- Synthesis, characterization, and antipeptic activity of a novel surfactant having an azulene moiety
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A novel surfactant having an azulene moiety, sodium 3-decyl-1- azulenesulfonate (CIOAS), has been synthesized. The surface-activity of C10AS is lower than that of its structural isomer, sodium 4-decyl-1-naphthalenesulfonate (C10NS), probably caused by the higher hydrophilicity of C10AS due to the dipole moment of azulene moiety. C10AS exhibits the higher antipeptic activity than the propyl derivative (C3AS) below its critical micelle concentration. Copyright
- Fujio, Katsuhiko,Kobayashi, Hideharu,Ozeki, Sumio,Fujimori, Kunihide
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- Formation and Structure of 2-Diazo-2,4-azulenequinone Derivatives
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The diazotization of methyl (and ethyl) 2-amino-3-cyano-4-methoxy(and ethoxy)azulene-1-carboxylate (1-4) was examined to determine whether the products are 2-diazo-2,4-azulenequinone derivatives (B) or azulene-2-diazonium-1-carboxylate derivatives (C).Since diazotization of 1 and 2 gave the same diazo compound 5 and diazotization of both 3 and 4 gave diazo compound 6, the diazo compounds are deduced to not be azulene-2-diazonium-1-carboxylate derivatives (7 and 8), but rather to be 2-diazo-2,4-azulenequinone (5 and 6).The diazo carbons of both 5 and 6 show 13C NMR signals at δ 66.3, and their carbonyl carbons resonate at δ 181.1, in good agreement with a 2-diazo-2,4-azulenequinone structure.The structures of diazo compounds 24 and 25, which we have previously reported, are reexamined on the basis of the analysis of their 13C NMR spectra.The contribution of a quinoid structure and a diazoazulenoeate structure to 5, 6, 24, and 25 is discussed by comparison of their 13C NMR spectral data with those of 4-diazo-2,5-cyclohexadien-1-one derivatives.It is concluded that the contribution of the quinoid structure is larger than that of the diazoazulenolate structure.
- Nozoe, Tetsuo,Asao, Toyonobu,Yasunami, Masafumi,Wakui, Hisamitu,Suzuki, Toshio,Ando, Masayoshi
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- Structural Biology-Guided Design, Synthesis, and Biological Evaluation of Novel Insect Nicotinic Acetylcholine Receptor Orthosteric Modulators
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The development of novel and safe insecticides remains an important need for a growing world population to protect crops and animal and human health. New chemotypes modulating the insect nicotinic acetylcholine receptors have been recently brought to the agricultural market, yet with limited understanding of their molecular interactions at their target receptor. Herein, we disclose the first crystal structures of these insecticides, namely, sulfoxaflor, flupyradifurone, triflumezopyrim, flupyrimin, and the experimental compound, dicloromezotiaz, in a double-mutated acetylcholine-binding protein which mimics the insect-ion-channel orthosteric site. Enabled by these findings, we discovered novel pharmacophores with a related mode of action, and we describe herein their design, synthesis, and biological evaluation.
- Montgomery, Mark,Rendine, Stefano,Zimmer, Christoph T.,Elias, Jan,Schaetzer, Jürgen,Pitterna, Thomas,Benfatti, Fides,Skaljac, Marisa,Bigot, Aurélien
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p. 2297 - 2312
(2022/01/20)
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- A practical approach for the preparation of monofunctional azulenyl squaraine dye
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The synthesis of monofunctional azulenyl squaraine dye NIRQ700 is described. The essential azulene intermediate 3, 1-(methoxycarbonyl)-2-methylazulene, was achieved via [8+2] cycloaddition between lactone 2, 2H-3-methoxycarbonyl-cyclohepta[b]furan-2-one, and the in situ generated vinyl ethers under high temperature and pressure conditions. Methylation on the cycloheptatriene ring of 2-methyl azulene 6 via Meisenheimer-type intermediate following Schrott's method formed the carboxylic acid intermediate 9, 3-(2-methyl-azulen-4-yl)-propionic acid. Condensation of 9 with squaric acid provided the title compound NIRQ700 at moderate yields. The non-fluorescent squaraine dye NIRQ700 absorbed in a 600-700 nm range and potentially can be used to quench a number of available NIR fluorochromes in order to extend the spectrum of biological quenching assays.
- Pham, Wellington,Weissleder, Ralph,Tung, Ching-Hsuan
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p. 3975 - 3978
(2007/10/03)
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- Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity.
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The relationship between free radicals and acute or chronic inflammation has been well established. We have previously reported the significant antioxidant activity of the natural azulene derivatives chamazulene and guaiazulene. Furthermore, some syntheti
- Rekka, Eleni,Chrysselis, Michael,Siskou, Ioanna,Kourounakis, Angeliki
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p. 904 - 907
(2007/10/03)
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- Catalyst component for use in the polymerization of α-olefins and process for producing α-olefin polymers using the same
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A catalyst component for use in the polymerization of α-olefins, comprising a compound represented by the following general formula I!: STR1 wherein R1 s represent a hydrogen atom, a C1-6 hydrocarbon group or a C1-12 hydrocarbon group containing silicon; each of R2 and R3 which forms the condensed ring represents a divalent C3-20 saturated or unsaturated hydrocarbon group, provided that at least one of R2 and R3 forms a ring condensed with the cyclopentadiene which is a seven- to twelve-membered ring having an unsaturated bond inherent in R2 or R3 ; Q represents a C1-20 divalent hydrocarbon group, a silylene group, a silylene group with a C1-20 hydrocarbon group, a germylene group, or a germylene group with a C1-20 hydrocarbon group; X and Y represent H, a halogen, a C1-20 hydrocarbon group, or a C1-20 hydrocarbon group containing oxygen, nitrogen or phosphorus; and M represents a Group IVB to VIB transition metal of the Periodic Table. Production of α-olefin polymers having a high melting point and a high molecular weight in a high yield and a process for producing α-olefin polymers is made possible upon the use of the catalyst.
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- Synthesis and analysis of positive inotropic effects of 3-substituted-2H-cyclohepta[b]furan-2-one derivatives
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Several 3-substituted-2H-cyclohepta[h]furan-2-one derivatives were prepared and tested in vitro for positive inotropic character. Introduction of an isopropyl group at the 5-position of compound 8a caused an increase of PIC50 (negative logarithm of the dosage which increases the contractile force by 50%) from 4.48 to 5.10. Among the 5-isopropyl-8-alkoxy compounds, the isopropoxy compound 12f had the most potent activity with a PIC50 value of 5.99. Conversion of the ester group at the 3-position to a methylene group and of the alkoxy group at the 8-position to a substituted amino group caused a decrease in activity. The most active compound, 12f, was also found to bave a weaker heart rate (HR)-increasing effect compared to milrinone and amrinone.
- Yokota,Yanagisawa,Kosakai,Wakabayashi,Tomiyama,Yasunami
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p. 865 - 871
(2007/10/02)
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