- Synthesis of poly(1-chloro-2-arylacetylene)s with high cis-content and examination of their absorption/emission properties
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A series of 1-chloro-2-arylacetylenes [Cl-C?C-Ar, Ar = C6H5 (1), C6H4-p-iPr (2), C6H4-p-OiPr (3), C6H4-p-NHC(O)OtBu (4), and C6H4-o-iPr (5)] were polymerized using (tBu3P)PdMeCl/silver trifluoromethanesulfonate (AgOTf) and MoCl5/SnBu4 catalysts. The corresponding polymers [poly(1)–poly(5)] with weight-average molecular weights of 6,500–690,000 were obtained in 10–91% yields. THF-insoluble parts, presumably high-molecular weight polymers, were formed together with THF-soluble polymers by the Pd-catalyzed polymerization. The Pd catalyst polymerized nonpolar monomers 1 and 2 to give the polymers in yields lower than the Mo catalyst, while the Pd catalyst polymerized polar monomers 3 and 4 to give the corresponding polymers in higher yields. The 1H NMR and UV–vis absorption spectra of the polymers indicated that the cis-contents of the Pd-based polymers were higher than those of the Mo-based polymers, and the conjugation length of the Pd-based polymers was shorter than that of the Mo-based polymers. Pd-based poly(5) emitted fluorescence most strongly among poly(1)–poly(5).
- Rodriguez Castanon, Jesus,Sano, Natsuhiro,Shiotsuki, Masashi,Sanda, Fumio
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- Catalytic cascade hydroalkoxylation/isomerization/[4 + 2] cycloaddition using enyne alcohols as latent dienes or dienophiles
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Enyne alcohols can react as precursors of either dienes or dienophiles with different substrates after hydroxylation and isomerization by gold catalysis. As such, oxa-bridged tricyclo[5.2.2.02,6]undec-8-ene-3,5-dione derivatives have been obtained by the Diels-Alder reaction and tetrahydro-1H-furo[3,4-c]pyran derivatives could be accessed by the hetero-Diels-Alder cycloaddition.
- Guo, Rui,Li, Kang-Nan,Gong, Liu-Zhu
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supporting information
p. 6707 - 6712
(2013/10/01)
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- 4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors
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A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT-702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-ylpyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed.
- Matulenko, Mark A.,Paight, Ernest S.,Frey, Robin R.,Gomtsyan, Arthur,DiDomenico Jr., Stanley,Jiang, Meiqun,Lee, Chih-Hung,Stewart, Andrew O.,Yu, Haixia,Kohlhaas, Kathy L.,Alexander, Karen M.,McGaraughty, Steve,Mikusa, Joseph,Marsh, Kennan C.,Muchmore, Steven W.,Jakob, Clarissa L.,Kowaluk, Elizabeth A.,Jarvis, Michael F.,Bhagwat, Shripad S.
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p. 1586 - 1605
(2008/02/01)
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- 5,6,7-Trisubstituted 4-Aminopyrido[2,3-d]pyrimidines as Novel Inhibitors of Adenosine Kinase
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The synthesis and structure-activity relationship of a series of 5,6,7-trisubstituted 4-aminopyrido[2,3-d]pyrimidines as novel nonnucleoside adenosine kinase inhibitors is described. A variety of alkyl, aryl, and heteroaryl substituents were found to be tolerated at the C5, C6, and C7 positions of the pyridopyrimidine core. These studies have led to the identification of analogues that are potent inhibitors of adenosine kinase with in vivo analgesic activity.
- Perner, Richard J.,Gu, Yu-Gui,Lee, Chih-Hung,Bayburt, Erol K.,McKie, Jeffery,Alexander, Karen M.,Kohlhaas, Kathy L.,Wismer, Carol T.,Mikusa, Joe,Jarvis, Michael F.,Kowaluk, Elizabeth A.,Bhagwat, Shripad S.
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p. 5249 - 5257
(2007/10/03)
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- 5,6,7-trisubstituted-4-aminopyrido[2,3-D] pyrimidine compounds
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A compound having the formula wherein R1, R2, R3, R4 and R5 are defined, a method for inhibiting adenosine kinase by administering a compound thereof, a pharmaceutical composition comprising a therapeutically effective amount of a compound thereof above i
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