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Volume 45, Issue 5
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Kunio HIROI, Masayuki UMEMURA, Yoko TOMIKAWA, Masamitsu KANEKO, Fumiko ...1997 Volume 45 Issue 5 Pages 759-764
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn asymmetric Diels-Alder reaction with a diene bearing a chiral sulfinyl group is described. The Lewis acid-catalyzed intramolecular asymmetric hetero Diels-Alder reaction of a chiral α'-sulfinyl-α, β-unsaturated ketone derived from 3-methylcitronellal produced optically active 4a, 5, 6, 7, 8, 8a-hexahydro-1H-2-benzopyran derivatives. On the basis of the stereochemical results obtained, a plausible mechanism for the asymmetric induction is presented.View full abstractDownload PDF (807K) -
Masaaki BAN, Kosuke OKAZAKI, Motoyasu OZAWA, Makio KITAZAWA, Akikazu K ...1997 Volume 45 Issue 5 Pages 765-768
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Friedel-Crafts acylation of 1-acetylindoline with (S)-2- or (R)-2-(methanesulfonyloxy)propionyl chloride, and aluminum chloride in dichloromethane at room temperature did not afford the expected (S)- or (R)-1-acetyl-5-[2-(methanesulfonyloxy)propionyl]indoline, but gave optically pure (R)- or (S)-1-acetyl-5-(2-chloropropionyl)indoline, whose stereochemistry at the asymmetric carbon was inverted during the reaction. Similar reaction of 1-acetylindoline with the same chiral acylating agents in the presence of aluminum bromide gave mainly the corresponding 2-bromopropionyl derivatives, but as stereo mixtures.View full abstractDownload PDF (612K) -
Kunio HIROI, Akira HIDAKA, Rie SEZAKI, Yumiko IMAMURA1997 Volume 45 Issue 5 Pages 769-777
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPalladium-catalyzed asymmetric α-allylations of carbonyl compounds were studied using various kinds of chiral sulfonamides derived from optically active α-amino acids as chiral ligands. Participation of the sulfonamide functionality in the palladium catalysis is discussed.View full abstractDownload PDF (1185K) -
Construction of 1, 3-Oxathiane Ring through Pummerer Reaction of γ, δ-Unsaturated Sulfinyl CompoundsHitoshi ABE, Hiroyuki FUJII, Chieko MASUNARI, Junko ITANI, Setsuo KASH ...1997 Volume 45 Issue 5 Pages 778-785
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral γ, δ-unsaturated sulfinyl compounds were prepared and their reactions with p-toluenesulfonic acid were examined. Conformationally rigid γ, δ-unsaturated sulfinyl compounds such as endo-(alkylsulfinyl)norbornene or 1-(alkylsulfinyl)-2-isopropenylbenzene derivatives afforded 1, 3-oxathianes through intramolecular Pummerer rearrangement.View full abstractDownload PDF (1279K) -
Isao KITAGAWA, Kazuyoshi OHASHI, Nam In BAEK, Masahiro SAKAGAMI, Masay ...1997 Volume 45 Issue 5 Pages 786-794
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new resin-glycosides, named mammosides A (10), B (11), H1 (12), and H2 (13), were isolated from the tuber of Merremia mammosa (Convolvulaceae), a Jamu raw material. Their chemical structures have been elucidated on the bases of chemical and physicochemical evidence, including synthesis of a glycosidic acid designated as mammoside I.View full abstractDownload PDF (1247K) -
Xue Long SUN, Toshitsugu KAI, Syuji FUJITA, Hiroaki TAKAYANAGI, Kimio ...1997 Volume 45 Issue 5 Pages 795-798
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn studies on the glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) derivatives, O-glycosides of furanose-type KDN were synthesized from benzyl 4, 5, 7, 8, 9-penta-O-acetyl-2-bromo-2, 3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate under Koenigs-Knorr reaction conditions. The furanoid structures of the KDN moiety were supported by with 1H-NMR experiments, and the reaction was considered as a novel glycosylation with ring contraction, which proceeded via in situ pyranose-furanose rearrangement of the KDN moiety, and subsequent coupling with acceptors.View full abstractDownload PDF (661K) -
Hideaki MURATAKE, Kazuaki OKABE, Michiko TAKAHASHI, Miyuki TONEGAWA, M ...1997 Volume 45 Issue 5 Pages 799-806
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTotal synthesis of furan and thiophene analogs 6 and 7 of duocarmycin SA was achieved in racemic forms, starting from methyl 4, 5-dibromo-2-furan- and thiophenecarboxylates (15a and 15b). Lithio derivatives 12a (a series : X=O) and 12b (b serie : X=S) were reacted with the aldehyde 22 for preparation of 25a and 25b, and successive synthetic operations, including Heck reaction of 25a and 25b to obtain 26a+27a and 26b+27b, and B ring aromatization, 28a and 28n→31a and 31b, based on our previous total synthesis of duocarmycin SA, afforded 36a and 36b. Treatment of 36a and 36b with potassium carbonate in methanol directly afforded cyclopropapyrroloindole derivatives 38a and 38b, whose condensation with the 5, 6, 7-trimethoxy-2-indolecarbonyl unit completed the synthesis of (±)-6 and (±)-7.View full abstractDownload PDF (1514K) -
Fumiyuki KIUCHI, Md.Abdul GAFUR, Tohoru OBATA, Akiko TACHIBANA, Yoshis ...1997 Volume 45 Issue 5 Pages 807-812
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2, 6-dimethyl-6-hydroxy-2, 7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2, 7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2, 7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.View full abstractDownload PDF (869K) -
Tatsumi SHINOHARA, Jun TODA, Takehiro SANO1997 Volume 45 Issue 5 Pages 813-819
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPummerer reaction of the sulfoxides 5 of N-acyl-N-(aryl)methyl-2-(phenylthio)ethylamines (4) on treatment with trifluoroacetic anhydride (TFAA) effectively caused intramolecular cyclization under a mild condition to give N-acyl-4-phenylthio-1, 2, 3, 4-tetrahydroisoquinolines (TIQs) (7). The reaction of the N-formyl sulfoxide 5c without a methoxy group in the benzene ring using a formyl group for N-protection is particularly efficient. Treatment of the N-formyl sulfoxide 5f with TFAA did not give any TIQ, but a sequential treatment using TFAA and BF3·Et2O afforded N-formyl-4-phenylthio-TIQ (7f) in quantitative yield. The efficiency of this method of preparing TIQs was demonstrated in the synthesis of 1, 4-dideuterio-TIQ (10D) and its N-methyl derivative (11D).View full abstractDownload PDF (1170K) -
Motohiko MORIHARA, Nobuko SAKURAI, Takao INOUE, Ken-ichi KAWAI, Masahi ...1997 Volume 45 Issue 5 Pages 820-823
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom Myrica gale var. tomentosa, two new diarylheptanoids, myricatomentosides I and II, were isolated together with a plane-chiral diarylheptanoid, galeon. The absolute stereochemistry of (+)-galeon was determined as R. Myricatomentoside I, was identified as the glucoside of myricatomentogenin, a new diarylheptanoid of diphenyl ether type, and myricatomentoside II, as the glucoside of 12-hydroxymyricanone.View full abstractDownload PDF (648K) -
Hiroyuki AKITA, Masako NOZAWA, Yoshiko FUTAGAMI, Maiko MIYAMOTO, Chika ...1997 Volume 45 Issue 5 Pages 824-831
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen the β-acyloxy esters (±)-10 and (±)-11 were exposed to the lipase OF-360 from Candida rugosa or immobilized lipase OF-360 in a water-saturated organic solvent, the hydrolyzed product (8aS)- was obtained in high chemical (40%) and optical (>99%ee) yields. The absolute structure of (8aS)-6 was confirmed by the fact that (8aS)-6 was converted into an authentic sample γ-keto nitrile (8aS)-17. Treatment of the diol (±)-12 with isopropenyl acetate in the presence of the lipase Godo E-4 from Pseudomonas sp. provided the unchanged (8aR)-12 (89%ee) in 42% yield.View full abstractDownload PDF (1084K) -
Taisuke ITAYA, Nobuaki ITO, Tae KANAI, Tozo FUJII1997 Volume 45 Issue 5 Pages 832-841
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn treatment with boiling H2O for 5-6h, 1-alkoxy-7-alkyladenines (13) underwent hydrolytic cleavage at the N(1)-C(2) and the N(1)-C(6) bonds to produce the imidazole-5-carboxamidines (14) in 53-60% yields and the imidazole-5-carboxamides (18) in 5-7% yields, respectively. The Dimroth rearrangement of 13 to N6-alkoxy-7-alkyladenine (15) was found to proceed through 14 more slowly than that of the 9-alkyl analogues 1 at pH 7 and above, being accompanied by hydrolysis to give the deformylated product (16) and by deamination through 18 leading to 7-alkylhypoxanthine (12), 1-alkoxy-7-alkylhypoxanthine (19), and 1-alkyl-4-aminoimidazole-5-carboxamide (20). Interestingly, the N(1)-C(6) bond fission product 17a was obtained from 13a by treatment with 0.01N aqueous NaOH at 4°C for 35d, but in only 2% yield, or more efficiently (in 56% yield) by pyrolysis at 150°C for 1h. On the other hand, 13 underwent acid hydrolysis faster than 1, providing the deformylated product 16 in 85-96% yields on treatment with 1-2N aqueous HCl at room temperature for 2-5h. 4-amino-N'-methoxy-1-methyl-5-carboxamidine (16a) was alternatively obtained in 59% yield by treatment of 1-methoxy-7-methyladenine (13a) with boiling 2N aqueous NaOH for 10min. Efficient preparations of the rearranged products 15 (80-86%) were accomplished by treating 13 with boiling 0.1N aqueous NaOH for 20-30min.View full abstractDownload PDF (1658K) -
Maria Angeles HONRUBIA, Jesus RODRIGUEZ, Rosa DOMINGUEZ, Estrella LOZO ...1997 Volume 45 Issue 5 Pages 842-848
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyproheptadine is a drug that shows high affinity for type 2 (5-HT2) receptors. We studied a series of compounds obtained by modification of the tricyclic system of Cyp (dibenzocycloheptadiene) : 2f (thioxanthene), 2g (xanthene), 2h (dihydrodibenzocycloheptadiene), 2j (diphenyl), 2i (fluorene), and 3b (phenylmethyl). Their activities at the rat cerebral cortex 5-HT2A receptor were (pKi±S.E.M) : 8.80±0.11 (Cyp), 8.60±0.07 (2f), 8.40±0.02 (2g), 8.05±0.03 (2h), 7.87±0.12 (2j), 6.70±0.02 (2i) and 6.45±0.02 (3b); those at the rat stomach fundus 5-HT2B receptor (pA2±S.E.M.) were : 9.14±0.25 (Cyp), 8.49±0.07 (2f), 7.58±0.58 (2g), 7.02±0.14 (2h), 6.07±0.20 (2j), and undetectable (2i, 3b); and those at the pig choroidal plexus 5-HT2C receptor (pKi±S.E.M.) were 8.71±0.08 (Cyp), 8.68±0.01 (2f), 8.58±0.20 (2g), 7.95±0.05 (2h), 7.57±0.04 (2j), 6.98±0.04 (2i) and 6.63±0.20 (3b). The slopes did not differ significantly from unity. The compounds exhibited the same order of activities at every type of receptor, and the most active molecules presented certain steric (butterfly conformation of the tricyclic system) and electrostatic (proton affinity on the top of the central rings) patterns. It is concluded that the activity of cyproheptadine derivatives at 5-HT2 receptors is related to these molecular features, which features, which make feasible a common disposition to interact with all three 5-HT2 subtypes.View full abstractDownload PDF (1060K) -
Shunichiro SAKURAI, Nobuo OGAWA, Yasuyo ONOGI, Makoto TAKESHITA, Hirom ...1997 Volume 45 Issue 5 Pages 849-862
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to find new antiasthmatic agents with dual antagonistic activity against thromboxane A2 (TXA2) and leukotriene D4 (LTD4) receptors, synthesis and pharmacological evaluation of various [4-[1-(benzenesulfonamido)-alkyl]phenyl]alkanoic acid derivatives were undertaken. TXA2 and LTD4 antagonistic activities in vitro were evaluated by measuring the inhibitory effects on U-46619-induced contraction of guinea-pig trachea and LTD4-induced contraction of guinea-pig ileum and trachea. Several compounds showed satisfactory dual antagonistic activities, and their effect (after oral administration) on LTD4-induced bronchoconstriction in guinea-pig in vivo was examined. The results demonstrated that both 4-[4-[1-(4-chlorobenzenesulfonamido)hexyl]phenyl]butyric acid (12e) and 4-[4-[1-(4-chlorobenzenesulfonamido)-5-methylhexyl]phenyl]butyric acid (12m) possessed good anti-LTD4 activities. Compounds 12e and 12m were then evaluated for other related pharmacological effects involving the arachidonic acid cascade. These compounds appear to be hybrid eicosanoids antagonists having antagonistic activity against contraction of guinea-pig trachea induced by prostaglandin D2 (PGD2) and PGF2α, as well as TXA2 and LTD4 antagonistic activities.View full abstractDownload PDF (1780K) -
Hirosato EBIIKE, Kaori MARUYAMA, Yukiyoshi YAMAZAKI, Yoshihiko HIROSE, ...1997 Volume 45 Issue 5 Pages 863-868
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChiral 4-aryl-1, 4-dihydro-2, 6-dimethyl-3, 5-pyridinedicarboxylates and 1, 4-dihydro-2, 4, 6-trimethyl-3, 5-pyridinedicarboxylate have been obtained in 80-99%ee by lipase-catalyzed hydrolysis of bis(acyloxymethyl) 1, 4-dihydro-3, 5-pyridinedicarboxylate in an H2O/organic solvent system. These chiral dihydropyridines were readily converted into chiral drugs, such as nicardipine, felodipine and PCA 4248.View full abstractDownload PDF (1026K) -
Hirosato EBIIKE, Kaori MARUYAMA, Yumi OZAWA, Yukiyoshi YAMAZAKI, Kazuo ...1997 Volume 45 Issue 5 Pages 869-876
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOptically active 2-hydroxymethyl-1, 4-dihydropyridines were obtained by lipase-catalyzed hydrolysis or transesterification of racemic materials. Chiral NB 818 and nilvadipine have been synthesized from chiral 2-hydroxymethyl-1, 4-dihydropyridine. On the other hand, chiral 1, 4-dihydropyridines obtained from prochiral substrates have been converted into (S)-NB 818 and (R)-nilvadipine via regioselective bromination of methyl groups under mild conditions.View full abstractDownload PDF (1064K) -
Masayuki YOSHIKAWA, Hiromi SHIMADA, Hajime KOMATSU, Tetsuo SAKURAMA, N ...1997 Volume 45 Issue 5 Pages 877-882
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new olean-12-ene-type triterpene oligoglycosides, named sandosaponins A and B, were isolated from kidney bean, the seed of Phaseolus vulgaris L., together with three known saponins, soyasaponins I and V and dehydrosoyasaponin I. The structures of sandosaponins A and B were determined on the basis of chemical and physicochemical evidence, which included the chemical derivation of sandosapogenol from a known sapogenol, soyasapogenol B. Five saponins obtained from kidney bean were found to inhibit histamine release from rat exudate cells induced by an antigen-antibody reaction and, among them, sandosaponins A and B showed the most potent inhibitory activity.View full abstractDownload PDF (936K) -
Hiroshi MORITA, Young Sook YUN, Koichi TAKEYA, Hideji ITOKAWA1997 Volume 45 Issue 5 Pages 883-887
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree-dimensional structures in dimethyl sulfoxide-d6 of two cyclic heptapeptides, segetalin D(1) : cyclo (-Gly-Leu-Ser-Phe-Ala-Phe-Pro-) and segetalin E (2) : cyclo (-Gly-Try-Val-Pro-Leu-Trp-Pro-), which have been isolated from the seeds of Vaccaria segetalis, were elucidated by computational and NMR methods. Distance geometry calculations using nuclear Overhauser effect (NOE) constraints resulted in uniquely determined backbone conformations of segetalins D and E : each had two β-turns, a βII turn at Pro7-Gly1 and a βI turn at phe4-Ala5 for segetalin D, and a βII turn at Pro7-Gly1 and a βVI turn at Val3-Pro4 for segetalin E, respectively. In addition, each had three intramolecular hydrogen bonds, which constructed a classical β-bulge conformation, as suggested by calculations and NMR studies.View full abstractDownload PDF (723K) -
Meselhy R. MESELHY, Norio NAKAMURA, Masao HATTORI1997 Volume 45 Issue 5 Pages 888-893
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe biotransformation of (-)-epicatechin 3-O-gallate (1) and related compounds was undertaken using a human fecal suspension. Of fifteen metabolites isolated, four compounds were new, namely, two epimers of 1-(3'-hydroxyphenyl)-3-(2", 4", 6"-trihydroxyphenyl)propan-2-ols (6, 19); 2", 3"-dihydroxyphenoxyl 3-(3', 4'-dihydroxyphenyl)propionate (14) and 1-(3', 4'-dihydroxyphenyl)-2-(2", 4", 6"-trihydroxyphenyl)propan-2-ol (18).(-)-Epicatechin (2), (-)-epigallocatechin (16) and their 3-O-gallates (1, 17) were extensively metabolized by a human fecal suspension after incubation for 24h, whereas the gallates (1, 17) resisted any degradation by a rat fecal suspension, even after a prolonged incubation time (48h), suggesting a difference in metabolic ability between two intestinal bacterial mixtures from different species.View full abstractDownload PDF (931K) -
Makoto OTSUKA, Hitoshi HASEGAWA, Yoshihisa MATSUDA1997 Volume 45 Issue 5 Pages 894-898
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of a solvent system on the pharmaceutical properties of carbamazepine (CBZ) granules containing a polymorphic form of bulk powder were investigated by X-ray diffraction analysis, thermal analysis, mercury porosimetry and Brunauer-Emmett-Teller (BET) surface area measurement. A powder mixture consisting of 20% CBZ form I, as a bulk powder, 56% crystalline α-lactose monohydrate and 24% corn starch was used as a pharmaceutical powder, with the three kinds of binder solutions (distilled water, 50% aqueous ethanol and ethanol) containing 5% hydroxypropylcellulose (HPC). After kneading with a binder solution, the granules were obtained using an extruding granulator. The X-ray diffraction and differential scanning calorimetry (DSC) results of the granules indicated that form I with 50% ethanol solution transformed into a dihydrate form during extruding granulation, but this did not occur with the distilled water or ethanol solutions. The order of hardness and specific surface area (Sw) of the granules was distilled water>50% ethanol>ethanol and 50% ethanol>ethanol>distilled water. The stress-thickness profiles of the tabletting compression processes of CBZ granules obtained using various binder solution systems were measured, and the initial compression process due to particle rearrangement was affected by the characteristics in the granules. The total pore volume of tablets obtained from 50% ethanol was the lowest, and their order was ethanol>distilled water>50% ethanol. Their order of tablet hardness reflected the total pore volume of the tablet, and was 50% ethanol>distilled water>ethanol. All pharmaceutical properties of the granules and/or tablets containing CBZ were affected by the characteristics of the solvent systems in binder solution.View full abstractDownload PDF (747K) -
Juziro NISHIJO, Yuko USHIRODA, Hiroe OHBORI, Makiko SUGIURA, Noriko FU ...1997 Volume 45 Issue 5 Pages 899-903
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction of 1-naphthalenesulfonate (1-NS) with β-cyclodextrin was investigated in a 0.1M phosphate buffer at pH7.4 by an LKB 2277 microcalorimeter, using a flow-mixed mode at 25°C. The thermodynamic parameters for inclusion complex formation obtained are as follows : ΔG°=-13.2kJ/mol (K=209M-1), ΔH°=-1.87kJ/mol, ΔS°=38.1J/mol K. The main driving force for inclusion complex formation was considered to be the hydrophobic interaction, whereas the contribution of the van der Waals-London dispersion force was minor. Also, from measurements of the proton nuclear magnetic resonance spectra and the model building with Corey-Pauling-Koltum atomic models, the probable structures of the inclusion complex were determined.View full abstractDownload PDF (772K) -
Toru MAEJIMA, Takashi OSAWA, Kingo NAKAJIMA, Masao KOBAYASHI1997 Volume 45 Issue 5 Pages 904-910
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe tumbling melt granulation (TMG) method by a centrifugal fluidizing granulator (CF) without any use of organic solvents was applied as a coating technique for preparing controlled-release spherical beads. The core beads containing four kinds of drugs with different solubilities : nicotinamide (NA), isoniazid (ISA), theophiline (THEO) and salicylic acid (SA), were driven in the CF and were previously heated at 61-63°C before feeding powdered hydrogenated castor oil (HCO) to the CF. HCO was gradually fed and adhered on the surface of the core beads. At the bed temperature of 61-63°C, about 20% of the HCO was presumed to have melted. After the adherence of HCO, the coated beads were cooled at room temperature and thus the controlled-release beads were obtained. The dissolution rates of these coated beads were determined by use of the JP paddle method. The rates seemed to increase with an increase in the solubility of the drug. To clarify the mechanism of drug transport through the coated layer of HCO, the superposition method was applied for the dissolution profile of the coated beads with various coating levels. Then, in each of ISA, THEO, and SA, the dissolution curves were superposed completely, irrespective of their coating level. Permeability coefficients, P values of each drug calculated for various pH media, were coincident, irrespective of pH. These facts indicated that the limiting factor of the dissolution of HCO coated beads was diffusion, and that the permeability of the coated layer was pH independent. The equilibrium P values decreased with the increase in solubility of the drug. The partition coefficient between the layer surface and inner core medium, activity coefficient, viscosity, diffusion through waxy phase and so on, might be attributed to these phenomena.View full abstractDownload PDF (972K) -
Fridrun PODCZECK1997 Volume 45 Issue 5 Pages 911-917
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAdhesion and friction forces are the main physical factors determining the re-suspension of a micronized drug from carrier particles during inhalation. Hence, it appears useful to link adhesion and friction force measurements to the in vitro testing of dry powder inhalations, namely the assessment of the mass median aerodynamic diameter (MMAD) using an eight-stage Andersen cascade impactor. Interactive mixtures of micronized Salmeterol Xinafoate adhered to irrespirable lactose monohydrate carrier particles were used as model dosage forms. The adhesion force between the drug and carrier particles was assessed using a centrifuge technique, and the MMAD was determined under standardized working conditions using the Andersen-Cascade impactor (Mark II). A cascade impactor simulator (CIS), which is a computer programm containing a re-suspension model to assess the amount of drug detached from the carrier particles during inhalation, was developed and validated using the experimental data. It could be shown, that the CIS provided a good estimate of the loss of drug due to adhesion to the carrier particles and the loss of drug on the cascade impactor walls. Small deviations between the theoretical and experimental mass median aerodynamic particle diameters however were found. These deviations were shown to be mainly due to the experimental error introduced by the cascade impactor, and that the error due to the exoperimental adhesion measurements is negligibly small. Hence, the CIS developed could be a useful tool in early development stages of dry powder inhalations to predict the in vitro aerodynamic performance of drug particles.View full abstractDownload PDF (1167K) -
Naomi YAGI, Takashi KIUCHI, Hayato SATOH, Yohko ISHIKAWA, Masahiko TAK ...1997 Volume 45 Issue 5 Pages 918-922
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSustained release granules of bumetanide (BN) were prepared to obtain mild and sustained diuresis. BN was dispersed in combined matrixes of ethylcellulose (EC) with hydroxypropylmethylcellulose phthalate (HPMCP), povidone (PVP) or cyclodextrins (CDs). Release of BN from these preparations was evaluated by the JP XIII dissolution test in JP disintegration media No. 1 (pH 1.2) and No. 2 (pH 6.8) at 37°C. The interaction of BN with CDs in buffer solutions with different pHs was also investigated, and BN from the preparation with the component of BN : γ-CD : EC=1 : 4 : 2 (weight ratio) showed the most favorable sustained release pattern. The apparent stability constant of the γ-CD system on the BN solubility was greater than those of the α- or β-CD systems. Crystalline BN was not observed in this system in studies using powder X-ray diffraction spectra and a differential scanning calorimeter.View full abstractDownload PDF (646K) -
Ryuji NIWA, Ryusei KONAKA, Midori HIRAMATSU, Hitoshi KAMADA1997 Volume 45 Issue 5 Pages 923-927
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSpin labels (7, 10, 13, 16, 22, 27) were synthesized from piperidinyloxyl (1), pyrrolidinyloxyl (2), and oxazolidinyloxyl (3). These compounds were injected into the carotid artery of anesthetized rats, and the ESR spectra of the rat brain were immediately recorded by the use of an L-band ESR spectrometer. Based on the spectra obtained, we considered whether or not these spin labels can pass the blood brain barrier and bind to brain tissue components.View full abstractDownload PDF (633K) -
Michiharu SUGIURA, Koosuke ASAI, Yoshiki HAMADA, Keiichiro HATANO, Yuk ...1997 Volume 45 Issue 5 Pages 928-931
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 2-acyl (or sulfonyl)-1-cyano-1, 2-dihydroisoquinolines with bromine and CH3OH gave 2-acyl (or sulfonyl)-4-bromo-1-cyano-3-methoxy-1, 2, 3, 4-tetrahydroisoquinolines in a highly stereoselective manner in high yields. The stereochemistry, with 1, 4-cis and 3, 4-trans configurations, was determined by X-ray crystallography.View full abstractDownload PDF (558K) -
Kazuyuki MIYASHITA, Katsunori KONDOH, Katsutoshi TSUCHIYA, Hideto MIYA ...1997 Volume 45 Issue 5 Pages 932-935
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral 2-trifluoromethyl derivatives of biologically active indoles, tryptamine, indole-3-acetic acid, oxypertine and tryptophan, were synthesized starting from 2-trifluoromethylindoles by use of the Mannich reaction and subsequent nucleophilic substitution reaction as key steps. In this study, chemoselective hydrolysis and reductions of the nitrile group to the respective carboxylic acid, amine and aldehyde in the presence of the trifluoromethyl group were achieved.View full abstractDownload PDF (682K) -
Koh-ichi YAMADA, Rieko ISHII, Hiroko NAKAGAWA, Hiroshi KAWAZURA1997 Volume 45 Issue 5 Pages 936-938
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRecemic 2-hydroxymethyltrithia[5]heterohelicene (2-HT), which has a labile helical structure was incorporated into serum albumins of nine species in 1% ethanolic aqueous solution, giving 1 : 1 complexes which exhibited induced circular dichroism spectra with species specificity. The application of 2-HT to bovine serum as a probe for chiral recognition revealed that the serum itself manifested an apparent chiral discrimination between enantiomers of 2-HT.View full abstractDownload PDF (480K) -
Masaru KIHARA, Motoki IKEUCHI, Aiko YAMAUCHI, Mamoru NUKATSUKA, Hirosh ...1997 Volume 45 Issue 5 Pages 939-943
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA phenolic 3, 4-diphenyl-1, 2-dihydroisoquinoline derivative (4a) as a new 4-hydroxytamoxifen analogue and a related compound (4c) were synthesized from 3, 4-diphenyl-1, 2, 3, 4-tetrahydroisoquinolin-ols (5a, c), which were prepared by intramolecular Barbier reaction of N-(2-iodobenzyl)phenacylamines. Anti-proliferative activities of 4a, c and 5a, c, as well as 4b and 5b prepared previously, against human mammary carcinoma MCF-7 cell line and human nasopharyngeal carcinoma KB cell line were evaluated. The 3, 4-diphenyl-1, 2-dihydroisoquinoline derivatives (4a, c) and isoquinolin-4-ols (5a, b) were active against MCF-7 cells and were nearly equipotent to the corresponding nonphenolic compound (1a). The mechanism of the anti-proliferative activity of 4a-c against MCF-7 cells is discussed.View full abstractDownload PDF (740K) -
Masa NAGANO, Junko YAMADA, Tomoko YAZAKI-YAGI, Masuo MORISAKI, Takayos ...1997 Volume 45 Issue 5 Pages 944-946
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFeeding of [26-13]desmosterol and [26-13C]Δ25(26)-cholesterol to cultured cells of Oryza sativa and hairy roots of Ajuga reptans var. atropurpurea followed by 13C-NMR analysis of the resulting 13C-labeled cholesteroldemonstrated that hydrogen introduction at C-25 occurs on the Si-face of desmosterol and on the Re-face of Δ25(26)-cholesterol.View full abstractDownload PDF (421K) -
Yoshiyasu FUKUYAMA, Atsuko KUWAYAMA, Hiroyuki MINAMI1997 Volume 45 Issue 5 Pages 947-949
Published: May 15, 1997
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGarsubellin A (1), a novel polyprenylated phloroglucin derivative, has been isolated from the wood of Garcinia subelliptica and its structure has been elucidated by spectroscopic analyses. Compound 1 could increase the ChAT activity at 10μM in P10 rat septal neuron cultures.View full abstractDownload PDF (449K)
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