-
MITSURU FURUKAWA, KAZUTADA MATSUOKA, TAKATOSHI YOSHIDA, YOKO KOJIMA, S ...
1974 Volume 22 Issue 1 Pages
1-7
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The reactions of N-amidino-O-alkylisourea and 1-substituted 3-amidino-2-thiourea with benzil were examined. The reaction of N-amidino-O-alkylisourea with an equivalent amount of benzil in ethanol gave 5, 5-diphenylglycocyamidine by heating for 10 hr under reflux, 5, 5-diphenylglycocyamidine and 2-alkoxyamidinylidene-5, 5-diphenylhydantoin by heating for 2 hr under the similar conditions and 2-alkoxyamidinylidene-5, 5-diphenylhydantoin and 3a, 6a-diphenylglycoluril-2, 5-dialkoximidoylimide by treatment for 1 hr at room temperature. Similarly, heating of 1-aryl-3-amidino-2-thiourea with benzil in ethanol for 10 hr under reflux gave 5, 5-diphenylglycocyamidine. On the other hand, by heating in ethanol in the presence of potassium hydroxide for 2 hr under reflux, 2-arylthiocarbamoyl-5, 5-diphenylglycocyamidine.
View full abstract
-
HIROSHI IWASE, ASAO MURAI
1974 Volume 22 Issue 1 Pages
8-14
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The L- and D-amino acids could be resolved by coupling N-trifluoroacetyl-prolyl chloride (L-TPC) as the resolving agent by gas chromatography. The reaction conditions were studied in detail, the solvents, the amount of resolving agent and reaction time for quantitative derivatization. The 22 stationary phases were studied for chromatographic separation. Relative retention times and separation factors were determined for each enantiomeric pair of 15 amino acids and glycine. Relation between separation factors and structure of amino acids were also discussed.
View full abstract
-
MIKIO HORI, TADASHI KATAOKA, CHEN-FU HSU
1974 Volume 22 Issue 1 Pages
15-20
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
By the reaction of selenopyrylium salts with phenyllithium, two selenabenzene analogs, namely, 10-phenyl- and 9, 10-diphenyl-10-selenaanthracenes have been prepared. The selenaanthracene derivatives are very stable against light, heat, and oxygen. The nuclear magnetic resonance and mass spectral data and the low dipole moment (1.08 D) strongly suggest a covalent aromatic structure for the selenaanthracene.
View full abstract
-
MIKIO HORI, TADASHI KATAOKA, CHEN-FU HSU
1974 Volume 22 Issue 1 Pages
21-26
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
It was confirmed that the nitration of 9-phenylselenoxanthylium salt (III) with a mixed acid (1 equivalent of HNO
3) gave 9-(p-nitrophenyl)- and 9-(m-nitrophenyl) selenoxanthylium salts in the product ratio of 1.0 to 1.5. On the other hand, the reaction of III with a mixed acid (5 equivalents of HNO
3 in H
2SO
4) gave 4-nitro-9-(p-nitrophenyl)- and 4-nitro-9-(m-nitrophenyl) selenoxanthylium salts in the product ratio of 1.0 to 1.25. Based on these results, the reactivity of III in the nitration has been discussed.
View full abstract
-
MIKIO HORI, TADASHI KATAOKA, CHEN-FU HSU, YUTAKA ASAHI, EIJI MIZUTA
1974 Volume 22 Issue 1 Pages
27-31
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
In order to investigate the reactivity of 9-phenylselenoxanthylium perchlorate (III), reaction of III and various nucleophiles have been examined. Theoretical consideration on the chemical reactivities of III in the electrophilic and nucleophilic reactions has been discussed, together with the reaction indices calculated from the ω-technique for 9-phenylxanthylium salt (I), 9-phenylthioxanthylium salt (II), and III.
View full abstract
-
MIKIO HORI, TADASHI KATAOKA, HIROSHI SHIMIZU, CHEN-FU HSU, YUTAKA ASAH ...
1974 Volume 22 Issue 1 Pages
32-41
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The mechanism of the reactions between 9-phenylselenoxanthylium perchlorate (IIb) with phenyllithium or Grignard reagents was clarified by the studies of the eloctron spin resonancl spectroscopy and the chemical reactivities of 9-phenylselenoxanthyl radical (V), which was a reaction intermediate. These experimental results show that the radical mechanism considerably contributes to the reactions between IIIb and organometallic reagents.
View full abstract
-
HIROSHI NAGASE
1974 Volume 22 Issue 1 Pages
42-49
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
By a novel addition reaction of o-aminobenzenethiol to 5-methoxycarbonylmethylidene-2-thioxo (or oxo)-4-thiazolidones (I) were obtained 5-(3-oxo-2, 3-dihydro-4H-1, 4-benzothiazin-2-yl)-2-thioxo (or oxo)-4-thiazolidones (III). I was also found to reat with thiols to afford 1 : 1 adducts (II and VI) in the presence of a catalytic amount of triethylamine. Thermal cyclization of the adducts (II) to III was observed. The adducts (VI) were proved to dissociate into I and thiols when heated above their melting points or dissolved in acetone or ethanol. Oxidation of III and VI gave the dehydro-compounds (IV and VIII), respectively.
View full abstract
-
YOSHIO SASAKI, AKIRA TAKAHATA, MICHIKO YORITAKA, HIDEKO KAWAKI, YUKO O ...
1974 Volume 22 Issue 1 Pages
50-54
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The S values, those are the paramagnetic shift parameters of deuterated and undeuterated and undeuterated para- and meta-substituted aniline derivatives induced by tris (dipivalomethanato) europium, were measured. The observed S values of compounds in the para-substituted series were linearly related with the substituent constants σ
π, whereas those of the meta-substituted series were linearly related with σ
i. The following results were obtained for the magnitudes, S
h and S
d, and the slopes, ρ
h and ρ
d, of the undeuterated and deuterated compounds in the two series : S
d>S
h and ρ
d/ρ
h=1.35.
View full abstract
-
TAKETO OGISO, KAZUO MORIYAMA, SANAE SASAKI, YOSHIKO ISHIMURA, AKIRA MI ...
1974 Volume 22 Issue 1 Pages
55-60
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
High dietary zinc resulted in the lowering of growth, hemoglobin concentration, ceruloplasmin activity and copper concentration in liver, kidney and serum with a marked increase in the concentration of zinc in these tissues. The preliminary experiments were made to determine the sites at which zinc interferes with copper metabolism. When copper was administered to the zinc-fed rats either orally or intraperitoneally, the depression in copper uptake into liver was clearly observed in the former case. Moreover, copper uptake into liver was depressed even when both copper and zinc were administered orally to the normal rats. By the short-period experiments using
64Cu, it was also shown that zinc interferes with the absorption and utilization of copper. These results indicate that the interference of copper metabolism by zinc feeding is mainly due to the inhibition of copper absorption at the intestinal level.
View full abstract
-
IKUO ADACHI, KIMIKO HARADA, RIE MIYAZAKI, HIDEO KANO
1974 Volume 22 Issue 1 Pages
61-69
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Thirteen N-substituted 4-isoxazoline derivatives were obtained by reaction of 3-unsubstituted and 3, 5-disubstituted isoxazolium salts with Grignard reagents. Similarly, 3-benzyl-2-methyl-2, 3, 4, 5-tetrahydronaphth [2, 1-d] isoxazoles and 3-benzyl-2-ethyl-2, 3-dihydrobenzisoxazole were produced by reaction of the corresponding quaternary salts with benzylmagnesium chloride. Thermal reactions of some 4-isoxazoline derivatives and 3-benzyl-2, 3, 4, 5-tetrahydronaphth [2, 1-d] isoxazole derivatives leading to substituted pyrrole derivatives and 3H-benz [e] indole derivatives were investigated. A tentative mechanism for the formation of pyrrole from 4-isoxazoline is also presented.
View full abstract
-
IKUO ADACHI, RIE MIYAZAKI, HIDEO KANO
1974 Volume 22 Issue 1 Pages
70-77
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Synthesis and thermal-reaction of 4-isoxazolines were investigated. Reaction of 3-unsubstituted isoxazolium salts with sodium borohydride yielded the corresponding 4-isoxazolines and their borane complexes together with β-hydroxyaminopropiophenone derivatives. Analogous reaction of 5-unsubstituted isoxazolium salt yielded two isomeric products, 4- and 3-isoxazoline derivatives. The 3-isoxazoline derivative underwent further reduction to give isoxazolidine derivatives. Thermal-conversion of some 4-isoxazolines and their borane complexes into 2-acylaziridine derivatives is also reported.
View full abstract
-
TETSURO IKEKAWA, YOSHIAKI IKEDA
1974 Volume 22 Issue 1 Pages
78-82
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A lipopolysaccharide, serratigen was isolated with weak acid extraction from the organisms of Serratia marcescens, and the purification and characterization were made. It had antigenic activity for rabbit antiserum and the total carbohydrate content was 75% and the molecular weight was 12600. A mannan was isolated from the same strain and had no antigenisity and the total carbohydrate content was 100% and the molecular was 10100.
View full abstract
-
YUZURU YAMAMOTO, TOSHIYUKI HIRAI, KEIKO OKADA, KAYOKO SAITO
1974 Volume 22 Issue 1 Pages
83-87
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
3, 4-Dihydroxytoluquinone and fumigatin chlorohydrin were isolated from a strain of Aspergillus fumigatus DH 413 and the biosynthetic position of these metabolites were discussed.
View full abstract
-
TAKUSHI KURIHARA
1974 Volume 22 Issue 1 Pages
88-92
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Condensation of nitrobenzylideneacetylacetone (Ia, b), which have double bond on 3 position of acetylacetone, with hydrazine dihydrochloride in several alcoholic solvents afforded 3, 5-dimethyl-4-nitrobenzylideneisopyrazolium alkyl chlorides. On the other hand, reaction of Ia, b with hydrazine dihydrochloride in acetonitrile gave 3, 5-dimethyl-4-nitrobenzylideneisopyrazole (IIa, b). These structures and chemical natures were examined.
View full abstract
-
ZEN-ICHI HORII, YUTAKA OZAKI, SHIRO YAMAMURA, TAKAKO NISHIKADO, MIYOJI ...
1974 Volume 22 Issue 1 Pages
93-98
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The synthesis of bisanhydrodaunomycinone (II) was achieved via bisanhydro-γ-rhodomycinone (III) by 7 step procedure envolving the transformation of ethyl side chain in III into acetyl group as shown in Chart 2. The formation of an ana-quinone system on methylation of 6, 11-dihydroxynaphthacenequinones (II and III) was discussed from infrared and ultraviolet spectral comparison.
View full abstract
-
SETSUO HARADA, TOYOKAZU KISHI
1974 Volume 22 Issue 1 Pages
99-108
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The structures of antibiotics, lankacidin A (T-2636 A), lankacidin C (T-2636 C), lankacidinol A (T-2636 D) and lankacidinol (T-2636 F) were elucidated by chemical degradations and spectral analyses. They all have the characteristic cyclo heptadeca carbon skeltone with a β-keto-δ-lactone ring. Of them lankacidin A and C have a pyruvamide group and the others have a lactamide group in their side chain. On the point of view from chemical and biological properties, these antibiotics might be in intermediate position between the macrolide and the polyene macrolide antibiotics.
View full abstract
-
ATSUSHI SUGII, YOSHIHUMI OHARA, KAZUTA KITAHARA
1974 Volume 22 Issue 1 Pages
109-114
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The color reaction of 3-methyl-2-thiohydantoin in alkaline medium was found to be mainly attributed to the formations of bis (3-methyl-2-thiohydantoinylidene-5) by the autoxidation effected by the dissolved oxygen. The presence of trace of manganese (II) ion showed remarkable effect to this color reaction.
View full abstract
-
KOTARO TAKAHASHI, MASAKO TAKANI, AKIKO FUKUMOTO
1974 Volume 22 Issue 1 Pages
115-122
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The structures of the photolysis products of dihydro- and Methyldihydro-usnic acids were studied and the mechanism of the photolysis was discussed.
View full abstract
-
MORIO IKEHARA, TAKEO NAGURA, EIKO OHTSUKA
1974 Volume 22 Issue 1 Pages
123-127
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
8, 5'-Anhydro-8-oxyadenosine was phosphorylated using cyanoethylphosphate and dicyclohexylcarbodiimide (DCC) in dimethylformamide-pyridine. Treatment of the products with a mixture of 50% aqueous pyridine-triethylamine and DEAE-cellulose chromatography gave 2', 3'-cyclic phosphate in a yield of 48%. 8, 5'-Anhydro-8-oxyadenosine 3'-phosphate was obtained by RNase M digestion of the cyclic phosphate. After protection with benzoic anhydride in tetraethylammonium benzoate buffer, the 3'-phosphate was condensed with 2'-O-benzoyluridylyl-(3'→5')-N
2, 2', 3'-O-triisobutyrylguanosine by the use of DCC. DEAE-cellulose, Sephadex G-25 and G-15 column chromatography gave 8, 5'-anhydro-8-oxyadenylyl-(3'→5')-uridylyl-(3'→5')-guanosine. The trinucleotide was characterized by degradation to cyclo Ap, Up and G with RNase M.
View full abstract
-
RYUJI MARUMOTO, MIKIO HONJO
1974 Volume 22 Issue 1 Pages
128-134
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The reaction of uridine with acyl bromide in acetonitrile (or ethyl acetate) afforded 3', 5'-di-O-acyl-2'-bromo-2'-deoxyuridine (II, V) in good yield, which was converted to 2'-deoxyuridine by hydrogenation and subsequent deacylation. A silmiar reaction of N
4-acetylcytidine with acetyl bromide yielded 1-(2, 5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-N
4-acetylcytosine (VIII), which was converted to 3'-deoxycytidine (X) by hydrogenation and subsequent deacylation with a concomitant formation of 2', 3'-dideoxycytidine (XII) and to 1-β-D-arabinofuranosyl cytosine (XI) by treatment with potassium hydroxide in ethanol. A similar reaction of cytidine with acyl bromide gave 2, 2'-anhydro-1-(3, 5-di-O-acyl-β-D-arabinofuranosyl) cytosine hydrobromide (XIV, XVI). These reaction mechanisms were also presented.
View full abstract
-
AKIRA OGISO, AIYA SATO, IKUKO KASHIDA, HARUMITSU KUWANO
1974 Volume 22 Issue 1 Pages
135-143
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Constituents of Leucothoe Keiskei, poriolide (1) and isoporiolide (2) have a novel structure of the macrocyclic biphenyl-type flavonoid glycosides. Results of the spectroscopic analysis and the chemical degradation of these compounds are discussed. The structure of isoporiolide, an isomer of poriolide, was derived from a comparison of the degradation products of poriolide, isoporiolide and their derivatives. On hydrolysis with barium hydroxide, both hexamethylethers (5 and 17) of poriolide and isoporiolide gave the identical propiophenone glycoside (12a), but the isoporiolide hexamethylether yielded an isomer (18a) of the carboxylic acid (13a) obtained from the poriolide hexamethylether.
View full abstract
-
AKIRA OGISO, AIYA SATO, IKUKO KASHIDA, YUKIO SUGIMURA
1974 Volume 22 Issue 1 Pages
144-151
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A key point of the synthesis of aglycones (12 and 33) derived from poriolide (1) and isoporiolide (2), the toxic constituents of Leucothoe keiskei, is the construction of the unsymmetric biphenyl compounds, this point was effected by application of the rearrangement reaction of suitable phenyltropone derivatives to biphenyl compounds.
View full abstract
-
TAKASHI SATO, TATSUZO FUJII
1974 Volume 22 Issue 1 Pages
152-156
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Incubation of human erythrocytes in lysolecithin-containing medium, prepared by an addition of purified lysolecithin to blood plasma or to phosphate-buffered saline, induced the increases in lysolecithin content of the erythrocyte membranes as well as morphological changes of the cells from normal biconcave disc to crenated or spherical forms. The erythrocytes with slight excess of lysolecithin incorporated, which take shapes of crenated disc or crenated sphere, rather have increased osmotic resistance, whereas those with much more lysolecithin, taking almost spherical form, show reduced osmotic resistance. After washing these erythrocytes with heated normal plasma to remove excess lysolecithin from the membrane, the increased osmotic resistance observed in the former erythrocyte preparation was restored to the normal level, whereas the decreased resistance in the latter cell preparation was never reversed, in spite of the restoration to the normal morphological shape.
View full abstract
-
YOSHIO ARATA, YOSHINOBU NAKAGAWA, YOSHIO ARAKAWA, MIYOJI HANAOKA
1974 Volume 22 Issue 1 Pages
157-164
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Oxidation of the anti- and syn-diamine (IX and X) with mercuric acetate gave the enaminolactam (XII). Treatment of the methiodides (XIII, XVIII, and XIX) with lithium in liquid ammonia afforded the ten-membered ring aminolactam (XX) in an excellent yield, which was reduced to the ten-membered ring diamine (XXI). Hofmann degradation of the carbamate (XXIII) derived from XXI provided the fourteen-membered ring aminocarbamate (XXVII) and the oxazolidone (XXVIII), which were converted to the fourteen-membered ring diamine (XXX) and the hydroxydiamine (XXXI), respectively.
View full abstract
-
KENJI KONO, YASUHIRO TAKEDA, HISASHI NOGAMI, TSUNEJI NAGAI
1974 Volume 22 Issue 1 Pages
165-170
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The complexes of polyethylene oxide (PEO) with guanidine hydrochloride and with phenobarbital were subjected to differential scanning calorimetry (DSC), polarized infrared (IR) spectroscopy and X-ray fiber photography, confirming the formations of the complexes and discussing the structures of PEO molecules in the complexes in comparison with PEO-urea complex or original samples of PEO. The formations of the complexes of PEO with urea, with guanidine hydrochloride and with phenobarbital were confirmed by DSC curves of physical mixtures of the respective original components. It may be concluded on the basis of the results by X-ray fiber photography that the three dimentional structure regarding the fiber identity period are different among ordinary PEO, PEO-guanidine hydrochloride complex and PEO-phenobarbital complex. The polarized IR spectroscopy informed that PEO molecule in PEO-guanidine hydrochloride complex may have a structure not so different from the 7
2 helix in the ordinary PEO. It was assumed that PEO molecule in PEO-phenobarbital complex is more distorted than that in PEO-guanidine hydrochloride complex in comparison with intact one, as the fiber identity period was considered to consist of one chemical unit.
View full abstract
-
TETSUYA KAMATAKI, HARUO KITAGAWA
1974 Volume 22 Issue 1 Pages
171-175
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Periodical change in the binding of carbon monoxide with P-450 reduced by NADPH was found to show diphasic pattern. Effect of concentration of oxygen in the atmosphere and effect of pretreatment of rats with phenobarbital and 3-methylcholanthrene on the first and second phases were investigated. Diphasic binding of carbon monoxide with NADPH-reduced P-450 suggested the existence of multiple P-450 species.
View full abstract
-
MASAZUMI WATANABE, MARIKO TOYODA, ISUKE IMADA, HIROSHI MORIMOTO
1974 Volume 22 Issue 1 Pages
176-182
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Urinary metabolites from rabbits dosed with phylloquinone and dl-α-tocopheryl acetate were examined. We found that phylloquinone was excreted as conjugate forms of 2-methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-naphthoquinone and 2-methyl-3-(3'-carboxybutyl)-1, 4-naphthoquinone, and dl-α-tocopheryl acetate was excreted mainly as the conjugate form of 2, 3, 5-trimethyl-6-(5'-carboxy-3'-hydroxy-3'-methylpentyl)-1, 4-benzoquinone lactone and in small amounts, as the conjugate form of 2, 3, 5-trimethyl-6-(3'-carboxybutyl)-1, 4-benzoquinone.
View full abstract
-
MASAZUMI WATANABE, RYOKICHI NEGISHI, ISUKE IMADA, MASAO NISHIKAWA, HIR ...
1974 Volume 22 Issue 1 Pages
183-188
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The effect on the stability of rat-liver lysosomal membrane was investigated with trans-2, 3, 5-trimethyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-benzoquinone (E Acid-I), 2, 3, 5-trimethyl-6-(3'-carboxybutyl)-1, 4-benzoquinone (E Acid-II), trans-2-methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-naphthoquinone (K Acid-I), 2-methyl-3-(3'-carboxybutyl)-1, 4-naphthoquinone (K Acid-II), trans, cis mixture (3 : 1) of 2, 3-dimethoxy-5-methyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-benzoquinone (Q Acid-I) and 2, 3-dimethoxy-5-methyl-6-(3'-carboxybutyl)-1, 4-benzoquinone (Q Acid-II). E Acid-I, E Acid-II, K Acid-I, K Acid-II and Q Acid-I, especially E Acid-I and K Acid-I, inhibited the release of acid phosphatase and β-glucuronidase from the heavy lysosomal fraction of rat-liver in vitro. Q Acid-II accerelated release of the hydrolases. Structure-activity relationships were considered.
View full abstract
-
SHIGEO SENDA, KOSAKU HIROTA, TETSUJI ASAO
1974 Volume 22 Issue 1 Pages
189-195
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
As a part of our studies on the structure-activity relationship of 1, 3-disubstituted 5-dimethylamino-6-methyluracil derivatives, the authors have synthesized 1, 3-disubstituted 5-dimethylaminouracils (B) and 1, 3-disubstituted 5-dimethylamino-6-ethyluracils (C) and investigated their pharmacological activity. In the synthesis, 1, 3-disubstituted uracils (7, 10-13) were made to react with bromine and the resulting 5-bromouracils (14-18) were heated with dimethylamine in DMF to give compounds (B). Ethyl 3-oxovalerate was condensed with phenylurea to afford 6-ethyl-3-phenyluracil (25) ; 3-position of it was alkylated and 5-position was brominated and further dimethylaminated to give compounds (C). In the pharmacological tests, compound (C) showed nearly same analgetic action as that of compounds (A) while compounds (B) scarcely showed such an action. Both (B) and (C) did not exhibit antipyretic action.
View full abstract
-
EIICHI FUJIHIRA, TAKASHI OHSHIMA, NORIMITSU TAKAHASHI, AKIRA MINATO, M ...
1974 Volume 22 Issue 1 Pages
196-200
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
TLC-analysis for bile acid composition was carried out on the bile samples obtained by bile duct-cannulation from the rats fasted for 48 hr and from those kept continuously on a diet supplemented with 1% cholesterol or 2% thyroid powder. The secretion of total taurine-conjugated bile acids decreased after fasting, only except the secretion of taurodeoxycholic acid which was maintained at normal level. The fasted group, thus, demonstrated an increase in the ratio of trihydroxy to dihydroxy bile acids and a decrease in another ratio of bile acid components, (taurocholic acid+taurodeoxycholic acid)/(taurochenodeoxycholic acid+tauromuricholic acid+taurohyodeoxycholic acid), as compared with the normal group. Cholesterol-feeding increased slightly the biliary output of total bile acids. However, both of the above ratios for this group were nearly the same to those for the normal group. On the other hand, thyroid powder-feeding caused an increase of taurocholic acid accompanied by a concomitant decrease of taurodihydroxy bile acids within the normal range of total bile acid secretion, resulting in increases of both the ratios over the normal levels. In all the experimental groups including the normal, the incorporation of intravenously injected taurine-
35S into biliary taurocholic, tauromuricholic and taurodihydroxy bile acids was approximately proportional to the secreted amounts of these fractions.
View full abstract
-
YOSHIKO KAMIYA, SHOJI TAKEMURA
1974 Volume 22 Issue 1 Pages
201-206
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Some oxidative cleavages of acetals with N, N-dibromobenzenesulfonamide (DBBS) have been presented. As a result of oxidative fission of C-O bond and simultaneous bromination, these reaction gave ester and alkyl bromide, or brominated esters (shown in Table I). The reaction mechanism has been discussed on the basis of the experiments and the previous investigation on the reaction of ethers with DBBS.
View full abstract
-
KIICHI ARAKAWA, TADASHI MIYASAKA, HISAO OCHI
1974 Volume 22 Issue 1 Pages
207-213
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
Acetylation of 3-methylpyrazol-5-one (I) with acetic anhydride produces five acetates according to the reaction condition : by heating in the presence of concentrated sulfuric acid 4-acetyl-3-hydroxy-5-methylpyrazole (II) ; by heating several minutes crystalline monoacetate, 2-acetyl-3-hydroxy-5-methylpyrazole (IV) and oily diacetate, 3-acetoxy-2-acetyl-5-methylpyrazole (V) ; by heating for several hours crystalline diacetate, 3-acetoxy-1-acetyl-5-methylpyrazole (VI) ; and by heating in the presence of pyridine monoacetate, 1-acetyl-3-hydroxy-5-methylpyrazole (VII). Basic hydrolysis of the acetates (IV, V, VI, and VII) gives the starting pyrazolone (I). The enol-acetate moiety of the diacetate (V or VI) is more susceptible to hydrolysis under mild condition to give the corresponding N-monoacetate (IV or VII). Inspection by nuclear magnetic resonance spectroscopy of the acetates reveals that the chemical shift of C
5-methyl grouping is observed at approximately 0.3 ppm lower field when acetylated at the adjacent nitrogen atom.
View full abstract
-
KIICHI ARAKAWA, TADASHI MIYASAKA, HISAO OCHI
1974 Volume 22 Issue 1 Pages
214-223
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
The individual reactions of acetyl group rearrangement are examined to elucidate the complicated formation of five acetylated products of 3-methylpyrazol-5-one (I). In heated acetic acid-anhydride mixture the initially formed 2-acetyl-3-hydroxy-5-methylpyrazole (II) reacts further to produce 1-acetyl-3-hydroxy-5-methylpyrazole (III), 3-acetoxy-2-acetyl-5-methylpyrazole (IV) and finally 3-acetoxy-1-acetyl-5-methylpyrazole (V), while inter- as well as intra-molecular acetyl transfer reaction takes place. The diacetate (V) is a sort of activated ester and is proved to be effective as a mild acetylating reagent of primary and secondary amines.
View full abstract
-
YOSHIO SASAKI, MAKIKO SUGIURA
1974 Volume 22 Issue 1 Pages
224-229
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
-
YOSHIFUMI MAKI, MIKIO SUZUKI, MASAHIRO TAKAYA
1974 Volume 22 Issue 1 Pages
229-232
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
-
NOBUYOSHI KANENIWA, AKIKO IKEKAWA, YUTAKA TOMITA, GIICHIRO NABEYAMA
1974 Volume 22 Issue 1 Pages
232-236
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
-
MASARU KOBAYASHI, KAGEMI TODO, HIROSHI MITSUHASHI
1974 Volume 22 Issue 1 Pages
236-238
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
-
TADAKAZU MURATA, KIYOSHI UKAWA
1974 Volume 22 Issue 1 Pages
240-241
Published: January 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS