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Mukund P Sibi - One of the best experts on this subject based on the ideXlab platform.
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lewis acid mediated diastereoselective intermolecular radical addition trapping with pyrazolidinone acrylimides
ChemInform, 2015Co-Authors: Takehiro Fujita, Mukund P SibiAbstract:A facile one-pot procedure for the radical conjugate addition of alkyl iodides to amides bearing a new pyrazolidinone chiral auxiliary and subsequent diastereoselective trapping of the intermediate radical by an Allyl Group is developed.
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lewis acid mediated diastereoselective intermolecular radical addition trapping with pyrazolidinone acrylimides
Tetrahedron Letters, 2015Co-Authors: Takehiro Fujita, Mukund P SibiAbstract:Abstract We report herein a new pyrazolidinone chiral auxiliary and its utility in Lewis acid-mediated conjugate addition followed by diastereoselective trapping of the intermediate radical by an Allyl Group. The Allylated products were obtained in good yields (up to 89%) and high diastereoselectivities (up to 94/6).
Takehiro Fujita - One of the best experts on this subject based on the ideXlab platform.
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lewis acid mediated diastereoselective intermolecular radical addition trapping with pyrazolidinone acrylimides
ChemInform, 2015Co-Authors: Takehiro Fujita, Mukund P SibiAbstract:A facile one-pot procedure for the radical conjugate addition of alkyl iodides to amides bearing a new pyrazolidinone chiral auxiliary and subsequent diastereoselective trapping of the intermediate radical by an Allyl Group is developed.
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lewis acid mediated diastereoselective intermolecular radical addition trapping with pyrazolidinone acrylimides
Tetrahedron Letters, 2015Co-Authors: Takehiro Fujita, Mukund P SibiAbstract:Abstract We report herein a new pyrazolidinone chiral auxiliary and its utility in Lewis acid-mediated conjugate addition followed by diastereoselective trapping of the intermediate radical by an Allyl Group. The Allylated products were obtained in good yields (up to 89%) and high diastereoselectivities (up to 94/6).
Dae Hyun Kim - One of the best experts on this subject based on the ideXlab platform.
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design and synthesis of a photocleavable fluorescent nucleotide 3 o Allyl dgtp pc bodipy fl 510 as a reversible terminator for dna sequencing by synthesis
Journal of Organic Chemistry, 2006Co-Authors: Qinglin Meng, Dae Hyun Kim, Xiaopeng Bai, Nicholas J TurroAbstract:DNA sequencing by synthesis (SBS) using reversible fluorescent nucleotide terminators is potentially an efficient approach to address the limitations of current DNA sequencing techniques. Here, we report the design and synthesis of a 3'-O-Allyl photocleavable fluorescent nucleotide analogue, 3'-O-Allyl-dGTP-PC-Bodipy-FL-510, as a reversible terminator for SBS. The nucleotide is efficiently incorporated by DNA polymerase into a growing DNA strand to terminate the polymerase reaction. After that, the fluorophore is photocleaved quantitatively by irradiation at 355 nm, and the Allyl Group is rapidly and efficiently removed by using a Pd-catalyzed reaction under DNA-compatible conditions to regenerate a free 3'-OH Group to reinitiate the polymerase reaction. Two cycles of such steps were successfully demonstrated to sequence a homopolymeric region of a DNA template, facilitating the development of SBS as a viable approach for high-throughput DNA sequencing.
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design and synthesis of a chemically cleavable fluorescent nucleotide 3 o Allyl dgtp Allyl bodipy fl 510 as a reversible terminator for dna sequencing by synthesis
Journal of the American Chemical Society, 2006Co-Authors: Dae Hyun KimAbstract:We report the construction of a novel chemically cleavable fluorescent labeling system based on an Allyl Group to modify nucleotide for DNA sequencing by synthesis (SBS). We have found that an Allyl moiety can be used successfully as a linker to tether a fluorophore to a 3'-O-Allyl-modified nucleotide, forming a chemically cleavable reversible terminator, 3'-O-Allyl-dGTP-Allyl-Bodipy-FL-510, for application in SBS. The fluorophore and the 3'-Allyl Group on a DNA extension product, which is generated by incorporating 3'-O-Allyl-dGTP-Allyl-Bodipy-FL-510, are removed simultaneously in 30 s by Pd-catalyzed deAllylation in aqueous buffer solution. The resulting DNA product is successfully used as a primer for further extension in polymerase reaction. This one-pot dual-deAllylation reaction thus allows the reinitiation of the polymerase reaction and increases the SBS efficiency.
Tadashi Kataoka - One of the best experts on this subject based on the ideXlab platform.
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synthesis and structure activity relationship of 3 substituted benzamide benzo b furan 7 carboxamide 2 3 dihydrobenzo b furan 7 carboxamide and indole 5 carboxamide derivatives as selective serotonin 5 ht4 receptor agonists
Chemical & Pharmaceutical Bulletin, 1998Co-Authors: Takuji Kakigami, Toshinao Usui, Katsura Tsukamoto, Tadashi KataokaAbstract:The title compounds (6-9) were prepared and evaluated for serotonin 5-HT4 agonistic activity in in vitro tests. Introducing a propyl or Allyl Group at the 3-position of benzamide caused only a slight enhancement of agonistic activity. Construction of the benzo[b]furan skeleton and 2, 3-dihydrobenzo[b]furan skeleton caused a significant enhancement of the activity. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2-methylbenzo[b]furan-7-carboxamide (7b) hemifumarate was as potent as cisapride. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-methylbenzo[b]furan-7-carboxamide (8a) hemifumarate, 4-amino-N-[2-(1-azabicyclo-[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2-ethylbenzo[b]furan-7-carboxamide (8c) hemifumarate, and 4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2, 3-dihydro-2, 3-dimethylbenzo[b]furan-7-carboxamide (8d) hemifumarate were potent than cisapride. Furthermore, 8a hemifumarate was free from dopamine D1, D2, serotonin 5-HT1, 5-HT2 and muscarine M1, M2 receptor binding activity in the in vitro tests. On the other hand, construction of the indole skeleton caused a remarkable decrease in activity.
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synthesis and structure activity relationship of 3 substituted benzamide benzo b furan 7 carboxamide 2 3 dihydrobenzo b furan 7 carboxamide and indole 5 carboxamide derivatives as selective serotonin 5 ht4 receptor agonists
Chemical & Pharmaceutical Bulletin, 1998Co-Authors: Takuji Kakigami, Toshinao Usui, Katsura Tsukamoto, Tadashi KataokaAbstract:The title compounds (6-9) were prepared and evaluated for serotonin 5-HT4 agonistic activity in in vitro tests. Introducing a propyl or Allyl Group at the 3-position of benzamide caused only a slight enhancement of agonistic activity. Construction of the benzo[b]furan skeleton and 2,3-dihydrobenzo[b]furan skeleton caused a significant enhancement of the activity. 4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro- 2-methylbenzo[b]furan-7-carboxamide (7b) hemifumarate was as potent as cisapride. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro- 2,3-dihydro-2-methylbenzo[b]furan-7-carboxamide (8a) hemifumarate, 4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro- 2,3-dihydro-2-ethylbenzo[b]furan-7-carboxamide (8c) hemifumarate, and 4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro- 2,3-dimethylbenzo[b]furan-7-carboxamide (8d) hemifumarate were more potent than cisapride. Furthermore, 8a hemifumarate was free from dopamine D1, D2, serotonin 5-HT1, 5-HT2 and muscarine M1, M2 receptor binding activity in the in in vitro tests. On the other hand, construction of the indole skeleton caused a remarkable decrease in activity.
M G Myskiv - One of the best experts on this subject based on the ideXlab platform.
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a novel copper i sulfamate π complex based on the 5 Allylthio 1 3 5 dimethylphenyl 1h tetrazole ligand alternating current electrochemical crystallization dft calculations structural and nlo properties studies
Polyhedron, 2018Co-Authors: Yu I Slyvka, A A Fedorchuk, N T Pokhodylo, Tadeusz Lis, I V Kityk, M G MyskivAbstract:Abstract Using the alternating-current electrochemical technique, the novel π-complex [Cu I ( m-dmphast )NH 2 SO 3 ] ( 1 ), based on the 5-(Allylthio)-1-(3,5-dimethylphenyl)-1 H -tetrazole ( m-dmphast ) ligand, was obtained and it was studied by single crystal X-ray diffraction as well as IR and UV–Vis spectroscopy. The structure 1 should be considered as the first known example of a metal sulfamate coordination compound with a tetrazole ligand. The copper(I) ion in 1 possesses a trigonal pyramidal environment, arranged from the N4 atom of the tetrazole core, the C C bond from the S-Allyl Group of the same m-dmphast ligand and O and N atoms of the NH 2 SO 3 − anions. The sulfamate anion is coordinated to the two neighboring Cu(I) ions in a bridged mode, occupying a basal plane (through the N atom) and an apical (through an O atom) position of the two neighboring metal trigonal pyramids. The bicolor coherent photoinduced treatment by a nanosecond Nd:YAG laser at a wavelength of 1064 nm caused the occurrence of charge density acentricity, which in turn favours an occurrence of second harmonic generation described by third rank polar tensors, that are usually forbidden for centrosymmerical crystals.
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copper i hexafluorosilicate π complex with n Allylmorpholinium cation a rare case of c c 3o copper i coordination in the structure of cu c4h8onh c3h5 h2o 2 sif6 h2o
Journal of Chemical Crystallography, 2010Co-Authors: Evgeny Goreshnik, M G MyskivAbstract:AbstractThe [Cu(C 4 H 8 ONH(C 3 H 5 ))(H 2 O) 2 ]SiF 6 ·H 2 O compound (I) was obtained by alternating current electrochemical synthesis, starting from a solution containing CuSiF 6 ·4H 2 O and N-Allylmorpholinium hexafluorosilicate. Compound I crystallizes in a trigonal P 3 1 space Group, a = 8.6449(4), c = 16.5629(11) Å, V = 1071.98(10) Å 3 , Z = 3 for Cu(C 7 H 14 NO)SiF 6 ·3H 2 O composition, R = 0.0569 for 2987 reflections and 182 refined parameters. The C=C bond of one N-Allylmorpholinium cation, elongated to 1.38(1) Å, the O-atom from another ligand moiety, and two oxygen atoms from two water molecules form the trigonal-pyramidal environment of the metal atom. The bridging function of the ligand moiety results in infinite metal-organic chains. One more water molecule is fixed in the crystal space by hydrogen bonds only.Graphical AbstractIn the structure of the title compound, the Cu I atom possesses rather unusual surrounding comprising the C=C-bond of the Allyl Group of one ligand moiety, two oxygen atoms from two water molecules, and one more oxygen atom from the morpholine ring of another ligand moiety. [IMAGE]
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1 Allylpyridinium cu2cl3 synthesis x ray structure and the regularity of crystal architecture of 1 Allyl amino pyridinium copper i chloride π complexes
Zeitschrift für anorganische und allgemeine Chemie, 2005Co-Authors: Oleksii Pavlyuk, Evgeny Goreshnik, Z Ciunik, M G MyskivAbstract:By alternating-current electrochemical technique crystals of copper(I) π-complex with 1-Allylpyridinium chloride of [C5H5N(C3H5)][Cu2Cl3] (1) composition have been obtained and structurally investigated. Compound 1 crystallizes in monoclinic system, space Group C2/c a = 24.035(1) A, b = 11.4870(9) A, c = 7.8170(5) A, β = 95.010(5)°, V = 2150.0(2) A3 (at 100 K), Z = 8, R = 0.028, for 4836 independent reflections. In the structure 1 trigonal-pyramidal environment of π-coordinated copper(I) atom is formed by a lengthened to 1.376(2) A C=C bond of Allyl Group and by three chlorine atoms. Other two copper atoms are tetrahedrally surrounded by chlorine atoms only. The coordination polyhedra are combined into an original infinite (Cu4Cl62—)n fragment. Structural comparison of 1 and the recently studied copper(I) chloride π-complexes with 3-amino-, 2-amino-, 4-amino-1-Allylpyridinium chlorides of respective [LCu2Cl3] (2), [L2Cu2Cl4] (3), and [LCuCl2] (4) compositions allowed us to reveal the trend of the inorganic fragment complication which depends on pKa (base) value of the corresponding initial heterocycle.