show that the novel compound shown in the formula (I) shows good TRK inhibitory
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Paragraph 0209-0211
(2021/06/23)
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- COMPOUNDS USEFUL IN HIV THERAPY
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The invention relates to compounds of Formula (I), (Ia), (Ib), (II) or (III), salts thereof, pharmaceutical compositions thereof, as well as therapeutic methods of treatment and prevention.
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Page/Page column 181; 182
(2020/06/19)
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- Aggregation-induced emission based on a fluorinated macrocycle: visualizing spontaneous and ultrafast solid-state molecular motions at room temperature: via F?F interactions
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We for the first time report the efficient construction of novel tetraphenethylene (TPE)-based macrocycles with various mechanofluorochromism (MFC) behaviors involving solid-state molecular motions. We were able to facilely regulate the diverse solid-stat
- Guo, Jingjing,He, Zhanyu,Irfan, Majeed,Liu, Tingting,Zeng, Zhuo,Zhang, Mei,Zhao, Zujin
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supporting information
p. 14919 - 14924
(2020/11/17)
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- Tetrastyrene macrocyclic compound with force-induced fluorescence color-changing performance and synthesis method and application thereof
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The invention discloses a tetrastyrene macrocyclic compound with force-induced fluorescence color changing performance. The compound is connected with an alkyl chain structural unit through the strongfluorescence property of the tetrastyrene macrocyclic c
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Paragraph 0059-0061
(2019/06/07)
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- A compound for PET imaging and use thereof
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The present invention provides a precursor compound for the production of a radioactive compound for efficient contrast of the heart, a radioactive compound prepared using the precursor compound, and uses as a contrast medium for a PET contrast medium.br
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Paragraph 0068-0070
(2018/04/21)
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- Synthesis, F-18 radiolabeling, and microPET evaluation of 3-(2,4-dichlorophenyl)-N-alkyl-N-fluoroalkyl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amines as ligands of the corticotropin-releasing factor type-1 (CRF1) receptor
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A series of 3-(2,4-dichlorophenyl)-N-alkyl-N-fluoroalkyl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amines were synthesized and evaluated as potential positron emission tomography (PET) tracers for the corticotropin-releasing factor type-1 (CRF1) receptor. Compounds 27, 28, 29, and 30 all displayed high binding affinity (≤1.2 nM) to the CRF1 receptor when assessed by in vitro competition binding assays at 23 °C, whereas a decrease in affinity (≥10-fold) was observed with compound 26. The log P7.4 values of [18F]26-[18F]29 were in the range of ~2.2-2.8 and microPET evaluation of [18F]26-[18F]29 in an anesthetized male cynomolgus monkey demonstrated brain penetrance, but specific binding was not sufficient enough to differentiate regions of high CRF1 receptor density from regions of low CRF1 receptor density. Radioactivity uptake in the skull, and sphenoid bone and/or sphenoid sinus during studies with [18F]28, [18F]28-d8, and [18F]29 was attributed to a combination of [18F]fluoride generated by metabolic defluorination of the radiotracer and binding of intact radiotracer to CRF1 receptors expressed on mast cells in the bone marrow. Uptake of [18F]26 and [18F]27 in the skull and sphenoid region was rapid but then steadily washed out which suggests that this behavior was the result of binding to CRF1 receptors expressed on mast cells in the bone marrow with no contribution from [18F]fluoride.
- Stehouwer, Jeffrey S.,Birnbaum, Matthew S.,Voll, Ronald J.,Owens, Michael J.,Plott, Susan J.,Bourke, Chase H.,Wassef, Michael A.,Kilts, Clinton D.,Goodman, Mark M.
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p. 4286 - 4302
(2015/08/03)
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- Synthesis and characterization of a novel series of agonist compounds as potential radiopharmaceuticals for imaging dopamine D2/3 receptors in their high-affinity state
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Imaging of dopamine D2/3 receptors (D2/3R) can shed light on the nature of several neuropsychiatric disorders in which dysregulation of D2/3R signaling is involved. Agonist D2/3 tracers for PET/SPECT imaging are considered to be superior to antagonists because they are more sensitive to dopamine concentrations and may selectively label the high-affinity receptor state. Carbon-11-labeled D2/3R agonists have been developed, but these short-lived tracers can be used only in centers with a cyclotron. Here, we report the development of a series of novel D2R agonist compounds based on the 2-aminomethylchromane (AMC) scaffold that provides ample opportunities for the introduction of longer-lived [ 18F] or [123I]. Binding experiments showed that several AMC compounds have a high affinity and selectivity for D2/3R and act as agonists. Two fluorine-containing compounds were [18F]-labeled, and both displayed specific binding to striatal D2/3R in rat brain slices in vitro. These findings encourage further in vivo evaluations.
- Van Wieringen, Jan-Peter,Shalgunov, Vladimir,Janssen, Henk M.,Fransen, P. Michel,Janssen, Anton G. M.,Michel, Martin C.,Booij, Jan,Elsinga, Philip H.
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p. 391 - 410
(2014/02/14)
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- Design and synthesis of polymeric chiral bicyclo[3.3.0] diene as reusable ligand for rhodium-catalyzed asymmetric 1,4-addition
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A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. With polymeric diene 6b, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. By using polymeric diene, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. Copyright
- Yang, Hongyu,Xu, Minghua
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supporting information
p. 119 - 122
(2013/08/24)
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- Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s
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The synthesis of well-defined polymer architectures is of major importance for the development of complex functional materials. In this contribution, we discuss the synthesis of a range of multifunctional star-shaped tosylates as potential initiators for the living cationic ring-opening polymerization (CROP) of 2-oxazolines resulting in star-shaped polymers. The synthesis of the tosylates was performed by esterification of the corresponding alcohols with tosyl chloride. Recrystallization of these tosylate compounds afforded single crystals, and the X-ray crystal structures of di-, tetra-and hexa-tosylates are reported. The use of tetra-and hexatosylates, based on (di)pentaerythritol as initiators for the CROP of 2-ethyl-2-oxazoline, resulted in very slow initiation and illdefined polymers, which is most likely caused by steric hindrance in these initiators. As a consequence, a porphyrin-cored tetratosylate initiator was prepared, which yielded a well-defined star-shaped poly(2-ethyl-2-oxazoline) by CROP as demonstrated by SEC with RI, UV and diode-array detectors, as well as by 1H NMR spectroscopy.
- Hoogenboom, Richard,Fijten, Martin W. M.,Kickelbick, Guido,Schubert, Ulrich S.
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experimental part
p. 773 - 783
(2011/03/19)
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- Synthesis of new bis-BINOL-2,2′-ethers and bis-H8BINOL-2,2′-ethers evaluation of their Titanium complexes in the asymmetric ethylation of benzaldehyde
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The preparation by means of different synthetic paths of a series of bis-BINOL and bis-H8BINOL ligands is described. The ligands consist of two BINOL or H8BINOL fragments, joined by diverse linkages through the oxygen at the 2′-position of the arylic fragments. These ligands were applied to the Ti(OiPr)4 catalyzed asymmetric alkylation of benzaldehyde with Et2Zn. The performance of these catalysts is very sensitive to the nature of the ether linkage. The ligand with a propylene link shows better enantioselectivity (ca. 70%) than those with two or four carbon atoms joining the BINOL fragments. Furthermore, using the propylene link, but replacing (R)-BINOL by (R)-H8BINOL, a significant improvement in the stereoselectivity of the catalysts was achieved (ca. 80% ee in (R)-1-phenylpropan-1-ol). A cooperative effect was observed between the chirality at the BINOL fragment and that of a (S,S)-4,5-bis(methylene)-2,2-dimethyl-1,3-dioxolane link, derived from tartaric acid. When this chiral link combines with two (S)-BINOL fragments, the alkylation of benzaldehyde in toluene produces 70% ee of (S)-1-phenylpropan-1-ol, while the (R)-BINOL derivative ligand with the same link, in identical conditions, yields only 40% ee of the (R)-alcohol.
- Abreu, Artur R.,Pereira, Mariette M.,Bayón, J. Carles
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experimental part
p. 743 - 749
(2010/09/14)
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- Tethered PProDOTs: Conformationally restricted 3,4-propylenedioxythiophene based electroactive polymers
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Herein we report a complete family of conformationally restricted PProDOT derivatives with varying alkylene tether lengths. It was found that variation of the tether length and structure of the electropolymerizable monomer was successful in the fine-tuning of the electrochemical and optical properties of the subsequent material. It was found that the band gap of the materials could be varied between 1.94 and 2.26 eV, with the "sweet spot" for obtaining the maximum electronic band gap existing at the n = 6 tether length, while maintaining low redox potentials. It was also found that these polymers exhibited stable electrochromic behavior with colors varying from blue-purple to orange in their neutral states and transmissive in their doped states. The Royal Society of Chemistry 2007.
- Walczak, Ryan M.,Cowart Jr., John S.,Reynolds, John R.
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p. 254 - 260
(2008/02/01)
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- Synthesis of a series of triaza-macrocyclicanes
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Condensation of the N, N′, N″-tris(p-toluenesulfonyl)diethylenetrimine-N,N″-disodium with bissulphonate esters of two-, three-, four- and six-carbon diols gives the corresponding 9-, 10-,11-, 13-membered triamine macrocycles containing N-ptoluenesulfonyl group, respectively. The p-tuluenesulfonyl groups are removed with concentrated sulfuric acid, acetic acidhydrobromic acid or LiAlH4 which give the ammonium salts of 1,4,7-triazacyclononane, 1,4,7-triazacyclodecane, 1,4,7-triazacycloundecane, 1,4,7-triazacyclotridecane, respectively. Comparison and details of the different synthetic procedures of the triamine macrocycles are described as well.
- Gao, Jinzhang,He, Hui,Zhang, Xuan,Lu, Xiaoquan,Kang, Jingwan
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p. 372 - 375
(2007/10/03)
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- Silver(I) oxide mediated highly selective monotosylation of symmetrical diols. Application to the synthesis of polysubstituted cyclic ethers
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(Matrix Presented) The reaction of symmetrical diols and oligo(ethylene glycol)s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver(I) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields. Polysubstituted cyclic ethers were obtained readily upon treatment of the corresponding diols with an excess of silver oxide. The high selectivity was explained on the basis of the difference in acidity between the two hydroxy groups, which undergo an intramolecular hydrogen bonding.
- Bouzide, Abderrahim,Sauve, Gilles
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p. 2329 - 2332
(2007/10/03)
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- Montmorillonite clay catalyzed tosylation of alcohols and selective monotosylation of diols with p-toluenesulfonic acid: An enviro-economic route
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An enviro-economic route for tosylation of alcohols and selective monotosylation of diols in good yield directly using p-toluenesulfonic acid together with metal-exchanged montmorillonite instead of p-toluenesulfonyl chloride or p-toluenesulfonic anhydrid
- Choudary, Boyapati M.,Chowdari, Naidu S.,Kantam, Mannepalli L.
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p. 7291 - 7298
(2007/10/03)
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- Synthesis of acyclic adenine 8,N-anhydronucleosides
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9-(4-Hydroxybutyl)adenine (10) was obtained by reaction of adenine with 4-[(2-tetrahydropyran-2-yl)oxy]butyl chloride (7) in the presence of DBU. 8-Bromo-9-(4-hydroxybutyl)adenine (13) was prepared by bromination of 10 or by alkylation of 8-bromoadenine (11) with 4-bromoethyl acetate followed by methanolysis. Tosylation of compound 13 afforded the 4-tosyloxy derivative 15 which gave on heating with methylamine or cyclopropylamine 6-methyl-(17a) or 6-cyclopropyl-7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17b), while the reaction with hydrazine afforded 7,8,9,10-tetrahydro-6H-[1,3]diazepino-[1,2-e]purine-4,6-diamine (17d). Treatment of compound 13 with thionyl chloride gave 9-(4-chlorobutyl)-8-chloroadenine (18) as the main product which was transformed to 17b, 6-propyl-7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17c) or 7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17e) by reaction with cyclopropylamine, propylamine or ammonia, respectively. Compound 17e was quite stable both in acid and alkaline solutions, at room temperature or at 90 °C. Compound 13 was converted to 9-(4-hydroxybutyl)-8-methylaminoadenine (19) by reaction with methylamine. Compound 19 failed to undergo intramolecular cyclization to diazepine 17a on treatment with diphenyl carbonate, bis(4-nitrophenyl) carbonate or 1,1′-carbonyldiimidazole.
- Meszarosova, Katerina,Holy, Antonin,Masojidkova, Milena
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p. 1109 - 1125
(2007/10/03)
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- Synthesis, modification, and characterization of a family of homologues of exo-calix[4]arene: exo-[n.m.n.m]Metacyclophanes, n,m ≥ 3
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A general strategy for the preparation of the family of exo-[n.m.n.m]metacyclophanes (n,m ≥ 3) in 6-steps (starting from 2-bromoanisole)that utilizes a [2 + 2] approach to furnish the exometacyclophane ring in good to moderate yield is described. The soluble copper catalyst [CuBr- LiSPh-LiBr-THF] is used to efficiently couple Grignard and alkyl or ether tosylate reagents in several of the synthetic steps, including the ring construction in the final step. The exo-[n.m.n.m]- metacyclophane ring is conformationally mobile on the NMR time scale, and X-ray crystallography reveals that exo-[3.3.3.3]metacyclophane 2a assumes a cone conformation, and that exo-[6.6.6.6]- metacyclophane 6a assumes a chair conformation. Molecular mechanics calculations show that both conformations for each exo-metacyclophane are very similar in energy. Regiocontrol over the alkylation and acylation of the phenolic oxygens of 2b is problematic, although the preparation of the tetraacetylated 18 and alkylation of 2b with CH2BrCl to furnish the methylene-linked mono- and bis-adducts 19 and 20 are straightforward.
- Burns, Dennis H.,Chan, Ho-Kit,Miller, Jeffrey D.,Jayne, Charles L.,Eichhorn, David M.
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p. 5185 - 5196
(2007/10/03)
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- Synthesis of New Diols Derived from Dianhydrohexitols Ethers under Microwave-Assisted Phase Transfer Catalysis
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Alkylation of mono-benzylated isosorbide and isomannide was performed under microwave assisted phase transfer catalysis (PTC). A small amount of solvent was necessary to provide good yields (90-96%) within 15 min. In order to minimize the competitive elimination, halide leaving group was changed to tosylate as competitive S(N)2-E2 processes were involved. After removal of benzyl moiety by hydrogenation, a series of new diols from dianhydrohexitols were thus prepared. (C) 2000 Elsevier Science Ltd.
- Chatti, Saber,Bortolussi, Michel,Loupy, André
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p. 5877 - 5883
(2007/10/03)
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- Formation and use of boron sulfonates
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Boric acid reacts swiftly with p-toluenesulfonyl chloride in pyridine-d5 to form the unstable boron sulfonate which is observed by NMR. The utility of this reaction is discussed.
- Braish
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p. 335 - 341
(2007/10/02)
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- Molecular Design of Crown Ethers. 1. Effects of Methylene Chain Length: 15- to 17-Crown-5 and 18- to 22-Crown-6
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The ring-enlarged crown ethers, 16- and 17-crown-5 and 19- to 22-crown-6, were synthesized and their cation-binding abilities were evaluated by solvent extraction of aqueous alkali metal picrates.The cation-binding abilities of less symmetrical crown ethers, 3a-e and 4a,b, were generally lower than those of the common symmetrical crown ethers 15-crown-5 (5a) and 18-crown-6 (5b), for which the less symmetrical arrangement of the donor oxygen atoms must be responsible.Compared with 18-crown-6 (5b), the ring-extended crown ethers, 3d, 3e, and 4b, showed a significant shift in cation selectivity, probably due to the enlarged cavity size.The thermodynamic parameters for the extraction of sodium and potassium picrates with 3a, 3c, and 5a,b were calculated from the change of the extraction equilibrium constants (Kex) between 10-25 deg C.The stability of the cation-crown ether complexes was shown to be governed in general by the enthalpy change.However, a significant contribution of the entropy factor was found in unfavorable size combinations of K+ with 3a and Na+ with 3c.
- Ouchi, Mikio,Inoue, Yoshihisa,Kanzaki, Takashi,Hakushi, Tadao
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p. 1408 - 1412
(2007/10/02)
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- COMPLEXATION DE L'ANION FLUORURE PAR DES TETRAMINES CYCLIQUES PROTONEES.
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The synthesis of the new tetraazamacrocycle N4 is briefly described; complexation of F(1-) by the fully protonated N4, N4 and N4 macrocycles is investigated.
- Suet, Elisabeth,Handel, Henri
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p. 645 - 648
(2007/10/02)
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- Synthesis of Selectively Protected Tri- and Hexaamine Macrocycles
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A general route to tri- and hexaamine macrocycles containing selectively protected diethylenetriamine units has been developed.Condensation of the N'-benzoyl-N,N"-bis(p-tolylsulfonyl)diethylenetriamine N,N"-disodium salt with bissulfonate esters of two-, four-, and six-carbon diols at high reactant concentrations gave the corresponding 9- and 18- (85percent and 1percent), 11- and 22- (30percent and 20percent), and 13- and 26- (56percent and 17percent) membered tri- and hexaamine macrocycles, respectively.The benzoyl group was selectively removed with potassium tert-butoxide in ca. 90percent yield, and the macrocycles were conveniently separated by chromatography.Details of the synthetic procedures and characterization of the new selectively protected tri- and hexaamine macrocycles are described.
- Martin, Andrea E.,Ford, Thomas M.,Bulkowski, John E.
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p. 412 - 415
(2007/10/02)
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- Co-ordinating Tendencies of a 14-Membered Tetra-aza Macrocycle which forms a Seven-membered Chelate Ring
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The basicity constant of 1,4,7,10-tetra-azacyclotetradecane (L5) and the stability constants of the complexes 5>(2+) and 5)>(3+) have been determined by potentiometry at 25 deg C in 0.5 mol dm-3 K
- Micheloni, Mauro,Paoletti, Piero,Poggi, Antonio,Fabbrizzi, Luigi
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