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KATSUHIDE MATOBA, NORIKO MIYABAYASHI, TAKAO YAMAZAKI
1973 Volume 93 Issue 11 Pages
1401-1405
Published: November 25, 1973
Released on J-STAGE: May 30, 2008
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With excess lithium aluminum hydride, 2-methyl-3-methoxy-2-cyclopentenone (III), 2-ethyl-3-methoxy-2-cyclopentenone (IV), and 2, 5-dimethyl-3-methoxy-2-cyclopentenone (VI) were reduced to the corresponding allyl alcohols, 2-methyl-2-cyclopentenol (Xa), 2-ethyl-2-cyclopentenol (XIa), and 2, 5-dimethyl-2-cyclopentenol (XIIa), respectively. On the other hand, 2, 4-dimethyl-3-methoxy-2-cyclopentenone (V) was reduced to 2, 4-dimethyl-2-cyclopentenol (XIVa), 2, 5-dimethyl-2-cyclopentenone (XIII
(v)e), and 2, 4-dimethyl-3-methoxy-2-cyclopenteno1-(XVc). Mechanism if this reduction and the substituent effect are described.
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KATSUHIDE MATOBA, TAKAO YAMAZAKI
1973 Volume 93 Issue 11 Pages
1406-1414
Published: November 25, 1973
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2-Methyl-3-methoxy-4-t-butyl-2-cyc1opentenone (VI) and 3-methoxy-4-t-butyl-2-cyclohexenone (IX) were reduced to the corresponding β-methoxy-allyl alcohols with excess lithium aluminum hydride. Under the same conditions, 2-methyl-3-methoxy-5-t-butyl-2-cyclopentenone (VII) was reduced to saturated ketones, allyl alcohols, and diols. On the other hand, from 3-methoxy-6-t-butyl-2-cyclohexenone (X), β-methoxyallyl alcohols, saturated ketones, allyl alcohols, and diols were obtained. The substituent effect of t-butyl group in five-membered and six-membered vinylogous esters was discussed, and a mechanism for the formation of diols was proposed.
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SATOSHI SUGIYAMA, SHIGEO SATO, KAZUTAKA YAMAGUCHI
1973 Volume 93 Issue 11 Pages
1415-1417
Published: November 25, 1973
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p-Toluidine derivatives of saturated fatty acids were found to be suitable as an internal standard substance for gas-liquid chromatography available in a wide range. Benzarone was assayed within 1% of standard deviation by the use of one of them, under the conditions of 5.9% SE-30 on Chromosorb W at 250°.
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SATOSHI SUGIYAMA, NOBUYUKI SASAKI, KYOKO NAGATSUMA, SHIGEO SATO, KAZUT ...
1973 Volume 93 Issue 11 Pages
1418-1421
Published: November 25, 1973
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It was found that alkaline hydrolysis of benzbromarone (II) proceeded by two kinds of cleavage, α and β. The former gave 3, 5-dibromo-4-hydroxybenzoic acid (VI) and 2-ethylbenzofuran (VIII), and the latter gave 3', 5'-dibromo-4'-hydroxy-2-(2-hydroxyphenyl) acetophenone (IV) and propionic acid (IX). IV was completely cyclized to 2-(3, 5-dibromo-4-hydroxyphenyl) benzofuran (V) by heating in the presence of an acid. Determination of the ratio of α and β cleavages was performed by gas chromatography and the predominance of β cleavage was recognized.
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YASUKATSU YUDA, HIROSHI MORIYA, CHIAKI MORIWAKI
1973 Volume 93 Issue 11 Pages
1422-1426
Published: November 25, 1973
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The role of kinins and their related substances in inflammatory process was studied by employing carboxymethylcellulose (CMC) pouch method in a rat. Kinin and kininase activities, pH value, and leucocyte migration in the effusion from experimental CMC pouch were measured, and kininase and kininogen levels in plasma were also determined. An increase of kinins in the effusion was found from 3 to 4 hr after CMC administration, and the content in the 3 hr effusion was higher than that at 4 hr, while an increase of leucocyte migration became significant at 4 hr. From these results, it seems plausible that the kinins found in effusion were not derived from migrated leucocytes but from plasma, because plasma kininogen decrease was found in inflammatory rat. Potent kininases were still found in the effusion in this investigation, and the activity in the effusion elevated parallel with kinin activity in it. Though it has been reported that pH value of inflammatory effusion was acidic and kininases were inactivated in acidic condition, the effusion from CMC-induced inflammation was found to be neutral. It has been widely accepted that kinins might be one of the chemical mediators in inflammatory processes, but the present results seem to indicate that the kinin system may participate only in the very early stage of the processes.
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KEIICHI WATANABE
1973 Volume 93 Issue 11 Pages
1427-1432
Published: November 25, 1973
Released on J-STAGE: May 30, 2008
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This kinetic study dealt with the hydrolysis of acetylsalicylic acid (ASP) in the aqueous solution of dimethyl sulfoxide (DMSO) at different solvent concentrations, pH, and temperature. The hydrolysis rate at pH 7 and 8 increased with increasing DMSO concentration, but that at pH6 especially decreased at higher concentration than 8 molal DMSO. The reaction rate in aqueous solution at the most stable pH, that is 2.3, also decreased by the addition of DMSO. The pH independent region of the hydrolysis rate observed in aqueous solution from pH 5 to 7 shifted to a higher pH from 9 to 13 by the addition of DMSO. Since the ionic dissociation of ASP observed by ultraviolet absorption was strongly suppressed by DMSO, the decrease of the rate in the aqueous DMSO solution at pH 6 could be mainly due to the decrease of the ASP anion which is a more reactive species. The first-order rate constant of ASP anion estimated by the observed pKa was almost constant below the molar ratio of [DMSO]/[H
2O]=0.3, but it increased at a higher concentration of DMSO. The relationship between the reaction rate constant and macroscopic dielectric constant of the solution could not be expressed by Awis' expression of anion-dipole reaction. The relationship between the activation enthalpy and entropy in various aqueous solution, i.e., EtOH, propylene glycol, dimethylacetamide, and DMSO was expressed by a straight line of Leffler's isokinetic equation.
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YOSHINORI TOMINAGA, REIKO NATSUKI, YOSHIRO MATSUDA, GORO KOBAYASHI
1973 Volume 93 Issue 11 Pages
1433-1436
Published: November 25, 1973
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3-Cyanoindoles were synthesized in a good yield by the reaction of methyl 3-indole-dithiocarboxylates and conc. ammonia water. This is a new synthetic method for 3-cyanoindole derivatives. The reaction of 2-hydroxy-3-indoledithiocarboxylates and hydroxylamine also afforded the corresponding 3-cyanoindoles.
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TETSUZO KATO, HIROSHI YAMANAKA, HIROSHI FUKUMI, MASAKI NODA
1973 Volume 93 Issue 11 Pages
1437-1444
Published: November 25, 1973
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3-Aminocrotonamide (II) reacted with α, β-unsaturated esters (III) in the presence of EtONa to give the corresponding 4-pyrimidone derivatives (VIIa-c) and glutarimide derivatives (VIIIa-c), whereas the use of tert-BuOK resulted in the formation of VIIIa-c and Xc-d. The mechanism of the formation of VII, VIII, and X is described.
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TAKAHIRO FUTAMI, JUNKO NAKAMURA, SHIZUO HAYASHI
1973 Volume 93 Issue 11 Pages
1445-1451
Published: November 25, 1973
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The effect of alkyldimethylbenzylammonium chloride (Alkyl-DBAC) on capillary permeability and on the activity of succinic dehydrogenase was studied in order to understand the inflammatory action of this drug. The capillary permeability increased from 45 min to 4.5 hr after C
12-DBAC was intracutaneously injected. The thresholds of capillary permeability fly was 0.01% When C
12-DBAC was intracutaneously injected in rabbit, 0.005% when intraperitoneally injected in mice, and 1.0% when externally applied on rabbit. The capillary permeability was influenced by the presence of keratinous layer. The capillary permeability depended on the chain length of Alkyl-DBAC and its maximum was at C
12. The activity of succinic dehydrogenase was inhibited by the high concentration of Alkyl-DBAC. The inhibitory action of Alkyl-DBAC reached a maximum at C
12. The threshold of C
12-DBAC on capillary permeability and the inhibitory concentration on the succinic dehydrogenase were nearly the same but the activity of liver homogenate succinic dehydrogenase was activated by the low concentration of C
12-DBAC ana this effect was inhibited by phospholipase C.
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MASANORI YOSHIDA
1973 Volume 93 Issue 11 Pages
1452-1456
Published: November 25, 1973
Released on J-STAGE: May 30, 2008
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The solubilizing action of N-substituted nicotinamides was studied in relation to the adsorption of nicotinamides by carbon black from aqueous solution, and to the partition coefficients in CHCl
3-H
2O and octanol-H
2O systems. The adsorption by carbon black was reversible and isotherms were well expressed by the Langmuir eqution. Amount of N-substituted nicotinamides adsorbed by carbon black increased with the chain length of the substituents in N-substituted nicotinamides. Formation constants of solubilizatenicotinamide complexes had a good correlation with the adsorbability of N-subetituted nicotinamides, except N, N-dialkyl substituents, by carbon black and with the partition coefficients in CHCl
3-H
2O and octanol-H
2O systems.
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TAKEO UEDA, ATSUSHI TAKADA, HITOSHI NISHIKAWA
1973 Volume 93 Issue 11 Pages
1457-1462
Published: November 25, 1973
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Nitrated products of Vitali-Freeman color reaction were investigated. It was concluded from the analytical results of the nitrated products of benzene derivatives in Vitali-Freeman condition that they can be clasified into two groups ; one was colored by their mononitrated product with tetraethylammonium hydroxide (TEAH), and the other, by their polynitrated product. In the nitration of atropine and hyoscyamine, seven compounds were separated by the chromatographic method, and their structures were investigated.
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JUTARO OKADA, KOICHI NAKANO, MICHIHIRO TSUCHIYA
1973 Volume 93 Issue 11 Pages
1463-1467
Published: November 25, 1973
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By gas phase reaction of trimethylenediamine and formaldehyde on alumina catalyst, 1-methyl-hexahydro-pyrimidine (I) and 1, 3-dimethyl-hexahydropyrimidine (II) were obtained in a good yield. In a molar ratio of ECHO to trimethylenediamine (TMDA) of 1.34, I was obtained selectively and in the highest yield when reacted at 220°. At the temperature higher than 350°, 2-methylpyridine was obtained. In molar ratio of 2.68, I was obtained more than II in the temperature range of 180° to 240°, but II was obtained more than I in the range of 250° to 290°. At 230°, only I was obtained from a molar ratio of 1.8, and only II in a molar ratio of 4.0. The yield of I and II increased with W/F, and the yield of I was maximum W/F : of 180, but that of II was maximum at W/F : of 220.
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JUTARO OKADA, KOICHI NAKANO, KOJI HAYAKAWA
1973 Volume 93 Issue 11 Pages
1468-1473
Published: November 25, 1973
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The reactions of ethylenediamine (ED) and formaldehyde (FA) in the alumina-packed bed reactor were studied. Methylpyrazine was obtained as the main product, and a small amount of dimethylpyrazine was also obtained. This reaction mechanism is yet unknown, and a statistical method was employed for the determination of optimum condition. The first part of the investigation consisted of 2
4 factorial design. Four variables were chosen-reaction temperature (A), catalyst weight (B), molar ratio of reactants (C), and the amount of water added (D). In the analysis of variance, all factors except (B) were significant at the 5% level. The interaction between (A) and (C) was checked in a wider range. Through experiments in the direction of the steepest ascent based on the first-order response function, it was found that the yield of methylpyrazine dropped suddenly beyond 410° and it was concluded that the optimum condition are follows : temprature 410°, catalyst weight, 21.92 g, molar ratio FA/ED=2.78, and dilution water 30.49 times mole, which gave the maximum yield of 42.5%.
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TAKEO UEDA, ATSUSHI TAKADA, KUNISHIGE KOSUGI
1973 Volume 93 Issue 11 Pages
1474-1480
Published: November 25, 1973
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1, 2-Naphthoquinone-2-acylhydrazones and their derivatives having a sulfonic acid group in 4-position were synthesized, and coloration of these compounds with various metal ions was examined. It was found that 1, 2-naphthoquinone-2-(p-nitrobenzoyl)-hydrazone was useful reagent for the detection of Hg
2+, and bis (1, 2-naphthoquinone-4-sulfonic acid)-2, 2-malonyldihydrazone was useful reagent for the detection and determination of Al
3+.
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TAKAJI KOYAMA, TAKASHI HIROTA, MASATOSHI YAMATO, SHINYA KOHKI
1973 Volume 93 Issue 11 Pages
1481-1483
Published: November 25, 1973
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α-Acyl-α-naphthylacetonitriles were heated with HCONH
2 and POCl
3, and the following results were obtained. 1) In the case of α-acyl-α-(1-naphthyl) acetonitriles, formyl derivative (IIa) gave 4-amino-5-(1-naphthyl) pyrimidine (IIIa), acetyl derivative (IIb) gave 4-amino-6-methy1-5-(1-naphthyl) pyrimidine (IIIb), and benzoyl derivative (IIc) gave IIIa and benzamide (IV). 2) In the case of α-acyl-α-(2-naphtyl) acetonitrilei, formyl derivative (VIa) gave 4-amino-5-(2-naphthyl) pyrimidine(VII), acetyl derivative (VIb) gave 6-methyl-5-(2-naphthyl)-4-pyrimidone.(VIII), and benroyl derivative (VIc) gave VII and IV.
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NOBORU SHIMAHARA, KENZO SIRAKAWA, HIROSHI HIRANO
1973 Volume 93 Issue 11 Pages
1484-1489
Published: November 25, 1973
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Reaction of thiol-type thiamine sodium salt (I) with dialkylaminosulfenyl halides, sodium dialkylaminothiosulfate or sodium dialkylaminosulfenylthiosulfate gave N-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-N-[4-hydrxy-1-methyl-2-(dialkylaminodithio)-1-butenyl] formamides (II) (thiamine dialkylamino disulfides) in a good yield. Treatment of II with amines was studied and discussed. II showed full thiamine activity in growth-promoting assay using thiamine-deficient rats.
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NOBORU SHIMAHARA, KENZO SIRAKAWA, HIROSHI HIRANO
1973 Volume 93 Issue 11 Pages
1490-1497
Published: November 25, 1973
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Reaction of N-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-N-[4-hydroxy-1-methyl-2-(dialkylaminodithio)-1-butenyl] formamides (I) (thiamine dialkylamino disulfides) with alkanethiols in ethanol containing 2 moles of hydrogen chloride gave N-[(4-amino-2-methyl-5-pyrimidinyl) methyl]-N-[4-hydroxy-1-methyl-2-(alkyltrithio)-1-butenyl] formamides (II) (thiamine alkyl trisulfides) in a high yield. The mechanism of this reaction was studied and discussed. When the propyl derivative (IIa) was treated with cycteine, thiamine (IX) and S-(propyldithio) cysteine (XI) were obtained. On the other hand, treatment of 1-adamantyl derivative (IId) with cysteine gave IX, cystine, and bis (1-adamantyl) tetra-sulfide (XII). II showed full thiamine activity in growth-promoting assay using thiamine-deficient rats.
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TSUGUJI NEGISHI, HIROSHI TAKAHIRA
1973 Volume 93 Issue 11 Pages
1498-1508
Published: November 25, 1973
Released on J-STAGE: May 30, 2008
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The incorporation of Adriamycin (14-hydroxydaunomycin), a new antibiotic possessing an antitumor activity, into Ehlrich ascites tumor cell nuclei and the interaction between Adriamycin and DNA were investigated. Intraperitoneal injection of Adriamycin[
3H(G)] to mice bearing Ehlrich ascites tumor demonstrated that silver grains in its autoradiogram were localized in tumor cell nuclei. The gel filtration of tumor cell chromatin over Sephadex G-25 and of chromatin digested by trypsin over Sephadex G-200 suggested that Adriamycin was bound to DNA and not to protein of chromatin. The binding of DNA and Adriamycin in vitro was supported by some physicochemical changes such as visible absorption spectrum fluorescence intensity, polarographic behavior, and possession of non-dialytic quality in Adriamycin and thermal denaturation-renaturation behavior of DNA. RNA, apurinic deoxyribonucleic acid, apyrimidinic deoxyribonucleic acid, hyaluronic acid, chondroitinsulfate, heparin, and a high concentration of AMP and TMP seeded to be bound to Adriamycin, but the physicochemical changes were not exactly the same as those induced by DNA. The quantitative investigation of interaction between Adriamycin and DNA was made by an equilibrium dialysis procedure. It was thereby found that Adriamycin was bound to DNA according to the Langmuir-type interaction and that free energy changes of binding were 8.4 kcal/mole. Calculations showed that the saturated binding site of DNA was 1 per 5.4 bases of DNA. It was suggested that more than two kinds of binding type, perhaps including hydrogen bond and ionic bond, were present in the Adriamycin-DNA complex. Adriamycin inhibited the RNA synthesis and DNA degradation by deoxyribonuclease, depending on the DNA-Adriamycin molar ratio. The formation of DNA-Adriamycin complex can be considered to be responsible for the biological effect of Adriamycin.
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KENJI OKAMOTO, SHINICHI SHIMAMURA
1973 Volume 93 Issue 11 Pages
1509-1513
Published: November 25, 1973
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Following the previous work, several new N-carbobenzoxyamino acid 4-morpholinyl esters (Arg (NO
2), Asp (β-OMe), Glu (γ-OMe), Ile, Leu, Met, Thr, and Trp) were prepared. Their coupling with Gly-OEt gave the corresponding N-carboenzoxydipeptide esters. Reactions of these 4-morpholinyl esters with amino acid sodium salts in aqueous organic solvent gave the corresponding N-carbobenzoxydipeptides, while good results were not obtained in the condensations which involved sterically hindered amino acids. Young's racemization test gave a high optical purity of 98%. Further, several reactions of N-benzoylglycine 4-morpholinyl ester were examined, and it was found that the ester was comparatively stable to acetic acid or 25% HBr in acetic acid, giving about 70% recovery in both media.
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SEIGO FUKUSHIMA, MASAHARU KINOSHITA, TADATAKA NORO
1973 Volume 93 Issue 11 Pages
1514-1516
Published: November 25, 1973
Released on J-STAGE: May 30, 2008
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The following compounds were synthesized : ω-(2-Methoxy-5-nitrophenyl)-2, 4-dihydroxyacetophenone (III), ω-(2-methoxy-5-nitrophenyl)-2, 4-dimethoxyacetophenone (IV), and 7-hydroxy-2'-methoxy-5'-nitroisoflavone (VI).
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SHIN MATSUURA, TOSHINOBU KUNII, MUNEKAZU IINUMA
1973 Volume 93 Issue 11 Pages
1517-1519
Published: November 25, 1973
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Eupatrin, sinensetin, and 3'-hydroxy-5, 6, 7, 4'-tetramethoxyflavone were isolated from Kumis-kuching (Orthosiphon stamineus BENTH.). These compounds were identified with the respective flavones synthesized from 2-hydroxy-4, 5, 6-trimethoxyacetophenone.
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YOSHINORI TOMINAGA, REIKO NATSUKI, GORO MATSUDA, GORO KOBAYASHI
1973 Volume 93 Issue 11 Pages
1520-1522
Published: November 25, 1973
Released on J-STAGE: May 30, 2008
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Application of sodium cyanide, to 3-bis (methylthiomethylene) oxindole (I) afforded 3-[cyano (methylthio) methylene] oxindole (II), and the reaction of II with nucleophilic reagents such as amines and active methylene compounds gave the corresponding products formed by substitution of the methylthio group of II.
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YOSHINORI TOMINAGA, REIKO NATSUKI, YOSHIRO MATSUDA, GORO KOBAYASHI
1973 Volume 93 Issue 11 Pages
1523-1525
Published: November 25, 1973
Released on J-STAGE: May 30, 2008
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Reaction of cyclic ketenethioacetal, 3-(methylthio) thiapyrano [3, 4-b] indol-1-one (Ia, b) and active methylenes was carried out and the corresponding products (IIIa-e) with the methylthio group substituted were obtained. Reaction of 4-(methylthio)-pyrano [3, 4-b] indol-2-one with active methylenes also afforded the corresponding substituted products (IVa-c).
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HIDEO NAKAO, MASAMI FUKUSHIMA, SHIN-ICHI SUGAWARA
1973 Volume 93 Issue 11 Pages
1526-1529
Published: November 25, 1973
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5-Cyano-2-furaldehyde and its derivatives were synthesized and their antimicrobial activities were tested. Neither series of compound possessed significant antimicrobial activity.
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TAKAO INOUE, HIROKO HIRASHIMA
1973 Volume 93 Issue 11 Pages
1530-1533
Published: November 25, 1973
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From the leaves of Sambucus sieboldiana BLUME, ex GRAEBN. var. Miquelii (NAKAI) HARA were isolated a colorless waxy substance which is almost composed of a mixture of α-amyrin and β-amyrin palmitates, ursolic acia, β-sitosterol, kaempferol, quercetin, sucrose, and a large amount of potassium nitrate (about 5% of dried leaves). Oleanolic acids, stigmasterol, and campesterol were detected by gas-liquid chromatography, and also glucose, fructose, and two flavonoid glycosides by paper chromatography. Chemotaxonomy of Sambucus species has been briefly discussed.
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ITSUO YOSHIZAWA, MICHIYA KIMURA
1973 Volume 93 Issue 11 Pages
1533-1536
Published: November 25, 1973
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A simple method to prepare 2-hydroxyestrone-6, 7-
3H in a high yield is described. The method is based on the benzoyloxylation of estrone-6, 7-
3H with benzoyl peroxide followed by acid hydrolysis as previously described.
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TAKAJI KOYAMA, TAKASHI HIROTA, MASATOSHI YAMATO, SHINYA KOHKI
1973 Volume 93 Issue 11 Pages
1536-1538
Published: November 25, 1973
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Treatment of α-formyl-(IIa) and α-acetyl-5, 6, 7, 8-tetrahydronaphthyl-2-acetonitrile (IIb) with formamide and phosphoryl chloride respectivily gave 4-amino-(IIIa) and 4-amino-6-methyl-5-(5, 6, 7, 8-tetrahydro-2-naphthyl) pyrimidine (IIIc). The same treatment of the benzoyl derivative (IIc) gave IIIa and benzamide (IV).
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KIYOKAZU TAKAISHI, YUZO KAWAHARA, KATSUHIKO IKEBE
1973 Volume 93 Issue 11 Pages
1538-1542
Published: November 25, 1973
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Maltol and sugars in the leaves of Cercidiphyllum japonicum were examined and the presence of maltol (1.8-2.3%), fructose (2.6%), glucose (3.0%), and sorbitol (1.1%) was confirmed. The high amount of sugars was correlated to the amount of maltol all the year. This correlation is interesting from biosynthetic point of view, since it has been expected that maltol is synthesized from a sugar.
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MASANORI OHNISHI, HIROYOSHI OHUE, HARUO MEGURI
1973 Volume 93 Issue 11 Pages
1542-1544
Published: November 25, 1973
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Two flavonoids, two toxic components, and ursolic acid were isolated from the flowers of Rhododendron linealifolium SIEB. et ZUCC. The two flavonoids were identified with azareatin and quercetin and the two toxic components were identified with grayanotoxin I and III.
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