- Synthesis of oligodiacetylene derivatives from flexible porous coordination frameworks
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Oligodiacetylenes (ODAs) with alternating ene-yne conjugated structure are significant materials for optical and electronic properties. Due to the low solubility of ODAs in common solvents, the synthetic approaches are limited. Here we disclose a new synthetic approach of ODAs without a side alkyl chain using a porous coordination polymer (PCP) as a sacrificial template. 1,2-Bis(4-pyridyl)butadiyne, which works as a monomer, was embedded in the flexible framework of the PCP, and ODAs were synthesized via utilization of the anisotropic thermal expansion of the PCP crystal. The oligomeric state of ODAs depends on the metal ion and coligand of the precursor.
- Fujiwara, Yu-Ichi,Kadota, Kentaro,Nagarkar, Sanjog S.,Tobori, Norio,Kitagawa, Susumu,Horike, Satoshi
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- Modulation on C- and N-terminal moieties of a series of potent and selective linear tachykinin NK2 receptor antagonists
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Herein we describe the synthesis of a series of new potent tachykinin NK2 receptor antagonists by the modulation of the Cand N-terminal moieties of ibodutant (MEN 15596, 1). The Nterminal benzo[b]thiophene ring was replaced by different substituted naphthalenes and benzofurans, while further modifications were evaluated at the C-terminal tetrahydropyran moiety. Most compounds demonstrated a high affinity for the human NK2 receptor and high in vitro antagonist potency, indicating that a wide range of substituents at both termini can be incorporated in the molecule without detrimental effects on the interactions with the NK2 receptor. Selected compounds were tested in vivo confirming their activity as NK2 antagonists. In particular, after both iv and id administration to guinea pig, compound 61b was able to antagonize NK2-induced colonic contractions with a potency and duration-of-action fully comparable to the reference compound 1 (MEN 15596, ibodutant).
- Gensini, Martina,Altamura, Maria,Dimoulas, Tula,Fedi, Valentina,Giannotti, Danilo,Giuliani, Sandro,Guidi, Antonio,Harmat, Nicholas J. S.,Meini, Stefania,Nannicini, Rossano,Pasqui, Franco,Tramontana, Manuela,Triolo, Antonio,Maggi, Carlo Alberto
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scheme or table
p. 65 - 78
(2010/11/16)
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- Folding of dihelicenetriamines in water
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Diastereomeric triamines containing two helicene moieties, 1,12-dimethylbenzo[c]phenanthrene, were synthesized and found to form folded structures in the water. Such folding was not observed for an achiral compound possessing a naphthalene moiety. The (M,M)-dihelicenetriamine with matching configuration at the helicene moieties formed a more stable folded structure than the (P,M)-isomer containing two enantiomeric helicene groups. The most stable folded conformation was predicted by the Monte Carlo method with Amber force field of the dihelicenetriamine.
- Honzawa, Shinobu,Okubo, Hitoshi,Nakamura, Keiichi,Anzai, Shuzo,Yamaguchi, Masahiko,Kabuto, Chizuko
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p. 1043 - 1052
(2007/10/03)
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- Molecular Recognition of Naphthalenedicarboxylic Acid Regioisomers by Cyclodextrins
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Complexation of cyclodextrins (CD's) with some regioisomers of naphthalenedicarboxylic acid (NDC) was examined in 0.1 mol dm-3 NaHCO3 at 25°C by means of 1H NMR spectroscopy, together with the measurement of induced circular dichroism spectra of NDC's with the addition of CD's. The 1H NMR spectra of 2,6- and 2,7-NDC's showed characteristic AB-type patterns, which changed continuously with increasing CD concentration in accord with the Pople theory. The binding constants (Ka) for β-CD complexes with NDC's increased in the order of: 1,4-NDC ≈ 1,5-NDC a values.
- Tan, Wei Hua,Niino, Noriaki,Ishikura, Takahiro,Maruta, Aya,Yamamoto, Tatsuyuki,Matsui, Yoshihisa
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p. 1285 - 1292
(2007/10/03)
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- An efficient synthesis of functionalized helicenes
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[5]- and [6]helicenebisquinones can be prepared easily and in quantity by combining enol ethers of 1,4 diacetylbenzene or 2,7-diacetylnaphthalene with p-benzoquinone. Similar diethenyl aromatics that either have no ether functions or have them attached to the double bonds, but to the aromatic rings, give the corresponding helicenes in only low yields and low purities. [6]Helicenebisquinone 11c is resolved into its enantiomers. An X-ray diffraction analysis of the adduct of one of these enantiomers and L-prolinol shows the absolute stereochemistry of 11c and the regiochemistry with which the amine adds to the quinone.
- Katz, Thomas J.,Liu, Longbin,Willmore, Nikolaos D.,Fox, Joseph M.,Rheingold, Arnold L.,Shi, Shuhao,Nuckolls, Colin,Rickman, Barry H.
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p. 10054 - 10063
(2007/10/03)
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- The Zinc(II)-Catalyzed Henkel Reaction of Dipotassium 1,8-Naphthalenedicarboxylate in a Dispersion Medium
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The Henkel reaction of dipotassium 1,8-naphthalenedicarboxylate in naphthalene as a dispersion medium gave dipotassium 2,6-naphthalenedicarboxylate (1) in a higher yield and with a better reproducibility than the reaction without a dispersion medium.Catalysts, particularly zinc catalysts, were examined in detail.The anion moiety of zinc catalysts affected the reaction, and the halide anion was effective for the selective formation of 1.The addition of potassium halide to the zinc catalysts also increased the yield of 1.The catalytic activity of the halide anion increased in the order: Cl---.The activity of the zinc catalysts was also compared with that of cadmium catalysts.
- Fujishiro, Koichi,Mitamura, Shuichi
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p. 786 - 790
(2007/10/02)
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