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Volume 19, Issue 1
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ISAO SEKI, HIROMU TAKAGI1971 Volume 19 Issue 1 Pages 1-5
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSyntheses and Pharmacology of some demethylated compounds related to 14-hydroxy-dihydro-6β-thebainol 4-methyl ether (oxymethebanol), a new potent antitussive, were presented with interest to the structure-antitussive activity relationship on the 6-hydroxyl group in the morphinans. It was suggested that the β (equatorial)-configuration in 6-hydroxyl group is one of essential factors for an appearance of strong antitussive action of the 3, 4, 6, 14-tetrahydroxy-morphinan 3, 4-diethers.View full abstractDownload PDF (556K) -
KAZUO YOSHIDA, NOBUKO IINO1971 Volume 19 Issue 1 Pages 6-10
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTransfer reaction of β-D-glucofuranose from phenyl β-D-glucofuranoside to methanol by almond emulsin was recognized. Extent of glucofuranosyl transfer from different aryl β-D-glucofuranoside to alcohol was determined. Influence of pH on the glucofuranosyl transfer was examined. The course of the transfer reaction was also reported. Enzymic transfer of β-D-galactofuranose and β-D-glucofuranosiduronic acid was also investigated. In view of the above facts, it was concluded that β-D-glycofuranosyl residue was transferred by β-glycosidase from phenol to alcohol and conversion of furanose ring to pyranose ring was not occured in the course of enzymic transfer reaction.View full abstractDownload PDF (623K) -
TETSURO MOHRI, CHIYOKO NAKAGAWA, HARUO KITAGAWA1971 Volume 19 Issue 1 Pages 11-15
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe uptake of glycine-1-14C and AIB-1-14C by HeLa cells into the 60% alcoholsoluble fraction and the effect of steroid (10 μg/ml of medium) on it were studied. After exposure of the cells to cortisol for 48 hr during culture, glycine uptake by the cells in 3, 5, 10 and 60 min of incubation in lactalbumin medium was depressed to 55 to 84% of the control. Larger depressing effect of cortisol on glycine uptake in 10 min of incubation was observed when the cells were incubated in Eagle's medium. Deoxycorticosterone also decreased glycine uptake to 55.6% of the control in 10 min of incubation in Eagle's medium. Cortisol decreased AIB uptake by 33 and 41%, and deoxycorticosterone by 9% (not significant) and 21% in 10 and 30 min of incubation, respectively. 17β-Estradiol and estriol did not significantly affect glycine uptake.View full abstractDownload PDF (666K) -
TOSHIO NAMBARA, KAZUTAKE SHIMADA1971 Volume 19 Issue 1 Pages 16-20
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to clarify the structure-activity relationship, synthesis of the titled compounds has been undertaken. The acid-cleavage of 14α, 15α-epoxyisobufadienolide (I) followed by oxidation with chromium trioxide gave the 14β-hydroxy-15-ketone (III). The ring opening of the β-epoxide (IV) and subsequent epimerization at C-14 resulted in formation of 15-oxo-14β-isobufadienolide (VI). Upon treatment with N-bromosuccinimide and then with lithium chloride or sodium iodide 14β, 17α- and 14α, 17β-isobufadienolides (IX and XIII) were led to Δ16, Δ14, 16 and Δ16-14β, 15β-epoxy derivatives (X, XV and XVI), respectively.View full abstractDownload PDF (663K) -
TOSHIO NAMBARA, KAZUTAKE SHIMADA, JUNICHI GOTO, SHUJIRO GOYA1971 Volume 19 Issue 1 Pages 21-24
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe attempts were made to synthesize 16-substituted 14, 17-cis-5α-cardenolides by the method worked out by Ruzicka, et al. starting from 16β-methyl-14α, 17α- and 16α-cyano-14β, 17β-pregnan-20-one derivatives (I and VI). Condensation with ethyl bromoacetate followed by dehydration gave the unsaturated acid esters, which on selenium dioxide oxidation were led to the desired cardenolides (IV and IX). However, Reformatsky reaction with 3β-acetoxy-16α-methyl-14β, 17β-pregn-5-en-20-one (V) resulted in failure probably due to the steric interaction with the methyl group at C-16.View full abstractDownload PDF (574K) -
TAKAO MURAKAMI, CHIUMING CHEN1971 Volume 19 Issue 1 Pages 25-30
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAus den Rhizomen von Woodwardia orientalis Sw. wurden eine Reihe von Phytosterin-Derivaten (freie Sterine, Sterin-Ester, Sterin-Glucoside, veresterte Sterin-Glucoside) und eine neue Triterpen-Verbindung, die wir Woodwardinsaure nannten, isoliert. Die Struktur der Woodwardinsaure wurde als 3β-Hydroxy-21β-H-Δ22(29)-hopen-23-carbonsaure aufgeklart.View full abstractDownload PDF (708K) -
MASAYUKI ONDA, KYOKO YONEZAWA, KAORU ABE1971 Volume 19 Issue 1 Pages 31-36
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnhydroprotopine and anhydromethylberberine were photocyclized to yield 5, 6, 11, 12-tetrahydrobenzo [c] phenanthridine derivatives, which were derived via two steps to sanguinarine and chelerythrine, respectively, in good yield. 5, 6, 11, 12-Tetrahydrobenzo [c]-phenanthridine derivative resulted from the initial photoproduct via rearrangement, which was trapped with dimethyl acetylenedicarboxylate as 4b, 12-etheno-compound.View full abstractDownload PDF (593K) -
TERUO KURIHARA, HIROKO ICHIMURA, TETSUO IGAKI, AKIHIRO OHTA1971 Volume 19 Issue 1 Pages 37-40
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was found that a certain relation seems to exist between the carcinogenic action of mononitroquinoline and the approximate superdelocalizabilities of the carbon atom to which the nitro group is attached. Referring to these results, the approximate superdelocalizabilities of some derivatives of 2- and 4-nitroquinolines were also calculated, and a relationship between the chemical structure and the carcinogenicity was discussed.View full abstractDownload PDF (525K) -
HIDETOSHI YOSHIMURA, HIROSHI SHIMENO, HISAO TSUKAMOTO1971 Volume 19 Issue 1 Pages 41-45
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the previous paper, it was shown that antipyrine was oxidized not only to 4-hydroxyantipyrine, but also to 3-hydroxymethyl-2-methyl-1-phenyl-3-pyrazolin-5-one which was characterized on the basis of analytical and spectral data. The present study established the latter pathway, the oxidation of methyl group at 3-position of pyrazolinone ring by the chemical synthesis of authentic sample, and also demonstrated chromatographically the subsequent pathway to 2-methyl-1-phenyl-5-oxo-3-pyrazolin-3-carboxylic acid. Possible importance of this serial oxidation steps was discussed concerning with antipyrine allergy problem. By the preliminary test it was shown that 3-hydroxymethyl metabolite did not retain the antipyretic acitivity.View full abstractDownload PDF (674K) -
NORIO NAKAMURA1971 Volume 19 Issue 1 Pages 46-51
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSdl-Ibotenic acid (I) was synthesized in a better yield than the known methods, starting from diethyl 3-chloroglutaconate (VII). Reaction of VII with hydroxylamine in the presence of sodium hydroxide followed by esterification afforded ethyl 3-hydroxy-5-isoxazoleacetate (IV), which was, after benzenesulfonylation, brominated with NBS to ethyl α-bromo-3-benzenesulfonyloxy-5-isoxazoleacetate (X). Hydrolysis and treatment with ammonia of X gave I. Synthesis of muscimol (II) from IV was also described.View full abstractDownload PDF (795K) -
SEIICHI SAKUMA, HIROYUKI ISHIZONE, RYOJI KASAI, SACHIKO KAWANISHI, JUN ...1971 Volume 19 Issue 1 Pages 52-59
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical structure of glycoside G (I), C36H56O13, mp 232-233°, [α]19D+30.2°(EtOH) and glycoside K (V), C40H66O16, mp 240-241°, [α]20D -27.58°(MeOH) were isolated from Bei-Wujiapi (cortex of Periploca sepium BGE.) and established to be periplocin and Δ5-pregnene-3β, 20α-diol(20)-β-D-glucopyranosyl (1glu→6glu)-β-D-glucopyranosyl (1glu→2dig)-β-D-digitalopyranoside. It should be noted that glycoside K is the first example of the pregnane type glycoside whose sugar moiety links to the hydroxyl group other than C3-hydroxyl group of the steroidal aglycone.View full abstractDownload PDF (924K) -
HIDEYO SHINDO, EIICHI NAKAJIMA, AKIRA YASUMURA, HISASHI MURATA, TAKASH ...1971 Volume 19 Issue 1 Pages 60-71
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe distribution of orally and intravenously administered 14C-oxazolam was studied in mice by means of whole-body autoradiography and in rats by scintillation counting of the organs and tissues. The radioactivity was found to be widely distributed in various tissues including the brain at 30 min after oral administration, reached the maximum levels within 1 hr and thereafter declined rather rapidly. The distribution patterns were similar for mice and rats, except that the brain uptake of the drug was appreciably higher in mice than in rats. A high affinity of oxazolam to the brain tissue was demonstrated by an extremely high and rapid uptake of radioactivity by the brain after intravenous injection in mice. The brain level reached its maximum at about 1 min after the injection and thereafter fell off rapidly, some retention of radioactivity being observed in the white matter of the brain-stem and in the trigeminal nerve. Autoradiographic studies in pregnant mice demonstrated that there is a slow and only a slight penetration of radioactivity through the placenta. A comparison of the excretion patterns of oxazolam after oral administration in mice, rats, dogs and man revealed that in mice and rats the excretion in the feces, mostly derived from the biliary excretion, was more important than that in the urine, while in dogs a larger part was excreted in the urine and in man the most part (ca. 80% of the dose) in the urine.View full abstractDownload PDF (2638K) -
KATSUTADA MASUDA, TAKAAKI KAMIYA, YOSHIO IMASHIRO, TATSUHIKO KANEKO1971 Volume 19 Issue 1 Pages 72-79
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA number of N-acyl and N-nitroso-3-dialkylaminosydnonimines (II) were synthesized by various acylating methods. In some cases, the acylation with activated esters, mixed anhydrides or dicyclohexylcarbodiimide was found to be more favorable. The reactivities of these derivatives towards acids and alkalis were investigated. Trifluoroacetyl (II-6) and formyl (II-1) compounds were easily deacylated in varuous conditions. Methylation took place at the acylated imino nitrogen of N-ethoxycarbonyl compound to give the quaternary salt (II-18). N-Acetyl compound (II-2) was compared with its 3-alkyl analog in the physicochemical properties ; its pKa values reveals that the morpholino group has little effect on the basicity of the compound.View full abstractDownload PDF (752K) -
RYUZO TAKESHITA1971 Volume 19 Issue 1 Pages 80-86
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA special chamber for thin-layer chromatography was devised in which compounds can be developed after adequate equilibration of the chromatographic media with the vapor of solvent systems. A comparison was made between the patterns of mobilities of several compounds when the compounds were developed using this chamber and a conventional chamber. Using the chamber, a well reproducible Rf value was obtained even when a compound was developed with the multicomponent solvent system and under different conditions of temperature.View full abstractDownload PDF (983K) -
HIROSHI HIKINO, NORIO SUZUKI, TSUNEMATSU TAKEMOTO1971 Volume 19 Issue 1 Pages 87-92
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom camphor blue oil, the high boiling fraction of the essential oil of camphor tree, Cinnamomum camphora (Lauraceae), new sesquiterpenic ketone and alcohol, campherenone and campherenol, have been isolated. Both terpenoids can be interconverted by reductionoxidation reactions. The physico-chemical properties of these substances and their derivatives and their transformation into β-santalene have established their stereostructures as I and II, respectively.View full abstractDownload PDF (741K) -
HIROSHI HIKINO, CHOHACHI KONNO, TSUNEMATSU TAKEMOTO1971 Volume 19 Issue 1 Pages 93-96
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom zedoary, Curcuma zedoaria (Zingiberaceae), a new sesquiterpenic diol has been isolated and named curcumadiol whose structure has been deduced as I on the basis of the chemical and physico-chemical study.View full abstractDownload PDF (486K) -
HARUO SAIKACHI, HARU OGAWA, KATUTOSHI SATO1971 Volume 19 Issue 1 Pages 97-103
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7, 8 : 17, 18-Dibenzo [20] annulene 1, 4 : 11, 14-dioxide all trans isomer (IV) has been synthesized from the Wittig reaction of di-trans 1, 2-bis [(β-5-formyl)-2-furyl]-vinyl benzene (IIIa) with o-xylene-bis-(triphenylphosphonium bromide) in fairly high yield (35%). The reaction of IIIa with o-phenylenediamine in tetrahydrofuran has been shown to yield three annelated products, i.e., 7, 8 : 17, 18-dibenzo-19, 20-dihydro-16, 19-diaza [20] annulene 1, 4 : 11, 14-dioxide (VI) in 15%, 16-H-7, 8 : 17, 18-dibenzo-15-keto-16, 19-diaza [20] annulene 1, 4 : 11, 14-dioxide (VII) in 1.0% and oxazirino [2, 3-s] 7, 8 : 17, 18-dibenzo-16-aza [20] annulene 1, 4 : 11, 14-dioxide (VIII) in 15.7% yield. The interrelationship among these products was discussed. The reaction of hydrazine hydrate and cis-α, β-di (5-formyl-2-furyl) ethylene (XIb) has been shown to yield dimeric [28] tetraazaannulene tetraoxide (XIII) in 2.5%, and no monomeric [14] diazaanulene dioxide (XII) or no other disproportionation products were obtained.View full abstractDownload PDF (849K) -
MORIO IKEHARA, SHOJI YAMADA1971 Volume 19 Issue 1 Pages 104-109
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to obtain 8-fluoroadenosine, 8-aminoadenosine was subjected to Schiemann reaction. However, presumably due to lability of the nucleosidic linkage of 8-fluoroadenosine, only 8-fluoroadenine and 8-oxyadenine were obtained as the product. When 2', 3', 5'-tri-O-acetyl-8-aminoadenosine, which was synthesized from 2', 3', 5'-tri-O-acetyl-8-bromoadenosine by way of 8-azido compound, was diazotized with sodium nitrite in 40% HBF4 at -20°, 2', 3', 5'-tri-O-acetyl-8-fluoroadenosine was obtained in yield around 10%. Optical properties and migratory behaviors in paper chromatography resembled those of 8-bromoadenosine derivative. 8-Fluoroinosine and 8-oxyadenine were also obtained as the byproduct. Deacetylation of triacetyl-8-fluoroadenosine gave 8-fluoroadenosine, which had circular dichroism (CD) profile similar to that of 8-bromoadenosine and a syn conformation was suggested to this compound. 8-Aminoguanosine gave 8-aminoxanthine and 8-fluoroxanthine by the Schiemann reaction.View full abstractDownload PDF (811K) -
KEIKI KOUNO, YO UEDA1971 Volume 19 Issue 1 Pages 110-118
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction products of the color reactions of butylurea and glucuronolactone with 1-phenyl-1, 2-propanedione, two positional isomers of its monoxime and diacetyl in aqueous phosphoric acid were investigated. The results showed that all reactions, regardless of the difference in the color developing reagent employed, gave 2, 2'-dioxo-4, 5'-diimidazolylmethane (I) derivatives as main products, and that the reactions of diacetyl and its monoxime gave tetrahydroimidazo [4, 5-d] imidazole-2, 5-dione (II) derivatives as common products. All of these compounds developed visible colors in acidic media, and the colors received strong hyperchromic shifts by the duration of the keeping time at room temperature. Because every color had close relations with the colors of the respective reaction mixtures, I and II derivatives were indicated to have significant responsibilities for the colorations. In spite of the poor reproducibility of isolation, an isolation of 1, 4-dimethyl-4-acetyl-3 (or 6)-butylcarbamoylimino-1, 2-cyclohexen-6 (or 3)-one (III) from the reaction mixture of butylurea, diacetyl and glucuronolactone was also mentioned, because its responsibility for the color reaction was not excluded. The influence of glucuronolactone on the formation of the reaction products was shown to be negligible and glucuronolactone was assumed to play its role in the process of the stabilization of the color developed.View full abstractDownload PDF (1023K) -
YASUMITSU TAMURA, TOMOHISA MIYAMOTO, KINO SHIMOOKA, TAKEHIKO MASUI1971 Volume 19 Issue 1 Pages 119-123
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclization of 2-acylamino-2-thiocarbamoylacetamides (Va, b) with acetic formic anhydride gave good yields of 5-formamidothiazole-4-carboxamides (VIa, b) which were converted to 5-aminothiazole-4-carboxamides (VIIa, b) by hydrolysis. For the purpose of the preparation of the free base (VIIa), however, cyclization of Va with polyphosphoric acid was proved to give better result, that is, heating of Va-c and ethyl 2-acylamino-2-thiocarbamoylacetates (Vd-f) in polyphosphoric acid gave VIIa-c and ethyl 5-aminothiazole-4-carboxylates (VIId-f) in excellent yields. 5-Aminothiazole-4-carbonitriles (VIIg, h) were prepared by treatment of Va, b with phosphorus oxychloride.View full abstractDownload PDF (731K) -
TAKAYOSHI OGUMA, TSUNEJI NAGAI, HISASHI NOGAMI1971 Volume 19 Issue 1 Pages 124-129
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEvaluating the extent of the hydrophobicity of 8 local anesthetics by the adsorbability on carbon black, discussions were made what kind of role the hydrophobicity plays in the nerve blocking. Additionally, the relationship between the partition coefficient in n-octanol/buffer solution and the blocking potency was investigated. The adsorbed amount (represented by a) increased with pH, while the reported data of minimum blocking concentration (MBC) decreased. There was no comparison between the increases of a and 1/(MBC) with pH, because the latter increase was so remarkable. The blocking potency (represented by -log (MBC)) increased with the adsorbability (represented by log b), where all the data were included between log b=2.8, and log b=4.1. The most available local anesthetics had the adsorbability around log b=4. The blocking potency increased with the decrease in the occupied area by one molecule. The increasing tendency of partition coefficient with pH was closer to that of 1/(MBC) than that of a or b. All the results suggested that a minimum adsorbability of drug is necessary in the nerve blocking and the behavior of drug under the surface of nerve membrane which may be related with the penetration forms a necessary factor affecting the activity.View full abstractDownload PDF (697K) -
YASUMITSU TAMURA, NOBUKO TSUJIMOTO, MITSUHIKO MANO1971 Volume 19 Issue 1 Pages 130-138
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPreparations of pyridine N-oxide (7a) and N-aminopyridinium chloride (10a) by ring opening of a quaternary pyridinium salt and successive recyclization were investigated, and the following methods established. Treatment of N-(2, 4-dinitrophenyl) pyridinium chloride (5a) with hydroxylamine, followed by refluxing the resulted 5-(2, 4-dinitroanilino)-2, 4-pentadienal oxime (6a) in dioxane-water (4 : 1) gave pyridine N-oxide (7a) in 87% yield from pyridine. Refluxing a mixture of N-(2, 4-dinitrophenyl) pyridinium chloride (5a) and hydrazine hydrate in dioxane-water (4 : 1) after being kept overnight at room temperature, gave N-aminopyridinium chloride (10a) in 50% yield from pyridine. The methods were proved to be applicable to conversions of β-, γ-picoline and 3, 5-lutidine into the corresponding N-oxides and N-amino derivatives.View full abstractDownload PDF (973K) -
EIKO OHTSUKA, HARUKO TAGAWA, MORIO IKEHARA1971 Volume 19 Issue 1 Pages 139-142
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA trinucleoside diphosphate, GpUpA was synthesized using a dinucleotide 2', 3'-cyclic phosphate as an intermediate. The synthetic approach involved a condensation of N, 2', 5'-O-triacetylguanosine 3'-phosphate (I) and uridine 2'(3')-phosphate (II) to yield the dinucleotide with 2', 3'-cyclic phosphate (III) (Chart 1). Pancreatic RNase treatment of the product was followed by acetylation of the 2'-hydroxyl group of uridine to give the protected dinucleotide (VII). The overall yield from the mononucleotide was 41%. The unfractionated dinucleotide was used for the condensation with the protected nucleoside bearing the 5'-hydroxyl group (VIII). The isolated yield of the unprotected product was 12% from the dinucleotide.View full abstractDownload PDF (532K) -
YASUMITSU TAMURA, NOBUKO TSUJIMOTO, MICHIKO UCHIMURA1971 Volume 19 Issue 1 Pages 143-147
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIsoquinoline N-oxide (5) and N-imine (8) were prepared by ring-opening reactions of quarternary isoquinolinium salts and successive ring-closures. The ring-opening reaction of N-(2, 4-dinitrophenyl) isoquinolinium chloride (1) with hydroxylamine gave o-[2-(2, 4-dinitroanilino) vinyl] benzaldehyde oxime (2), which cyclized by refluxing in concentrated hydrochloric acid-ethanol (3 : 40) to isoquinoline N-oxide (5) in 53% yield from isoquinoline. This method was applied to the preparation of isoquinoline N-imine (8). An equimolar mixture of N-(2, 4-dinitrophenyl) isoquinolinium chloride (1) and hydrazine hydrate in dioxane-water (4 : 1) was heated under reflux to give isoquinoline N-imine (8) in 50% yield from isoquinoline.View full abstractDownload PDF (587K) -
MASAYOSHI OKIGAWA, HISAKATSU HATANAKA, NOBUSUKE KAWANO, ISAO MATSUNAGA ...1971 Volume 19 Issue 1 Pages 148-152
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new glycoside (I) was isolated from the leaves of Clerodendron trichotomum THUNB. and confirmed to be acacetin-7-β-D-glucurono-(1→2)-β-D-glucuronide, the sugar part of which was the same as that of glycyrrhizin in licorice.View full abstractDownload PDF (653K) -
TOSHIO NAMBARA, MITSUTERU NUMAZAWA, SETSUKO AKIYAMA1971 Volume 19 Issue 1 Pages 153-158
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to examine the occurrence of "NIH shift"during hydroxylation of the aromatic steroid, 2-and 3-deuterio-3-deoxyestrones (IIIb, V) were synthesized as substrate. After oral administration of these labeled steroids to a rabbit, two principal metabolites, 2-hydroxy-3-deoxyestrone (Ib) and 17α-estradiol, were isolated from the collected urine specimen. Inspection of mass and nuclear magnetic resonance spectra revealed that aryl hydroxylation was accompanied by a migration of deuterium from the initially labeled site to an adjacent position. The direction and extent of isotope migration are listed in Table I.View full abstractDownload PDF (638K) -
TAKAO YAMAZAKI, MASANORI NAGATA, FUJIO NOHARA, SIRO URANO1971 Volume 19 Issue 1 Pages 159-165
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnhydro 4-hydroxy-pyrido [1, 2-b] pyridazinium hydroxide derivatives were prepared starting with ethyl 2-piperidine-carboxylate (I). I was, via the N-nitroso compound (II), converted into the corresponding N-amino derivative (III), which was condensed with ethyl acetoacetate to give ethyl 1-(ethoxycarbonyl-isopropylidene) amino-2-piperidine carboxylate (IV) in a good yield. The Dieckmann condensation of IV led to the corresponding cyclic compound (V), mp 152-153°, contaminated with a small amount of a 4-hydroxy-pyrido [1, 2-b] pyridazinium hydroxide derivative (VI), mp 135-136° (anhydronium base). V and VI are transmutable each other by oxido-reduction. VI was readily hydrolysed to the corresponding carboxylic acid (VII), which was decarboxylated to anhydro 4-hydroxy-2-methyl-5, 6, 7, 8-tetrahydro-pyrido [1, 2-b] pyridazinium hydroxide (VIII), mp 142°. The C3-position of VIII was subject to both the electrophilic and the nucleophilic attacks ; VIII was readily brominated with bromine to give the 3-bromo compound (IX) which led, via the corresponding thiouronium bromide, to the 3-mercapto compound (XII), and to the anilino derivative (X) reacted with aniline. Furthermore, VIII was treated with hydrogen peroxide to give 3-hydroxy derivative (XV). The above synthesis has been applicable to a general method for the preparation of anhydro 1-substituted or 1, 6-disubstituted 5-hydroxy-pyridazinium hydroxides, a type of zwitterionic heterocyclic compounds.View full abstractDownload PDF (816K) -
KEIJIRO SAMEJIMA, MASANORI YOSHIOKA, ZENZO TAMURA1971 Volume 19 Issue 1 Pages 166-177
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSProcedures for the purification of acidic growth factors for Bifidobacterium bifidum from carrot were developed. These involved adequate solvent extraction and subsequent successive chromatography on Amberlite IR-45, IRC-50, IRA-68, and SE, DEAE, QAE Sephadex which included a proper precipitation procedure for the SE-Sephadex eluate, and preparative paper electrophoresis. Among five kinds of growth factors separated, the major growth factor and the most acidic factor were highly purified. Both factors differed from coenzyme A and its known precursors, while one of the weaker acidic factors coincided with D-pantetheine 4'-phosphate in chromatographic and electrophoretic behaviors.View full abstractDownload PDF (1365K) -
MASANORI YOSHIOKA, ZENZO TAMURA1971 Volume 19 Issue 1 Pages 178-185
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMolecular weight of the major bifidus factor (I) in carrot was less than 700. I was strongly acidic and converted to a still strongly acidic active compound (II) with alkaline phosphatase. I and II changed to D-pantetheine 4'-phosphate (P-PaSH) and D-pantetheine (PaSH) with KCN or 2-mercaptoethanol, conversely in 0.1M NaHCO3, P-PaSH and PaSS (D-pantethine) gradually and partially changed to I and II, respectively. These fact suggested that I and II were oxidation products of P-PaSH and PaSS. Among possible oxidation products of PaSS synthesized, D-Pantetheine-S-sulfonic acid (PaSSO2H) was active and coincided with II. Synthesized 4'-phospho-D-pantetheine-S-sulfonic acid (P-PaSSO3H) was also active and identified with I by the behaviors in thin-layer chromatography, paper electrophoresis, amino acid analysis, infrared and nuclear magnetic resonance spectra. The possibility to be an artifact of P-PaSSO3H was deniable, since a column chromatogram on DEAE-Sephadex of direct methanol extract of raw carrot root showed the identical peak. The biochemical and medical significances of the new compound P-PaSSO3H are discussed.View full abstractDownload PDF (874K) -
MASANORI YOSHIOKA, ZENZO TAMURA1971 Volume 19 Issue 1 Pages 186-189
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMolecular weight of the minor bifidus factor (III) in carrot was 700-800. III was converted to 3'-dephospho-coenzyme A (DP-CoA) with KCN or 2-mercaptoethanol. It suggested that III was 3'-dephospho-coenzyme A-S-sulfonic acid (DP-CoASSO3H). This was confirmed by amino acid and phosphoric acid analysis and ultraviolet spectrum. Further synthesized DP-CoASSO3H coincided with III in behaviors of gel filtration, paper electrophoresis, thin-layer chromatography and ultraviolet spectrum. Coenzyme A-S-sulfonic acid (CoASSO3H) was also synthesized, and significances of these S-sulfonated compounds are discussed.View full abstractDownload PDF (497K) -
Effect of Anti-inflammatory Drugs on Glucosamine-6-phosphate Synthetase from Inflamed Tissue of RatsEIICHI FUJIHIRA, NOBUYUKI TSUBOTA, MASAO NAKAZAWA1971 Volume 19 Issue 1 Pages 190-195
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1) The in vitro synthesis of glucosamine-6-phosphate (Gm-6-P) was inhibited effectively by adding aurothiomalate and acid non-steroidal anti-inflammatory drugs to the incubation mixtures. The drug-action was more sensitive in the reaction with the supernatant fluid of the croton oil-induced granulation tissue homogenate using as a source of Gm-6-P synthetase, as compared to the case of the liver homogenate. Potency of each compound was in the following descending order ; aurothiomalate, flufenamic and mefenamic acids, phenylbutazone and salicylic acid. Chloroquine and aminopyrine had no effect on Gm-6-P synthesis with the enzymes from both sources at 10-3M. 2) A markedly high activity of Gm-6-P synthetase was found in the swollen hind paws of the rats which were suffered from adjuvant disease. pH-difference was seen in the maximum production of Gm-6-P between the inflamed tissue and liver enzymes. The optimum pH was 6.8 for the reaction with the homogenates of the swollen paws and croton oil-induced granulation tissue, while that for the liver enzyme was in the range from 7.7 to 8.3. 3) Good correlation was seen between increases of the enzyme activity and the swelling in the hind paws as adjuvant disease appeared and developed in rats. On the other hand, the activity of the liver enzyme was not changed significantly by the development of the typical inflammatory lesions. 4) The drug-action to Gm-6-P synthesis with the paw enzyme was much clearer in the reaction at pH 6.8 than pH 7.7.View full abstractDownload PDF (716K) -
ATSUKO NODA, YOSHIYUKI HIRAKAWA, NORIKO FUJII, SADAO IGUCHI1971 Volume 19 Issue 1 Pages 196-199
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
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MIKIO YAMAZAKI, YUKIO MAEBAYASHI, KOMEI MIYAKI1971 Volume 19 Issue 1 Pages 199-201
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (480K) -
YOSHIMASA SATO, MIHO HIRANO, ISAO NITTA, JUNKO AZUMA, KOJI HAYASHI, HI ...1971 Volume 19 Issue 1 Pages 202-205
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (486K) -
SADAO NISHIGAKI, SHINOBU FUKAZAWA, KAZUKO OGIWARA, FUMIO YONEDA1971 Volume 19 Issue 1 Pages 206-207
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (359K) -
VERAPONG PODIMUANG, STANG MONGKOLSUK, KUNITOSHI YOSHIHIRA, SHINSAKU NA ...1971 Volume 19 Issue 1 Pages 207-208
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
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HIROAKI KUBO, TERUMI NAKAJIMA, ZENZO TAMURA1971 Volume 19 Issue 1 Pages 210-211
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
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HIROSHI HIKINO, TOMIHISA OHTA, TSUNEMATSU TAKEMOTO1971 Volume 19 Issue 1 Pages 212-213
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
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KAZUYA KOHASHI, YOSUKE OHKURA, TSUTOMU MOMOSE1971 Volume 19 Issue 1 Pages 213-214
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
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KEITARO SENGA, FUMIO YONEDA, SADAO NISHIGAKI1971 Volume 19 Issue 1 Pages 215-216
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
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HIDEO INATOMI, FUMITO INUKAI, TAKAO MURAKAMI1971 Volume 19 Issue 1 Pages 216-217
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
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KOUICHIRO UMEMOTO, KEIICHIRO HOZUMI1971 Volume 19 Issue 1 Pages 217-219
Published: January 25, 1971
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (400K)
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