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Volume 87, Issue 5
Displaying 1-30 of 30 articles from this issue
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Teisuke Okano, Shujiro Goya, Tokio Kaizu1967 Volume 87 Issue 5 Pages 469-472
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIsoguanine, 2, 6-dimethylpurine, 9-methyl- and 9-cyclohexylguanine, guanine, and xanthine were methylated in N, N-dimethylacetamide, and the reaction products were identified by UV spectrophotometry and paper chromatography. 6-Aminopurines gave 3, 9-dimethyl derivatives regardless of the substituent at the 2-position. 7, 9-Dialkylpurine betaines were obtained when xanthine, guanine, and 9-alkylguanines were treated with methyl p-toluenesulfonate.View full abstractDownload PDF (494K) -
Teisuke Okano, Kazuyuki Tsuji1967 Volume 87 Issue 5 Pages 473-478
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSElectronic state of flavin core of riboflavin has been studied making use of the absorption and fluorecence emission spectra of various nonaqueous solutions of riboflavin tetrabutyrate (RTB). The absorption spectra of RTB in nonpolar solvents, such as carbon tetrachloride and diethyl ether, showed two new bands or shoulders in the vicinity of 420 and 470 mμ in addition to the well-known bands (α and β maxima at about 450 and 340 mμ, respectively). While the position of the a band maximum remained unaffected, the β band shifted toward longer wave length with increasing polarity of solvent, indicating that the latter is associated with π→π* transition. Two fluorescence maxima were observed in the emission spectra of RTB in nonpolar solvents, viz. at about 500 and 520 mμ. The fluorescence maximum of the shorter wave length migrates with solvent polarity corresponding to the migration of the β absorption band maximum, and has been ascribed to monomeric form of RTB. With the increase of RTB concentration, fluorescence intensity at 520 mμ increased while that of the 500 mμ decreased, indicating that the former maximum resulted from molecular association of the solute. A vertically stacked model was proposed for the dimerized complex, taking account of the electronic map of isoalloxazine.View full abstractDownload PDF (708K) -
Eiichi Tomita, Yuusaku Hirota, Yoshihiro Nitta1967 Volume 87 Issue 5 Pages 479-484
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAcid-catalyzed reaction of β-D-glucopyranosiduronic acid was examined and a linear relation was found between the logarithm of the first-order rate coefficient and Hammet's acidity function, the slope of the line being approximately 1. This relationship agrees with the reaction mechanism known as the A-1 reaction among the Zucker-Hammet hypotheses, although there was a difference in the slope of the line according to various acids. The straight line obtained on addition of a salt to the acid solution agreed approximately with the straight line obtained without the addition of a salt. Rate of acid hydrolysis in heavy water solution was greater than that in aqueous solution. These results suggest that the acid-catalyzed reaction of β-D-glucopyranosiduronic acid has the same reaction mechanism as that of A-1 reaction proposed for glucopyranosides.View full abstractDownload PDF (617K) -
Eiichi Tomita1967 Volume 87 Issue 5 Pages 485-489
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSEffect of the electron affinity of the aglycone group in the rate of acid hydrolysis of alkyl-β-D-glucopyranosiduronic acid was examined. Electron-attracting aglycone was found to decrease the acid hydrolysis rate greatly, while the electron releasing aglycone greatly increased the rate. The Hammet-Taft rule was applied to the acid hydrolysis rate of glucopyranosiduronic acid and glucopyranoside, and the result suggested that the mechanism of hydrolysis was the same for glucopyranosiduronic acid (ρ*) and for glucopyranoside (ρ1*) having an electron releasing aglycone, but differed from that of glycopyranoside(ρ2*)having an electron-attracting aglycone. The activation energy has the greatest effect on the acid hydrolysis rate constant of glucopyranosiduronic acid and the entropy of activation has no part in it.View full abstractDownload PDF (578K) -
Eiichi Tomita1967 Volume 87 Issue 5 Pages 490-494
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSEffect of the electron affinity of the aglycone group in the alkaline hydrolysis rate of alkyl- and aryl-β-D-glucopyranosiduronic acid was examined. Electron-attracting aglycone increased the hydrolysis rate of the acid while the electron-releasing aglycone decreased this rate. This relationship is the reverse of the same effect in acid hydrolysis. Hammett value in the rate of alkaline hydrolysis of aryl-βD-glucopyranosiduronic acid was about 1.5 in either N, 2N, or 4N sodium hydroxide at 100°.View full abstractDownload PDF (538K) -
Eiichi Tomita, Yoshihiro Nitta1967 Volume 87 Issue 5 Pages 495-499
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSRate of acid and alkaline hydrolyses of glucofuranosiduronic acid 3, 6-lactone and glucopyranosiduronic acid, and their α- and β-anomers was examined. The 3, 6-lactone was hydrolyzed much faster than the acid by either acid or alkali, and the β-anomer of the acid was more rapidly hydrolyzed than the α-anomer. The fairly large minus value of the entropy of activation in the acid-catalyzed hydrolysis of the 3, 6-lactone suggested this to be an A-2 reaction. Comparative considerations were made on the kinetic data of glucuronoside and glucoside.View full abstractDownload PDF (534K) -
Koji Kuroda, Genzo Hashizume1967 Volume 87 Issue 5 Pages 500-506
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDetermination of hydrocortisone acetate, chloramphenicol, and tetracycline hydrochloride in an ointment was carried out by the X-ray diffraction analysis. The concentration of these chief components in the ointment was so small that the intensity of diffraction lines was weak, and some of the strongest peaks were close to the halo of white petrolatum used as the ointment base. Consequently, relative error of the determined values became fairly large but the method seemed to be practicable.View full abstractDownload PDF (576K) -
Taketo Ogiso1967 Volume 87 Issue 5 Pages 507-510
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSPolarographic studies were made on copper-histidine chelate to determine the composition and stability constant in aqueous solution. The results of polarographic analysis of a solution containing cupric nitrate (5×10-4M) and excess histidine (2.5×10-2M) at 25° are given in Table I. The electrode reaction for the copper-histidine chelate indicated that two electrons were involved, as shown by the values of (E3/4∼E1/4). The two molecules of histidine were found to be coordinated with each cupric ion from the slope of the plot of equation (5), as shown in Fig. 3. Further, stability constant of copper-histidine chelate was calculated to be log β=18.40 from equation (5).View full abstractDownload PDF (501K) -
Akiko Kubodera, Tetsuro Mori, Susumu Tsurufuji1967 Volume 87 Issue 5 Pages 511-515
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSEffect of 10 chelating agents on the excretion of radiostrontium from the body was investigated in mice. Sodium salts and/or monocalcium-sodium salts of these chelating agents were used as test materials. Preliminery toxicity tests were carried out to estimate their approximate maximum safety doses. The sodium salts were generally more toxic and brought about some convulsion with occasional death which were attributed to the decrease of Ca2+ ion in the blood. The monocalcium-sodium salts were applicable in 10-folds as compared with their equivalent sodium salts. The chelating agents and radioactive strontium were simultaneously injected into different parts of the body. The animals were killed 24 hours after the injection, and then reduced to ashes individually in an electric furnace after removing the digestive tracts and bladders. Radioactivity of the ashes was assayed to determine the percentage retention of radioactive strontium in the carcasses. Monocalcium-disodium salt of bis(dicarboxyaminoethyl) ether was found to be one of the most effective agents, same as calcium sodium citrate which had been previously reported.View full abstractDownload PDF (597K) -
Yukio Nishimoto, Etsuo Tsuchida, Shoji Toyoshima1967 Volume 87 Issue 5 Pages 516-523
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSConditions for separatory determination of 11 kinds of tetracycline by thin-layer chromatography were examined. These compounds were found to show tailing on the usual silica gel layer and this was considered to be due to chelation of tetra cyclines with trace metals in the silica gel. In order to stop this reaction, the thin layer was treated with disodium-EDTA and a good result was obtained. Further, changes in the behavior of tetracycline and oxytetracycline by pH and temperature were examined, and the effect of citric acid, boric acid, and calcium ion on these compounds was also examined. At pH 4.0, oxytetracycline undergoes specific decomposition and the solution colors pink. Two kinds of decomposition product were isolated and these were examined by thin-layer chromatorarhy, and by ultraviolet and infrared spectra.View full abstractDownload PDF (796K) -
Tadashi Hashimoto1967 Volume 87 Issue 5 Pages 524-527
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSExaminations were made on the products obtained by the nitration of (trimethylsilyl)benzene (I) in acetic anhydride with cupric nitrate (Cu(NO3)2·3H2O) at 40° for 6 hours. The molar percentage yields of the products, o-(II), m-(III), and p-(trimethylsilyl)nitrobenzene (IV), and nitrobenzene (V), were examined by gas chromatography and the results obtained are listed in Table I. The partial rate factors at 1-/2-/3-/4- and at 2-/3-/4- are 18/12/17/23 and 15/21/29, respectively. Warming of a mixture of I, II, III, IV, and V in acetic acid, in the presence of nitric acid, at 40° for 6 hours results in protodesilylatiom of only a small amount of I and the others are not decomposed. Consequently, the formation of V is not due to protodesilylation of III, as had been thought, but is due to the nitrodesilylation of I.View full abstractDownload PDF (465K) -
Tadashi Hashimoto1967 Volume 87 Issue 5 Pages 528-529
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSBromination of trimethylsilylbenzoic acids was examined. Addition of equimolar amount of bromine to the acetic acid solution of o-, m-, and p-(trimethylsilyl)benzoic acid, and heating of this mixture in a sealed tube at 100° for 5, 12, and 13 hours respectively afforded o-, m-, and p-bromobenzoic acids. The ease or difficulty of this bromination by desilylation was found to be proportional to the activity of the ortho, meta, and para positions of the benzoic acid.View full abstractDownload PDF (332K) -
Tadashi Hashimoto1967 Volume 87 Issue 5 Pages 530-534
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSReaction of o-(trimethylsilyl)phenol (I) with various electrophilic reagents was examined. Acid and alkali treatment of I results in the severance of silicon-aryl bond and phenol is formed. Bromination of I results in substitution of the position para to the hydroxyl, accompanied by desilylation and p-bromophenol is formed. Coupling reaction of I with benzenediazonium chloride results in the substitution first in the position para to the hydroxyl and then at ortho to form 2-trimethylsilyl-4-(phenylazo)phenol (IV) and then 2-trimethylsilyl-4, 6-bis(phenylazo)phenol (IX), and no further substitution occurs. This is considered to the due to the stabilization of the silicon-aryl bond by the -I effect of the second substitution. Nitration of I with acetyl nitrate at 20° or -50° failed to produce any nitrated product. The Reimer-Tiemann reaction of I gave salicylaldehyde, while the Friedel-Crafts reaction of the methyl ether (XV) of I with aluminum chloride and acetyl or benzoyl chloride afforded p-methoxyacetophenone or p-methoxybenzophenone.View full abstractDownload PDF (637K) -
Tadashi Hashimoto1967 Volume 87 Issue 5 Pages 535-538
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSA satisfactory result was obtained by a modified method for the synthesis of 2-trimethylsilyl-p-benzoquinone (I). Application of p-diazobenzenesulfonic acid to m- (VI) or o-(trimethylsilyl)phenol (VII) affords p-(2-trimethylsilyl-4-hydroxyphenylazo)-(VIII) or p-(3-trimethylsilyl-4-hydroxyphenylazo)-benzenesulfonic acid (X) which is reduced with sodium thiosulfate to 3-(IX) or 2-trimethylsilyl-4-aminophenol (XI). I is obtained in a good yield by the oxidation of IX or XI with dichromic acid. Addition reaction of I was then examined. I undergoes reaction with hydrochloric acid in methanol or with hydrogen chloride in chloroform to afford 2-chloro-p-hydroquinone. Refluxing of I with butylamine in methanol gives 2-butylamino-p-hydroquinone but I does not react with phenol. Reduction of I with sodium thiosulfate, hydroxylamine, or p-nitrophenylhydrazine affords 2-trimethylsilyl-p-hydroquinone (XIV) but I is not reduced by sulfur dioxide gas.View full abstractDownload PDF (454K) -
Masumi Ito1967 Volume 87 Issue 5 Pages 539-542
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSome nitrofuran derivatives were synthesized as potential chemotherapeutic agents. 2-(4-bromo-3-oxo-1-butenyl)-5-nitrofuran (I) was reactea with thiourea, acetone thiosemicarbazone, thiosemicarbazide, semicarbazide hydrochloride, and potassium thiocyanate to give l, 3-thiazoles, 6H-1, 3, 4-thiadiazine, and other derivatives (II∼IX), respectively. Their antimicrobial activities are described in the text.View full abstractDownload PDF (474K) -
Masumi Ito1967 Volume 87 Issue 5 Pages 543-546
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSReaction of 2-(4-Bromo-3-oxo-1-butenyl)-5-nitrofuran (I) with hydrazine gave 5-methyl-3-(5-nitro-2-furyl)pyrazole (II), which was identified with an autihentic sample prepared by the nitration of 3-(2-furyl)-5-methylpyrazole (III). Some derivatives (IV∼VI) of II werealso prepared. Antimicrobial activities of II and its derivatives are listed in the Table.View full abstractDownload PDF (476K) -
Shunsaku Shiotani, Katsumi Sakai, Kenmotsu Mitsuhashi1967 Volume 87 Issue 5 Pages 547-549
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSCatalytic reductions of 4-amino-, 4-acetamido-, and 4-benzamidoisoquinoline under several conditions were examined. Reduction of 4-acetamido- and 4-benzamidoisoquinoline over Adams catalyst in acetic acid or over Raney nickel in ethanol afforded the corresponding 1, 2, 3, 4-tetrahydro derivatives ; whereas their reduction over Adams catalyst in acetic acidsulfuric acid gave the corresponding 5, 6, 7, 8-tetrahydro derivatives. 4-Aminoisoquinoline was reduced to 5, 6, 7, 8-tetrahydro derivative either over Adams catalyst in acetic acid or over Raney nickel in ethanol.View full abstractDownload PDF (437K) -
Masayasu Kimura, Eizaburo Osada, Soichi Kagami, Den-itsu Shiho1967 Volume 87 Issue 5 Pages 550-553
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe cholagogic action of the crude drug, oriental bezoar, was examined by dividing the action into contraction of the gall bladder and relaxation of Oddi's sphincter. It was thereby found that, among the components of bezoar, the substance that causes contraction of the smooth muscle, found earlier, was the only one that showed contraction of the gall bladder and Oddi's sphincter, and most of other bite acid salts showed a relaxing effect. Deoxycholate showed the strongest a relaxing action on Oddi's sphincter and this was proved to be the principle of the cholagogic action of bezoar. The substance which contracts the smooth muscle was found to inhibit the relaxing action of deoxycholate in the gall bladder and to take part in the mechanism of contractive excretion. It was concluded from these results that pharmacologucally antagonistic substances, acting on the same point, formed a functionally co-operating system to effect cholagogic activity.View full abstractDownload PDF (585K) -
Hiroshi Tomisawa, Hiroshi Hongo, Hisae Haruta1967 Volume 87 Issue 5 Pages 554-557
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSReaction between 1-methyl-2(1H)-quinolone (I) and phenyl-metal compound was carried out. Reaction conditions (reagent, solvent, and catalyst combination) and yields are given in Table I. The results of these reactions may be summarized into the following two points. (i) Reaction points of the phenyl-metal compound against I are considered to be at 2-, 4-, 5-, and 7-positions, but the reaction occurred only in the 2-position, in spite of various combinations of the reagent, solvent, and catalyst. The identified product was always only II. (ii) The yield of II was 48% at maximum but was calculated to be about 6O% when recovery of the starting material was taken into consideration.View full abstractDownload PDF (489K) -
Tetsuji Kametani, Kazuo Kigasawa, Mineharu Hiiragi1967 Volume 87 Issue 5 Pages 558-562
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSReduction of 1-methyl-4-(2-hydroxyethyl)-3, 4-dihydrocarbostyril (VIII) by the Ladenburg method or with lithium aluminum hydride afforded the objective cyclized product, 3-methyl-2, 3, 4, 5, 6-7-hexahydro-8H-2, 6-methanobenzo[d]-1, 3-oxazocine (IX), whose catalytic reduction or reduction with lithium aluminum hydride gave 1-methyl-4-(2-hydroxyethyl)-1, 2, 3, 4-tetrahydroquinoline (X). IX was also obtained on the reduction of 1-methyl-4-methoxycarbonylmethyl-3, 4-dihydrocarbostyril (VII) with lithium aluminum hydride. The same Ladenburg reduction of VIII or its reduction with lithium aluminum hydride did not afford the expected cyclization product (XIV) but produced 4-(2-hydroxyethyl)-1, 2, 3, 4-tetrahydroquinoline (XIII). It is interesting that a six-membered ring lactam like VII and VIII underwent reductive cyclization to form oxygen-containing heterocyclic compound with Ph-N-C-O-skeleton.View full abstractDownload PDF (587K) -
Tetsuji Kametani, Kazumi Ohkubo, Seiichi Takano1967 Volume 87 Issue 5 Pages 563-569
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSyntheses of sendaverine and its related compounds were carried out, and their infrared and NMR spectra were examined. It was thereby found that the infrared spectra of 13 kinds of 2-substituted 1, 2, 3, 4-tetrahydroisoquinoline derivatives, excluding XX and the N-methylated compound, show characteristic absorption band very similar to the Bohlmann band which is considered to be the characteristic absorption of trans-quinolizidine. In the NMR spectra of these compounds, the proton signals of the methylene groups in 3- and 4-positions show a characteristic broad, singlet-like absorption, irresuctive of the substituent on the ring-nitrogen or on the benzene ring, as long as there are substituents like methoxyl, beozyloxyl, and hydroxyl group in the 6- or 7-position and the substituent in the 2-position is a unit higher than ethyl or benzyl group, but not methyl group.View full abstractDownload PDF (654K) -
Eisaku Hayashi, Takeo Nakura1967 Volume 87 Issue 5 Pages 570-577
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSReaction of acridine (I) with various ketones (II), in the presence of sodium methoxide at ordinary temperature, was examined. Ketones used were acetophenone, propiophenone, butyrophenone, valerophenone, isobutyrophenone, isovalerophenone, acetone, diethyl ketone, diisobutyl ketone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, cyclohexinone, and cyclopentanone. From the results of this reaction, following points were clarified. 1) When the reaction is effected, the carbonatom of the methyl or methylene group adjacent to the carbonyl group in the ketone is bonded to 9-position of I to form the acridanyl derivative (III). 2) Although the examples are small, the reaction seemed difficult when the alkyl group in the ketone possessed a branched chain in the α- and or β-position. 3) The carbon bonded to the carbonyl group in the ethyl or propyl group seemed to have greater reactivity than the carbon in the methyl group bonded to the carbonyl. The actidanyl derivatives (III) are derived to the corresponding acridine derivatives (IV) by oxidation with chloranil. However, in the case of 2-(9-acridanyl)cyclopentanone (IIIn), 9-acridine-valeric acid (Vn), considered to be formed by the hydrolysis of 2-(9-acridinyl)-1-cyclopentanone (IV) during the treatment, was obtained. Hydrolysis of the acridine derivatives (IV) with sodium hydroxide afforded 9-alkylacridine (V) except in the case of 2-(9-acridinyl)-1-cyclohexanone (IVm) which formed 9-acridine-caproic acid (Vm).View full abstractDownload PDF (696K) -
Eisaku Hayashi, Takeo Higashino, Shigeru Tomisaka1967 Volume 87 Issue 5 Pages 578-580
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS4-Aminoquinazoline 3-oxide (I) had been obtained by Adachi1) by the application of hydroxylamine to 4-methoxy-(II) or 4-phenoxyquinazoline (III) and this reaction route was assumed to be as shown in Chart 1. I is an acid substance and would probably be present in a tautomeric system in a solution, as shown in Chart 2. Application of diazomethane to I afforded 3-methoxy-4-methylimino-3, 4-dihydroquinazoline (V) and 3-methoxy-4-imino-3, 4-dihydroquinazoline (VI), and the route of their formation was assumed to be as shown in Chart 3.View full abstractDownload PDF (354K) -
Masaiti Yasue, Toyo Kaiya, Akira Wada1967 Volume 87 Issue 5 Pages 581-584
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe leaves of Lyonia ovalifolia SIEB. et ZUCC. var. elliptica HAND.-MAZZ. were extracted successively, with benzene and methanol From the benzene extract, nonacosane, 2-nonacosanone (a new compound), 1-triacontanol, ursolic acid, lyofolic acid (a new compound), and a trace of β-sitosterol were isolated. From the methanol extract, β-sitosteryl β-D-glucoside was separated. 2-Nonacosanone C29H58O, colorless plates, m.p. 81°, whose infrared spectrum is shown in Fig. 1, gave nonacosane C20H60, m.P. 63∼64°, by the Huns-Minlon reduction. Lyofolic acid, C58H62O1O·2H2O, colorless plates (from ethyl acetate), m.p. 136°, or C38H62O10, colorless grains (from boiling benzene), m.p. 192°, is a hydroxytriterpenecarboxylic acid, containing a glucose residue and an O-acetyl group [C29H47(COOH)(OC6H11O5)(OCOCH3)].View full abstractDownload PDF (572K) -
Juichiro Shibasaki, Etsuko Sadakan1967 Volume 87 Issue 5 Pages 585-590
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe metabolism of three hydroxylated derivatives of N-methylthiocarbanilide, namely, 4'-hydroxy-, 4-hydroxy-, and 4, 4'-dihvdroxy-N-methylthiocarbanilide, was studied. Examinations were made on the urinary metabolites in rabbits after oral administration of these compounds, tested by paper and thin-layer chromatography. The major metabolism of the respective derivatives is summarized as follows. 1) The fate of 4'-hydroxy derivative is quite similar to that of N-methylthiocarbanilide. Its main metabolite is the glucuronide at the 4'-hydroxyl group and the sulfuric acid conjugation was not observed. 2) The metabolism of 4-hydroxy derivative is different from that of 4'-hydroxy derivative since the former is conjugated with both glucuronic acid and sulfuric acid at the 4-hydroxyl group. In addition the glucuronide of p-methylaminophenol is also excreted. 3) 4, 4'-Dihydroxy derivative is excreted mainly as the monoglucuronide in which the conjugation occurs exclusively at the 4'-hydroxyl group and the ethereal sulfate was not detected.View full abstractDownload PDF (760K) -
Yoshiki Hamada, Hisayoshi Sugihara, Yosio Ito, Kasuke Ito, Sumio Tomom ...1967 Volume 87 Issue 5 Pages 591-596
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS1) Application of 2, 4-dichloronitrobenzene to the potassium salts 2, 5-dichloro-, 2, 4, 5-trichloro-, p-fluoro-, and p-iodophenols, and p-chlorothiophenol, in the presence of copper powder, afforded (2-phenoxy-5-chloro)nitrobenzenes (III to VI) and [2-(4-chloro-phenylthio)-5-chloro] nitrobenzene (VII). These nitre compounds were reduced to the amino compounds (XI to XVIII) with stannous chloride and hydrochloric acid. Thiocyanation of these compounds, 2-amino-4-chlorophenol, and XIX, by treatment with ammonium thiocyanate and bromine in acetic acid afforded the thiocyano compounds (XXI to XXX). 2) Reaction of the potassium salts of p-chloro- and p-bromophenols with 2-chloro-, 4-bromo-, 2-chloro-4-fluoro-, and 2-chloro-4-iodo-nitrobenzenes, in the presence of copper powder, afforded the nitro compounds (XXXI to XXXVI), which were reduced with stannous chloride and hydrochloric acid to the amino compounds (XXXVII to XLII), and further derived to the thiocyano compounds (XLIII to XLVII) by treatment with ammonium thiocyanate and bromine. 3) All these thiocyanate compounds were submitted to antifungal tests against Candida and Trichophyton. None of the compounds showed much activity against Candida but some of the compounds had activity against Trichophyton comparable to or better than that of I.View full abstractDownload PDF (591K) -
Tetsuzo Kato, Takeshi Kawamata1967 Volume 87 Issue 5 Pages 597-602
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS2-Methyl-12a, 13-dihydro-4H-pyrano[2, 3-b]-2H-benzo[a]quinolizine-4, 5-dione (I) was synthesized from quinoline and diketene and its treatment with ammonia water gave the pyridone compound (II) and the 4-amino compound (III). Treatment of II with phosphoryl chloride gave the 4-chloro compound (IV) which, when treated with sodium methoxide or hydrazine in dehyd. methanol, formed the 4-methoxy compound (VIII) or 4-hydrazino compound (VIII) respectively. Reduction of IV over Raney nickel gave the 4-chloro-11, 12-dihydro compound (VI), while catalytic reduction over palladium-carbon gave the dechlorinated compound (V) of VI. III was derived to its acetate (VI) by its treatment with acetic anhydride. Reduction of III was also attempted. The NMR spectra of these products were examined.View full abstractDownload PDF (654K) -
Teishiro Kushima1967 Volume 87 Issue 5 Pages 603-605
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSulfadimethoxine-N1-β-D-glucopyranuronamide was synthesized, and it was found to have no antibacterial activity in the range examined.View full abstractDownload PDF (425K) -
Tetsuzo Kato, Masatsugu Kondo1967 Volume 87 Issue 5 Pages 605-608
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe reaction of ethyl γ-bromoacetoacetate (I) with 2-picoline 1-oxide under ice cooling and basification of the reaction mixture with sodium carbonate resulted in the formation of diethyl 2, 5-dihydroxyterephthalate.View full abstractDownload PDF (464K) -
Mikio Yamazaki, Tsuneko Kawana1967 Volume 87 Issue 5 Pages 608-610
Published: May 25, 1967
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSHydroxyevodiamine (rhetsinine), which was synthesized by the KMnO4-oxidation of evodiamine by Asahina and Ohta, and whose structure was recently altered to IV from Asahina's formula (III) by Pachter et al., was isolated from the fruits of Evodia rutaecarpa HOOK fil. et THOMSON. Hydroxyevodiamine (rhetsinine) was also obtained by the photoxidation of evodiamine and the possibility of rhetsinine formation as an artefact was discussed.View full abstractDownload PDF (444K)
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