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Volume 44, Issue 2
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Takeshi IMANISHI, Satoshi OBIKA, Toshihiko NISHIYAMA, Masahiro NISHIMO ...1996 Volume 44 Issue 2 Pages 267-272
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel NADH model compounds, (SS)-1-alkyl-3-(p-tolylsulfinyl)-1, 4-dihydropyridines (2) and (RS)-1-benzyl-3-[1-oxo-2-(p-tolylsulfinyl)ethyl]-1, 4-dihydropyridine (3), were synthesized. 1H-NMR study and X-ray analysis of 2 revealed its preferred conformation.View full abstractDownload PDF (909K) -
Ken TANAKA, Takako INOUE, Yasuhiro TEZUKA, Tohru KIKUCHI1996 Volume 44 Issue 2 Pages 273-279
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of illudin S with cysteine derivatives (cysteine methyl ester, glutathione and a peptide, Cys-Asp-Pro-Gly-Tyr-Ile-Gly-Ser-Arg) were investigated. In the reaction with cysteine methyl ester, four products (P1, P2, P3, P4) were obtained and their structures were determined, on the basis of MS and NMR data, to be adducts of the mercapto group of cysteine methyl ester with the α, β-unsaturated carbonyl group of illudin S. In the reactions with glutathione and the peptide, two addition products in each case were identified by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and NMR analyses. The structures of these adducts also indicated that the α, β-unsaturated carbonyl group in illudin S behaves as a Michael acceptor for the mercapto group in cysteine.View full abstractDownload PDF (838K) -
Toshiyuki TAKAGI, Junko TAKAHASHI, Hirokazu NAKATSUKA, Mayumi KOYAMA, ...1996 Volume 44 Issue 2 Pages 280-283
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe have reported an abnormal Grignard reaction of halothane (1) with carbonyl compounds (2). The reaction afforded 1-bromo-1-chloro-2, 2, 2-trifluoroethylcarbinols (3) as the major products at -53°C, while at 0°C, the main products were the dehalogenation products, 1-chloro-2, 2-difluoroethenyl carbinols (4). Treatment of 4 with hydrogen fluoride (HF) afforded 1-chloro-1-(trifluoromethyl)ethene derivatives (5) in good yields. However, this reaction required HF, a dangerous reagent. Here, we describe a much easier and safer synthesis of 5. Thus, treatment of 3 with zinc chloride and acetic anhydride gave acetoxy compounds (6). The acetates were converted to the olefins (5) by reductive debromoacetoxylation with zinc in the presence of a catalytic amount of copper(I) iodide. Application of this reaction to an α, β-unsaturated ketone, benzalacetone, gave the diene bearing a trifluoromethyl group.View full abstractDownload PDF (670K) -
Eiji YOSHIDA, Haruhiro FUJIMOTO, Mikio YAMAZAKI1996 Volume 44 Issue 2 Pages 284-287
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new azaphilones, named luteusins C, D, and E, were isolated from an Ascomycete, Talaromyces luteus, together with luteusins A and B (previous tentative designations : TL-1 and -2, respectively), which had formerly been isolated as monoamine oxidase (MAO)-inhibitory azaphilones from the fungus. The new compounds had no MAO-inhibitory activity.View full abstractDownload PDF (641K) -
Noriaki MINAKAWA, Yoshimasa SASABUCHI, Arihiro KIYOSUE, Naoshi KOJIMA, ...1996 Volume 44 Issue 2 Pages 288-295
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn efficient and large scale chamical synthesis of 5-aminoimidazole-4-carboxamide (AICA) 2'-deoxyriboside (5a) and its 3'-deoxyriboside 5b is described. Treatment of 3', 5'-di-O-acetyl-N1-triphenylmethyl-2'-deoxyinosine (3a) with 5 N NaOH in EtOH, followed by anhydrous trifluoroacetic acid gave 5a in 59% yield from 2'-deoxyinosine (1a). AICA 3'-deoxyriboside (5b) was also obtained in a similar manner as for 5a in 73% yield from 3'-deoxyinosine (1b). Conversion of these AICA derivatives (5a, b) into 3-deazapurine derivatives (9a, b, 15a, b, 20a, b) is also described.View full abstractDownload PDF (1263K) -
Tomohiko OHWADA, Masanobu UCHIYAMA, Motonori TSUJI, Iwao OKAMOTO, Koic ...1996 Volume 44 Issue 2 Pages 296-306
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe characterized experimentally the substituent effect of a 5-exo substituent on the π facial selectivities of bicyclo[2.2.2]octenes toward electrophilic oxidative reactions such as epoxidation and dihydroxylation, and we discuss the underlying orbital interactions of vicinal σ orbitals and the olefinic π orbital involved in bicyclo[2.2.2]octenes, and commonly in methylenenorbornanes. Of significance is the out-of-phase motif of these σ-π couplings. Electron-withdrawing substituents such as cyano and carboxylic acid groups unequalize the relevant σ-π coupling, leading to the observed syn-facial preference. Alkyl substituents exhibit an electron-donative perturbing effect, depending on the bicyclic ring system.View full abstractDownload PDF (1616K) -
Masahiro EDA, Tadahiro TAKEMOTO, Takehiro OKADA, Hiroshi SAKASHITA, Su ...1996 Volume 44 Issue 2 Pages 307-313
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of amino acid conjugates of N-(6-amino-3-pyridyl)-N'-[exo-bicyclo[2.2.1]hept-2-yl]-N"-cyanoguanidine (4) were prepared and evaluated as antihypertensive agents. The parent compound 4 showed potent potassium channel-opening and antihypertensive activities, but with undesirable changes of the urinary balance of electrolytes. Howere, alanine and histidine congeners (9, 19) reduced this undesirable side effect of 4 through improved pharmacokinetics without loss of antihypertensive activity. They also provided additional information on the structural requirements for pinacidil-type potassium channel openers.View full abstractDownload PDF (1096K) -
Tomoyuki KITAZAKI, Norikazu TAMURA, Akihiro TASAKA, Yoshihiro MATSUSHI ...1996 Volume 44 Issue 2 Pages 314-327
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new series of optically active antifungal azoles, N-[(1R, 2R)-2-(2, 4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-N'-(4-substituted phenyl)-3(2H, 4H)-1, 2, 4-triazolones (1, 2) and 5(1H, 4H)-tetrazolones (3), were prepared from the triflate derivative of (1S)-1-[(2R)-2-(2, 4-difluorophenyl)-2-oxiranyl]ethanol (13) by an SN2 displacement reaction with the anion of an azolone (17-19) and subsequent ring-opening reaction with 1H-1, 2, 4-triazole. The optically active oxiranylethanol 13 was synthesized from methyl (R)-lactate in a stereo-controlled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.View full abstractDownload PDF (1768K) -
Masayo SAKATA, Takanori SUEDA, Hirotaka IHARA, Chuichi HIRAYAMA1996 Volume 44 Issue 2 Pages 328-332
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel copolymeric adsorbents for the selective removal of endotoxin from an acidic protein solution were prepared. The adsorbents comprise spherical copolymers derived from N, N-dimethylaminopropylacrylamide (DMAPAA) and divinylbenzene (DVB). When the molar ratio of DMAPAA to DVB was 80/20 (amino-group content : 5.1 meq/g) and the pore size (molecular mass exclusion of polysaccharide, Mlim) was 4000 to 10000, DMAPAA/DVB showed high endotoxin-adsorbing activity at pH 5.0 to 9.0 and ionic strengths of μ=0.05 to 0.4. The capacity of the adsorbent (Mlim : 4000) was 390 μg of endotoxin (lipopolysaccharide purified from E. coli O111 : B4) per ml of the adsorbent using the batchwise method. The apparent dissociation constant between endotoxin and the adsorbent was 2.2×10-12 M. On the other hand, the adsorption of bovine serum albumin, an acidic protein, by the adsorbent increased with an increase in Mlim from 4000 to 10000, but decreased with an increase in ionic strength (μ) from 0.05 to 0.2 As a result, DMAPAA/DVB (80/20)(Mlim : 4000)selectively removed endotoxin from various acidic protein solutions at pH 7.0 and μ=0.05. The residual concentration of endotoxin in the protein solution always decreased to a concentration lower than 0.1 ng/ml, and recovery of the protein was more than 97%.View full abstractDownload PDF (869K) -
Emi OKUYAMA, Yoshiko OKAMOTO, Mikio YAMAZAKI, Motoyoshi SATAKE1996 Volume 44 Issue 2 Pages 333-336
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom Jatropha cilliate M. ARG., a Peruvian medicinal plant, isoorientin and orientin were isolated anxiolytic components by using the isolation guide of anti-conflict effect in mice. Several related flavonoids were also tested for this effect. Another bioassay-guided isolation using the acetic acid-induced writhing method gave a coumarin compound, fraxetin, as an analgesic principle.View full abstractDownload PDF (665K) -
Masateru ONO, Yasuyuki ITO, Thoru ISHIKAWA, Junichi KITAJIMA, Yasuko T ...1996 Volume 44 Issue 2 Pages 337-342
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new monoterpene glycosides, foeniculosides V, VI, VII, VIII and IX, were isolated form Foeniculi Fructus (fruit of Foeniculum vulgare MILLER) along with seven known compounds, zizybeoside I, icaviside A4, syringin, sinapyl alcohol 1, , 3'-di-O-β-D-glucopyranoside, adenosine, threo-anethole glycol and erythro-anethole glycol. The structures of foeniculosides V, VI, VII, VIII and IX were characterized as β-D-glucopyranosides of (1S, 2R, 4S)-2, 4-dihydroxy-1, 8-cineole-2-O-, (1R, 4R, 6R)-4, 6-dihydroxy-1, 8-cineole-6-O-, (1R, 4R, 6R)-4, 6-dihydroxy-1, 8-cineole-4-O-, (1S, 2R, 4R, 6S)-2, 6-dihydroxy-1, 8-cineole-2-O- and (1S, 2R, 4S, 5R)-2, 5-dihydroxy-1, 8-cineole-2-O-, respectively, on the basis of chemical and spectroscopic data.View full abstractDownload PDF (900K) -
Kensuke SAKURAWI, Fumio YASUDA, Takehiko TOZYO, Miharu NAKAMURA, Tomoh ...1996 Volume 44 Issue 2 Pages 343-351
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs the first non-peptide endothelin receptor antagonist form a higher plant, a new triter penoid, myiceric acid A (50-235) (1) was isolated from the bayberry, Myrica cerifera. myriceric acid A (1) inhibited not only an endothelin-1-induced increase in cytosolic free Ca&glt;2+> concentration (IC50=11±2nM) but [<125&t;I]endothelin-1 binding in rat aortic smooth muscle cells (Ki=66±15nM). Two new related triterpenoids, myriceric acid C (6), and myriceric acid D (8), were also isolated. Furthermore, the chemical modification of these natural products led to the synthesis of sulfated derivative (13, 14, 15) which showed 1.5 to 20 times higher affinity for endothelin receptors. The structure activity relationships of myriceric acids and their derivatives are discussed.View full abstractDownload PDF (1518K) -
Hiroshi KOHDA, Akira NAMERA, Atsuko KOYAMA, Kazuo YAMASAKI, Tadato TAN ...1996 Volume 44 Issue 2 Pages 352-357
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of growth hormones and nutrients on growth and alkaloid production in callus cultures of Uncaria rhynchophylla (MIQ.) MIQUEL (Rubiaceae) were investigated. Gamborg B5 (B5) medium supplemented with indoleacetic acid (10-4M) and 6-benzylaminopurine (3×10-5M) was optimized both for the growth (1.8g fresh weitht/5 weeks) and alkaloid production (1.73 mg/g dry weight/5 weeks). The influence of sucrose concentration was examined, and 2% sucrose was found to be the most appropriate for the growth and alkaloid production. The effect of the composition of nitrogen sources was examined. Maximal growth and alkaloid production were obtained when 6 mM ammonium chloride and 25mM potassium nitrate were added to the B5 medium. Hirsuteine, hirsutine, 3α-dihydrocadamibine and ursolic acid were isolated from the callus. The 3α-dihydrocadambine concentration of callus was ca. 50-fold higher than that of the hooks and stems of U. rhynchophylla.View full abstractDownload PDF (798K) -
Tsutomu WARASHINA, Tadataka NORO1996 Volume 44 Issue 2 Pages 358-363
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe roots of Cynanchum caudatum M. (Asclepiadaceae) affored 21 new pregnane glycosides which had sibirigenin, cynanchogenin, gagaminin, 12-O-nicotinoyllineolon and rostratamine as the aglycone moiety and 2, 6-dideoxy-3-O-methylhexopyranoses as component sugars. The structures of these compounds were elucidated by spectroscopic methods and chemical evidence.View full abstractDownload PDF (788K) -
Hideshi SUZUKI, Norifumi MIYAMOTO, Tomoaki MASADA, Eiji HAYAKAWA, Kuni ...1996 Volume 44 Issue 2 Pages 364-371
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solid dispersion technique has been widely utilized to improve the dissolution profile and oral bioavailability of water insoluble drugs. Benidipine hydrochloride, a calcium-antagonist, is a slightly soluble compound in a weak acid, so that its bioavailability is liable to be influenced by the gastric acidity of patients. In the preparation of solid dispersions by the solvent removal process, organic solvents are used as agents to intimately mix a drug or drugs and carrier molecules. Benidipine hydrochloride is also poorly soluble in commonly used organic solvents. The application of the solvent removal prosess for preparing solid dispersions of the drug makes it necessary to enhance the organic solubility of the drug. Two kinds of solvent systems have been investigated : one in an organic solution of Eudragit[○!R] E-100 (OSE) and the other in binary solvent mixtures (BSM). In the OSE, the presence of Eudragit[○!R] E-100 in dichloromethane resulted in an appreciable increase in drug solubility. However, in ethanol, this solubilization effect of the polymer was completely inhibited. In the BSM, enhanced solubility of the drug was obtained in ethanol-dichloromethane mixtures. Further, the addition of polyvinylpyrrolidone (PVP) or hydroxypropylmethyl-cellulose (HPMC) to this system did not deposit the dissolved drug. In these two solvent systems, solubilization of benidipine hydrochloride was presumed to be caused by intermolecular interactions. It enabled the preparation of solid dispersions of benidipine hydrochloride with Eudragit[○!R] E-100, PVP or HPMC. Especially, when dispersed in PVP or HPMC, the dissolution rate of the drug improved remarkably in a weak acid (pH 6.0).View full abstractDownload PDF (1231K) -
Hideshi SUZUKI, Norifumi MIYAMOTO, Tomoaki MASADA, Eiji HAYAKAWA, Kuni ...1996 Volume 44 Issue 2 Pages 372-377
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solubilization mechanism of benidipine hydrochloride in two kinds of organic solvent systems has been investigated : one in an organic solution of Eudragit[○!R] E-100 (OSE), and the other in binary solvent mixtures (BSM) of alchol-cosolvent. In the OSE, the organic solubility of the drug was increased in proportion to the polymer concentration. Fourier transform infrared spectroscopy clearly demonstrated the existence of hydrogen bonds between dimethylamino groups of the polymer and piperidine NH+ of the drug. The ultraviolet absorption maximum of the drug in the 350 nm region blue-shifted in dichloromethane or chloroform with polymer, whereas this shift was not found in ethanol or acetonitrile with the polymer. In the BSM, the logarithmic maximum solubility of the drug in ethanol-cosolvent mixtures was linearly related to the π* (dipolarity-polarizability) value of the cosolvent. The initial slope of the drug solubility curve in alcohol-dichloromethane mixtures was in good correlation with the α (hydrogen-bond donor acidity) value alcohol. Therefore, it was understood that the solubilization of benidipine hydrochloride in the OSE resulted form the drug-polymer complexation with the intermolecular hydrogen bonding and dipolar interactions, and the solubilization effect in the BSM arose from the enhancement of the proton donor ability of alcohol molecules by the dipolar interactions with the cosolvent.View full abstractDownload PDF (1025K) -
Hiroshi YUASA, Masashi AKUTAGAWA, Takashi HASHIZUME, Yoshio KANAYA1996 Volume 44 Issue 2 Pages 378-382
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe aim of this study was to reduce the stress concentration of a medicine by dispersing the stress in tablets at tableting by addition of excipients. The mechanism of the stress dispersion was elucidated.Phenacetin (PHE) was used as a model of crystalline medicine with a high brittleness, and the degree of stress dispersion was evaluated by the change in the exposed surface area of PHE. To learn the mechanical strength of tablets, the crushing strength and friabillity were measured, their internal structure was analyzed by the porosity and pore size distribution, and stress relaxation experiments were performed. The results were as follows.Calcium silicate (Florite[○!R] RE, FLR) showed a high stress dispersion effect, adding a high formability and mechanical strength to tablets. It was thought that the high stress dispersion resulted from the rapid stress relaxation caused by the plastic deformation and brittleness fracture of pores in FLR under a low compression pressure. Thus the stress caused locally on PHE particles may disperse.View full abstractDownload PDF (1186K) -
Hideki ICHIKAWA, Shuji KANEKO, Yoshinobu FUKUMORI1996 Volume 44 Issue 2 Pages 383-391
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn aqueous composite latex which suppressed particle adhesion by electrostatic charge and agglomeration in coating and had self-film-formability in dissolution was developed as a coating meterial for subsieve-sized particles using the Wurster process. This composite latex was composed of a poly(ethyl acrylate (EA)/methyl methacrylate(MMA)/2-hydroxyethyl methacrylate (HEMA)) core and a thermosensitive poly(N-isopropylacrylamide (NIPAAm)) shell. The polymer yield in coating of 53-63μm lactose with homogeneou latices without poly(NIPAAm) shell exhibited a remarkable particle size dependency because of particle adhexion arising form the electrostatic charge. On the contrary, composite latices reduced the production of poorly particles and the particle size dependency of polymer yield, when the coating operation was done at temperatures where poly(NIPAAm) shells were swellable, i.e., below the lower critical solution temperature (LCST; 32°C) of poly(NIPAAm). Agglomeration tendency strongly depended on the hardness of the poly(EA/MMA/HEMA) cores. Microcapsules coated with composite latices exhibited a temperature-sensitive release of water-soluble lactose, while with homogeneous latices the release was simply enhanced with rise in temperature. When the microcapsules coated with composite latices were exposed to a critical temperature around LCST during the dissolution process, the lactose release from them was most suppressed, suggesting that shrinkage of the dehydrated poly(NIPAAm) shells in the coat of the microcapsules at the critical temperature would contribute to formation of a compact film which could strongly suppress water- and lactose-permeation.View full abstractDownload PDF (1473K) -
Kaori JONO, Hideki ICHIKAWA, Yoshinobu FUKUMORI, Ryuichi KANAMORI, Yas ...1996 Volume 44 Issue 2 Pages 392-398
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA phase diagram of a soybean lecithin (SL)-cholesterol (CH)-stearic acid (SA) system incorporating 42% polyvinylpyrrolidone was estimated by differential scanning calorimetry (DSC), X-ray diffiractometry (XRD) and polarizing microscopy in order to relate it to the dissolution and disintegration properties of microcapsules whose membranes consisted of these compounds. At the weight ratio of SL : CH=4 : 1, SL : SA=4 : 1 or SL : CH : SA=3 : 1 : 1, SL liquid crystalline phase (SL(LCP)) dissolved the maximum amount of CH and/or SA without any other crystalline phases detected on DSC and XRD. The existence of SL(LCP) was confirmed by observation under polarizing microscope : mixtures remained anisotropic over 20-90°C or SA-containing anisotropic phases became isotropic at 70-80°C without any peaks on DSC. With increase in CH and /or SA, these were separated from SL(LCP) dissolving CH and/or SA. The separated CH (CH(c)) was found to have the same crystalline structure as the parent CH from XRD. The separated SA, in contrast, showed two types of XRD patterns : one had the same pattern as the parent SA (SA(c)) and the other had a pattern with some peaks shifted to shorter spacings(SA(c')). The mixtures gave a phase diagram with six regions, each of which had the following phase(s) : 1)SL(LCP);2) SL(LCP) and CH(c); 3) SL(LCP), CH(c) and SA(c'); 4) CH(c), SA(c') and SA(c); 5) SA(c) and SA(c'); 6) SL(LCP) and SA(c'). It was not clear whether SL(LCP) was present in the fourth and fifth zones or not.View full abstractDownload PDF (1059K) -
yoshimi SHIRAI, Kiyomi SOGO, Hiroshi FUJIOKA, Yasuhiko NAKAMURA1996 Volume 44 Issue 2 Pages 399-402
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influence of heat treatments on the dissolution and the masking degree of the bitter taste for the coated fine granules with water-insoluble film composed of ethylcellulose, hydroxypropylmethylcellulose, titanium dioxide and sucrose fatty acid ester (SS) (4 : 2 : 1 : 1), containing sparfloxacin (SPFX) and low-substituted hydroxypropylcellulose in the cores was investigated.The dissolution rate of SPFX from the coated fine granules in water was increased by heat treatment of the granules. Dissolution percentage at 30 min in water after heat treatment at 70°C for more than 4h reached almost 100%, whereas it was about 90% before the heat treatment. The masking degree of the bitter taste for the coated fine granules was improved by the heat treatment. Differential scanning calorimetry (DSC) analysis of the coating film indicates that the endothermic peak due to melting of SS in the film disappeared with the heat treatment at 70°C for 4h, and also that the tensile strength of the film was reduced to one-half of the inital value after the heat treatment.It is thought that heat treatment caused changes of film properites, i.e. that tensile strength and wettability are attributable to the melting and diffusing of SS in the film, resulting in the dissolution level being increased to about 100% and the masking degree of the bitter taste being greatly improved.View full abstractDownload PDF (648K) -
Yoshie MAITANI, Kazue SHIMADA, Tsuneji NAGAI1996 Volume 44 Issue 2 Pages 403-408
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism of l-menthol, oleic acid and lauricidin as enhancers on percutaneous absorption was examined using diclofenac (DH) as a hydrophobic drug and sodium diclofenac (DNa) as a hydrophilic drug in in vitro diffusion experiments with two kinds of membranes : ethanol-treated and untreated silicone membranes; these were models for the lipid and pore pathways of skin. A 20% w/w ethanol-aqueous solution decreased the flux of DH but increased the flux of DNa significantly across the treated membrane compared with those fluxes across the untreated membrane, suggesting that DH penetrated by the lipid pathway and DNa by the pore pathway. The permeability of DNa through the pore pathway decreased significantly across the treated membrane with the addition of oleic acid and lauricidin. l-Menthol increased the permeability coefficients of DH and DNa more in a treated membrane than in an untreated one, showing the same tendency as in rat skin. Thus, while oleic acid and lauricidin did not increase the permeation of DNa by the pore pathway, l-menthol appeared to enhance the permeation of the drug by both the lipid and pore pathways.View full abstractDownload PDF (910K) -
Satoru WATANO, Takashi MORIKAWA, Kei MIYANAMI1996 Volume 44 Issue 2 Pages 409-415
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA population balance equation, in which moisture content was taken into consideration for the coalescence probability of two colliding granules, was proposed to investigate the kinetics of granule growth in agitation fluidized bed granulation. The effects of operating variables such as moisture content, damping speed and operation time on the granule growth and its rate were numerically examined. It was found that the theoretical results intrinsically revealed these effects on granule size, size distribution and granule growth rate. The theory also showed good agreement with the experimental granulation data for pharmaceutical powders. As a result, the granule growth mechanism in agitation fluidized bed granulation was elucidated in detail.View full abstractDownload PDF (887K) -
Muneo TANAKA, Hajime MATSUDA, Hideyuki SUMIYOSHI, Hidetoshi ARIMA, Fum ...1996 Volume 44 Issue 2 Pages 416-420
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe potential use of three kinds of 2-hydroxypropylated cyclodextrins [HP-CyDs : 2-hydroxypropyl-α-cyclodextrin (HP-α-CyD), 2-hydroxypropyl-β-cyclodextrin (HP-β-CyD) and 2-hydroxypropyl-γ-cyclodextrin(HP-γ-CyD)] in the solubilizing of fragrance materials and the retarding of their release rates was examined. Of the HP-CyDs, HP-β-CyD significantly increased the solubility of six fragrance materials in water, and the apparent 1 : 1 stability constant of the HP-β-CyD complexes was higher than those of the HP-α-CyD and HP-γ-CyD complexes. Ultraviolet, circular dichroism and unclear magnetic resonance spectroscopic studies suggested that the inclusion mode of eugenol is different between the HP-β-CyD complex and the HP-α- or HP-γ-CyD complexes. The release rates of d-camphor and 3-l-methoxypropane 1, 2-diol from water were remarkably decreased by the addition of HP-CyDs, where the rate of decrease was in agreement with that of the stability constant ranking of the complexes, i.e., fragrance materials alone<HP-α-CyD<HP-γ-CyD<HP-β-CyD. In order to retard the transport of fragrance materials to skin, the suppressive effect of HP-CyDs was examined in vitro. The mean transit time for eugenol through the skin barrier increased in the order of eugenol alone<HP-γ-CyD<HP-α-CyD<HP-β-CyD, and the suppressive effects of HP-α-CyD and HP-β-CyD were remarkably greater than that of the nonionic surfactant, HCO-60. The present data suggest that HP-β-CyD has a significant advantage over the other HP-CyDs and HCO-60 with respect to providing high aqueous solubility and the sustained release of fragrance materials while maintaining a lack of toxicity in topical liquid preparations of fragrance materials.View full abstractDownload PDF (795K) -
Masaru KIDO, Daisuke NOMI, Koji HASHIMOTO1996 Volume 44 Issue 2 Pages 421-423
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe optically active (+)-enantiomer of 5, 6-difluoro-2-methyl-1, 2, 3, 4-tetrahydroquinoline was obtained as a salt with dibenzoyl-D-tartaric acid by the optical resolution method and was determined to be R-configuration by X-ray analysis. Since (R)-(+)-5, 6-difluoro-2-methyl-1, 2, 3, 4-tetrahydroquinoline is the optically resolved synthetic intermediate of optically active (+)-enantiomer of nadifloxacin[9-fluoro-6, 7-dihydro-8-(4-hydroxy-1-piperidyl)-5-methyl-1-oxo-1H, 5H-benzo[i, j]quinolizine-2-carboxylic acid, OPC-7251, 1], the absolute configuration of (±)-1 was assigned to R.View full abstractDownload PDF (474K) -
Yohko SAKAMOTO, Toshikazu AOKI, Shigeru OHSHIMA1996 Volume 44 Issue 2 Pages 424-428
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA thorough NMR spectroscopic investigation was made on 7, 12-dimethylbenz[α]anthracene (1) and the 1H-and 13C-NMR spectra were completely assigned. We compared the 13C-NMR chemical shifts (δ) of three benz[α]anthracenes, including compound 1, whose carcinogenicities vary largely, and investigated the relationship of the δ and carcinogenicity. It was found that the δ values at the C1, C2, and C6 positions differed significantly between the carcinogenic and noncarcinogenic compounds.View full abstractDownload PDF (518K) -
Yueh-Hsiung KUO, Zong-Shiow CHEN, Yun-Lian LIN1996 Volume 44 Issue 2 Pages 429-436
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSExtracts of the leaves of Druanta repens LINN. were found to contain two new iridoids, durantoside IV and durantoside V together with several known compounds, oleanolic acid, ursolic acid, (E)-cinnamic acid, β-sitosteryl-3-O-β-D-glucopyranoside, (E)-p-methoxycinnamic acid, KNO3 KCl, kusaginin, glucose, durantoside I, and durantoside II. Their structures was elucidated on the basis of spectral and chemical evidence. The absolute configuration of durantoside was determined by using the benzoate rule.View full abstractDownload PDF (1054K) -
Eisuke KAJI, Yumiko OSA, Mutsumi TANAIKE, Yugo HOSOKAWA, Hiroaki TAKAY ...1996 Volume 44 Issue 2 Pages 437-440
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA chemical synthesis has been achieved for β-D-ManNAc-(1→4)-α-D-Glc-(1→3)-L-Rha, a trisaccharide repeating unit of the capsular polysaccharide of Streptococcus pneumoniae serotype 19A, by stepwise link-up of the suitably functionalized, constituent sugar units. A β-selective glycosylation of trimethylsilylethyl glucoside having free 4-OH with 2-(benzoyloxyimino)-2-deoxyglycosyl bromide, followed by manno-selective hydroboration, N-acetylation, and functionalization of the anomeric center (1-OSE→1-OH→1-F), gave a key disaccharide donor, β-D-ManNAc-(1→4)-α-D-Glc-(1→F. Ensuing glycosylation of an L-rhamnosyl acceptor with the donor substrate afforded, after deblocking, the target trisaccharide in 6.5% yield over 13 steps from D-glucose.View full abstractDownload PDF (670K) -
Chihiro ITO, Yoshiaki MIYAMOTO, K. Sundar RAO, Hiroshi FURUKAWA1996 Volume 44 Issue 2 Pages 441-443
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConstituents of an EtOH extract of the stem bark of Calophyllum panciflorum A. C. SMITH (Guttiferae) collected in Central Province of Papua New Guinea were studied. A novel dibenzofuran named calophyfuran (1) and two new xanthones named pancixanthone-A (3) and pancixanthone-B (4), respectively, were isolated as well as four kinds of known xanthones, and their structures were elucidated by spectrometric methods. Among these components, calophyfuran (1) is the first example of dibenzofuran derivatives having a five-carbon unit (prenyl) as a substituent to be found in nature.View full abstractDownload PDF (605K) -
Byoung-Mog KWON, Ji-Youn NAM, Seung-Ho LEE, Tae-Sook JEONG, Young-Kook ...1996 Volume 44 Issue 2 Pages 444-445
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe have isolated cholesteryl ester transfer protein (CETP) inhibitors from the extract of Korean Panax ginseng C. A. MEYER roots and identified them as polyacetylene analogs. These compounds inhibit human CETP with IC50 values of around 20-35 mg/ml.View full abstractDownload PDF (388K) -
Pengyue SUN, Wen YE, Guifang ZHENG, Zhixue WANG, Yingjie CHEN, Yukio O ...1996 Volume 44 Issue 2 Pages 446-447
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new flavonol glycoside named epimedin K was isolated from the aerial parts of Epimedium koreanum NAKAI (Berberidaceae). Its chemical structure was found to be anhydroicaritin 3-O-β-D-(2, 6-di-O-acetyl) glucopyranosyl (1→3)-α-L-(4-O-acetyl) rhamnopyranoside-7-O-β-D-glucopyranoside on the basis of spectroscopic and chamical evidence.View full abstractDownload PDF (494K) -
Akira MIYASHITA, Yoshiyuki MATSUOKA, Atsushi NUMATA, Takeo HIGASHINO1996 Volume 44 Issue 2 Pages 448-450
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe anions derived form O-aroylmendelonitriles 1 reacted with Michael addition acceptors such as acrylonitrile (7) and methyl acrylate (10) to give the corresponding 1, 4-diketones 12, 13, and 15 in moderate to good yields. Under acidic conditions, the 1, 4-diketones 12, 13, and 15 were converted into the furans 17, 18 and 19 in good yields.View full abstractDownload PDF (481K) -
Toshiaki NAGATA, Yuuki KOIDE, Kazumasa NARA, Etsuko ITOH, Mitsuhiro AR ...1996 Volume 44 Issue 2 Pages 451-453
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPreparation of the 1-methoxycarbonyl-3-phenylthio-2-quinolinone (10) from dihydro-2-quinolinone (5) and its Diels-Alder reaction with 2-trimethylsilyloxy-1, 3-butadiene under Lewis acid catalyst is described. Conversion of the D-A adduct (11) to 9-phenenthridinone ketal (16) will open a new synthetic route to a dynemicin A core structure.View full abstractDownload PDF (479K) -
Yukio MASAKI, Yukihiro SATOH, Takechi MAKIHARA, Min SHI1996 Volume 44 Issue 2 Pages 454-456
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA chiral C2-symmetric N-(β-mercaptoethyl)pyrrolidine bearing 6-membered benzylidene acetal functionalities fused at the 2, 3- and 4, 5-positions was found to exhibit high efficiency in the asymmetric addition reaction of aldehydes with diethylzinc.View full abstractDownload PDF (457K) -
Kazuyuki MIYASHITA, Masahiro NISHIMOTO, Hidenobu MURAFUJI, Satoshi OBI ...1996 Volume 44 Issue 2 Pages 457-459
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe C-6 methyl group of methyl (4R, SS)-2, 4, 6-trimethyl-5-(p-tolylsulfinyl)-1, 4-dihydropyridine-3-carboxylate (2) was found to be regioselectively lithiated by participation of the neighboring sulfinyl group, giving rise to the 6-modified Hantzsch-type compounds by treatment with n-butyllihium and the electrophiles.View full abstractDownload PDF (445K) -
Hiroyuki KAGECHIKA, Isao AZUMAYA, Kentaro YAMAGUCHI, Koichi SHUDO1996 Volume 44 Issue 2 Pages 460-462
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN, N'-Dimethyl-N, N'-[2-(3-methylureido)pyrid-5-yl]urea (5) was designed and synthesized as a guanylyl-guanosine equivalent molecule. (E)-Perference of the urea bond of 5 enhanced the formation of highly associated complexes of 5 with bis(cytosyl)derivatives.View full abstractDownload PDF (498K) -
Kazuyuki SUGITA, Daisuke SAWADA, Mikiko SODEOKA, Hiroaki SASAI, Masaka ...1996 Volume 44 Issue 2 Pages 463-465
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS13-Deacetoxy-11-demethyl-phorbol derivatives with acyl groups of various lengths (from hexanoyl to tetradecanoyl) at the C-12 position were synthesized in an optically active from. Although considerable binding affinities to PKC were observed by analogs 3-7, no activation of PKC was seen even at 10 μM.View full abstractDownload PDF (468K) -
Katsumi HOTODA, Mitsuaki AOYAGI, Toshikatsu TAKANAMI, Kohji SUDA1996 Volume 44 Issue 2 Pages 466-468
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSthe reaction of 3-alkylidene-4-trimethylsilylazetidin-2-ones with aldehydes in the presence of fluoride ion gave 3-alkylidene-4-(α-hydroxy)-alkylazetidin-2-ones in good to moderate yields.View full abstractDownload PDF (430K) -
Nobutoshi MURAKAMI, Toshiyuki MURAKAMI, Masashi KADOYA, Hisashi MATSUD ...1996 Volume 44 Issue 2 Pages 469-471
Published: February 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInvestigation of hypoglycemic activity of major saponin constituents from "gymnemic acid", a crude saponin fraction of G. sylvestre, exposed non only two new saponins, gymnemosides a (1) and (2), but also gymnemoside b and gymnemic acid V (7) as active principles. Fruthermore, an acetyl group linked 16- or 22-hydroxy group in 1 and 2 was found to migrate easily to primary 28-hydroxyl group, while acyl migration from 28-hydroxy group in 3 was little observed.View full abstractDownload PDF (488K)
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