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Volume 42, Issue 12
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Yuko YOSHIKAWA, Hiroshi TERADA1994 Volume 42 Issue 12 Pages 2407-2411
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIon-pair partition of methyl orange anion with aminoalkanol and alkylamine cations between n-octanol and buffer solution was studied under various conditions. Transfer of methyl orange from the aqueous to the octanol phase increased with increase in the concentration of amines, and with increase in their alkyl chain length. The ion-pair partition consists of two steps : formation of the ion-pair complex in the aqueous phase and its transfer into the octanol phase. Although the ion-pair formation constant was almost independent of alkyl chain length of the amine and temperature, the ion-pair partition coefficient increased with increase in the chain length, both of these parameters being greater with alkylamines than with aminoalkanols. From the values of thermodynamic parameters, the mechanism of ion-pair partition of methyl orange with amine cation was discussed.View full abstractDownload PDF (740K) -
Shin-ichi KONDO, Katsuyuki MURASE, Masayuki KUZUYA1994 Volume 42 Issue 12 Pages 2412-2417
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHydrophilic polymeric prodrugs have been prepared by the mechanochemical copolymerization of methacryloyl derivatives of bioactive compounds with acrylamide, which is a hydrophilic conventional vinyl monomer. The polymeric prodrugs homogeneous in composition, since mechanochemical copolymerization is ideal copolymerization under the present experimental conditions. It is also shown that the polymeric prodrugs have a narrow molecular weight distribution.The alkaline hydrolysis of polymeric prodrugs prepared by mechanochemical copolymerization has been examined in a heterogeneous system. Though the degree of hydrolysis of polymeric prodrugs increases with increasing the content of hydrophilic monomer in the copolymer, there exists a limit to the degree of hydrolysis attainable due to the retardation by the carboxylic group produced as a side chain of the polymer hydrolyzate. The rate of hydrolysis depended largely on the structural feature of the polymer hydrolyzate; the use of carbamoyl derivatives of bioactive compounds is valuable for improving the nature of hydrolysis, since the amino group formed with the progress of hydrolysis does not cause any retardation of the nucleophilic reaction of the hydroxyl anion.View full abstractDownload PDF (828K) -
Yoshihiro KURODA, Misako WAKITA, Terumichi NAKAGAWA1994 Volume 42 Issue 12 Pages 2418-2425
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction between amine local anesthetic dibucaine and pig erythrocyte membranes has been studied by 1H-NMR spectroscopy. Two-dimensional NOESY spectra were observed to obtain the conformations of cationic and uncharged forms of dibucaine. The NMR spectra were measured at pH 7.4, and the temperature was raised (318-348 K) to increase the concentration of the uncharged form of dibucaine, taking the temperature dependence of the pKa value of dibucaine into consideration. The dibucaine in a buffered solution showed the presence of two kinds of distinctly different species; one is assignable to the cationic form and the other to the uncharged form of dibucaine, suggesting that the protonation equilibrium between the two forms is slow in the presently employed experimental condition. The uncharged dibucaine showed well-defined NOE cross-peaks in the NOESY spectra of the solution containing no erythrocyte membranes, suggesting that its conformation is relatively fixed. Interestingly, however, it was only the cationic dibucaine that showed NOE cross-peaks when the solution contained the membranes, and expriments were performed at a much shorter mixing time for the buildup of NOEs, suggesting that it appeared only the cationic form of dibucaine is interacting with the membranes. It was concluded that the uncharged form of dibucaine, which was produced by raising the temperature, formed micelles in a buffered solution. Thus formed micelles didn't interact with membranes owing to the repulsive forces between the structured water surrounding the micelles and those at the surface of the membranes. This conclusion could be a promising reason why the cationic local anesthetics are much more active than their uncharged counterparts in blocking nerve conduction.View full abstractDownload PDF (1172K) -
Kazuhiro NOJIMA, Chiho ISOGAMI1994 Volume 42 Issue 12 Pages 2426-2429
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree toluene oxides reacted with nitrogen dioxide in air to give nitrocresols. 1-Methylbenzene oxide (1) and 3-methylbenzene oxide (2) gave the same nitrocresols, including 2-methyl-6-nitrophenol (1b) and 2-methyl-4-nitrophenol (1c), while 4-methylbenzene oxide (3) gave only 4-methyl-2-nitrophenol (3b). Irradiation with a xenon lamp through a Pyrex filter (cut-off below 290 nm) did not affect the product distribution. Only 1-methylbenzene oxide (1) generated fog when it was brought into contact with nitrogen dioxide in air.View full abstractDownload PDF (653K) -
Masayuki YOSHIKAWA, Shoko YAMAGUCHI, Hisashi MATSUDA, Nobumitsu TANAKA ...1994 Volume 42 Issue 12 Pages 2430-2435
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the water-soluble portion of Chinese Alismatis Rhizoma, four bioactive sesquiterpenes, sulfoorientalols a, b, c, and d, were isolated and their structures having a sulfonic acid function were established on the basis of chemical and physicochemical evidence. In addition, two sulfoorientalol congeners were derived from alismol by sulfonation of the exo-methylene moiety. Sulfoorientalols and the synthetic congeners were found to inhibt the carbachol-induced contraction of isolated bladder smooth muscle of guinea pig.View full abstractDownload PDF (872K) -
Yuko TAKEMURA, Motoharu JU-ICHI, Keiichiro HATANO, Chihiro ITO, Hirosh ...1994 Volume 42 Issue 12 Pages 2436-2440
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel bicoumarins named furobinordentatin (1) and furobiclausarin (3) have been isolated from the roots of Citrus yuko and C. hassaku, respectively. The structures were elucidated by single crystal X-ray analysis and/or spectroscopic studies as 1 and 3. The structural characteristic of these new bicoumarins is the presence of a tetrahydrofuran ring connecting two nordentatin or clausarin units.View full abstractDownload PDF (788K) -
Shin-ichi SHIRATORI, Shuji YASUIKE, Jyoji KURITA, Takashi TSUCHIYA1994 Volume 42 Issue 12 Pages 2441-2448
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFlash vacuum pyrolysis of 2a, 7b-dihydrocyclobuta[b]-1-benzometalloles (6a-e), prepared from the corresponding 1-benzometalloles (3) containing Si, Ge, P, or As via three steps, resulted in valence isomerization with ring-opening to give 1, 1-dimethyl-1-benzosilepine (7a), 1-methyl-1-phenyl-1-benzosilepine (7b), 1, 1-dimethyl-1-benzogermepine (7c), 1-phenyl-1-benzophosphepine 1-oxide (7d), and 1-phenyl-1-benzarsepine 1-oxide (7e). The oxides (7d, e), on treatment with trichlorosilane, underwent deoxygenation to afford 1-phenyl-1-benzophosphepine (7f) and 1-phenyl-1-benzarsepine (7g). The 1-benzometallepines (7a-g) thus obtained are hitherto unknown heterocyclic ring compounds, and their thermal stabilities and several reactions were examined.View full abstractDownload PDF (1138K) -
Motomasa KOBAYASHI, Shunji AOKI, Katsuhiko GATO, Katsuyoshi MATSUNAMI, ...1994 Volume 42 Issue 12 Pages 2449-2451
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new antibiotic indole trimer named trisindoline (1) was isolated, together with a known dioxopiperazine brevianamide F (2), from the culture of a bacterium of Vibrio sp., which was separated from the Okinawan marine sponge Hyrtios altum. The structure of trisindoline (1) has been determined on the bases of physicochemical evidence and chemical synthesis.View full abstractDownload PDF (574K) -
Noriaki KASHIWABA, Shigeo MOROOKA, Michiko KIMURA, Yoshie MURAKOSHI, J ...1994 Volume 42 Issue 12 Pages 2452-2454
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new morphinane alkaloids named cephamonine (1) and cephamuline (2) were isolated from the tuber of Stephania cepharantha HAYATA (Menispermaceae), cultivated in Japan, along with eleven known alkaloids. By comparison of spectroscopic data with those of sinomenine (3), the structures of 1 and 2 were elucidated to be the 8-methoxy derivative of 3 and its C-14 stereoisomer, respectively.View full abstractDownload PDF (514K) -
Kazuko YOSHIKAWA, Hitomi TANINAKA, Yukiko KAN, Shigenobu ARIHARA1994 Volume 42 Issue 12 Pages 2455-2460
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fresh stem of Stephanotis lutchuensis var. japonica, five new oleanate-type triterpenoid glycosides named sitakisosides VI-X (1-5) were isolated. Their structures were determined on the basis of spectroscopic data and chemical evidence. Sitakisosides VI and VII are 3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosido-21-O-(6-N-methylanthranilyl)-β-D-glucopyranosyl and 3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosido-21-O-(4-N-methylanthranilyl)-β-D-glucopyranosyl sitakisogenin, respectively. Sitakisoside VIII is 3-O-β-d-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosido-21-O-N-methylanthranilyl-3β, 16β, 21β, 28-tetrahydroxyolean-12-ene-22-one. Sitakisoside IX is 3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosido-21-O-(6-N-methylanthranilyl)-β-D-glucopyranosyl gymnestrogenin. Sitakisoside X is 3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl longispinogenin.View full abstractDownload PDF (898K) -
Tozo FUJII, Tohru SAITO, Jun CHIKAZAWA, Yuko NAKAMURA, Masashi OHBA1994 Volume 42 Issue 12 Pages 2461-2466
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour-step synthetic routes from 3-methyladenine (10) to 7-benzyl-N6, 3-dimethyladenine (1b) and 7-benzyl-1, 2-dihydro-1, 3-dimethyladenine (2b), selected as models for the marine sponge alkaloids agelasimine-A (1a) and agelasimine-B (2a), respectively, have been established. The key steps involved are regioselective methylations of 7-benzyl-3-methyladenine (8) and 7-benzyl-1, 2-dihydro-3-methyladenine (11). The reaction of 1b with acetic anhydride in pyridine was found to give the monocyclic imidazole derivative 29b. A similar acetylation of 2b yielded the N6-acetyl derivative 20b. When treated with boiling H2O, 20b afforded 7-benzyl-2, 3-dimethylhypoxanthine (21b) and a compound inferred to be the dihydrohypoxanthine derivative 30. Probable pathways to 29b from 1b and to 21b and 30 from 20b are proposed.View full abstractDownload PDF (939K) -
Haruki MATSUMURA, Yoshihito NOZAKI, Makoto SUNAGAWA1994 Volume 42 Issue 12 Pages 2467-2471
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of the 1β-methylcarbapenem key intermediate 2 from the enamino ketone 6 was investigated. Stereoselective reduction of 6 and effective lactonization of the crude reduction product are described. The methyl group in 6 was shown to play an important role in these steps.View full abstractDownload PDF (717K) -
Masahiro MAKINO, Shin OHTA, Hiroshi ZENDA1994 Volume 42 Issue 12 Pages 2472-2474
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the previous paper, we described the synthesis of new quaternary ammonium salts with antimicrobial activity : N-alkyl-N-2-hydroxyethyl-N, N-dimethylammonium butyl phosphate (4) and N-alkyl-N-(2-hydroxy-3-phenoxyl)-propyl-N, N-dimethylammonium butyl phosphate (5). In this study, we examined the relationship between the MIC (minimum inhibitory concentration) of these new cationic disinfectants, 4 (six compounds) and 5 (three compounds), and the ζ-potential against Escherichia coli in solutions of these compounds. The MIC values of these disinfectants against E. coli were highly correlated with the concentration that induced electric charge inversion (ζ-potential=0) of E. coli from negative to positive.View full abstractDownload PDF (528K) -
Tatsuo NAKAJIMA, Toshio IZAWA, Tomoko KASHIWABARA, Shohachi NAKAJIMA, ...1994 Volume 42 Issue 12 Pages 2475-2482
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious heteroaromatic cyanoamidines were synthesized starting from nitriles via cyanoimidates or from amides via thioamides. The compounds were tested for inhibitory effect on the 40 mM K+-induced contraction of rat aorta strips and selected compounds were also evaluated for antagonism of the norepinephrine-induced contraction. Most of the cyanoamidines showed vasodilatory activities. Potent vasoactive compounds were also examined for stimulation of the 86Rb+ efflux to determine their potassium channel opening actions. Maximum potency was displayed by N-cyano-N'-(2-nitroxyethyl)-3-pyridinecarboxyamidine (3h). The methanesulfonate of 3h, which was designated as KRN2391, has been selected for further development as an antianginal agent.View full abstractDownload PDF (1171K) -
Tatsuo NAKAJIMA, Shohachi NAKAJIMA, Toshio IZAWA, Tomoko KASHIWABARA, ...1994 Volume 42 Issue 12 Pages 2483-2490
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new series of cyanoamidines, N-arylalkyl-N'-cyano-3-pyridinecarboxyamidines was synthesized and evaluated for inhibitory effects on 40 mM KCl-induced contraction and norepinephrine (NE)-induced contraction of rat aorta strips. The N-phenethyl cyanoamidine 4c showed potent vasodilatory action. Further in vitro screening program using 4c as a lead compound resulted in the discovery of highly potent N-[2-(2-chlorophenyl)ethyl]-N'-cyano-3-pyridinecarboxamidine (5j). Compound 5j induced the greatest increase in 86Rb+ efflux among cyanoamidine series. Subsequent modification of the pyridine ring of 5j was performed with evaluation for intravenous and oral antihypertensive activities. Introduction of an amino group at the 5-position of the pyridine ring furnished the new potassium channel opener, 5-amino-N-[2-(2-chlorophenyl)ethyl]-N'-cyano-3-pyridinecarboxamidine (9e; KRN4884), which showed highly potent antihypertensive activity and a long duration of antihypertensive action after oral administration. KRN4884 is under further development as an antihypertensive agent.View full abstractDownload PDF (1046K) -
Michiko NAGAHARA, Jun NAKANO, Mitsuo MIMURA, Tsutomu NAKAMURA, Katsuhi ...1994 Volume 42 Issue 12 Pages 2491-2499
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious azaazulene derivatives were synthesized and their antiallergic activity was examined. The structure-activity relationship among various derivatives modified by introducing substituents at the 1-, 2-, or 3-position of the azaazulene ring was investigated.The inhibitory activities on allergic histamine release of the compounds bearing a 5-tetrazolyl group at the 3-position were more potent than those of the corresponding compounds with other groups (CN, COOH, and CHO). The compounds substituted with amino, azide and carboxymethylamino groups at the 2-position showed strong inhibitory activity. The compounds with various phenylalkyl groups at the 1-position showed a greater activity than those with other substituents. Among the compounds with substituents at the 1-, 2-, or 3-position of the azaazulene ring, 1-benzyl-7-isopropyl-3-(5-tetrazolyl)-1-azaazulen-2-one (18f) and 1-(4-fluorobenzyl)-7-isopropyl-3-(5-tetrazolyl)-1-azaazulen-2-one (19c) had the most potent inhibitory activities on histamine release from mast cells and on passive cutaneous anaphylaxis (PCA) in rats after oral administration (ED50=0.56 and 0.58 mg/kg, respectively).View full abstractDownload PDF (1110K) -
Shirou MAEDA, Hiroshi MASUDA, Takashi TOKOROYAMA1994 Volume 42 Issue 12 Pages 2500-2505
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe parent benzofuran lignan 4 of schizotenuins 1-3 and related compounds were efficiently prepared by a judicious use of the oxidative coupling reaction, and were tested for their inhibitory effects on lipid peroxidation in rat brain homogenate and rat liver microsomes. Among twelve compounds tested in rat brain homogenate, compounds 13, 14 and 16 showed prominent inhibitory activity. Compounds 13 and 16 were then tested in rat liver microsomes, and their activity was found to be more potent than schizotenuin A (1) and much more potent than that of (±)-α-tocopherol.View full abstractDownload PDF (834K) -
Shirou MAEDA, Hiroshi MASUDA, Takashi TOKOROYAMA1994 Volume 42 Issue 12 Pages 2506-2513
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxidative coupling reaction of methyl (E)-3-(4, 5-dihydroxy-2-methoxyphenyl)propenoate (10), obtainable from esculetin, has been studied using silver oxide and potassium hexacyanoferrate(III). The products were separated, after acetylation, by silica gel column chromatography. 1-Aryl-1, 2-dihydronaphthalene derivative 12 was obtained as a major product, accompanied by the benzo[kl]xanthene derivative 13. In the oxidation with silver oxide, a benzodioxane compound 14a was produced additionally in a minor amount. Thus, the course of the reaction differed notably from those of ferulic or caffeic acid derivatives.The compounds 11, 12, 13 and 14a were tested for their inhibitory effects on lipid peroxidation in rat brain homogenate and rat liver microsomes. They showed activities more effective than that of idebenone in rat brain homogenate, and were found to be more potent than benzofuran lignans 4 and 5, and much more potent than (±)α-tocopherol in rat liver microsomes.View full abstractDownload PDF (1060K) -
Hitoshi ISHIDA, Nobu YAMAMOTO, Haruo NUKAYA, Kuniro TSUJI, Takuo KOSUG ...1994 Volume 42 Issue 12 Pages 2514-2517
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSodium chimaerol sulfate (1) was isolated from the bile of Lamna ditropis and Rhizoprionodon acutus by chromatography on silica gel and Sephadex LH-20, together with sodium scymnol sulfates, (24R, 25S)- and (24R, 25R)-(+)-3α, 7α, 12α, 24, 26-pentahydroxy-5β-cholestan-27-yl sodium sulfates (3 and 4) and 3, respectively. On acid hydrolysis, compound 1 afforded chimaerol (2), which was identified as (24R, 25R)-(+)-5β-cholestane-3α, 7α, 12α, 24, 26-pentol by direct comparison with an authentic sample, prepared by reduction of (24R, 25S)-(+)-24, 26-epoxy-5β-cholestane-3α, 7α, 12α, 27-tetrol (5) with LiAlH4. The structure of 1 was concluded to the (24R, 25R)-(+)-3α, 7α, 12α, 24-tetrahydroxy-5β-cholestan-26-yl sodium sulfate, based on the chemical transformation and spectral data.View full abstractDownload PDF (722K) -
Takashi YAEGASHI, Seigo SAWADA, Hiroshi NAGATA, Tomio FURUTA, Teruo YO ...1994 Volume 42 Issue 12 Pages 2518-2525
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwenty-six novel A-ring-modified 7-ethylcamptothecins (6) were synthesized by Friedlander's condensation of the chiral tricyclic ketone (5) with aminopropiophenones (4). The compounds substituted with fluorine at the 11 position showed strong cytotoxicity to KB and L1210 cells. The 11-fluoro derivatives also exhibited strong inhibitory activity on DNA topoisomerase I. Nine compounds 6 with four to ten times stronger cytotoxicity than that of camptothecin were selected and converted into water-soluble 17-O-acyl amide derivatives (8). Compounds 8e (10-Me, O-COCH2CH2SCH3) and 8f (11-F, O-COC2H5) showed activity towards Meth A in mice that was comparable to that of CPT-11, at lower doses than CPT-11.View full abstractDownload PDF (1123K) -
Yoshitomo SUHARA, Misa ARAKAWA, Kiyoshi IKEDDA, Kazuo ACHIWA1994 Volume 42 Issue 12 Pages 2526-2531
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew β-N-acylated L-asparagine-linked D-glucosamine derivatives, in which the reducing unit of lipid A has been mimicked by a lipoamino acid, have been synthesized. Compounds 1 and 2 exhibit mitogenicity and nitric oxide (NO) productivity.View full abstractDownload PDF (1001K) -
Hitoshi ISHIDA, Shunya KINOSHITA, Nobu YAMAMOTO, Haruo NUKAYA, Kuniro ...1994 Volume 42 Issue 12 Pages 2532-2535
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of scymnol, chimaerol and sodium scymnol sulfate, prepared from the bile of Rhizoprionodon acutus, on cerebral anoxia were investigated in experimental models of hypoxia, ischemia and histotoxic anoxia in mice. Scymnol, at a dose of 100 mg/kg, showed a significant protective action against cerebral anoxia in all of the models studied and significantly increased the partial oxygen pressure of the arterial blood. The anti-anoxic actigvity of scymnol was found to be slighly greater than that of idevenone. A similar protective effect of sodium scymnol sulfate was seen at does higher than 100 mg/kg. The survival time on hypoxia was significantly prolonged in the animals pretreated with chimaerol.View full abstractDownload PDF (628K) -
Shirou MAEDA, Hiroshi MASUDA, Takashi TOKOROYAMA1994 Volume 42 Issue 12 Pages 2536-2545
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree dihydrobenzofuran derivatives 11, 19, 22, a Pummere's ketone 20 and a dimeric phenylpropanoid 24 were synthesized by oxidative coupling reaction of methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate 10, which was prepared from umbelliferone. The major product 11 was converted into its acetate 21 and schizotenuin D analogs 27, 28, 29. A new coumestan derivative 13 was synthesized from 29. Ten synthetic compounds thus obtained were tested for inhibitory effects on lipid peroxidation in rat brain homogenate.View full abstractDownload PDF (1282K) -
Masayuki KATO, Kiyotaka ITO, Shigetaka NISHINO, Hisashi YAMAKUNI, Hisa ...1994 Volume 42 Issue 12 Pages 2546-2555
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of pyrido[1, 2-α]indol-6(7H)-ones was prepared and evaluated for 5-HT3 receptor antagonist activity. The structural requirements for the 5-HT3 receptor antagonist have been defined as an aromatic moiety, a basic nitrogen, and a linking acyl group. The (5-methylimidazol-4-yl)methyl group as a basic nitrogen moiety was an important element for high potency. The highest potency was observed for compounds which have 7- and 10-methyl substituents on the pyrido[1, 2-α]indol-6(7H)-one ring. From this series, (+)-11b (FK 1052) was selected for further evaluation. FK 1052 was a potent 5-HT3 receptor antagonist in the Bezold-Jarisch reflex test in rats (ED50 0.9 μg/kg, i.v.) and a very effective antiemetic agent against cisplatin-induced emesis in dogs (ED50 1.1×2 μg/kg, i.v. and 2.7×2 μg/kg, p.o.).View full abstractDownload PDF (1449K) -
Masayuki KATO, Shigetaka NISHINO, Kiyotaka ITO, Hisashi YAMAKUNI, Hisa ...1994 Volume 42 Issue 12 Pages 2556-2564
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of pyrimido[1, 6-α]indol-1(2H)-ones was prepared and evaluated for 5-HT3 receptor antagonist activity. The compounds in this series were regarded as bioisosters of the pyrido[1, 2-α]indol-6(7H)-ones previously reported. High potency was found for compounds having 5-methyl substituents on both the pyrimido[1, 6-α]indole ring and the imidazole ring. Optimized members of this series, 8b and (+)-26a, were potent 5-HT3 receptor antagonists as determined by measuring inhibition of the Bezold-Jarisch reflex in anesthetized rats (ED50 0.6 and 0.8 μg/kg i.v., respectively), being equipotent to or more potent than FK 1052 (1) in the previous paper and 20- to 30-fold more potent than ondansetron (2).View full abstractDownload PDF (1277K) -
Kiyoshi SUGIYAMA, Harumi UEDA, Yoshitomo SUHARA, Yasuhiro KAJIMA, Yosh ...1994 Volume 42 Issue 12 Pages 2565-2568
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of ingredients of Shi-Quan-Da-Bu-Tang (Juzen-taiho-to) on the nephrotoxicity and bone marrow toxicity caused by i.p. administration of 3 mg/kg cis-diamminedichloroplatinum (II) (CDDP) 9 times (on days 3, 4, 5, 6, 7, 8, 10, 11, 12) were examined in ddY mice s.c. inoculated with sarcoma 180 (S-180) cells on day 1. Angelicae Radix showed the strongest protective effect against the toxicity among the ingredients. The ED50 of a water extract of Angelicae Radix was 17.8 mg/kg for nephrotoxicity (indicated by an increase in blood urea nitrogen) and 59.4 mg/kg for bone marrow toxicity (indicated by a decrease in white blood cell count), when it was administered perorally (p.o.) on days 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15. The water extract did not exert any significant effect on the antitumor activity of CDDP. Bioassay-directed fractionation of the water extract resulted in isolation of a constituent having protective effects against the toxicity : sodium L-malate, C4H4Na2O5, was found to exhibit protective effects against both nephrotoxicity (ED50 : 0.4 mg/kg, p.o.) and bone marrow toxicity (ED50 : 1.8 mg/kg, p.o.), without reducing the antitumor activity of CDDP. These findings indicate that Angelicae Radix and its constituent sodium L-malate could provide significant protection against CDDP-induced nephrotoxicity and bone marrow toxicity without reducing the antitumor activity.View full abstractDownload PDF (735K) -
Yozo TODO, Hiroyasu TAKAGI, Fumihiko IINO, Yoshikazu FUKUOKA, Masahiro ...1994 Volume 42 Issue 12 Pages 2569-2574
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of the title compounds listed in Chart 1 have been synthesized to study the effects of 3-alkyl substituents on the antibacterial potency and in vivo efficacy of 10-(1-aminocyclopropyl)-9-fluoro-7-oxo-2, 3-dihydro-7H-pyrido[1, 2, 3-de]-1, 4-benzoxazine-6-carboxylic acid and its 1-thio and 1-aza variants. Compound (S)-1, which proved most active in vitro against five representative gram-positive and gram-negative organisms, was assayed in vivo using Staphylococcus aureus and Pseudomonas aeruginosa mouse infection models. It exhibited an excellent in vivo efficacy, being superior to ofloxacin and ciprofloxacin, and was then assayed for convulsion-inducing activity, mammalian cell cytotoxicity, and topoisomerase II inhibition. The biological results showed that (S)-1 displayed antibacterial and toxicological advantages over ofloxacin and ciprofloxacin. Compound (S)-1 and its methanesulfonate showed high serum concentrations after oral and intravenous administrations to mice.View full abstractDownload PDF (929K) -
Laurence EYROLLES, Emiko KAWACHI, Hiroyuki KAGECHIKA, Yuichi HASHIMOTO ...1994 Volume 42 Issue 12 Pages 2575-2581
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of new quinoline, quinolone, and quinazolinedione derivatives was synthesized and tested for retinoid activity in the human promyelocytic cell line HL-60 differentiation assay. All the quinoline compounds exhibited significant activity, depending on the substituent on the heterocycle. However, the quinolone and quinazolinedione derivatives were poor inducers of the differentiation of the HL-60 cells, the activity depending strongly on the polarity of the molecule.View full abstractDownload PDF (1080K) -
Yasushi MATSUNAGA, Nobuyuki BANDO, Hiroshi YUASA, Yoshio KANAYA1994 Volume 42 Issue 12 Pages 2582-2587
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(E)-4-[1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-(4-isopropyl)phenyl]-1-butenyl]phenyl monophosphate (TAT-59) is a new drug for the treatment of breast cancer. Physical and chemical stability of mixtures of TAT-59 and microcrystalline cellulose (1 : 9) compressed at 0, 300, 600 and 1400 kg/cm2 was evaluated by determination of water content, porosity and the amount of hydrolysis product, DP-TAT-59, formed.The water contents and porosity of these tablets scarcely changed during 57 d at 25-60°C under 50% relative humidity (RH). The degradation rate of TAT-59 increased with increasing compression pressure as well as temperature. The apparent activation energy and frequency factor were determined from an Arrhenius plot of the degradation rate. Activation energy of these tablets was almost the same, while the frequency factor tended to increase with increasing compression pressure. The porosity and pore sizes in TAT-59-containing tablets decreased with increasing compressive force. We speculated from these observations that the increase in compression pressure decreased the distance and increased the contact area between TAT-59 and microcrystalline cellulose. The proximity between TAT-59 and moisture presented at the surface of microcrystalline cellulose by compression was considered to enhance the degradation of TAT-59.View full abstractDownload PDF (661K) -
Susumu KITANAKA, Michio TAKIDO1994 Volume 42 Issue 12 Pages 2588-2590
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new bitetrahydroanthracene derivative, torosaol-III, was isolated from the flowers of Cassia torosa CAV. along with physcion, 5, 7'-physcionanthrone-physcion, 5, 7'-biphyscion, torosanin-9, 10-quinone, 5, 7-dihydroxychromone, naringenin, and chrysoeriol. The structure of torosaol-III was established as 3, 3', 4, 4'-tetrahydro-3, 3', 8, 8', 9, 9'-hexahydroxy-6, 6'-dimethoxy-3, 3'-dimethyl-1(2H), 1'(2H)-5, 7'-bianthracenone on the basis of spectral and chemical evidence. Dimeric tetrahydroanthracenes exhibited cytotoxic activity against KB cells in the tissue culture.View full abstractDownload PDF (539K) -
Midori TAKASAKI, Takao KONOSHIMA, Mutsuo KOZUKA, Mitsumasa HARUNA, Kaz ...1994 Volume 42 Issue 12 Pages 2591-2597
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new euglobals with acylphloroglucinol-monoterpene structures (C23H30O5), named euglobals-G1 (1), -G2 (2), -G3 (3), -G4 (4), and -G5 (5) were isolated from the chloroform extract of the juvenile leaves of Eucalyptus grandis W. HILL (Myrtaceae). The structures and relative stereochemistries of 1-5 have been elucidated on the basis of their two-dimensional (2D)-NMR spectra and difference in nuclear Overhauser effects (NOE) experiments.View full abstractDownload PDF (945K) -
Kazumi DANJO, Hironobu KATO, Akinobu OTSUKA, Kouichi USHIMARU1994 Volume 42 Issue 12 Pages 2598-2603
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCompaction mechanisms and the strength required for compacting granular particles are considered to be influenced by granular particle strength. A fundamental study evaluating the crushing strength of particles by various methods was performed, and value obtained by the various methods were compared. Firstly, the particle diameter and crushing load for 140 particles were measured individually, and the single particles strength (σg) was calculated. The crushing strength exponentially decreased with an increase in particle diameter up to about 500 μm, and thereafter showed a constant value.Next, the compression of multiple particles was measured. A linear relationship existed between the crushing load and the number of particles, and the average particle strength (σ^^-g) was found to be lower than σg in every sample. This may be due to a variety of factors such as the distribution of particle diameter, shape, and crushing strength in multiple particles.Finally, compaction tests of the particle bed were performed, and the parameters of some compression equations, which were recognized as values related to the particle strength were determined. The inflection points of the compression curve were also examined. The strength obtained from the first inflection point appeared to be in fairly good agreement with σ^^-g.View full abstractDownload PDF (797K) -
Yoshinobu FUKUMORI, Hideki ICHIKAWA, Kaori JONO, Hiroyuki TOKUMITSU, T ...1994 Volume 42 Issue 12 Pages 2604-2611
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMicrocapsules with a soybean lecithin coat as a short-term controlled release dosage form were successfully prepared using the Wurster process. Each of them was composed of a lactose core of 75-106 μm, a drug-layer of carbazochrome sodium sulfonate (CCSS, a model drug), soybean lecithin (SL), cholesterol (CH), stearic acid (SA) and polyvinylpyrrolidone (PVP) and a coat of SL, CH, SA and PVP. Their release properties were evaluated at 37°C in a 0.9% saline solution by a column method. When the coat lacked either or both CH and SA, the microcapsules showed rapid burst in CCSS release. However, the release of CCSS exhibited a short-term delayed and subsequently prolonged profile when the coat was composed of all of four components; the lag time and the subsequent release rate were sensitive to the composition of coat and the coating level. As a dosage form with a short-term controlled release property, the microcapsules more than 100% coated with a SL-CH-SA mixture of 5 : 5 : 2 weight ratio and 42% PVP based on this mixture were found.View full abstractDownload PDF (1707K) -
Yasuhiro TEZUKA, Qing HUANG, Tohru KIKUCHI, Arasuke NISHI, Keisuke TUB ...1994 Volume 42 Issue 12 Pages 2612-2617
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix new α-pyrone derivatives, named cladobotrins I-VI (1-3, 5, 10, 11), and a know one, rosellisin aldehyde (6), were isolated from the culture broth of a mycoparasitic fungus, Cladobotryum varium NEES et DUBY (=Didymocladium ternatum BON.). Their structures were established by spectroscopic methods including two-dimensional NMR techniques. Among the compounds obtained, three α-pyrone derivatives, having a formyl group at the C-5 position, showed inhibitory activity against the mycelial growth of a fungus, Ganoderma lucidum (FR.) KARST., the fruit bodies of which are used as the oriental crude drug "Lin-Chi".View full abstractDownload PDF (830K) -
Yasuhiro SOEJIMA, Aru AKAGI, Nobuo IZUMIYA1994 Volume 42 Issue 12 Pages 2618-2620
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMolecular rotations of Nα-acyl-L-lysines were determined in water and in water containing various amounts of HCl or NaOH. The acyl groups were formyl, acetyl, propionyl, and butyryl. Each Nα-acyl-L-lysine exhibited more negative rotation in HCl or NaOH solution than in water. The plot of molecular rotation against amount of HCl or NaOH resembled that of a D-α-amino acid even though Nα-acyl-lysine was of L-form. The reason for this is discussed from the standpoint of steric factors. Nε-Acyl-L-lysines corresponding to the Nα-acyl-L-lysines were synthesized as reference compounds. It was found that water-soluble Nε-acyl-L-lysines can be easily prepared by acylation of the Cu complex solution of L-lysine hydrochloride in the presence of triethylamine. The molecular rotation plots for Nε-acyl-L-lysines were typical of L-α-amino acids.View full abstractDownload PDF (495K) -
Yaeko KONDA, Tomomitsu SASAKI, Xue-Long SUN, Xian LI, Masayuki ONDA, H ...1994 Volume 42 Issue 12 Pages 2621-2624
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree taxane diterpenes, taxinine (1), taxinine B (2), and 2'-desacetoxyaustrospicatin (3), have been isolated from Taxus cuspidata SIEB et ZUCC. The absolute stereostructure of 3 has been determined by a combination of X-ray analysis and circular dichroism (CD) spectroscopy. Complete assignments of 1H- and 13C-nuclear magnetic resonance (NMR) signals for 1 and 2 have been made on the basis of two-dimensional (2D) NMR techniques.View full abstractDownload PDF (571K) -
Min SHI, Kenichi KAZUTA, Yukihiro SATOH, Yukio MASAKI1994 Volume 42 Issue 12 Pages 2625-2628
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSC2-Symmetric optically active pyrrolidinium salts were synthesized by the reaction of 2, 3 : 4, 5-di-O-benzylidene-(3R, 4R)-dihydroxy-(2S, 5S)-bis(hydroxymethyl)pyrrolidine (2), (3R, 4R)-dimethoxy-(2S, 5S)-bis(methoxymethyl)-pyrrolidine (3), 2, 3 : 4, 5-Di-O-benzylidene-(3R, 4R)-dihydroxy-N-(2-hydroxyethyl)-(2S, 5S)-bis(hydroxymethyl)-pyrrolidine (5), and (3R, 4R)-dimethoxy-N-(2-hydroxyethyl)-(2S, 5S)-bis(methoxymethyl)pyrrolidine (7) with methyl iodide or α, ω-dibromoalkanes. They exhibited low chiral induction activity in the epoxidation of chalcone and in the Darzens condensation of p-chlorobenzaldehyde and phenacyl chloride under phase-transfer conditions.View full abstractDownload PDF (588K) -
Yozo TODO, Hiroyasu TAKAGI, Fumihiko IINO, Kazuya HAYASHI, Makoto TAKA ...1994 Volume 42 Issue 12 Pages 2629-2632
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn economical 11-step synthesis of T-3761 (1), a new quinolone antibacterial agent discovered by us, has been developed. Commercially available 2, 3, 4, 5-tetrafluorobenzoic acid (2) has been transformed to 4-(1-acetaminocyclopropyl)-2, 3, 5-trifluorobenzoic acid (10) in 6 steps (68% yield), including cyclopropane-ring formation of the 4-cyanomethylbenzoate intermediate (6) at its side chain. Conversion of 10 to the β-keto ester 11 and a subsequent 2-step pyridoxazine annulation procedure afforded 13 (80% yield), which, on N, O-deprotection, provided 1 (48% overall yield from 2). The overall reaction sequence can be carried out without chromatographic purification of intermediates.View full abstractDownload PDF (587K) -
Akira MIYASHITA, Yumiko SUZUKI, Ken-ichi IWAMOTO, Takeo HIGASHINO1994 Volume 42 Issue 12 Pages 2633-2635
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBenzoins 4 (2-hydroxyethanones substituted with aryl groups at the 1- and 2-positions) were prepared by self-condensation of aromatic aldehydes 3 using catalytic amounts of azolium salts 1 and 2 in excellent yields.1, 3-Dimethylbenzimidazolium iodide (2) was an effective catalyst for the preparation of acyloins 6 (2-hydroxyethanones substituted with alkyl groups at the 1- and 2-positions) by self-condensation of aliphatic aldehydes 5. On the other hand, an attempt at the condensation of hexanal (5d) catalyzed by 1, 3-dimethylimidazolium iodide (1) failed to yield the acyloin 6d, and instead the aldol-type condensed product 8d was obtained.View full abstractDownload PDF (556K) -
Tomoyuki KITAZAKI, Tsuneo ASANO, Koichi KATO, Shoji KISHIMOTO, Katsumi ...1994 Volume 42 Issue 12 Pages 2636-2640
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTripeptide analogues 2 and 3 containing a dioxoethylene moiety were designed based on the characteristic structure of the naturally occurring human immunodeficiency virus (HIV)-1 protease inhibitors RPI-856 A, B, C and D (1). The compounds (2, 3) prepared showed high inhibitory activity, comparable to that of RPI-856 A, against HIV-1 protease in vitro.View full abstractDownload PDF (741K) -
Mireille MOUTIEZ, Djalal MEZIANE-CHERIF, Marc AUMERCIER, Christian SER ...1994 Volume 42 Issue 12 Pages 2641-2644
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to compare the non-enzymatic capacities of the xenobiotic conjugation of trypanothione (a spermidine-glutathione conjugate unique to kinetoplastidae) and glutathione, the reactivity of their respective thiols was investigated. The acido-basic properties of both compounds and their nucleophilicity toward Elliman's reagent and 1-chloro-2, 4-dinitrobenzene were studied. Our results show that although glutathione is a better nucleophile than trypanothione, the latter is more reactive because it is more ionized in a large pH range. This pH range likely includes the pH to which such conjugation reactions are expected to happen in vivo. Thus, the better conjugation capacity of trypanothione could make it the cornerstone for the xenobiotic detoxication of trypanosomatidae.View full abstractDownload PDF (691K) -
Sanan SUBHADHIRASAKUL, Hiromitsu TAKAYAMA, Yuhko MIYABE, Norio AIMI, D ...1994 Volume 42 Issue 12 Pages 2645-2646
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new corymine-related indole alkaloids, Na-demethylcorymine (2) and Na-demethyldeformylcorymine (4), were isolated from the leaves of Hunteria zeylanica native to Thailand. Their structures were determined by spectroscopic analysis and chemical correlation.View full abstractDownload PDF (477K) -
Shigetoshi KADOTA, Dong HUI, Purusotam BASNET, Jeevan Kumar PRASAIN, G ...1994 Volume 42 Issue 12 Pages 2647-2649
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree novel diarylheptanoids, calyxin A (1), calyxin B (2) and 3-epi-calyxin B (3), have been isolated from ethanolic extract of seeds of Alpinia blepharocalyx K. Schum. and their structures determined by the use of 2D NMR spectroscopy including NOE and HMBC experiments and chemical analyses.View full abstractDownload PDF (544K) -
Motoo TORI, Katsuyuki NAKASHIMA, Shigeru TAKAOKA, Yoshinori ASAKAWA1994 Volume 42 Issue 12 Pages 2650-2652
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFusicorrugatol, a new fusicoccane-type diterpene alcohol, has been isolated from the Venezuelan liverwort Plagiochila corrugata and its structure determined on the basis of spectroscopic evidence and X-ray crystallography.View full abstractDownload PDF (415K) -
EXPLANATION FOR STEREOSELECTIVITY OF THS CIS-DIHYDROXYLATION OF CIS-3, 5-DISUBSTITUTED CYCLOPENTENESNobuya KATAGIRI, Yumiko ITO, Kenji KITANO, Akemi TOYOTA, Chikara KANEK ...1994 Volume 42 Issue 12 Pages 2653-2655
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStereoselectivity of the cis-dihydroxylation of cis-3, 5-disubstituted cyclopentenes has been found to depend on the conformation of cyclopenetenes and has been explained by both steric and Cieplak effects.View full abstractDownload PDF (524K) -
Fumihiro NAGASHIMA, Hironao TANAKA, Shigeru TAKAOKA, Yoshinori ASAKAWA1994 Volume 42 Issue 12 Pages 2656-2658
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new 6, 7-seco-kaurane-type diterpenoids, secoexsertifolins A (1) and B (2), and a new bis-kaurane-type diterpenoid, exsertifolin A (3), have been isolated and their structures determined by extensive spectroscopic and X-ray crystallographic analysis.View full abstractDownload PDF (439K) -
Yuko KATSUTA, Yukiko AOYAMA, Hisa OSONE, Akimori WADA, Shimami UCHIYAM ...1994 Volume 42 Issue 12 Pages 2659-2661
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew retinoic acid (RA) analogs 9E-locked-RA 3 and 9Z-locked-RA 4 were synthesized from dithiane 6 and β-cyclocitral 13, respectively. Both analogs behaved as agonistic ligands for a mixture of retinoic acid receptor (RAR) and retinoid X receptor (RXR).View full abstractDownload PDF (442K) -
Masayuki YOSHIKAWA, Yoshihiro YOKOKAWA, Yasuhiro OKUNO, Nobuhiro YAGI, ...1994 Volume 42 Issue 12 Pages 2662-2664
Published: December 15, 1994
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight new myriocin analogs, 2-epi-myriocin, Z-14-deoxomyriocin, and nor-deoxomyriocins, and a known myriocin derivative, 14-deoxomyriocin, were synthesized from 2-deoxy-D-glucose via common intermediates in previous myriocin and Z-myriocin syntheses. The immunosuppressive activities of new myriocin analogs and Z-myriocin on mouse allogeneic mixed lymphocyte reaction were examined, and, by comparing with those of myriocin and 14-deoxomyriocin, some structure-activity relationships have been found.View full abstractDownload PDF (472K)
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