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Volume 31, Issue 12
Displaying 1-50 of 56 articles from this issue
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HIROSHI NAKAHARA, SATOSHI OKADA, KENSHU MOCHIDA, HIDENOBU OHMORI, MASA ...1983 Volume 31 Issue 12 Pages 4213-4219
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPancreatic lipase activity toward a series of fatty acid vinyl esters with different chain lengths, solubilized in sodium deoxycholate (NaDC) micelles, was investigated kinetically. The kinetic data could be analyzed on the basis of a fully competitive inhibition mechanism, where substratefree NaDC micelles act as a competitive inhibitor. The values of inhibition constant (K4), which is the dissociation constant of lipase-NaDC micelle complex, obtained from the reaction of each substrate were in reasonable agreement with one another. On the other hand, the maximum velocity (V) and the Michaelis constant (Km) increased with decrease in the fatty acid chain length (C14≃C12<C10<C8). The V/Km values indicate that vinyl dodecanoate and tetradecanoate are better substrates than vinyl decanoate and octanoate in this micellar system. The Km/K4 values suggest that the lipase-substrate-solubilizing NaDC micelle complex is less stable than the lipase-substrate-free NaDC micelle complex. The changes in the V and Km values with chain length were ascribed to the difference in the interaction between the substrate molecule and NaDC micelles.View full abstractDownload PDF (695K) -
TOSHIMASA ISHIDA, HIDEKO USAMI, MASATOSHI INOUE1983 Volume 31 Issue 12 Pages 4220-4229
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to elucidate the energetically stable conformations of 9-[3-(3-indolyl) propyl] adenine and 9-[3-(3-indolyl) propyl]-1-methyladeninium, as intramolecular stacking models for the indoleadenine and indole-adeninium interactions, respectively, empirical energy calculations considering nonbonded, electrostatic and torsional energies were carried out. Two or one out of four kinds of stacking modes were considered to be energetically stable for the former or latter molecule, respectively. These stacking modes were significantly stabilized by the orbital interaction between the highest occupied molecular orbital of the indole ring and the lowest unoccupied one of the adenine or the adeninium ring.View full abstractDownload PDF (809K) -
JUNZO SUNAMOTO, KIYOSHI IWAMOTO, HIROAKI IKEDA, KAZUMARO FURUSE1983 Volume 31 Issue 12 Pages 4230-4235
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe release of a water soluble material, carboxyfluorescein (CF), from the interior of liposomes induced by several spermicidal agents, nonionic surfactants (TS-88, INP-90, and NOP-90), has been investigated. The efficiency of the agents for CF-release was significantly correlated with that for the inhibition of fertilizing ability of sea urchin sperm (p<0.01). On the other hand, it was also found that these nonionic surfactants promote the aggregation of liposomes at a concentration just below the cmc. The efficiency and the minimum concentration able to induce both CF-release and the aggregation of liposomes were closely related with not only the hydrophobicity but also the geometry of the hydrophobic moiety of the surfactant.View full abstractDownload PDF (634K) -
HIROSHI HARA, RYUICHI SHIRAI, OSAMU HOSHINO, BUNSUKE UMEZAWA, YOICHI I ...1983 Volume 31 Issue 12 Pages 4236-4246
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid treatment of the p-quinol acetate (23), obtained from the phenolic amine (14) gave (±)-2-hydroxy-3-methoxyhomoproaporphine (20) in excellent yield. However, similar treatment of other p-quinol acetates (24 and 25) afforded no cyclized products. Reaction of 24 or 25 with Ac2O-conc. H2SO4 gave two diastereoisomeric 4, 7-diacetates (36a and 36b or 38a and 38b). The stereostructures of 36a and 36b were decided by nuclear magnetic resonance study, while those of 38a and 38b were determined by chemical transformations and X-ray analyses. The stereoselectivity of acetoxylation is discussed.View full abstractDownload PDF (942K) -
SADAKATSU SHIMADA, TOSHIAKI TOJO1983 Volume 31 Issue 12 Pages 4247-4258
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIntramolecular cycloaddition of N-allyl-4-methyloxazole-5-carboxamides (1) gave the corresponding 6a-acetyl-2-hydroxy-6-oxotetrahydrofuro [2, 3-c] pyrrolidines (3). Tricycloadducts (6) were obtained by the intramolecular Diels-Alder reaction of N-(3-butenyl)-4-methyl-N-phenyloxazole-5-carboxamides (4). Hydrolysis of the tricycloadducts (6) afforded 7a-acetyl-2-hydroxy-7-oxo-6-phenyl-tetrahydrofuro [2, 3-c] piperidines (8). Treatment of the tricycloadducts (6) with acetic acid gave 1, 2, 3, 4-tetrahydroisoquinolin-1-ones (10), 8a-hydroxy-1, 2, 3, 4, 5, 6-hexahydroisoquinoline-1, 6-diones (9') and 8a-hydroxy-1, 2, 3, 4, 5, 8-hexahydroisoquinoline-1, 8-diones (9). Similar intramolecular cycloaddition of alkenyl 4-methyloxazole-5-carbamates (11) is also described.View full abstractDownload PDF (963K) -
NOBUTAKA FUJII, SHINICHI KATAKURA, HARUAKI YAJIMA, YOSHIHIRO NAKATA, A ...1983 Volume 31 Issue 12 Pages 4259-4262
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHylambates-kassinin, a new amphibian skin dodecapeptide of the tachykinin family, was synthesized in a conventional manner using thioanisole-mediated deprotection with trifluoromethanesulfonic acid. The contractile potency of synthetic hylambates-kassinin in isolated guinea-pig duodenum was 1.4 times higher than that of synthetic kassinin.View full abstractDownload PDF (547K) -
TAISEI UEDA, JINSAKU SAKAKIBARA, JOZI NAKAGAMI1983 Volume 31 Issue 12 Pages 4263-4269
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Acylation and N-alkylation of 5-amino-6-methyl-3-phenyl-4 (3H)-pyrimidinone (I) were carried out and the products were examined for analgesic and antiinflammatory activities. The reaction of I with α-bromopropionyl bromide or chloroacetyl chloride followed by treatment with 40% aqueous dimethylamine gave 5-(α-dimethylaminopropionamido)- or 5-(N, N-dimethylglycyl) amino-6-methyl-3-phenyl-4 (3H)-pyrimidinone (IIc or IIe). The reaction of 3, 4-dihydro-1, 6-dimethyl-5-dimethylamino-4-oxo-3-phenylpyrimidinium iodide (IV) with several alkylamines such as propylamine, isobutylamine, sec-butylamine, and allylamine in acetonitrile gave 5-alkylamino-3, 4-dihydro-1, 6-dimethyl-4-oxo-3-phenylpyrimidinium iodides (IVa-d), whose reduction with sodium borohydride in methanol gave 5-alkylamino-1, 2-dihydro-1, 6-dimethyl-3-phenyl-4 (3H)-pyrimidinones (VIIa-d). The reaction of I with benzaldehyde or p-methoxybenzaldehyde gave 5-benzylidene (or p-methoxybenzylidene) amino-6-methyl-3-phenyl-4 (3H)-pyrimidinones (VIIIa, b). Compounds I and VIIIa showed analgesic and antiinflammatory activities in mice and rats.View full abstractDownload PDF (628K) -
TOZO FUJII, TOHRU SAITO, TAKASHI MURAMOTO1983 Volume 31 Issue 12 Pages 4270-4276
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethylation of N6-methoxyadenine (3) with an excess of Mel in AcNMe2 at 40°C was found to give the 3-methylated product 8 (17% yield), 9-methylated product 4 (2%), N6, 9-dimethylated product 5 (9%), 7, 9-dimethylated product 6 (27%). 3, 7-dimethylated product 7 (10%), and N6, 3-dimethylated product 9 (11%). Similar treatment of N6-benzyloxyadenine (12) with Mel also afforded a mixture of several products, from which the 7, 9-dimethylated product 13 (X=1) was isolated in 30% yield. Similar methylation of N6-methyladenine (17), prepared in 65% yield from 1-methyladenine (16) by a Dimroth-type rearrangement. gave the 3-methylated product 18 (82% yield), 9-methylated product 20 (1.3%), 3, 7-dimethylated product 19 (1.8%), and 1, 9-dimethylated product 21 (0.3%). On methylation under similar reaction conditions, 18 furnished the 9-methylated product 22 (15% yield) as well as the 7-methylated product 19 (29%), and 20 produced 22 (17%) and 21 (11%). The probable pathways to the six methylated products from 3 and those to the four methylated products from 17 are discussed.View full abstractDownload PDF (706K) -
REIKO TODORIKI, MACHIKO ONO, SHINZO TAMURA1983 Volume 31 Issue 12 Pages 4277-4285
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Substituted 1-arylamino-3-arylimino-1-propenes (III) were prepared by the reaction of N-lithio derivatives of 1-arylamino-3-arylimino-1-propenes (malonaldehyde dianil derivatives) (II) and substituted benzyl bromides. 2-Allyl and 2-(2, 4-dinitrophenyl) derivatives of II were prepared by the same method. However, the alkylation failed with less reactive alkyl halides such as ethyl iodide as alkylating agents. Hydrolysis of III afforded α-substituted β-(arylamino) acroleins (IV), which afforded 3-substituted quinolines (V) on heating with aluminium chloride.View full abstractDownload PDF (901K) -
SHUNJI NARUTO, ATSUSUKE TERADA1983 Volume 31 Issue 12 Pages 4286-4294
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title compound, which was newly synthesized, showed good anti-inflammatory and analgesic activities. Optical resolution was performed by the following procedures : 1) condensation of the acid with (-)-1-phenylethylamine followed by separation of diasteromeric amides ; 2) reduction of the cyclopentanone moiety and then acylation with optically active acid ; 3) separation of epimeric esters followed by saponification of esters ; 4) oxidation of alcohols to ketones ; 5) saponification of amides. The absolute configurations of the four optically active compounds thus obtained were confirmed by circular dichroism spectroscopy.View full abstractDownload PDF (811K) -
HIROSHI TAKAHASHI, YUJI SUZUKI1983 Volume 31 Issue 12 Pages 4295-4299
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA chiral hydrazone, (E)-(S)-N'-benzylidene-N, 3-dimethyl-2-hydrazinobutanol (6), was synthesized from (S)-valinol. Compound 6 was reacted with Grignard reagents to give optically pure (2S, 1'S)-N, 3-dimethyl-N'-1'-phenylalkyl-2-hydrazinobutanols (7a and 7b). However, N'-2'-aryl-1'-phenylethyl-N, 3-dimethyl-2-hydrazinobutanols (7c and 7d) were each obtained as a mixture of two diastereomers. Nitrogen-nitrogen bonds of 7a and 7b were cleaved by hydrogenolysis to give (S)-1-phenylalkylamines (8a and 8b), and their absolute configurations and optical purities were confirmed. These reactions were assumed to proceed via the chelated sixmembered ring intermediates.View full abstractDownload PDF (610K) -
MASAYUKI SATO, HIROMICHI OGASAWARA, KEIKO KATO, MASAKO SAKAI, TETSUZO ...1983 Volume 31 Issue 12 Pages 4300-4305
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiketene-acetone adduct (1) generates acetylketene (2) under heating. In order to compare the reactivity of 2 with that of diketene, the reaction of 1 with electron-rich olefins was investigated. On heating with 1, primary enamines (3a-d) produced the corresponding 3-substituted 2, 6-dimethyl-4 (1H)-pyridones (4a-d), while the tertiary enamine 3e gave the 4-pyrone derivative (7). The reaction of 1 with ketene acetals (8) gave the 2, 2-diethoxy-2, 3-dihydro-4-pyrone derivatives (9). The vinyl ether derivatives 13 similarly reacted with 1 to give the 4-pyrone derivative 15 or 16 as the major product. The result shows that both diketene and 2 react with electron-rich olefins in a similar manner.View full abstractDownload PDF (596K) -
MANABU NODE, KIYOHARU NISHIDE, TAKEO KAWABATA, KEIICHIRO OHTA, KHOJI W ...1983 Volume 31 Issue 12 Pages 4306-4311
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxygen functions and halogens at the peri-carbon atom in polyarenes were reductively removed with the AlCl3-EtSH reagent system to afford the parent polyarenes in high yield. The reaction consists of two steps of reactions involving displacement of a functionality with an alkylthio group followed by reductive removal of the introduced alkylthio moiety. A radical cation induced mechanism for the latter process is proposed on the basis of several observations.View full abstractDownload PDF (585K) -
MIKIO KUROKAWA, KOJI YOSHIDA, YASUTAKA NAGAI, HITOSHI UNO1983 Volume 31 Issue 12 Pages 4312-4318
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new partially saturated tricyclic ring systems, 6, 6a, 7, 8, 9, 10, 10a, 11-octahydro-11-oxodibenz [b, e] oxepins (3a and 3b), and -thiepins (4a and 4b) were synthesized. Compounds 4a and 4b were desulfurized to give a pair of isomeric 2-methylbenzoylcyclohexanes (10a and 10b). Deuterated 4a and 4b (11a and 11b) were prepared starting from butadiene-d6 (12). The stereochemical features of 3a (trans), 3b (cis), 4a (trans) and 4b (cis) are compared with those of 10a, 10b, 11a and 11b on the basis of proton nuclear magnetic resonance data.View full abstractDownload PDF (614K) -
SHUNJI NARUTO, ATSUSUKE TERADA1983 Volume 31 Issue 12 Pages 4319-4323
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA recently synthesized compound, (±)-2-[4-(2-oxocyclopentylmethyl) phenyl] propionic acid, had good anti-inflammatory and analgesic activities. One of the metabolites of this compound showed more potent prostaglandin synthetase inhibitory activity than the parent acid. For the structural determination and absolute configurational assignment of the metabolites, we synthesized the eight possible title alcohols and carried out stereochemical assignment of these alcohols.View full abstractDownload PDF (539K) -
KIMIHIRO YOSHIMOTO, YOSHISUKE TSUDA1983 Volume 31 Issue 12 Pages 4324-4334
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlthough the migration pattern was dependent on the conditions of the reaction, a general path of acyl migration for O-myristoyl-D-glucoses and -glucosides could be identified as follows : (1) The well known O-1α→ -2 and O-4→ -6 migrations take place easily. Evidence for the reverse process (O-6→ -4) of the latter migration was obtained for O-myristoyl-D-glucosides. (2) For trans-migrations, the O-2→ -3 process was confirmed. It was apparently reversible for O-myristoyl-D-glucosides and also for O-myristoyl-D-glucose with pyridine. However, O-3→ -4 and O-1β→ -2 migrations were not observed. (3) O-3→ -6 Migration (through the 1C4 (D) conformation) was common for either O-myristoyl-D-glucoses or -glucosides. The reverse migration (O-6→ -3) was also observed, though to a small extent, for an O-myristoyl-α-D-glucoside. However, the O-2→-4 migration in an O-myristoyl-α-D-glucoside and -D-glucose was not observed, but instead the reverse O-4→ -2 process occurred, although only to a small extent. These results suggest that the migrations through the 1C4 (D) conformation occur much more readily for the α- than the β-D-anomer. (4) The O-myristoyl-1β group was rather stable to acyl migration. Upon heating in pyridine, the group migrated to O-3, and then to O-6. In contrast to the other O-myristoyl-D-glucoses, the O-myristoyl-1β derivative was solvolyzed to D-glucose and methyl myristate merely when kept in methanol solution.View full abstractDownload PDF (1025K) -
KIMIHIRO YOSHIMOTO, YOSHISUKE TSUDA1983 Volume 31 Issue 12 Pages 4335-4340
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to clarify whether or not direct O-1β→ -6 acyl migration in O-acyl-D-glucose derivatives really occurs, 3-O-methyl-1-O-myristoyl-β-D-glucopyranose and 3-deoxy-1-O-myristoyl-β-D-glucopyranose were synthesized and their acyl migration was examined under thermal, solvolytic, and base- and acid-catalyzed conditions. Neither compound showed any tendency for acyl migration under these conditions (only partial solvolysis was observed under solvolytic conditions). Consequently, it was concluded that O-1β→ -6 acyl migration does not occur directly, but proceeds through the path O-1β→ -3→ -6.View full abstractDownload PDF (742K) -
SHIRO URANO, SHUNICHIRO NAKANO, MITSUYOSHI MATSUO1983 Volume 31 Issue 12 Pages 4341-4345
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Tocopherol (1) and α-tocotrienol (2) were synthesized in racemic form by a method in which their side chains were constructed by the coupling reaction of a key intermediate, 6-methoxymethoxy-2, 5, 7, 8-tetramethyl-2-(5-mercaptothiazolinyl-4-methyl-3-penten-1-yl) chroman (7), with geranyl bromide. Desulfurization of the reaction product and then hydrolysis afforded α-tocotrienol, which, upon reduction, gave the desired α-tocopherol in good yield. This method, using a mercaptothiazolinyl derivative, is more convenient than previous approaches which use the Wittig or Grignard reaction for the synthesis of the side chain.View full abstractDownload PDF (586K) -
YOSHIHITO ABE, MASAYUKI SATO, HIROYUKI GOTO, RIE SUGAWARA, ERI TAKAHAS ...1983 Volume 31 Issue 12 Pages 4346-4354
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of diketene (1) with some organometallics was investigated. The reaction of 1 with benzyl Grignard reagents in the presence of nickel (II) chloride afforded 3-benzyl-3-butenoic acids 2a-e. In the presence of dichloro [1, 3-bis (diphenylphosphino) propane] nickel, primary alkylmagnesium bromides reacted with 1 to give 3-methylenealkanoic acids 2g-i. (E)-1-Alkenyldiisobutylaluminiums, in the presence of Pd (0)-catalyst, reacted with 1 to give 3-methylene-4-alkenoic acids 5a-c. Similarly, alkynyl-and aryl-zinc chlorides gave 3-methylene-4-alkynoic acids 7a-d and 3-aryl-3-butenoic acids 8a-c, respectively.View full abstractDownload PDF (770K) -
NAOKI TAKEUCHI, NAOMI OKADA, SEISHO TOBINAGA1983 Volume 31 Issue 12 Pages 4355-4359
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of the enaminones 1 with dimethyl 3-oxoglutarate in the presence of KF-AcOH or AcONa-AcOH and 18-crown-6 gave the dimethyl 2-hydroxy-1, 3-benzenedicarboxylates 3, providing a new aromatic annelation reaction.View full abstractDownload PDF (443K) -
NAOKI TAKEUCHI, KAZUE OCHI, MASAYUKI MURASE, SEISHO TOBINAGA1983 Volume 31 Issue 12 Pages 4360-4363
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(±)-Phyllodulcin (1), a sweet dihydroisocoumarin of Hydrangea serrata SERINGE var. thunbergii SUGIMOTO, was synthesized by aromatic annelation of two synthons 2 and 3 to yield 5, followed by successive debenzylation, hydrolysis, lactonization, and decarboxylation in the sequence 5→9→10→11→1.View full abstractDownload PDF (468K) -
TETSUYA TAKEYA, HIROSHI MATSUMOTO, EIICHI KOTANI, SEISHO TOBINAGA1983 Volume 31 Issue 12 Pages 4364-4367
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidations of 1-aryl-1-propenes with new reagent systems, CrO3-HBF4-MeCN and CrO3-HClO4-MeCN, gave the 4-aryltetralones 1a and 1c, and the tetrahydrofuran 4, which are precursor molecules for aryltetrahydronaphthalene and tetrahydrofuran neo-lignans.View full abstractDownload PDF (523K) -
KATSUHIDE MATOBA, TAKASHI MORITA, TAKAO YAMAZAKI1983 Volume 31 Issue 12 Pages 4368-4375
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5, 5-Dimethyl-2-cyclohexenone (Ia) and isophorone (Ib) were nitrated with isoamyl nitrate using potassium metal in liquid ammonia to give 5, 5-dimethyl-2-nitro-1, 3-cyclohexadienol (III) and 3, 5, 5-trimethyl-2-nitro-2-cyclohexenone (IVb), respectively. Compound III was treated with diazomethane to give an oxime (VI) and an intermediate to VI (V). Compound VI was derived to 2-methoxy-4, 4-dimethyl-2, 5-cyclohexadienone (IX) via the nitrone (VIII) and then the hydroxydienone (IIb). On the other hand, the reduction of IVb with sodium borohydride (SBH) was examined. The products were two epimeric nitro alcohols (Xa and XIa), a nitroketone (XII), and a nitro ester (XIII). Compound XIa was converted to Xa by using SBH or aqueous sodium hydroxide. Although the compound with axial acetate (XIc) was deacetoxylated under SBH reduction conditions, that with equatorial acetate (Xc) was inert to this reduction.View full abstractDownload PDF (864K) -
HIROYUKI AKITA, AKIYA FURUICHI, HIROKO KOSHIJI, KOKI HORIKOSHI, TAKESH ...1983 Volume 31 Issue 12 Pages 4376-4383
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of optically active α-methyl β-hydroxy esters I by means of microbiological reduction of the corresponding β-keto esters II was carried out. Benzyl 2-methyl-3-oxobutyrate 1 was found to be reduced by a variety of yeasts to the α-methyl β-hydroxy esters with (2R, 3S)- and (2S, 3S)-configurations (2 and 3, respectively), and by carrying out screening experiments, yeasts which give each product with high optical purity were isolated. Moreover, the absolute configuration and the optical purity of the reduction products were found to be determinable from the 400 MHz nuclear magnetic resonance spectra of the (+)-α-methyoxy-α-trifluoromethylphenylacetyl esters of the alcohols produced.View full abstractDownload PDF (786K) -
HIROYUKI AKITA, AKIYA FURUICHI, HIROKO KOSHIJI, KOKI HORIKOSHI, TAKESH ...1983 Volume 31 Issue 12 Pages 4384-4390
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to synthesize four optically active methyl 2-methylmalates (10-13), microbiological asymmetric reduction of the corresponding dimethyl 2-methyl-3-oxosuccinate (9) was carried out. The β-keto diester 9 was found to be reduced by fermenting baker's yeast (Saccharomyces cerevisiae) and Candida albicans to afford a mixture of the (2R, 3R)-isomer 10 and the (2S, 3R)-isomer 11. Although the optical purity of 10 produced by Candida albicans was reasonably high (95% e.e.), optical yields of other products were unexpectedly low. However, identification of the four possible isomers 14-17 was found to be easily carried out by means of nuclear magnetic resonance spectroscopy.View full abstractDownload PDF (699K) -
HISASHI ISHII, YASUOKI MURAKAMI, TOSHIKO WATANABE, HIDEHARU SUZUKI, ZE ...1983 Volume 31 Issue 12 Pages 4391-4400
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Fischer indolization of ethyl phenylpyruvate 2-[(1, 4-dimethoxy-2-naphthyl) hydrazone] (2) with ethanolic hydrogen chloride gave four angular benz [e] indole products (ethyl 4-chloro-5-ethoxy-(14a), ethyl 4-chloro-5-methoxy-(14b), ethyl 5-ethoxy-(14c), and ethyl 5-methoxy-(14d)-1-phenyl-3H-benz [e] indole-2-carboxylates), instead of the anticipated linear benz [f] indole, ethyl 4, 9-dimethoxy-3-phenyl-1H-benz [f] indole-2-carboxylate (3). Oxidation of these benz [e] indole derivatives (14b and 14d) with chromic acid in acetic acid provided an o-quinone derivative (15) which showed anti-viral activity in a preliminary biological test.View full abstractDownload PDF (1033K) -
HISASHI ISHII, YASUOKI MURAKAMI, TOSHIKO WATANABE, HIDEHARU SUZUKI, HI ...1983 Volume 31 Issue 12 Pages 4401-4408
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEthyl 4-methoxy- (7) and ethyl 5-methoxy- (3) -1-phenyl-3H-benz [e] indole-2-carboxylates were prepared by Fischer indolization of ethyl phenylpyruvate 2-naphthylhydrazone derivatives bearing a methoxy group at the C3-(26) and the C4-(8) positions, respectively.View full abstractDownload PDF (807K) -
TADAYUKI KURAISHI, TAKAO TANIGUCHI, KAZUYUKI HORI, TAKAO MURAKAMI, NOB ...1983 Volume 31 Issue 12 Pages 4409-4416
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reinvestigation of Microlepia marginata (PANZER) C. CHR. afforded in addition to the previously reported ent-kaurane glycosides three new ent-pimarene derivatives, which were named fumotoshidin A (I), B (II) und C (III). The structures of the new compounds were characterized by spectroscopic methods and some chemical transformations as 2β, 15 (R), 16-trihydroxy-entpimar-7-en-3-one (1), 3α, 15 (R), 16-trihydroxy-ent-pimar-7-en-2-one (II) and 2, 15 (R), 16-trihydroxy-ent-pimar-1, 7-dien-3-one (III).View full abstractDownload PDF (881K) -
YASUHIKO OZAKI, SADAO MAEDA, TAMEO IWASAKI, KAZUO MATSUMOTO, AKIO ODAW ...1983 Volume 31 Issue 12 Pages 4417-4424
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethyl 5-substituted oxazole-4-carboxylates were synthesized by the reaction of methyl α-isocyanoacetate with acylating reagents in the presence of bases. The oxazole methyl esters were converted into the carboxylic acids and the carboxamides. Then, N-alkyl-oxazole-4-carboxamides were prepared through the oxazole-4-carboxylic acid chloride. Furthermore, 2-substituted oxazoles were synthesized by cyclization of N-acyl-α-benzoylglycine methyl esters. which were obtained by acylation of α-benzoylglycine methyl ester followed by ammonolysis of the resulting oxazole methyl esters. These oxazole compounds were evaluated for inhibitory activity on blood platelet aggregation in vitro and ex vivo. Some of these compounds showed the inhibitory activity comparable to that of aspirin. Of these, 5-(3, 4, 5-trimethoxyphenyl) oxazole-4-carboxamide was the most active compound in the ex vivo test.View full abstractDownload PDF (663K) -
AKIRA TOKUMURA, YASOMI HANDA, YASUKO YOSHIOKA, HIROAKI TSUKATANI1983 Volume 31 Issue 12 Pages 4425-4435
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe electron impact and chemical ionization mass spectra of 1-O-hexadecyl- and 1-palmitoyl-2-O-acetyl-sn-glycero-3-phosphocholines and their lyso derivatives were measured by insertion of the compounds into a direct inlet system. The lysophospholipids were decomposed by heating at over 300°C into multiple compounds that volatilized together and gave several characteristic ion peaks when subjected to electron impact or interaction with an ion plasma of reactant gas. The mass spectral data indicated that the major pyrolysis products of these lysophospholipids were produced by elimination of methanol or N, N-dimethylethanolamine. When sn-2-acetyl phospholipids were introduced on the direct insertion probe and heated, several pyrolysis products volatilized together at above 350°C. The results suggested the major pyrolysis mechanism was loss of the phosphorylcholine moiety, together with some deacetylation and subsequent elimination of methanol and N, N-dimethylethanolamine from the sn-2-acetyl phospholipids.View full abstractDownload PDF (914K) -
JUN HAGINAKA, HIROYUKI YASUDA, TOYOZO UNO, TERUMICHI NAKAGAWA1983 Volume 31 Issue 12 Pages 4436-4447
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkaline degradation of clavulanic acid in methanol and in aqueous solution has been investigated. Potassium clavulanate was degraded in methanol and in NaOH-saturated methanol to yield methyl 8-hydroxy-6-oxo-4-aza-2-octenoate (I). which showed ultraviolet (UV) absorption with λmax 268nm (methanol). The UV absorption of I almost disappeared in acidic conditions, and reappeared on subsequent realkalization, suggesting interconversion between I and its protonated form. It was suggested that potassium clavulanate might be rapidly hydrolyzed in alkaline aqueous solutions to 8-hydroxy-6-oxo-4-aza-2-octenoic acid (II), which has strong UV absorption around 260 nm. The acid-base interconversion was also observed between II and its protonated form, the latter exhibiting almost no UV absorption around 260 nm. An ion-pair reversed-phase high performance liquid chromatography method with the alkaline degradation reaction incorporated into post-column has been developed for the determination of clavulanic acid in plasma and urine. After separation from regular components of plasma and urine, clavulanic acid is degraded in NaOH solution in a reaction coil followed by detection of the UV absorbance of the degradation product at 270 nm. The procedure was quantitative over a wide range of clavulanic acid concentrations in plasma and urine down to 0.1 μg/ml.View full abstractDownload PDF (1002K) -
KATSUHIKO ISEKI, TOSHIAKI MASE, TOKUJI OKAZAKI, MASAKATSU SHIBASAKI, S ...1983 Volume 31 Issue 12 Pages 4448-4455
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBiologically interesting 9 (O)-methano-△6-prostaglandin I1 (9 (O)-methano-△6-PGI1), a chemically stable analog of prostacyclin (PGI2), was efficiently synthesized from 1, 3-cyclooctadiene with high stereo- and regiochemical control. In all three biological test systems examined, 9 (O)-methano-△6-PGI1 was found to be considerably less active than prostaglandin E1 (PGE1).View full abstractDownload PDF (821K) -
TAMIO MAITANI, KAZUO T. SUZUKI1983 Volume 31 Issue 12 Pages 4456-4463
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAge and sex dependencies of iron. calcium and zinc levels in liver, kidney and spleen were investigated in male and female mice (3-12 weeks old). To clarify the age and sex dependencies of responses to dextran sulfate treatment. 4- and 12-week-old mice were injected intraperitoneally with dextran sulfate and killed 24 h later. The most striking change was observed in splenic iron level. The level increased with age and a five (male)- or eight (female)-fold increase was observed within the experimental period. Dextran sulfate treatment produced a marked decrease of the splenic iron level and the response was larger in 12-week-old mice. The alterations of metal levels after dextran sulfate treatment in the supernatant and precipitated fractions were also studied.View full abstractDownload PDF (743K) -
YOSHIHIKO INAMORI, YOSHIAKI KATO, MAYURI KUBO, KIMIYE BABA, YOUKO MATS ...1983 Volume 31 Issue 12 Pages 4464-4468
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt has already been reported that among the constituents of the root of Anthriscus sylvestris HOFFM., deoxypodophyllotoxin (anthricin : I), anthriscinol methyl ether and (Z)-2-angeloyl-oxymethyl-2-butenoic acid show insecticidal action against several species of insects. In order to clarify the mechanisms of insecticidal action of I, which showed the strongest action among the above chemicals, the distribution of I in the tissues of the 5th instar larvae of silkworm, Bombyx mori, fed on mulberry leaves treated with I was investigated. I was analyzed by high-pressure liquid chromatography. The amount of I in the blood increased rapidly after the administration and no decrease was seen even after 96 h. Compound (I) accumulated in the fat body in a larger amount for a longer time, as compared with the other tissues. It was also accumulated at the skin, the ventriculus and the Malpighian tubules in somewhat higher amounts than in other tissues. Degeneration of the skin and the fat body were observed in the intoxicated insects. The concentration of I in feces reached its peak at 48 h after administration.View full abstractDownload PDF (532K) -
KAZUO T. SUZUKI, TAMIO MAITANI1983 Volume 31 Issue 12 Pages 4469-4475
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactivity of two isometallothioneins (two isoforms of rat liver zinc- and cadmiumthioneins) was compared in vitro. Reactions characteristic of metal-thiol mercaptide bonds were selected as follows; oxidative formation of intramolecular disulfide bonds by 5, 5'-dithiobis (2-nitrobenzoic acid), intra- and inter-molecular oxidations by air and ligand substitution reaction with ethylenediaminetetraacetic acid (EDTA). The relative ratio of the two isometallothioneins and the reaction products were determined by high performance liquid chromatograph-atomic absorption spectrophotometry. Metallothionein-I was shown to be more reactive than metallothionein-II in all reactions tested in this study.View full abstractDownload PDF (710K) -
YOSHIYUKI KOIDA, GOICHI HIRATA, MASAYOSHI SAMEJIMA1983 Volume 31 Issue 12 Pages 4476-4482
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMicrocapsules of ascorbic acid were prepared by phase separation of ethylcellulose (EC) from cyclohexane solution by lowering the temperature. The effects of molecular weight of EC on the aggregation of microcapsules and on the sustained release of the microencapsulated ascorbic acid were investigated. Polyisobutylene (PIB) was used as a coacervation-inducing agent. The molecular weight of EC significantly affected the aggregation of microcapsules ; the aggregation decreased with increasing molecular weight of EC. The release rate of ascorbic acid from microcapsules was influenced significantly by the molecular weight of EC and the minimum release rate was given by EC with a molecular weight of 13×104 if PIB with a molecular weight of 1.12×106 was used. The molecular weight of EC which gave minimum release rate was affected by the molecular weight of PIB used. The relationship between the release rate and molecular weight of EC depended mainly on the compactness of the wall rather than the thickness of the wall.View full abstractDownload PDF (924K) -
AKINOBU OTSUKA, KOTARO IIDA, KAZUMI DANJO, HISAKAZU SUNADA1983 Volume 31 Issue 12 Pages 4483-4488
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of temperature on the adhesive force between particles of powdered organic substances (butyl p-hydroxybenzoate and sulfadimethoxine) and a glass substrate was investigated by means of the impact separation method using a pendulum-type shock testing machine. At elevated temperatures, a remarkable increase in adhesive force with heating time was observed. The adhesive force at a given heating time increased with rising temperature and a linear relationship existed between the logarithm of adhesive force and the reciprocal of temperature (°K) for each sample. The results were interpreted in terms of the growth of a solid neck between a particle and the substrate.View full abstractDownload PDF (535K) -
MAKOTO OTSUKA, NOBUYOSHI KANENIWA1983 Volume 31 Issue 12 Pages 4489-4495
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of grinding on the degree of crystallinity of cephalexin (CEX) powder was investigated. The intensities of the X-ray diffraction peaks of crystalline CEX decreased with increasing grinding time in an agate shaker mill, and after 4 h showed the same halo pattern as the noncrystalline solid (NC) obtained by the freeze-drying method. The crystallinity of CEX ground for various times was determined by two X-ray diffraction methods, that is, by the internal standard method using lithium fluoride as the internal standard, and by Hermans method, as well as by the infrared (IR) spectral method, for which standard samples were obtained by physically mixing crystalline monohydrate (phase IV) and NC-H2O. The degree of crystallinity determined by Hermans' method was considerably larger than that determined by the X-ray internal standard method for short grinding times (up to about 1 h), but CEX ground for 3-4 h showed 0% crystallinity by both methods. The crystallinity determined by the IR-spectral method accorded quite well with that determined by the X-ray internal standard method for grinding times up to about 30 min, but remained approximately constant at about 15% for longer grinding times. Thus, the state of noncrystalline CEX produced by grinding differs from that of the material obtained by freeze-drying.View full abstractDownload PDF (644K) -
KOZO TAKAYAMA, NAOKI NAMBU, TSUNEJI NAGAI1983 Volume 31 Issue 12 Pages 4496-4507
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA computer optimization technique was applied to obtain flufenamic acid (FFA)/polyvinylpolypyrrolidone (PVPP)/methyl cellulose (MC) solid dispersions which provide a high dissolution rate and high stability of FFA. The amounts of PVPP, MC and ethanol were selected as independent variables. Both PVPP and MC are formulation variables, and ethanol, which was used for the preparation of solid dispersions, is a process variable. Twelve dissolution parameters were selected as dependent variables for deciding the optimum formulation. These dissolution parameters were predicted quantitatively by the best combination of independent variables. The physical significance of the regression equation for each dissolution parameter was defined with the application of contour graphs. The optimum formulation of FFA/PVPP/MC solid dispersions was obtained by placing a set of restrictions on the regression equations. Experimental results for the optimum formulation agreed well with the predictions.View full abstractDownload PDF (817K) -
TARO OGISO, MASAHIRO IWAKI, MASAE KURANARI1983 Volume 31 Issue 12 Pages 4508-4516
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo clarify the differences in hemolytic activities between basic drugs and to identify the major factors inducing hemolysis, some tranquilizers and antihistaminics were compared with each other as regards hemolytic activities, van der Waals volume (V), pKa, partition coefficient (octanol/water, P), lipid spin labeling and membrane/buffer partition ratio (Pm/b), and correlation analyses were carried out among these parameters. The best correlation was between logarithmic Pm/b for drugs and 1/C1 (C1 ; the initial concentration inducing hemolysis, r=0.877, p<0.01) or 1/C50 (C50 ; the concentration inducing 50% hemolysis, r=0.924, p<0.01). Less good correlations were observed between the logarithmic V (r=0.708, p<0.05 ; r=0.780, p<0.05) or the fluidity of lipids (r=0.711, p<0.05 ; r=0.619) and 1/C1 or 1/C50, respectively. No correlation, however, was found between P and hemolytic concentrations. These results indicate that the amount of drugs penetrated into the membrane is probably a major factor in the induction of hemolysis, and that large molecular volume of a drug, increased fluidity of the membrane lipids and un-ionized concentration of the drug significantly affect the drug-induced hemolytic process.View full abstractDownload PDF (791K) -
NOBUHIRO MURAMATSU, TAMOTSU KONDO1983 Volume 31 Issue 12 Pages 4517-4523
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAdhesion of rabbit platelets to microcapsules having different numbers of carboxyl groups was examined. The platelets adhered more easily to microcapsules having higher negative charges than to those having lower ones. It was strongly suggested that this trend was caused by plasma components adsorbed on the microcapsules ; the difference in surface negative charge caused a difference in adsorption of plasma components, which would in turn result in the difference in platelet adhesion. Among various plasma components, the major proteins, albumin, γ-globulin and fibrinogen, were all found to inhibit platelet adhesion to the microcapsules, while fresh rabbit serum facilitated it, irrespective of surface negative charge. On the other hand, heat-inactivated rabbit serum was found to inhibit platelet adhesion almost completely. These findings led us to conclude that certain complement adsorbed on the microcapsule surface facilitate platelet adhesion, and the difference in platelet adhesion, which is dependent on the surface negative charge of the microcapsules in the presence of plasma, can be explained in terms of competitive adsorption of the complement and fibrinogen.View full abstractDownload PDF (992K) -
JUNICHI SUDO, ATSUSHI ISHIHARA, TSUNEYOSHI TANABE1983 Volume 31 Issue 12 Pages 4524-4529
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMean blood pressure, renal clearances of electrolytes and urinary volume, in addition to renal hemodynamics and functions, were comparatively investigated in rats subjected to ureteral catheterization by the ventral and the retro-peritoneal approach procedures in order to determine the validity of each of these procedures. From 60 min after the operation, the mean blood pressure in the case of ventral approach gradually decreased, while the pressure in the case of retroperitoneal approach remained constant. The urinary volume and the urinary sodium excretion in the case of the ventral approach decreased about a half in comparison with those in the retroperitoneal one, although the plasma sodium concentration was well maintained in both cases. The renal hemodynamics and functions remained normal in both cases. The decrease of urinary volume and urinary sodium excretion observed in the case of the ventral approach is considered to be due to the homeostatic protection against loss of body fluid as well as against the decrease of pressure in the abdominal cavity, both of which are caused by the opening of the abdominal cavity. It is accordingly considered that the retro-peritoneal approach procedure should be adopted for pharmacological and pharmacokinetical studies on the clearances of electrolytes and water in comparison with the clearance (s) of drug (s).View full abstractDownload PDF (598K) -
HIROTERU SAYO, YASUSHI YAMADA, TAKASHI MICHIDA1983 Volume 31 Issue 12 Pages 4530-4532
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethyl 2-nitrobenzenesulfenate (5) was formed by controlled potential electrolysis (CPE) of N-(2-nitrophenylthio) amines (morpholine (1), piperidine (2), pyrrolidine (3), thiomorpholine (tetrahydro-4H-1, 4-thiazine) (4)) in methanol at a glassy carbon anode. A yellow powder obtained by the electrolysis of 1 reacted with triethylamine to give 2, 4-bis (o-nitrophenylthio)-5, 6-dihydro-1, 4-oxazine (7). CPE of 1-4 in acetonitrile gave 2, 2'-dinitrodiphenyldisulfide (6). These results suggest that the initial step of anodic oxidation of 1-4 in acetonitrile is an EC process (an electron transfer process followed by a chemical reaction), while that in methanol is an ECE process (an electron transfer process followed by a chemical reaction and then an electron transfer process). Enamine is considered to be one of the intermediates in the anodic oxidation of 1-4 in methanol.View full abstractDownload PDF (375K) -
TAKAO SAKAMOTO, HIROSHI YOSHIZAWA, SOHICHI KANEDA, YOSHIAKI HAMA, HIRO ...1983 Volume 31 Issue 12 Pages 4533-4538
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 2, 6-dimethyl-4-phenylpyrimidine 1-oxide with phosphoryl chloride gave 4-chloromethyl-2-methyl-6-phenylpyrimidine exclusively. In contrast, 2, 6-dimethyl-4-methoxypyrimidine 1-oxide and 2, 6-dimethyl-4-dimethylaminopyrimidine 1-oxide reacted with the same reagent to give the corresponding 2-chloromethylpyrimidines predominantly.View full abstractDownload PDF (694K) -
MAGOICHI SAKO, KAZUKI AKIRA, KOSAKU HIROTA, YOSHIFUMI MAKI1983 Volume 31 Issue 12 Pages 4539-4542
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermal reactions of (2R, 5S, 6S)-2-(1-methylethenyl)-6-phenylacetamido-4-oxa-1-azabicyclo [3.2.0] heptane-3, 7-dione (1) with alcohols gave 2-phenylmethyl-4-{N-[(1R)-1-carboxy-2-methylprop-2-enyl] carbamoyloxazole (2a), (3S, 4S)-4-alkoxy-1-[(1R)-1-carboxy-2-methylprop-2-enyl]-3-phenylacetamidoazetidin-2-ones (3a, c), and (2S)-N-[(1R)-1-carboxy-2-methylprop-2-enyl]-3, 3-dialkoxy-2-phenylacetamidopropionamides (4a, c), probably via an intramolecular ring transformation of 1 into (1S, 5R)-3-phenylmethyl-6-[(1R)-1-carboxy-2-methylprop-2-enyl]-4-oxa-2, 6-diazabicyclo [3.2.0] hept-2-en-7-one (5a) in the initial stage of the reaction.View full abstractDownload PDF (492K) -
YOSHIHIKO INAMORI, YOSHIAKI KATO, MAYURI KUBO, TERUO KAMIKI, TSUNEMATS ...1983 Volume 31 Issue 12 Pages 4543-4548
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA fungus which was identified as Aspergillus terreus var. aureus showed antifungal and antibacterial activities. Through the investigation of its metabolites, six compounds (1-6) were isolated ; emodin (1), dihydrogeodin (2), questin (3), sulochrin (5), the new metabolite 2-(3-chloro-4-methyl-γ-resorcyloyl)-5-hydroxy-m-anisic acid methyl ester (4), which is a monochloro derivative of sulochrin (5), and compound (6), the chemical structure of which has not yet been clarified. Dihydrogeodin (2), sulochrin (5), 4 and 6 showed antifungal and antibacterial activities, and 6 had especially strong antifungal activity towards Trichophyton mentagrophytes.View full abstractDownload PDF (640K) -
HIROSHI YAMANAKA, MICHINAO MIZUGAKI, TAKAO SAKAMOTO, MATAICHI SAGI, YO ...1983 Volume 31 Issue 12 Pages 4549-4553
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to investigate the generality of a chain-elongation reaction observed in the metabolism of fusaric acid (5-butyl-2-pyridinecarboxylic acid) and its derivatives, various heteroaromatic (diazine, 1, 3-azole, and 1, 2-azole) carboxylic acids with a normal alkyl side-chain were synthesized.View full abstractDownload PDF (545K) -
TAKAO SAKAMOTO, TAKEJI SAKASAI, HIROSHI YOSHIZAWA, KENICHI TANJI, SUMI ...1983 Volume 31 Issue 12 Pages 4554-4560
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 4-alkylpyrimidines with propyl nitrite under acidic conditions followed by deoximation of the resulting ketoximes gave alkyl pyrimidinyl ketones in satisfactory yields. As compared with the direct oxidation of the alkylpyrimidines with selenium dioxide, the nitrosation followed by deoximation has some advantages for the synthesis of alkyl 4-pyrimidinyl ketones.View full abstractDownload PDF (628K) -
MASAMI ISHIDA, NAOKI NAMBU, TSUNEJI NAGAI1983 Volume 31 Issue 12 Pages 4561-4564
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new type of highly viscous ointment containing Carbopol-934 (CP) for application to the oral mucosa was formulated. The release properties of Brilliant Blue FCF (B.B.FCF) and the absorption of sodium salicylate through the oral mucosa from the ointment were studied. In release test using the agar gel bed method, there was no significant difference in % release of B.B. FCF after 12 h from ointments containing glycerin and polyethylene glycol (PEG) as excipients. However, the form of the ointment containing glycerin was maintained for 24 h whereas the ointment containing PEG liquefied. The 50% release time (T50) decreased with increase of glycerin content, but the difference of water absorption was negligible. Therefore, the release rate of B.B. FCF was related to the consistency of CP gel ointment rather than to water absorption. In vivo absorption of sodium salicylate from the ointment in hamster cheek pouch was also investigated. Absorption was fast from both 12.5 and 20% CP ointments, and the drug absorption was sustained for 5 h from 12.5% CP ointment.View full abstractDownload PDF (450K) -
TAKASHI MIZUMA, HIROYUKI YAMAGUCHI, MASAHIRO HAYASHI, SHOJI AWAZU1983 Volume 31 Issue 12 Pages 4565-4567
Published: December 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSp-Nitrophenol (PNP) sulfate conjugation in rat liver cytosol fraction was investigated over a wide PNP concentration range (1.25 μM-5 mM). The PNP sulfate synthesis rate in the liver cytosol decreased in the low PNP concentration range (10-500 μM) and increased again at concentrations above approximately 500 μM, as was previously found in isolated liver cells (J. Pharm. Dyn., 5, 811 (1982)). This apparent substrate at low PNP concentration was found in the sulfotransferase reaction when the cosubstrate, 3'-phosphoadenosine-5'-phosphosulfate (PAPS), had been generated in advance as well as in the overall reaction (i.e., including the generation process of PAPS), suggesting that the inhibition was due to direct interaction between PNP and aryl sulfotransferase, and not to inhibition of PAPS generation by PNP.View full abstractDownload PDF (387K)