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KAZUO KIGASAWA, HIDEKI IIMURA, AKIRA TANIZAKI, HIDEAKI SUGIMURA, HIROA ...
1975 Volume 95 Issue 7 Pages
769-773
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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In order to examine the influence of tablet formula and tablet shape on the distribution of hardness inside a tablet, the hardness inside each tablet was measured by using a boring hardness measuring apparatus. The sample tablets with ingredients used in general, lactose and crystalline cellulose, of different formula were formed in the plane and convex type by using an ordinary tableting machine. Measurement of the hardness inside various tablets gave curves for the distribution of hardness, in which compressibility by the difference in the ratio of ingredients was observed as a marked difference in the distribution of hardness inside each tablet. As to the distribution of hardness by the difference in the tablet shape, in the case of convex type, the smaller the radius of curvature, the larger was the difference in the distribution of hardness in each layer and, in the case of the tablet with ingredients of poor compressibility, the tablet shape had a larger effect on the distribution of hardness. It was found that the presence and position of a capping can be confirmed from the distribution of hardness.
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EISAKU HAYASHI, AKIKO UTSUNOMIYA
1975 Volume 95 Issue 7 Pages
774-777
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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Reaction of 2-(methylsulfonyl)quinoxaline (I) and acetophenone (IIIa) in dimethyl sulfoxide, in the presence of potassium cyanide, at 100° results in the formation of 2-pheny1furo[2, 3-b]quinoxaline (VIa) accompanying 2-quinoxalinecarbonitrile (IV) and 2, 3-quinoxalinedicarbonitrile (V). In order to examine the process of formation of VIa, the same reaction was carried out with IV or V in place of I, and VIa was formed in either case, as well as by the application of potassium cyanide to 2-(2-quinoxalinyl)-acetophenone (VIIa). Therefore, formation of VIa cannot be concluded as a single process. The use of propiophenone (IIIb) as the ketone gave 3-methyl-2-phenylfuro-[2, 3-b] quinoxaline (VIb). The same reaction with ketones was carried out with 2-chloroquinoxaline (II) in place of I, and V was obtained in all cases. In addition, VIb was obtained from IIIb and 3-ethyl-2-phenylfuro[2, 3-b]quinoxaline (VIc) from butyrophenone (IIIc). In these reactions, yield of furo[2, 3-b]quinoxaline derivatives was extremely low, and it seems better to use the reaction of 2, 3-dichloroquinoaline (IX) with various ketones in benzene, in the presence of sodium amide,
3) to obtain such derivatives, but this reaction can also be carried out in dimethyl sulfoxide, in the presence of potassium cyanide ; for example, VIb is obtained from IX and IIIb.
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MASAAKI KATAI, TAMOTSU MATSUSHIMA, TADAMASA TERAI, HARUO MEGURI
1975 Volume 95 Issue 7 Pages
778-783
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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The methanolic extract of the leaves of Pieris japonica D.DON was purified and the final extract was submitted to column chromatography from which pieristoxin-F, pieristoxin-G, deacylpieristoxin-B, pieristoxin-C, asebotoxin-I, grayanotoxin-II, and, as the main poisonous principle, grayanotoxin-III (2.7 g, 0.013% yield) were isolated. Hydrolysis of pieristoxin-F affordea 7-hydroxygrayanotoxin-III. Nuclear magnetic resonance (NMR) spectrum of pieristoxin-F indicated the presence of one O-acetyl and one O-propionyl groups, and partial structures of ≡CCH(OR)CH(OH)C≡and-CHOR. Pieristoxin-F is not oxidized by sodium periodate, and its acetate does not agree with tetraacetyl-asebotoxin-IV. Therefore, the structure of pieristoxin-F was presumed to be 6-acetyl-7-hydroxy-14-propionylgrayanotoxin-III. The composition of pieristoxin-G was found to be C
20H
32O
8·H
2O from its elemental analytical values and highresolution mass spectrometry, while its infrared spectrum did not show absorptions for carbonyl and unsaturated bond(s). Pieristoxin-G is reduced by lithium aluminum hydride and consumes sodium periodate. Its NMR spectrum indicated the presence of a partial structure of≡CCH(OH)-CH(OH)C≡ and an epoxide ring. These facts suggested the structure of pieristoxin-G as 7, 9-dihydroxy-2, 3-epoxygranotoxin-III.
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CHIHOKO IIJIMA, TEIKO MORIKAWA, EISAKU HAYASHI
1975 Volume 95 Issue 7 Pages
784-792
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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Application of sodium amide to 2, 3-diethoxyquinoxaline (I) and 3-substituted [methoxy (II), isopropyl (V), tert-butyl (VI), phenyl (VII)] 2-methoxyquinoxaline in dehyd. benzene, in the presence of methyl ethyl ketone gives 3-substituted [ethoxy (III), methoxy (IV), isopropyl (VIII), tert-butyl (IX), phenyl (X)] 2-aminoquinoxalines. IV and III are respectively obtained from 2-methoxyquinoxaline (XXVIII) and 2-ethoxyquinoxaline (XXIX) by the same reaction. In the case of 2-ethyl-3-methoxyquinoxaline (XXV), 2, 2'-[α, α'-dimethyethylenebis(3-methoxyquinoxaline)] (XXVI) is obtained mainly, with 2-amino-3-ethylquinoxaline (XXVII) as a minor product. In the case of 2-methoxy-3-methylquinoxaline (XVII), IV is obtained contrary to expectations, accompanied by 2, 2'-methylenebis(3-methoxyquinoxaline) (XIX), 2, 2'-ethylenebis(3-methoxyquinoxaline (XX), and 3-methoxy-3'-methyl-2, 2'-methylenediquinoxaline (XXI).
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KIYOSHI YAMADA, MAMORU TERADA, KAZUYUKI NAKANISHI, NOBUKO MAKIHATA, MA ...
1975 Volume 95 Issue 7 Pages
793-802
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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It was reported previously that hypoglycemic sulfonylureas turned into hyperglycemic when a cyclized urea structure was involved in their molecules. The mechanism of the hyperglycemic action of 1-(p-chlorophenylsulfonyl)-2-imidazolidinone (CPSI), a derivative of chlorpropamide (P-607), was compared with the hypoglycemic action of the parent P-607, and the results obtained were summarized as follows. 1) An enhanced blood sugar level in rabbits induced by CPSI administration (100 mg/kg, p.o.) was decreased transiently by insulin (0.2 IU/kg, i.v.) and consistently by P-607 (100 mg/kg, p.o.). 2) An ora1 administration of P-607 (100 mg/kg) to the hyperglycemized rabbits treated with CPSI (100 mg/kg, p.o.), resulted in a rapid and transient increase of the peripheric blood insulin level, followed by a rapid decrease of blood glucose. In contrast, these phenomena were not observed when animals were not pretreated with CPSI. 3) Pretreatment of rats with CPSI (100 mg/kg, p.o.) inhibited the increase of periphericblood insulin level induced by glucose administration (2400 mg/kg, p.o.). 4) An oral administration of a relatively large quantities of CPSI (300 mg/kg) to rats, resulted in a more prolonged low peripheric blood insulin level, followed by a marked increase of pancreas insulin and the hyperglycemic state was observed. In contrast, when P-607 (300 mg/kg, p.o.) was administered, a transient and a marked increase of peripheric blood insulin level together with a decrease of pancreas insulin, was observed and a lasting hypoglycemic state was induced. 5) When rats were dosed orally for four consecutive weeks with CPSI (100 mg/kg daily), the hyperglycemic phenomenon was constantly reproduced during the whole experimental period. No histopathological abnormalities were noticed on the pancreas Langerhan's island. It was concluded that unlike alloxan, the hyperglycemic action of CPSI might be induced by its inhibitory effect on the process of insulin release from pancreatic β cells.
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KIYOSHI YAMADA, MAMORU TERADA, KAZUYUKI NAKANISHI, NOBUKO MAKIHATA, MA ...
1975 Volume 95 Issue 7 Pages
803-808
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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In a previous paper we have reported that, unlike alloxan, the hyperglycemic action of 1-(p-chlorophenylsulfonyl)-2-imidazolidinone (CPSI) might be induced by its inhibitory effect on the releasing process of insulin from pancreatic β cells. In this paper, influences of CPSI on carbohydrate and lipid metabolism have been investigated comparatively with that of chlorpropamide (P-607). The results obtained were summarized as follows. 1) The muscular and liver glycogen levels in rats were both lowered by P-607 (100 mg/kg, p.o.), whereas CPSI (100 mg/kg, p.o.) increased the liver glycogen level and lowered the muscular glycogen level significantly. 2) The serum free fatty acids and triglycerides levels in the fasted rats were both lowered by P-607 (100 mg/kg, p.o.), whereas increased by CPSI (100 mg/kg, p.o.). These phenomenon were markedly manifested when a relatively large quantities of CPSI and P-607 (both 300 mg/kg, p.o.) were dosed to the fed rats. 3) The serum total cholesterol level in the fed rats were lowered by P-607 (300 mg/kg, p.o.), whereas increased by CPSI (300 mg/kg, p.o.). The results obtained seems to give a good explanation for the behavior of the peripheral blood insulin level toward to CPSI and P-607. They may support our suggestion strongly that CPSI have an inhibitory effect on the releasing process of insulin from pancreatic β cells and that P-607 have a stimulatory effect on the same process.
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TSUNEO NAMBA, MASAO YOSHIZAKI, TSUYOSHI TOMIMORI, MASAHIKO TSUBOI, KIM ...
1975 Volume 95 Issue 7 Pages
809-814
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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A new method for the determination of glycyrrhizin in liquorice roots was devised by the use of thin-layer chromatography over silica gel sintered rod with hydrogen flame ionization detector. It was found that glycyrrhizin was specifically absorbed on polyamide powder, and the test solution had to be prepared especially. Typical chromatograms obtained by this method are shown. Determination of glycyrrhizin in liquorice roots from China, Afghanistan, Iran, and U.S.S.R., and their processed goods on the Japanese market was made and the recovery rate was found to be more than 95% on the average.
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NOBUYOSHI MINAMI, YASUSHI SUZUKI
1975 Volume 95 Issue 7 Pages
815-821
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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Reaction of 2-acyl-1-tetralones with hydroxylamine was carried out. The reaction of 2-methoxalyl-1-tetralones (IIa-d) with hydroxylamine hydrochloride in methanol gave the cyclized compounds, 3-methoxycarbonyl-4, 5-dihydronaphth[2, 1-d]isoxazoles (IIIa-d), which were converted to the corresponding 2-cyano-1-tetralones (Va-d) under alkaline conditions. The reaction of 2-acetyl-1-tetralones (IIe, f) with hydroxylamine hydrochloride gave 3-methyl-4, 5-dihydronaphth[2, 1-d]isoxazo1es (IIIe, f). IIIa, c were reduced by LiAlH
4 or NaAlH
2(OCH
2CH
2OCH
3)
2 to 3-hydroxymethyl-4, 5-dihydronaphth-[2, 1-d] isoxazoles (VIa, c), which, on treatment with PCl
5, gave 3-chloromethyl-4, 5-dihydronaphth[2, 1-d]isoxazoles (VIIa, c). Reduction of VIIa, c with zinc dust in acetic acid afforded IIIe, f. When one equivalent of 3-hydroxymethyl-7-methoxy-4, 5-dihydronarhth[2, 1-d]isoxazo1e (VIc) was allowed to react with 2 equivalents of PCl
5, 6-chloro-3-chloromethyl-7-methoxynaphth[2, 1-d]isoxazo1e (VIIIc) and VIIc were obtained. The structure of VIIIc was supported by its spectral data.
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HARUSHIGE FUJITA, MASATARO YAMASHITA
1975 Volume 95 Issue 7 Pages
822-824
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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In anticipation of pharmacological activities in synthesized compounds containing methylenedioxy or ethylenedioxy groups in chemically active positions of 4-methyl-coumarin derivatives, alkylenation of 4-methyl-5, 6-dihydroxy-(I), 4-methyl-6, 7-dihydroxy-(IV), 4-methyl-7, 8-dihydroxy-(VI), and 3, 4-dimethyl-7, 8-dihydroxycoumarin (VIII) was examined in a noncatalytic heterogeneous reaction system, and high purity alkylenated ether derivatives corresponding to I, IV, VI, and VIII were obtained to a good yield for a short reaction period, when dimethyl sulfoxide was used as a solvent and potassium carbonate as a base.
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YASUO TOKUOKA, KOJI DAIGO, TSUNEMATSU TAKEMOTO
1975 Volume 95 Issue 7 Pages
825-829
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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Two flavonoids, compounds A and B, were isolated from the herb of Epimedium grandiflorum MORR. (Berberidaceae). Their structures were established from their chemical and spectroscopic evidence as 4'-O-methyl-8-γ, γ-dimethylallylkaempferol 3-rhamnosido-7-glucoside and 4'-O-methyl-8-γ, γ-dimethylallylkaempferol 7-glucoside, respectively. It was presumed that compound A is icariin and compound B is icarisid I, and it is propose to correct their chemical structures as above.
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HIDEO KATO
1975 Volume 95 Issue 7 Pages
830-837
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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Reduction of both methiodides, II and XI, with lithium in liquid ammonia or sodium amalgam gave nine-membered aminolactams, III and XII, respectively, which, on treatment with lithium aluminum hydride, afforded the correspouding diamines, IV and XIII. Diamines (IV and XIII) were also obtained by lithium aluminum hydride reduction of II and XI, respectively. Reduction of XV with lithium in liquid ammonia yielded XVI.
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CHIAKI TANI, NAOTAKA NAGAKURA, NOBUKO SUGIYAMA
1975 Volume 95 Issue 7 Pages
838-842
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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With the droplet countercurrent chromatography, using the multi-buffered solution as the moving phase, tertiary bases were isolated from Corydalis speciosa MAXIM. and identified as corypalline, protopine, α-allocryptopine, capaurimine, capaurine, and dltetrahydropalmatine.
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ITSUO YOSHIZAWA, MICHIYA KIMURA
1975 Volume 95 Issue 7 Pages
843-848
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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A synthetic method is described for the haptenyl compound, 3α, 20α-dihydroxy-5β-pregnan-7-one O-carboxymethyloxime (VII) for the radioimmunoassay of pregnanediol from chenodeoxycholic acid (Ia).
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MASAMI INOUE, SABURO ENOMOTO, JUNKI IMAMURA
1975 Volume 95 Issue 7 Pages
849-852
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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The vapor phase dehydrogenation of piperazine to pyrazine on palladium was examined by using a flow method and a pulse technique. When Pd supported on Al
2O
3 was used as the rare metal catalyst in a stationary process, the activity decreased in a few hours by carbon deposition, although a high initial activity was observed. In contrast, Pd (1%)-UO
3 (5%)-Al
2O
3 continued a higher level yield of 65% at 400°. The effectiveness of the rare earth metal oxides as the catalyst support of Pd was in the order of CeO
2> UO
2≫ThO
2. Dehydrogenation rates among six-membered saturated ring compounds were estimated as cyclohexane≃piperizine≪piperazine. The steric configuration significantly influenced the rate of dehydrogenation ; cis-2, 3-dimethylpiperazine was dehydrogenated faster than the trans isomer. From these results a geometrically plane intermediate structure of piperazines on Pd was suggested.
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KUNIHARU SUMIDA, HIROSHI KISHIMOTO, SABURO SIMABAYASHI, MASAYUKI NAKAG ...
1975 Volume 95 Issue 7 Pages
853-858
Published: July 25, 1975
Released on J-STAGE: May 30, 2008
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In order to elucidate the behavior of sodium dodecyl sulfate (NaDS) bound on nonionic polymers, the molar enthalpy of binding of NaDS on polymers, ΔH^
-bound, as well as the amount of bound NaDS, n
bound, in 1 kg of 0.5% aqueous solutions of poly (vinylpyrrolidone) (PVP) and poly (vinyl alcohol) (PVA) with various NaDS concentrations at 25° and 37° was determined by means of calorimetric and equilibrium dialysis measurements, respectively. The n
bound isotherm against the total concentration of NaDS showed S-shaped curves with PVP as well as PVA at both temperatures. By considering the data of ΔH^
-bound and n
bound as a whole, two regions with respect to the behavior of NaDS bound on polymers could be distinguished, corresponding to the smaller absolute values of n
bound and ΔH^
-bound (I) and to the larger values (III). Between these, an intermediate region (II) exists. The values of ΔH^
-bound in the regions (I) and (III) were -0.2 (I) and -0.55 (III) kcal·mol
-1 at 25°, -1.2 (I) and -2.2 (III) kca1·mo1e
-1 at 37° in PVP-NaDS system, and -0.2 (I) and -0.45 (III) kcal·mol
-1 at 25° in PVA-NaDS system, respectively. The number of NaDS bound on a single polymer chain of PVP or PVA was found to be confined to 0-16 in the region I and reach the micellar number of NaDS, i.e., 50-120 in the region III. Also, the difference in ΔH^
-bound between regions I and III was found to be nearly equal to the molar micelle formation enthalpy of NaDS in aqueous media. From these results, it was inferred that the bound NaDS molecules behave independently of each other on polymer chains in the region I, while they behave co-operatively to form micellelike aggregates in the region III.
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HISASHI FUKUZAWA, EIHEI FUKUOKA, SHINTARO KIMURA
1975 Volume 95 Issue 7 Pages
859-864
Published: July 25, 1975
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The six methods generally believed to be capable of estimating the flowing ability of a powder, were tested and results obtained were compared with cohesiveness (α
c), whose measurement was reported previously. Correlation was recognized between the angle of repose (θ
p, θ
d) and α
c. The values of h
o were obtained by extrapolation of height of the powder cone heap (h) to h axis, using the Train's method. Correlation between h
o and α
c seemed to exist when α
c exceeded 3. There were no relations between packed porosity (ε
p) and α
c, but a correlation was observed between Δε and α
c. In the range of α
c smaller than 2, all samples were judged as freely drainable and at α
c above 3.2, all samples was undrainable. It is concluded that the free flowing of a powder is one of the forms of flowing which can be done only by migration of the surface particle of the bed by gravitational force and, in connection with this, the definition of ability to flow freely is given as easiness to remove the particles sitting on the surface of the loosely packed powder bed. As was defined earlier, cohesiveness (α
c) is also the easiness to remove the particles sitting on the surface of the powder bed so that, in the case of the loosely packed powder bed, the ability to flow freely and cohesiveness are different manifestation of the same property of a powder bed.
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YASUMASA KOYAMA, YUICHI FUKAKUSA, NOBUO KYOMURA, SABURO YAMAGISHI
1975 Volume 95 Issue 7 Pages
865-871
Published: July 25, 1975
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Luteoreticulin, mp 184.5-185°, is a new nitro-containing metabolite which has been isolated from the mycelial cake of Streptomyces luteoreticuli KATOH et ARAI along with the known nitro-containing metabolite, aureothin (I). Chemical and spectroscopic investigations have shown that luteoreticulin has the structure shown by formula II.
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SHIKIFUMI KITAZAWA, ATSUSHI MAEDA, YOKO ITO, JUTARO OKADA
1975 Volume 95 Issue 7 Pages
872-878
Published: July 25, 1975
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Comparative examinations of dissolution testers were made, using seven iron agents of different manufactures, including quick- and slow-releasing preparations. The dissolution testers investigated were rotating basket method of U.S.P. XVIII or N.F. XIII and the solubility simulator method which was devised recently by Sartorius Membrane-Filter Company. Despite little difference in the dissolution patterns obtained by these two methods in the case of quick-releasing preparations, apparent and serious differences were revealed in the case of slow-releasing iron preparations. The results obtained by the solubility simulator method had a tendency of accelerating the dissolution of sustained release preparations. The reason for these differences was considered to be disintegration or scratching of the film surface of the preparations by glass balls (approximately by 247 balls) in the dissolution chamber of the solubility simulator during the course of testing.
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Isoo ITO, TAISEI UEDA, NORIICHI ODA
1975 Volume 95 Issue 7 Pages
879-882
Published: July 25, 1975
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1-Methyl-4-oxo-2-phenyl-1, 2, 4, 5-tetrahydro-3(7H)-thiopyrano[3, 4-c]pyrazolone (IV) and its derivatives were synthesized. The reaction of 4-hydroxyimino-1-methyl-2-phenyl-1, 2, 4, 5-tetrahydro-3(7H)-thiopyrano[3, 4-c]pyrazo1one (VI) with phosphorus pentachloride gave 2-[(4-chloro-2-methyl-1-phenyl-3-pyrazoline-3-methyl)thio]acetonitrile (X).
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SHIGETAKA YOSHINA, AKIRA TANAKA, CHIING-HSING WU, HSIEN-SAW KUO
1975 Volume 95 Issue 7 Pages
883-888
Published: July 25, 1975
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5-(3-Pyridyl)-2-furaldehyde (III) and 5-(3-quinolyl)-2-furaldehyde (IV) were prepared by the Meerwein arylation. III and IV were derived to Schiff's bases in order to investigate their antibacterial activity. An unusual phenomenon was observed when III was reacted with 2-aminopyridine or 3-aminopyridine for formation of the Schiff's bases. Their antibacterial activities are generally low, but only 5-(3-pyridyl)-2-furaldehyde thiosemicarbazone (IX) shows high activity to Mycobacterium tuberculosis.
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MASAHARU KOJIMA, YUKIHIKO TOMIOKA
1975 Volume 95 Issue 7 Pages
889-892
Published: July 25, 1975
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meso-cis-Cyclohexenimine (Ia) or N-benzylsulfonyl-meso-cis-cyclohexenimine (Ib) reacted with sodium ethyl malonate in ethanol or diethyl carbonate to afford 2-oxo-3-ethoxycarbonyl-trans-octahydroindole (IIa) or N-benzylsulfonyl-2-oxo-3-ethoxycarbonyl-trans-octahydroindole (IIa). Reduction of octahydro-2-oxoindole (IV), which was obtained after hydrolysis and decarboxylation of IIa, with LiAlH
4 gave trans-octahydroindole (V).
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RYOHEI KIMURA, MASAKO KURITA, TOSHIRO MURATA
1975 Volume 95 Issue 7 Pages
892-895
Published: July 25, 1975
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Both theanine (L-N-ethylglutamine) and L-glutamine were found to have a weak depressing effect on the spontaneous activity of mice and to decrease the activity enhanced by the administration of caffeine. These amides, however, did not depress the activity induced by pipradrol or methamphetamine and the hyperactivity produced with hexobarbital. Sodium glutamate did not show any depression on the activity increased by caffeine in mice, while γ-aminobutyric acid depressed it to a lesser extent than theanine. Studies on the effects of theanine and L-glutamine at various periods after administration of these chemicals suggested that the depression mechanisms of these amides might be similar on the caffeine-increased spontaneous activity of mice.
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