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Volume 46, Issue 11
Displaying 1-37 of 37 articles from this issue
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Yasushi KANZAKI, Yuko SHIMOYAMA, Maki TSUKAMOTO, Motoko OKANO, Noriko ...1998 Volume 46 Issue 11 Pages 1663-1666
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe intercalation of layered inorganic materials, synthetic mica (TSM), with drugs and their drug release characteristics were investigated using intermediate intercalation compounds with phosphatidylcholine (H-PC). Oil-soluble indomethacin and water-soluble imipramine chloride were selected as model drugs. The drug intercalation compounds were prepared by two methods. The first one was the "solvent method" in which the intermediate intercalation compound of TSM with H-PC was prepared in advance using a chloroform solution of H-PC. The intermediate was then mixed with a drug and heated at 180°C to prepare the ternary TSM/H-PC/drug compound. The second one was the "heating method" in which the mixture of (TSM+H-PC+drug) was heated at 180°C to prepare TSM/H-PC/drug directly. The release rate was controlled using a disintegrator (L-HPC). In the case of a tablet sample, the release rate indomethacin was controllable from 60 min (10% L-HPC) to longer than 420 min (3% L-HPC) in the case of the solvent method. A similar result was obtained in the case of imipramine chloride.View full abstractDownload PDF (628K) -
Kuniharu UTSUNO, Katsuko KOJIMA, Yoshimi MAEDA, Masamichi TSUBOI1998 Volume 46 Issue 11 Pages 1667-1671
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of chromomycin A3 binding on the geomtery of DNA deplex (plasmid pBR322) has been examined using topoisomerase I relaxation followed by gel electrophoresis. To determine the equilibrium constant of this drug-DNA binding-dissociation reaction in the same concentration range (ca. 10-5M) in the same buffer as those for the topoisomerase reaction (at 37°C), fluorescence measurements were made of the same plasmid-drug system, followed by a Scatchard plot and an analysis using McGhee-von Hippel's exclusion site model. The binding constant has been fouond to be 3.8×105M-1 in the particular buffer (buffer-T) at 37°C, and the number of base pairs involved in the site of one chromomycin molecule on the duplex has been found to be 5. It has been concluded that one chromomycin molecule, bound to the duplex, unwinds it by 11.8±1.1 degress. In addition, the enthalpy of binding was determined to be 31.81 kJ/mole using a titration calorimeter with a more concentrated (6.2 mM) solution.View full abstractDownload PDF (765K) -
Elzbieta MASIUKIEWICZ, Barbara RZESZOTARSKA1998 Volume 46 Issue 11 Pages 1672-1675
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple, large-scale synthesis of a cytokine, methionine-enkephalin, Tyr-Gly-Gly-Phe-Met, has been elaborated. Classical solution peptide chemistry methods without protection of amino acid side-chain functions and 1+(2+2) segment condensation were used. A nine-step synthesis from commercial amino acid derivatives was developed with yields ranging from 86% to 99%, averaging 92%. The purity of all intermediates was found to be 99.0-100% by HPLC. The process has been used to prepare greater than 150 g quantities of the pentapeptide as a monohydrate of 100% purity. Hydantoin formation was observed during saponification of Boc-Tyr-Gly-Gly-Phe-Met-OMe and minimised.View full abstractDownload PDF (725K) -
Keisuke MIYAJIMA, Takahiro NEKADO, Kiyoshi IKEDA, Kazuo ACHIWA1998 Volume 46 Issue 11 Pages 1676-1682
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConjugates (3-5) of Tn, sialyl Tn and HIV-1-derived peptide antigen with a N-tetradecanoyl L-serine-β-alanine-containing D-glucosamine derivative, structurally related to lipid A, as an immunoadjuvant for the development of totally synthetic vaccines against cancers or HIV were synthesized. The mitogenic activity of compounds 3, 4 and 5 was stronger than that of lipid A analogs (1, 2).View full abstractDownload PDF (1208K) -
Kozo SAWADA, Hideo HIRAI, Patrick GOLDEN, Satoshi OKADA, Yuki SAWADA, ...1998 Volume 46 Issue 11 Pages 1683-1687
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel series of indole-3-alkanoic acids with varied N-benzyl substituents were synthesized as nonsteroidal inhibitors of steroid 5α-reductase. The structure-activity relationship in this series were studied and the optimum carboxylic acid side chain was butyric acid. Furthermore, compounds with a diaryl substituent at the 1-position of the indole ring displayed strong inhibitory activities in vitro. Amongst these derivatives, 4-[1-(6, 6-dimethyl-6H-dibenzo[b, d]pyran-3-yl)methylindol-3-yl]butyric acid (FR119680) displayed very high inhibitory activity in vitro against rat prostatic 5α-reductase (IC50=5.0 nM) and good in vivo activity in the castrated young rat model.View full abstractDownload PDF (965K) -
Shuji JINNO, Takaaki OKITA1998 Volume 46 Issue 11 Pages 1688-1694
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTotal synthesis of a novel long chain alkyl phenol, phaffiaol (1), a potent antioxidant isolated from Phaffia rhodozyma, was achieved via three reaction steps starting from 3, 5-dibromosalicylaldehyde (2). We also prepared several types of long chain alkyl phenol having different aromatic rings or different carbon length, and evaluated their antioxidative activity using the rabbit erythrocyte membrane ghost system. Amongst these compounds, the novel methoxy phenol derivatives (6c, d, 7) having a heptadecyl moiety at the ortho-position to the hydroxy group, were approximately 2 times more active than α-tocopherol. In addition, 4-methoxy-2-pentadexylphenol (10h), which has a 15-carbon length in the side chain moiety, showed the maximum activity.View full abstractDownload PDF (976K) -
Hiroshi NAGASE, Koji KAWAI, Jun HAYAKAWA, Hisanori WAKITA, Akira MIZUS ...1998 Volume 46 Issue 11 Pages 1695-1702
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe designed highly selective non-peptide agonists for the δ-opioid receptor. On the basis of the "message-address" concept in this field and the accessory site hypothesis, a novel class of hetericycle-fused octahydroisoquinoline derivatives were synthesized. One of these compounds (4aS*, 12aR*)-4a-(3-hydroxyphenyl)-2-methyl-1, 2, 3, 4, 4a, 5, 12, 12a-octahydropyrido[3, 4-b]acridine, TAN-67 (2)] showed high selectivity for the δ-opioid receptor (Ki=1.12 nM) in guinea-pig cerebrum with a 2070-fold lower affinity for the μ-opioid receptor and a 1600-fold lower affinity for the К-opioid receptor. TAN-67 was a potent δ-opioid receptor agonist with an IC50 value of 6.61 nM in the mouse vas deferens assay that was reversed by naltrindole (NTI) (Ke=0.21). Moreover, TAN-67 was shown to have antinociceptive activity following subcutaneous administration in the mouse acetic acid abdominal constriction assay that was antagonized by NTI (δ1-and δ2-antagonist) and 7-benzylidinenaltrexone (δ1-antagonist), but not by naltriben (δ2-antagonist). This systemically applicable non-peptide agonist will be useful for elucidating the pharmacological properties of the δ-opioid receptor.View full abstractDownload PDF (1309K) -
Makoto TAKEUCHI, Shunichi SAKAMOTO, Kousei KAWAMUKI, Hiroyuki KURIHARA ...1998 Volume 46 Issue 11 Pages 1703-1709
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new series of fused aza-heteroarylbisphosphonates (5, 8), which are structurally quite different from incadronate (YM175), and related compounds were synthesized and evaluated for antiresorptive activity using a parathyroid hormone (PTH)-induced hypercalcemia model in rats (PIH model). Among these compounds, several exhibited more potent antiresorptive activity than pamidronate. In particular, [1-hydroxy-2-(imidazo[1, 2-α]pyridin-3-yl)ethylidene]bisphosphonic acid (5b, minodronate) was 100-fold more potent than pamidronate in not only the PIH model, but also in an immobilization bone atrophy model in rats (DA model), and was selected for clinical development. The structure-activity relationships in these new series of bisphosphonates are discussed.View full abstractDownload PDF (1047K) -
Katsuhiro KAWAKAMI, Shohgo ATARASHI, Youichi KIMURA, Makoto TAKEUMURA, ...1998 Volume 46 Issue 11 Pages 1710-1715
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of novel LVFX (7) analogues bearing 4, 4-dialkyl-3-aminopyrrolidines at the C-10 position of pyridobenzoxazine was synthesized and their antibacterial activities, pharmacokinetics and acute toxicities in animals were evaluated. Non-alkylated pyrrolidine derivative 26a showed greater activity than LVFX (7) against gram-positive and gram-negative bacteria including Pseudomonas aeruginosa, but 26a possessed high acute toxicity in mice and unfavorable pharmacokinetics in rats. When compared with 26a, 4, 4-dialkylated derivatives 26c, e, g showed more potent activity against gram-positive bacteria along with an improvement of pharmacokinetics and reduction of acute toxicity. Increases in lipophilicity by alkylation on the pyrrolidine ring resulted in a good influence on the above profiles.View full abstractDownload PDF (942K) -
Takeshi YAMAMOTO, Manabu HORI, Ikuo WATANABE, Hisayoshi TSUTSUI, Kengo ...1998 Volume 46 Issue 11 Pages 1716-1723
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-(3-Oxo-3, 4-dihydro-2H-benzo[1, 4]oxazine-6-carbonyl)guanidines 4 were prepared and tested for Na/H exchange inhibitory activities in order to clarify the structure-activity relationship (SAR). Quantitative SAR (QSAR) analysis of 6-carbonylguanidines 4 indicated that the length of the 4-substituent was parabolically related to activity and that the calculated optimum 4-substituents were propyl, ethyl and isopropyl groups. This SAR was similar to the SAR of the 2- and 4-substituents of 7-carbonylguanidine derivatives 3, although the position relative to the essential guanidinocarbonyl group was different. Larger 2-substituents, such as a phenyl group were unfovorable. The most potent derivative in this series was N-(4-isopropyl-2, 2-dimethyl-3-oxo-3, 4-dihydro-2H-benzo[1, 4]oxazine-6-carbonyl)guanidine 4g, with an IC50 value of 0.12 μM. The methanesulfonate salt (KB-R9032) of 4g had excellent water-solubility and showed anti-arrhythmia activity against a rat acute myocardial infarction model. KB-R9032 was selected for further investigation as a therapy for ischemia-reperfusion induced injury.View full abstractDownload PDF (967K) -
Nobuo CHO, Yoshi NARA, Mioko HARADA, Tsukasa SUGO, Yasushi MASUDA, Ake ...1998 Volume 46 Issue 11 Pages 1724-1737
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn the basis of structural information for the cyclic hexapeptide endothelin (ET) receptor antagonist, TAK-044, a series of thieno[2, 3-d]pyrimidine-2, 4-dione derivatives bearing a carboxyl group and aromatic rings that were important for receptor binding were designed, synthesized, and evaluated for ET receptor binding affinities and inhibitory activities against ET-induce vasconstriction.Optimization of each substituent in the thieno[2, 3-d]pyrimidine ring led to the discovery of a novel and potent nonpeptide ET receptor antagonist, 6-(4-methoxymethoxyphenyl)-5-methylsulafonylminomethyl-1-(2-methylthiobenzyl)-2, 4-dioxo-1, 2, 3, 4-tetrahydrothieno[2, 3-d]pyrimidine-3-acetic acid (32 g), which binded to human ETA and ETB receptor subtypes with affinities (IC50) of 7.6 and 100 nM, respectively.Compound 32 g effectively antagonized ET-induced vasconstriction and the inhibitory effect mediated by the ETB receptor was more potent than that of bosentan, while the inhibitory effect mediated by the ETA receptor was slightly less potent than that of bosentan.View full abstractDownload PDF (2042K) -
Toru ISHIKAWA, Junichi KITAJIMA, Yasuko TANAKA, Masateru ONO, Yasuyuki ...1998 Volume 46 Issue 11 Pages 1738-1742
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour stereoisomers of 2-hydroxy-1, 8-cineole β-D-glucopyranoside were isolated together with five new 1, 8-cineole glycosides and five new dihydroxy-1, 8-cineoles from the water-soluble portion of fennel. Their structures were clarified by spectral methods.View full abstractDownload PDF (738K) -
Junichi KITAJIMA, Nobuyuki SUZUKI, Yasuko TANAKA1998 Volume 46 Issue 11 Pages 1743-1747
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the water-soluble portion of the methanolic extract of Torillis japonica D. C. fruit (Umbelliferae), nine new guaiane-type sesquiterpenoid glycosides, including three kessane derivatives, have been isolated. Their structures were clarified by spectral and chemical investigations.View full abstractDownload PDF (775K) -
Toru ISHIKAWA, Yasuko TANAKA, Junichi KITAJIMA1998 Volume 46 Issue 11 Pages 1748-1751
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the water-soluble portion of the methanol extract of the herbal medicine fennel, six new acyclic monoterpenoid glycosides, three of which contained an oxide linkage, were obtained. Their structures were clarified by spectral investigations.View full abstractDownload PDF (599K) -
Tsutomu WARASHINA, Tadataka NORO1998 Volume 46 Issue 11 Pages 1752-1757
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFifteen new steroidal glycosides were obtained from the roots of Metaplexis japonica M. (Asclepiadaceae). These glycosides were confirmed to have ramanone, 12-O-acetylramamone, pergularin, 12-O-acetylpergularin and deacylmetaplexigenin as the aglycone and 2, 6-dideoxyhexopyranoses as the sugar sequence by spectroscopic methods and chemical evidence.View full abstractDownload PDF (916K) -
Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Masashi KADOYA, Johji YAMAHARA ...1998 Volume 46 Issue 11 Pages 1758-1763
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFollowing the elucidation of betavulgarosides I, II, III, and IV, betavulgarosides VI, VII, VIII were isolated from the roots of sugar beet (Beta vulgaris L.), while betavulgarosides V, IX, and X were isolated from the leaves of this plant. The structures of betavulgarosides V-X were determined on the basis of chemical and physicochemical evidence.View full abstractDownload PDF (866K) -
Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Johji YAMAHARA, Hisashi MATSUD ...1998 Volume 46 Issue 11 Pages 1764-1769
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew acylated polyhydroxyoleanene triterpene oligoglycosides, escins IIIb, IV, V, and VI and isoescins Ia, Ib, and V, were isolated from the seeds of horse chestnut tree (Aesculus hippocastanum L.). Their structures were elucidated on the basis of chemical and physicochemical evidence.View full abstractDownload PDF (823K) -
Yoshiyasu FUKUYAMA, Yuuko KIRIYAMA, Mitsuaki KODAMA1998 Volume 46 Issue 11 Pages 1770-1775
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe convergent synthesis of ardisiaquinones D (1), E (3) and F (4), isolated as 5-lipoxygenase inhibitors from Ardisia sieboldii, has been achieved efficiently by a cross-coupling reaction via an acetylene between two benzene units bearing appropriate functional groups readily derived from 2, 5-dimethoxy-1, 4-benzoquinone.View full abstractDownload PDF (1016K) -
Yukio TAKENAKA, Takao TAKAHASHI, Naotaka NAGAKURA1998 Volume 46 Issue 11 Pages 1776-1780
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInvestigation of the crude drug "Ye su xin", the dried flowers of Jasminum polyanthum, has led to the isolation of eight secoiridoid glucosides esterified with a linear monoterpene unit, jaspofoliamosides C-G, jaspogeranosides A and B, and jaspolinaloside B. The structures of these compounds were elucidated on the basis of chemical and spectroscopic evidence.View full abstractDownload PDF (732K) -
Keisuke KOJIMA, Kimio ISAKA, Ondognii PUREV, Gonbovanjilin JARGALSAIKH ...1998 Volume 46 Issue 11 Pages 1781-1784
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new sesquiterpenoid derivatives, 1-(2, 4-dihydroxyphenyl)-2-hydroxy-5, 9, 13-trimethyl-4(E), 8(E), 12-tetradecartien-1-one, 1-(2, 4-dihydroxyphenyl)-3, 7, 11-trimethyl-3-vinyl-6-(E), 10-dodecadiene-1-one, 1-(2, 4-dihydroxyphenyl)-3, 7, 11-trimethyl-3-vinyl-6(E), 10-dodecadiene-1, 9-dione and 1-(2, 4-dihydroxyphenyl)-3, 7-dimethyl-3-vinyl-8-(4-methyl-2-furyl)-6(E)-octen-1-one, were isolated from roots of Ferula ferulioides. The structures of these new compounds were establiished by comprehensive spectral analysis. The biosynthetic pathway leading to these compounds is proposed based on their structures.View full abstractDownload PDF (481K) -
Yasuyuki ASAI, Sumio WATANABE1998 Volume 46 Issue 11 Pages 1785-1789
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStable aqueous dispersions of α-tocopherol acetate (α-TA) were obtained by cosonication with dipalmitoylphosphatidylcholine (DPPC) in the α-TA mole fraction range of 0.1-0.8. In order to clarify the dispersal mechanism, the dispersed particles were characterized and the interaction between α-TA and DPPC was investigated using several physicochemical techniques. Dynamic light scattering measurements showed that the diameter of the dispersed particles was 50-75 nm. The trapped aqueous volume inside the particles was determined fluorometrically using the aqueous space marker calcein. The trapped volume in the α-TA/DPPC particles decreased remarkably with the addition of α-TA into small unilamellar vesicles of DPPC. The decline in the fraction of vesicular particles was also confirmed by fluorescence quenching of N-dansylhexadecylamine in the DPPC membrane by the addition of the quencher CuSO4. These results indicate that the excess α-TA separated from the DPPC bilayers is stabilized as emulsion particles by the DPPC surface monolayer. The monolayer-bilayer equilibrium of α-TA/DPPC mixtures was estimated by measurement of spreading and collapse pressures. The results showed that the coexistence of emulsion particles (surface monolayer of DPPC+core of α-TA) with vesicular particles (bilayer) was critically important for the formation of the stably dispersed particles of the lipid mixture.View full abstractDownload PDF (790K) -
Juziro NISHIJO, Yuko USHIRODA1998 Volume 46 Issue 11 Pages 1790-1796
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction of 2-naphthalenesulfonate (2-NS) with β-cyclodextrin (β-CD) was investigated in a 0.1 M phosphate buffer at pH 7.4 using an LKB 2277 microcalorimeter and a flow-mixed mode at 25°C. The thermodynamic parameters for inclusion complex formation obtained were as follows : ΔG°=-14.7 kJ/mol (K=381 M-1), ΔH°=-26.4 kJ/mol, ΔS°=-39.1 J/mol K. The formation constant K was determined as 428 M-1 at the same temperature from the change in chemical shift of the proton nuclear magnetic resonance spectra (1H-NMR) in 0.1 M phosphate buffered deuterium oxide solution at pD 7.4. The main driving force for inclusion complex formation was considered to be the van der Waals-London dispersion force. From measurements of the 1H-NMR and model building with Corey-Pauling-Koltun atomic models, the probable structure of the complex was determined to be : the naphthalene ring of 2-NS is included deeply at the head of 6-H and 7-H of 2-NS in the cavity of β-CD from the secondary hydroxy group side, the sulfonate group being outside the cavity.View full abstractDownload PDF (953K) -
Yoichi KOBAYASHI, Misao MIYAMOTO, Kenji SUGIBAYASHI, Yasunori MORIMOTO1998 Volume 46 Issue 11 Pages 1797-1802
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe enhancing effects of various vehicles on the in vitro permeation of a hydrophilic model drug, 5-fluorouracil (5-FU), or a lipophilic model drug, tolnaftate (TN), through human nail plates were investigated using a modified side-by-side diffusion cell. Tip pieces from the 5th finger-nail, clipped from healthy volunteers, were used in this permeation study. The swelling and softening properties of the nail pieces were also measured in each vehicle. The weights and stresses of the nail pieces were dramatically changed after immersion in aqueous solvents containing N-acetyl-L-cysteine (AC) or 2-mercaptoethanol (ME). However, no significant change in the physicochemical properties of the nail pieces was found in the lipophilic vehicles. Thus, the water content in the nail plates absorbed from vehicles may relate to their physicochemical properties. Although keratin-softerning agents and new skin permeation enhancers did not significantly promote 5-FU permeation compared with water alone, the flux from solvent systems containing AC or ME was substantially higher. In addition, TN permeation from solvents containing AC or ME could be measured, whereas that from other solvents was undetectable. When the AC concentration was increased, the 5-FU permeation and the nail weight increased and the stress of each nail piece decreased. It is concluded from these experimental results that AC and ME may be useful as enhancers for increasing drug permeation through the human nail plate.View full abstractDownload PDF (867K) -
Hiroyasu KOKUBO, Sakae OBARA, Yuichi NISHIYAMA1998 Volume 46 Issue 11 Pages 1803-1806
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPellet film coating has very limited applicability compared with tablet film coating, because of the problem of sticking during fluidized bed operation. We have prepared an extremely low viscosity methylcellulose (MC) (4 mPA·s), and examined its solution and film properties and its suitability for pellet film coating.MC lost its adhesivenes at a relatively high moisture content and pellet film coating could be achieved without agglomeration of the pellets within a reasonable operating time. The coated pellets were covered with a continuous film of MC, and drug release from the coated pellets was as rapid as that from the core. These findings suggest that MC (4 mPa·s) is applicable for pellet film coating in an aqueous system.View full abstractDownload PDF (754K) -
Yun-Lian LIN, Jun-Chih OU, Chief-Fu CHRN, Yueh-Hsiung KUO1998 Volume 46 Issue 11 Pages 1807-1809
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new eremophilane-type sesquiterpenes, petasinones A (1), B (2), C (3), and D (4), together with petasin (5), isopetasin (6), petasol (7), isopetasol (8), S-petasin (9), and S-isopetasin (10) were isolated from the aerial parts of Petasites formosanus. The structures of new compounds were determined by chemical and spectroscopic methods.View full abstractDownload PDF (514K) -
Yoshimitsu KIRYU, Satoshi ITOH, Kimiyoshi KANEKO, Hajime KATAYAMA1998 Volume 46 Issue 11 Pages 1810-1813
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of cyclohexene oxide with 1-aminoindoline under neat conditions gave a C-C bond-cleavage product of cyclohexene oxide as a dihydrozone and a 1, 2-aminoalcohol-type product. No hydrazinoalcohol was obtained.View full abstractDownload PDF (660K) -
Makoto NAKAJIMA, Shun-ichi HASHIMOTO, Masahiro NOJI, Kenji KOGA1998 Volume 46 Issue 11 Pages 1814-1815
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAerobic oxidative coupling of naphthols catalyzed by a copper-amine complex was found to proceed without solvent in high efficacy. The present reaction was applied to a practical synthesis of 1, 1'-binaphthalene-2, 2'-diol on multi-gram scale.View full abstractDownload PDF (432K) -
Hiroki SATO, Jun-ichi KITAGUCHI, Sei-ichi NAKAMURA, Shun-ichi HASHIMOT ...1998 Volume 46 Issue 11 Pages 1816-1819
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn optically pure C-1 side chain equivalent of zaragozic acid C, (4R, 5R)-4-benzyloxy-5-methyl-6-phenyl-1-hexyne, has been synthesized in ten steps from (E)-4-phenyl-2-buten-1-ol with an overall yield of 50%, involving a Sharpless asymmetric epoxidation as a key step, followed by regio- and stereocontrolled ring-opening of the epoxide with the trimethylaluminum/n-butyllithium system.View full abstractDownload PDF (754K) -
Marianne DUPUY, Frederic PINGIET, Yves BLACHE, Olivier CHAVIGNON, Jean ...1998 Volume 46 Issue 11 Pages 1820-1823
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-1 and N-2 substituted pyrazolo[4, 5-g]pyrido[1, 2-a]benzimidazoles were prepared regioselectively, and cytotoxicities evaluated in vitro against K562 and HL60 cells. All compounds displayed weaker activity than doxorubicin against sensitive lines, but showed the same activity against resistant cell lines (multidrug resistance +, (MDR+); K562R and HL60R) indicating no resistance phenomena.View full abstractDownload PDF (661K) -
Toshihiro AKIHISA, Yumiko KIMURA, Kazuo KOIKE, takaaki TAI, Ken YASUKA ...1998 Volume 46 Issue 11 Pages 1824-1826
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of astertarone A isolated from the root extract of Aster tataricus L. (Compositae) was established to be D : A-friedoeuph-21-en-3-one (1) based on spectroscopic methods. This is the first example of a naturally occurring triterpenoid with a D : A-friedoeuphane skeleton. Isolation and identification of epishinol (2), shionone (3), friedelin, epifriedelinol, and Ψ-taraxasterol are also described.View full abstractDownload PDF (559K) -
Odontuya GENDARAMYN, Keisuke KOJIMA, Sylvain RODRIGUEZ, Purev ONDOGNII ...1998 Volume 46 Issue 11 Pages 1827-1828
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new xanthone, a new xanthone glycoside and a known xanthone have been isolated from the chloroform and ethyl acetate fractions of Halenia corniculata (Gentianaceae). They were identified as 1, 3-dihydroxy-2, 4, 5, 7-tetramethoxyxanthone, 1-hydroxy-2, 7-dimethoxy-3-O-β-D-glucopyranosylxanthone and 1, 2, 3-trihydroxy-5-methoxyxanthone. 1, 3-Dihydroxy-2, 4, 5, 7-tetramethoxyxanthone is a revised structure from 1, 6-dihydroxy-2, 3, 4, 8-tetramethoxyxanthone reported by our previous paper.View full abstractDownload PDF (485K) -
Yoshihiro MIMAKI, Tadashi SATOU, Minpei KURODA, Yutaka SASHIDA, Yoshio ...1998 Volume 46 Issue 11 Pages 1829-1832
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight spirostanol saponins, including four new compounds, and two known furostanol saponins were isolated from the fresh bulbs of Lilium candidum. The structures of new compounds were determined to be (25R, 26R)-26-methoxyspirost-5-ene-36β, 17α-diol 3-O-{O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside}, (25R, 26R)-26-methoxyspirost-5-ene-3β, 17α-diol 3-O-{O-α-L-rhamnopyranosyl-(1→2)-O-[6-O-acetyl-β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside}, (25R, 26R)-26-methoxyspirost-5-ene-3β, 17α-diol 3-O-{O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside} and (25S)-spirost-5-ene-3β, 27-diol 3-O-{O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopuranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside}, respectively, on the basis of spectroscopic analysis, including two-dimensional NMR techniques, and the result of hydrolysis. The inhibitory activity of the isolated saponins on Na+/K+ ATPase was evaluated.View full abstractDownload PDF (737K) -
Naoyoshi KOBAYASHI, Izumi SAITOH1998 Volume 46 Issue 11 Pages 1833-1835
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solubility of a drug in an ointment base is an important factor determining the efficacy of the formulation. However, it is difficult to measure the solubility of drugs in ointment bases. Thus, a rapid and simple method to determine the solubility of drugs in ointment bases was investigated.Using oxybenzone as a model drug, the bleeding liquid which leaked out from various ointments was collected, and the drug concentration in the bleeding liquid was measured. The drug concentrations in the bleeding liquid collected from soluble type ointments in which the drug is dissolved in bases were in accord with that in the ointments. On the other hand, the drug concentrations in the bleeding liquid collected from crystal dispersion type ointments in which drug crystals are dispersed in bases were the same in spite of the variance in total drug concentrations in the ointments. It was confirmed by microscopic examination that crystals do not flow out into bleeding liquid in the crystal dispersion type ointment. It was also confirmed that the solubility of the drug obtained in the present study was in a solubility range consistent with microscopic examination. Furthermore, an increase in the drug solubility was detected by this method when the drug solubility in the base was raised by adding a detergent into the base. And the results from this method were in accord with the results from microscopic examination. These results suggest that the drug concentration in bleeding liquid represents the solubility of the drug in an ointment.View full abstractDownload PDF (561K) -
Yukiko ASO, Sumie YOSHIOKA, Shigeo KOJIMA1998 Volume 46 Issue 11 Pages 1836-1839
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCrosslinked dextran hydrogels were prepared from glycidyl methacrylate (GMA)-derivatized dextran by gammma-irradiation initiation in the presence of insulin and lysozyme as model protein and peptide drugs. The diffusion coefficient of insulin and lysozyme in the hydrogels was determined sucessfully by a pulsed-field-gradient stimulated-echo method. A conventional NMR probe which can impose a relatively small magnetic field gradient (30 Gauss/cm) was used for the measurements. This method seems to be applicable to proteins and peptides with a molecular weight of about 10000 or less. The diffusion coefficient determined by the NMR method almost agreed with that calculated from the drug release profiles, indicating the usefulness of the diffusion coefficient determined by the NMR method as a measure of the release rate from hydrogels.View full abstractDownload PDF (605K) -
Tomohiro ENDO, Hiromasa NAGASE, Haruhisa UEDA, Atsushi SHIGIHARA, Shoi ...1998 Volume 46 Issue 11 Pages 1840-1843
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUnder standard conditions, i.e. use of natural starches as substrates and long reaction times, it has been confirmed that cyclodextrin glucotranferase (CGTase) produces not only conventional α-, β-, and γ-cyclodextrins (CDs) but also large-ring CDs (LR-CDs) composed of 9 to 17 glucopyranose units as minor products. Recently, it was reported that CGTase produced cyclic α-1, 4-glucans with degrees of polymerization ranging from 9 to more than 60 units under different reaction conditions such as the use of synthetic amyloses as substrates and short reaction times. However, the maximum size of LR-CDs which can be produced by CGTase under standard conditions, has not yet been determined. Therefore, in the present study we searched for LR-CDs composed of more than 18 glucopyranose units in commercially available CD powder produced by CGTase from potato starch. We found 4 new kinds of LR-CD, cyclomaltooctadecaose (v-CD), cyclomaltononadecaose (ζ-CD), cyclomaltoeicosaose (o-CD) and cyclomaltoheneicosaose (π-CD), and these were purified by a combination of HPLC and column chromatography. Their molecular weights were determined by FAB-MS, and their α-(1→4)-linked cyclic structures were identified by 1H-NMR and 13C-NMR. The 13C-NMR chemical shifts of these new LR-CDs were elucidated and compared with 9 kinds of previously reported LR-CDs. Their structures were predicted to be similar to those of cyclomaltodecaose (ε-CD) and cyclomaltotetradecaose (l-CD). These results indicate that CGTase can produce LR-CDs consisting of up to about 20 glucopyranose units under standard reaction conditions.View full abstractDownload PDF (537K) -
Yukio NOHARA, Toshihiko HANAI, Junko SUZUKI, Gou MATSUMOTO, Fumio IINU ...1998 Volume 46 Issue 11 Pages 1844-1845
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn automated HPLC system coupled with fluorometry was established for the sensitive, rapid and accurate assay of serum guanidines. Naturally fluorescent materials characteristic of the sera of uremic patients (uremic fluorescences) which interfere with the assay were removed simultaneously with deproteinization. Application of this method revealed that the uremic patients who are capable of excreting urine under hemodialysis therapy show low serum guanidinosuccinic acid levels. The interval between hemodialysis sessions in one of these patients was prolonged while monitoring guanidinosuccinic acid level using the present method without any hazardous effect.View full abstractDownload PDF (456K) -
Weisum RAO, Daniel J. SMITH1998 Volume 46 Issue 11 Pages 1846-1847
Published: November 15, 1998
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWater-insoluble diazeniumdiolates with extended nitric oxide (NO) release half-lives were synthesized based on diester of spermic acid. These diesters were prepared via Michael addition reactions from 1, 4-diaminobutane and various acrylate esters. synthesis and NO release profiles of dimethyl, diethyl, dibutyl, dihexyl, and dilauryl spermate diazeniumdiolates are reported.View full abstractDownload PDF (380K)
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