All issues
Predecessor
Volume 83, Issue 7
Displaying 1-20 of 20 articles from this issue
- |<
- <
- 1
- >
- >|
-
Ester Type DerivativesTadao Ida, Shoji Takahashi, Kazuo Noda, Isamu Utsumi1963 Volume 83 Issue 7 Pages 663-671
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSVarious O-acyithiamines were prepared by the oxidation of O-acrylate, O-methacrylate, O-crotonate, and O-undecylenate of thiothiamine and high-molecular derivatives of thiamine were obtained by their polymerization. Copolymer of these with vinyl compounds was also prepared.
Oral administration of these high-molecular derivatives in man and measurement of the amount of thiamine excreted in the urine showed that the total amount excreted during 24 hours was 1/2 to 1/4 of that after administration of thiamine hydrochloride. The peak of excretion appeared much later, 7-12 hours later than that of thiamine, and indicated the lasting effect of high-molecular derivatives. Of these derivatives, those with smaller molecular weight were excreted in larger amount, and copolymers were excreted in larger amount than homopolymers. Greater urinary excretion was found in basic comonomers than acid comonomers among these copolymers.
These experimental results showed the same tendency as that shown by hydrolysis of high molecular derivatives with alkali or diastase. O-Methacryloyl derivative was not hydrolyzed by alkali or diastase but was hydrolyzed in vivo to be excreted into urine in a similar manner as the other derivatives.View full abstractDownload PDF (1234K) -
Triterpenoids of the Flowers of Pieris japonica. (1)Yoshikazu Kondo, Tsunematsu Takennoto1963 Volume 83 Issue 7 Pages 671-673
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSTriterpenoid components were examined in the flowers of Pieris japonica (THUNBERG) D. DON, and β-amyrin, oleanolic acid, ursolic acid, and β-sitosterol were isolated and identified. In addition, a hitherto unknown neutral triterpenoid (C32H52O2, m. p. 188-189°) was isolated. Its infrared spectrum suggested the presence of endo-methylene group and the spectrum was similar to that of lupeol acetate except for the region of 1000-1100cm-1. It was therefore assumed that this new triterpenoid is its epimer with respect to its 3-hydroxyl group but no evidence has yet been obtained.View full abstractDownload PDF (429K) -
Constituents of Tripetaleia paniculata. (1)Yoshikazu Kondo, Tomiko Nagaya, Yasuyoshi Takeuchi, Tsunematsu Takemot ...1963 Volume 83 Issue 7 Pages 674-676
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe present series of work was carried out in order to extract and isolate poisonous component from the leaves of Tripetaleia paniculata SIEB. et ZUCC. Presence of grayanotoxin series substance was assumed from the toxic symptoms of the leaves to mice and such a fraction was obtained but did not crystallize. At the same time, hexa-consane (?), 1-triacontanol, 1-octacosanoi, ursolic acid, and quercetin were separated and identified. Presence of kaempferol was observed in paper chromatography. A new triterpenoid of m. p. 210-211°, C30H50O (acetate, m. p. 210.5-211°), was also isolated.View full abstractDownload PDF (510K) -
Structure of Trilobine and Isotrilobine. (15). Synthesis of Isotrilobine Antipode from EpistephanineMasao Tomita, Hiroshi Furukawa1963 Volume 83 Issue 7 Pages 676-679
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSY. Inubushi and K. Nomura reported a ring cleavage reaction of natural isotrilobine with sodium in liquid ammonia and represented its structure by II. In the present paper authors showed that the demethylation and dehydration of N-methyldihydroepistephanine (V) with hydrobromic acid followed by O-methylation gave O-methylanhydrodemethyl-N-methyldihydroepistephanine (VIII) (picrate, m. p. 188-189° (decomp.), [α]D -226.7° (acetone)), which is the antipode of natural isotrilobine (cf. Table I).View full abstractDownload PDF (583K) -
A New Synthesis of 2, 3, 4, 4a, 5, 6-Hexahydro-1H-pyrazino[1, 2-a]quinolineMasanori Nagata, Takao Yamazaki1963 Volume 83 Issue 7 Pages 679-682
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS2-Aminomethylquinoline was converted to the corresponding haloacetyl compound (V, VI), followed by cyclization to the corresponding quinolinium salt (VII) by warming in a sealed tube at 90° for 2hr. The salt (VII) was then reduced with lithium aluminum hydride to 2, 3, 4, 4a, 5, 6-hexahydro-1H-pyrazino [1, 2-a] quinoline (IV), identified with the authentic specimen. The compound (IV) was also prepared by the reduction of I with lithium aluminium hydride.View full abstractDownload PDF (597K) -
Synthesis of 2, 3, 4, 4a, 5, 6-Hexahydro-1H-pyrimido[1, 2-a]quinoline DerivativesMasanori Nagata, Takao Yamazaki1963 Volume 83 Issue 7 Pages 682-689
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSReaction of 2-chloroquinoline with 3-amino propanol gave 2-(3-hydroxypropylamino)-quinoline (I). I was treated with phosphoryl chloride to give the corresponding 4-aza-benzo[c]quinolizine derivative (III). III was reduced to 2, 3, 4, 4a, 5, 6-hexahydro-1H-pyrimido[1, 2-a]quinoline (IVa) over platinium oxide catalyst.
The hydrochloride of IVa absorbed one mole of hydrogen over platinium oxide catalyst to give 1-(3-aminopropyl)-1, 2, 3, 4-tetrahydroquinoline (IVb), whose structure was elucidated by another method of its synthesis. The compound IVa was prepared also by another method, according to the following process. 2-Aminoquinoline was reacted with ethyl 3-chloropropionate to give 1, 2-dihydro-3H-pyrimido[1, 2-a]quinolin-3-one (VII), followed by its catalytic reduction over platinium oxide catalyst to give 1, 2, 4, 4a, 5, 6-hexahydro-3H-pyrimido[1, 2-a]quinolin-3-one (XIII), which was reduced with lithium aluminum hydride to IVa.View full abstractDownload PDF (1215K) -
Syntheses of N-(Dimethylaminoalkyl) anilinesKazuo Kigasawa, Hiroshi Sugahara, Mineharu Hiiragi1963 Volume 83 Issue 7 Pages 689-695
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBy the reaction of N, N-dimethyl-2-chloropropylamine (or N, N-1-trimethyl-2-chloro-ethylamine), Y-C6H4NRH (Y=H, OC2H5; R=H, CH3, CH2C6H5) represented by the general formula produced a mixture of two kinds of Y-C6H4NRCH(CH3)CH2N(CH3)2 (III) and Y-C6H4NRCH2CH(CH3)N(CH3)2 (IV). A series of such compounds (III) and (IV) was synthesized aiming the analgesics shown in Table I and II. A mixture of two kinds was separated by recrystallization as maleates and picrates and the structure was determined by the method shown in Chart 2.
In order to obtain the III-type compound, N-(1-methyl-2-dimethylaminoethyl)-p-phenetidine was prepared by the reductive reaction of p-phenetidine and CH3COCH2-N(CH3)2 in the presence of PtO2 catalyst.View full abstractDownload PDF (1057K) -
Syntheses and Pharmacological Action of N-(Dimethylaminoalkyl) anilinesKazuo Kigasawa, Hiroshi Sugahara, Mineharu Hiiragi, Kazunaga Fukawa1963 Volume 83 Issue 7 Pages 696-700
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn continuation to the previous report, aminobenzene derivatives, represented by the general formula, Y-C6H4NR-CH2CH2CH2N(CH3)2, Y-C6H4NRCH2CH2N(CH3)2 (Y=H, OC2H5; R=H, CH3, CH2C6H5, COCH3, COC6H5) being also ethylenediamine derivatives, were synthesized as is shown in Table I and II. All of the analgesic activities were examined and some of the superior derivatives to aminopyrine were shown in Table III and IV.View full abstractDownload PDF (738K) -
Synthesis of Bound Compounds of Thioctic Acid Derivatives and Vitamin B1. (1)Yoshio Deguchi, Kazuo Nakanishi1963 Volume 83 Issue 7 Pages 701-704
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBoth thioetic acid and thiamine play important rôle in the metabolic process of pyruvic acid and preparation of their conjugate would be significant for biological studies. The present series of synthetic work was undertaken in order to obtain such compounds.
Attempt was first made to synthesize a compound in which the sulfur atoms in 6- and 8-positions of thioctlc acid was bonded in disulfide-form to thiamine. Application of sodium thiosulfate to methyl 6, 8-dichloroöctanoate (VI) to obtain the Bunte salt (VII) showed that chlorine in 6-position is less reactive and, by the use of the methyl ester (VIII) and amide (XIV) of 6-bromo-8-chloroöctanoic acid, the objective 6, 8-bis{2-{N-[(4-amino-2-methyl-5 -pyrimidinyl) methyl] formamido}-1-(2-hydroxyethyl) propenyldithio}-octanoic acid was obtained as its methyl ester (II) and amide (IV). Although II retained its thioctic acid activity in approximately 90% of the original acid, transition of thiamine into blood cells was hardly observed.View full abstractDownload PDF (588K) -
Synthesis of Bound Compounds of Thioctic Acid Derivatives and Vitamin B1. (2)Yoshio Deguchi, Kazuo Nakanishi1963 Volume 83 Issue 7 Pages 704-707
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFollowing the previous work*1 on the disulfide conjugate (I) of thioctic acid and thiamine, whose thiamine did not transit into blood cells, attempt was made to obtain compounds (IIa and IIb), in which the sulfur atom at 6- or 8-position of thioctic acid was bonded in disulfide form to thiamine and the other sulfur was in a dimer form. Methyl 8-chloro-6-hydroxyoctanoate (III), which was easily available, was converted into methyl 8-mercapto-6-bromo-octanoate (VIa) and from it, methyl 8, 8′-dithiobis[6-{2-{N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]formamido}-1-(2-hydroxyethyl)propenyl-dithio}öctanoate] (IIa) was obtained. Although transition of thiamine into blood cells was observed in II, its thioctic acid activity was abnormally low.View full abstractDownload PDF (610K) -
Synthesis of Bound Compounds of Thioctic Acid Derivatives and Vitamin B1. (3)Yoshio Deguchi, Kazuko Miura1963 Volume 83 Issue 7 Pages 708-713
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn continuation of previous works, attempt was made to synthesize a compound in which the sulfur atom at 6-position of thioctic acid was bonded in disulfide form to thiamine and the sulfur atom in 8-position was acetylated, i.e. methyl 8-acetylthio-6-{2-{N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]formamido}-1-(2-hydroxyethyl)propenyldithio}octanoate (IIIa). This compound, IIIa showed satisfactory result in thioctic acid activity and transition of its thiamine into blood cells. Among the various methods of synthesis tried, even that showing the highest yield gave the objective substance in a total yield of ca. 6% from methyl 8-chloro-6-hydroxyoctanoate (IV). It was found that the one of the reasons for this poor yield was the extremely slow reaction of the halogen atom in 6-position of methyl 8-acetylthio-6-halogenoöctanoate (VII) to form the Bunte salt (VIII) by the action of sodium thiosulfate and the fact that VIII is easily decomposed by heat.View full abstractDownload PDF (992K) -
New Synthesis of 6-Acylthio-8-chloroöctanoic EstersYoshio Deguchi, Kazuko Miura, Masumi Ito1963 Volume 83 Issue 7 Pages 713-717
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIt had been found that derivatives of haloöctanoic acid in 6- and 8-positions differed in their behavior towards sodium thiosulfate and that the use of 8-substituted derivative would be more desirable. In the present series of work, methyl 8-chloro-6-hydroxy-octanoate was derived to methyl 8-chloro-6-tosyloxyoctanoate (VII) by the action of tosyl chloride and methyl 6-acetylthio-8-chioroöctanoate (Va) was finally synthesized in a high yield of 73% by the application of thioacetic acid and calcium hydroxide in acetone.View full abstractDownload PDF (744K) -
Synthesis of Bound Compounds of Thioctic Acid Derivatives and Vitamin B1. (4)Yoshio Deguchi, Kazuko Miura1963 Volume 83 Issue 7 Pages 717-721
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSStarting with methyl 6-acetylthio-8-chloroöctanoate (Ia) obtained in a previous work, the objective methyl 6-acetylthio-8-{2-{N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-formamido}-1-(2-hydroxyethyl)propenyldithio}octanoate (IIIa) hydrochloride was obtained in 42% yield from methyl 8-chloro-6-hydroxyoctanoate.
The values of thioctic acid activity of the conjugates of thioctic acid deriyatives and thiamine obtained in this series of work and transition of thiamine into blood cells, using washed blood cell suspension from a rabbit, are presented.View full abstractDownload PDF (807K) -
Gas Chromatography of PreservativesSadao Iguchi, Magobei Yamamoto, Toshinobu Aoyama1963 Volume 83 Issue 7 Pages 721-723
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSeparatory detection of preservatives by gas chromatography was examined. A mixture of sorbic acid, benzoic acid, salicylic acid, dehydroacetic acid, menadione, and methyl, ethyl, butyl, and propyl p-hydroxybenzoate was separated completely into the componental compounds without any pretreatment, under the conditions of 30% DC 550 silicone on Celite 545, at 190°, with carrier gas of hydrogen. Salicylic acid tended to undergo thermal decomposition and phenol peak sometimes appeared in the product but no such decomposition occurred in other compounds.View full abstractDownload PDF (386K) -
Tsutomu Momose, Akira Inaba1963 Volume 83 Issue 7 Pages 724-725
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS3, 6-Dinitrophthalic acid underwent degradation with aqueous sodium hydroxide at a room temperature in about 60 days to 3-hydroxy-6-nitrophthalic acid, which gave a yellow color in alkaline medium. The degradation also occurred gradually in aqueous sodium carbonate, but the acid was very stable when it was stored in tablets mixed with anhydrous alkali carbonate.View full abstractDownload PDF (334K) -
Ring Contraction Reaction from Pyridazone Derivatives to Pyrazoione DerivativesYoshifumi Maki, Hiroko Kizu, Kazunaga Obata1963 Volume 83 Issue 7 Pages 725-728
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1-Phenyl-3, 5-dichloro-6(1H)-pyridazinone (IV) was converted into 1-phenyl-3-hydroxy-pyrazolecarboxylic acid (VI) by treatment with alkali hydroxide solution. The structure of VI was established mainly from infrared spectra of VI and its derivatives. The mechanism of this ring-contraction reaction was assumed.View full abstractDownload PDF (684K) -
Synthesis and Antibacterial Activity on Mycobacterium tuberculosis of 4-Thienyl-3-buten-2-one DerivativesFukujiro Fujikawa, Kunio Hirai, Otokichi Sawada, Junko Goto, Masukazu ...1963 Volume 83 Issue 7 Pages 728-731
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSNineteen kinds of 4-thienyl-3-buten-2-one derivatives were synthesized and their antibacterial activity was examined with a sensitive strain of human-type tubercle bacilli H37Rv and a strain resistant to INH, PAS, and streptomycin. Thiosemicarbazone, 4-methyl-, 4-ethyl, and 4-allyl-thiosemicarbazones of 4-thienyl-3-buten-2-one showed antibacterial activity against both sensitive and resistant strains at 6.25γ/ml. and salicyloylhydrazone at 12.5γ/ml., while 4-propyyl-, 4-butyl-, 4-(p-tolyl)-, 4-(o-methoxyphenyl)-, 4-(p-methoxyphenyl)-thiosemicarbazones, p-hydroxybenzoylhydrazone, p-aminobenzoylhydrazone, phenylhydrazone, and p-nitrophenylhydrazone at 25γ/ml.View full abstractDownload PDF (601K) -
Triterpenoids of Leucothoe GrayanaYoshikazu Kondo, Toshimi Sugiyama, Yuriko Tuchide, Tsunematsu Takemoto1963 Volume 83 Issue 7 Pages 731-733
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSUrsolic acid and oleanolic acid were isolated and identified newly from Leucothoe Grayana MAXIM. (Japanese name, “Hanahirinoki”), besides a paraffin, considered to be nonacosane or triacontane.View full abstractDownload PDF (470K) -
Synthesis of N-Thioctoylamino AcidsYoshio Deuchi, Kazuko Miura1963 Volume 83 Issue 7 Pages 733-737
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn the previous report, the synthesis of thioctamide which shows normal ultraviolet absorption spectra was reported. In this report, a comparison between the synthetic method of N-thioctoylamino acid and the other method which have been known so far, has been made. Especially, N-thioctoylamino acid (methionine, glycine, valine and glutamic acid) which indicates normal ultraviolet absorption spectra was obtained from the reaction of thioctoyl chloride and amino acid ester easily in a better yield.View full abstractDownload PDF (723K) -
Flavonoid Constituents in the Leaves of Acer palmatum THUNBEAGMasakazu Aritomi1963 Volume 83 Issue 7 Pages 737-740
Published: July 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBesides vitexin, saponaretin, orientin, and homo-orientin have now been isolated in pure state from the leaves of Acer palmatum THUNBERG and identified as such.View full abstractDownload PDF (647K)
- |<
- <
- 1
- >
- >|