All issues
Predecessor
Volume 72, Issue 12
Displaying 1-50 of 114 articles from this issue
-
Isomerism of Hydrazodithiodicarbamide, 2-Amino-5-mercapto-, and 2-Amino-5-hydroxythiodiazoleMasaki Ohta, Hiroaki Koyama1952 Volume 72 Issue 12 Pages 1533-1535
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIt has been found that the report by Janniah and Guha should be denied regarding the existence of two isomers of hydrazodithiodicarbamide (I) as thiol type, m.p. 223°, and dithiol type, m.p. 203°. These two show identical absorption curves and should, therefore, be polymorphs. The two authors' report that there is an endo-form, m.p. 245°, to 2-amino-5-mercaptothiodiazole, m.p. 234°, obtained by the hydrochloric acid cyclization of (I), should also be denied, since no compound with m.p. 245° was obtained in the present experiments in this authors' laboratory. Further denial has been obtained on the report by Janniah and Guha that the substance of m.p. 177° obtained by the conc. hydrochloric acid cyclization of hydrazomonothiodicarbamide is 2-amino-5-hydroxythiodiazole (II), and that of m.p. 235° obtained by acetic anhydride cyclization of (II) is the endo-form. The latter compound is 2-amino-5-hydroxythiodiazole. No definite confirmation has yet been obtained as to the structure of the substance with m.p. 177°.View full abstractDownload PDF (515K) -
Synthesis of Carboxylic Acid DerivativesMasaki Ohta1952 Volume 72 Issue 12 Pages 1536-1537
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBy the condensation of malonic or succinic ester chlorides respectively with thiosemi-carbazide, in the presence of phosphorus trichloride, ethyl 2-amino-1, 3, 4-thiodiazole-5-acetate and methyl 2-amino-1, 3, 4-thiodiazole-5-propionate were obtained. Their hydrolyses afforded the corresponding acids. Their respective acid amides and acid hydrazides were also prepared.View full abstractDownload PDF (326K) -
A New Method for the Preparation of Isoquinoline Derivatives. (2). Reaction of Methyleugenol on Acid Amide in the Presence of POCl3Tetsuji Kametani1952 Volume 72 Issue 12 Pages 1537-1539
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAs described in the previous report, 1-substituted 3-methyl-6, 7-methylenedioxy-3, 4-dihydroisoquinoline is formed by reacting safrol and acid amide in a suitable solvent in the presence of phosphoryl chloride. Application of this reaction to methyleugenol successfully yielded 1-substituted 3-methyl-6, 7-dimethoxy-3, 4-dihydroisoquinoline. For example, the use of acetamide, benzamide, 3, 4-dimethoxybenzamide, 3, 4-methylenedioxy-benzamide, and phenylacetamide as acid amide in the reaction of methyleugenol and phosphoryl chloride respectively yielded 1-methyl-, 1-phenyl-, 1-(3′, 4′-dimethoxyphenyl)-, 1-(3′, 4′-methylenedioxyphenyl)-, and 1-benzyl-3-methyl-6, 7-dimethoxy-3, 4-dihydroiso-quinolines.View full abstractDownload PDF (619K) -
A New Method for the Preparation of Isoquinoline Derivatives. (3). Condensation Agents, Mechanism of New Syntheses, and a Synthesis of 3, 4-DihydroneupaverineTetsuji Kametani, Kichijiro Ninomiya1952 Volume 72 Issue 12 Pages 1539-1541
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to increase the yield of dihydroisoquinoline derivatives obtained by the condensation of safrol or methyleugenol with various acid amides, several kinds of condensation agents were tried but phosphoryl chloride seemed to be the most effective. In the preparation of 3, 4-dihydroneupaverine, i.e. 1-(3′, 4′-methylenedioxyphenyl)-3-methyl-6, 7-methylenedioxy-3, 4-dihydroisoquinoline, 3, 4-methylenedioxybenzonitrile is formed as a by-product, and therefore, p-nitrobenzonitrile or p-nitrobenzamide was applied to safrol by which the objective isoquinoline derivative was obtained in either case but it required a long period of time in the case of the former with a very poor yield. It is assumed, from this result, that nitrile itself does not directly react with safrol in this reaction but the amide adds to the double bond in safrol and then undergoes isoquinoline cyclization by the action of phosphoryl benzamide. It can also be assumed that the initially formed nitrile by the dehydration of acid amide also takes part in the reaction.View full abstractDownload PDF (630K) -
On the Alkylaminoacetanilides Containing Thioalkyl SubstituentsTozaburo Kurihara, Hirosi Niwa, Fumihiko Tanaka1952 Volume 72 Issue 12 Pages 1541-1545
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to find the effect of thioalkyl group introduced into a benzene nucleus on local anesthetic properties, 15 kinds of alkylaminoacetanilide substituted in the ortho and para positions with thioalkyl group were prepared and their local anesthetic properties were compared. In general, the anesthetic action increased with the increase of the number of carbon atoms in the thioalkyl group, with attendant increase in toxicity. The maximum efficacy was found in p-thioamyldiethylaminoacetanilide which possessed 2.3 times the surface anesthetic power of cocaine. These substances possess a certain amount of local irritating action, similar to the corresponding alcoxyl compounds, but it was observed that their anesthetic properties are slightly better than those of oxygen compounds. Reduction of alcoxyl compounds, to decrease irritating action, to hydroxyl derivatives resulted in the loss of local anesthetic action together with the decrease of irritating properties.View full abstractDownload PDF (1015K) -
Tatsuo Kariyone, Hajime Yamada, Mitsuo Takahashi, Teruo Omiya, Kihachi ...1952 Volume 72 Issue 12 Pages 1545-1547
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFor the purpose of preparing antispasmodics with strong effect and small toxicity, glycerol ethers of nitrogen-free bicyclic compounds were prepared and pharmacological tests were carried out. Of the new compounds prepared, 3-(1, 2, 3, 4-tetrahydro-7-naphthyloxy)-1, 2-propanediol was found to be better than Myanesin in slackening and paralysing the muscles, toxicity, action time, safety rate, and inhibition of convulsions induced by spasmodic poisons. 3-(1, 2, 3, 4-Tetrahydro-8-naphthyloxy)-1, 2-propanediol was found to be the next, with properties slightly lower than those of Myanesin. Such actions were found to be weak in compounds of this series such as 3-methylphenoxy-, 3-m-propylphenoxy-, and 3-m-butylphenoxy-1, 2-propanediols.View full abstractDownload PDF (516K) -
On the Steric Inversion of N-MethylephedrineKuniyosi Tanaka, Tosio Sugawa1952 Volume 72 Issue 12 Pages 1548-1551
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSRelationship between substitution reaction and steric rearrangement in N-methylephedrine was examined and the result was compared with that in the case of ephedrine. Application of phosphorus pentachloride to d-N-methylephedrine (I) and to l-φ-N-methylephedrine (II) respectively yielded (-)-φ-1-phenyl-1-chloro-2-dimethylaminopropane hydrochloride (III) from (I), and (III) and (+)-1-phenyl-1-chloro-2-dimethylaminopropane hydrochloride (IV) from (II). Application of aqueous solution of silver nitrate to (III) yielded a mixture of (I) and (II), while heating (III) with aqueous solution of sodium hydroxide gave (II) alone. Application of sodium hydroxide to (IV) gave (I). It was assumed that ethylene-immonium ion is formed as an intermediate in the reaction of (III) to (II), and two Walden inversions occurred consecutively during its cyclization and cleavage. Exactly the same relationships were found to exist in l-N- and d-φ-N-methylephedrines.
In the previous paper, the ethylene-imine derivative, formed during the formation of φ-1-phenyl-1-chloro-2-acylmethylaminopropane (VII) through N-methyl-1-phenyl-2-methylethylene-imine (VI) from φ-1-phenyl-1-chloro-2-methylaminopropane, derived from ephedrine or φ-ephedrine, was assumed to belong to the pseudo series, but later experimental results seem to point that the compound belongs to the normal (cis-form) series and that Walden inversions occured during its cyclization and cleavage.View full abstractDownload PDF (780K) -
On the Steric Inversion of 1, 2-Diphenyl-2-methylaminoethanol-(1)Kuniyosi Tanaka, Tosio Sugawa1952 Volume 72 Issue 12 Pages 1551-1554
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSRelationship between substitution reaction and steric rearrangement between erythro and threo compounds of 1, 2-diphenyl-2-methylaminoethanol-(1) was examined and it was found that the situation identical with ephedrine also existed. Treatment of the N-acetyl derivative (VI) of erythro-1, 2-diphenyl-2-methylaminoethanol-(1) (I) with alcoholic hydrochloric acid results in its rearrangement to the O-acetyl derivative (VIII) of the threo series while the threo-1, 2-diphenyl-2-aminoethanol-(1) (II) obtained by the hydrolysis of (VIII) undergoes rearrangement to the N-acetyl (VI) or O-acetyl (VIII) derivative of the erythro-series via threo-chloro (III), erythro-ethylene-imine (IV), and threo-N-acetylchloro (V) derivatives. Hydrolysis of (VI) or (VIII) was found to yield (I).View full abstractDownload PDF (810K) -
Reaction of Periodic Acid on Two HexasaccharidesShichiro Akiva, Seiiehi Okui, Shigeo Suzuki1952 Volume 72 Issue 12 Pages 1554-1558
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe hexasaccharides of Schardinger and Akiya-Watanabe were oxidized with periodic acid to aldehydes and derived to p-nitrophenylhydrazones. The hydrazone obtained from Schardinger's hexasaccharide contained four p-nitrophenylhydrazine groups bonded on both sides of glyoxal and erythrose. The hydrazone obtained from Akiya-Watanabe's hexasaccharide contained six p-nitrophenylhydrazine goups in a molecule, bonded to the glyoxal sides alone. Acid decomposition of the two hydrazones were also carried out.View full abstractDownload PDF (766K) -
Preparation of Glyoxal p-NitrophenylhydrazoneShichiro Akiya, Seiichi Okui1952 Volume 72 Issue 12 Pages 1558-1560
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOxidation of the p-nitrophenylhydrazone of D-glucose with periodic acid gave glyoxal p-nitrophenylhydrazone. This compound was stable in a neutral medium but easily changed to glyoxal p-nitrophenylosazone and free glyoxal in an acid medium.View full abstractDownload PDF (399K) -
Kaneo Imai, Kiyoshi Furuya1952 Volume 72 Issue 12 Pages 1560-1564
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAttempt was made to find a simple and rapid determination method for rutin in Kaika, a crude drug composed of the flower buds of Sophora japonica L. The reaction conditions of rutin-Al complex, and the correlation between rutin concentration and absorption were statistically examined. The flower buds were extracted with 99% methanol, using a new type extractor, treated with ether to remove quercetin, and diluted with a suitable amount of methanol to prepare a sample solution. To 2cc. of this sample solution, 3cc. of 0.1 mole aqueous solution of aluminum chloride and 5cc. of 1 mole aqueous solution of potassium acetate were added, allowed to stand at a room temperature for two hours, and the absorption (y) of rutin-Al complex was measured by a photoelectric colorimeter, using S-47 filter. The percentage of rutin (x) at 95% confidence limit was calculated from the following equation: x=(0.0612y-0.00072)±0.00049.View full abstractDownload PDF (705K) -
Takeshi Oda1952 Volume 72 Issue 12 Pages 1564-1566
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSPenitrinic acid, C15H17O5N, was isolated from the culture medium of Penicillium notatum P176. α- and β-Penitrin were obtained by the respective cleavage of peni-trinic acid by sulfuric acid and alkali. A new, nitrogen-free phenol, penitrinol, C13H18O3, was obtained by the hydrogenolysis of penitrinic acid.View full abstractDownload PDF (618K) -
Wataru Nagata, Ken'ichi Takeda1952 Volume 72 Issue 12 Pages 1566-1570
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFollowing considerations were made regarding the so-called second-type Beckmann rearrangement by which nitrile is formed from ketoxime.
1) Such rearrangement easily occurs with compounds in which C-C bond (C-H bond in aldoxime) in the transposition of the oxime group is easily cleaved.
2) Such rearrangement was confirmed to occur primarily by cleavage without passing through an intermediate of acid aride or imide, by detailed studies on camphor oxime and anti-α-isonitrosocamphor.
3) It was pointed out that the rearrangement agent does not directly attack the β-carbon, the carbon atom next to the carbon bonding with nitrogen.View full abstractDownload PDF (928K) -
Genshun Sunagawa, Teishiro Kushima, Takeshi Ichii1952 Volume 72 Issue 12 Pages 1570-1574
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) The benzylamine derivatives possessing a substituent with comparatively strong -E effect in the para-position, such as the methoxyl, and an aromatic residue bonded to its nitrogen, easily undergo decomposition by acids.
2) Respective decomposition by hydrochloric acid of 2-p-methoxybenzylaminopyrimidine and p-methoxybenzylaniline yielded α-aminopyridine, 2-anzinopyrimidine, and aniline, as the bases, with p, p′-dimethoxydiphenylmethane and formaldehyde.View full abstractDownload PDF (925K) -
Derivatives of Phenyl(1)-methylphenyl(2)-glucosazoneShichiro Akiya, Setsuzo Tejima1952 Volume 72 Issue 12 Pages 1574-1576
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBy the methylation of phenylglucosazone, phenyl(1)-methylphenyl(2)-glucosazone was isolated. Condensation of acetone to the latter resulted in the bonding of acetone at C5 and C6, to form 5, 6-monoacetone-phenyl(1)-methylphenyl(2)-glucosazone, whose further methylation gave 3, 4-dimethyl-5, 6-monoacetone-phenyl(1)-methylphenyl(2)-glucosazone. Phenyl(1)-methylphenyl(2)-glucosazone required 3 moles of periodic acid to form 2 moles of formic acid and precipitated yellow needles of mesoxaldehyde-phenyl(1)-methylphenyl-(2)-osazone, whose color changed to blood red on irradiation of sunlight. However, the melting point of the red crystals was no different from that of the yellow one, the color being recovered on recrystallization. This change was reversible and could be repeated number of times.View full abstractDownload PDF (522K) -
Condensation Products of D-Glucose with Alkyl- or Aryl-phenyl-hydrazines and their Degeneration Products by Periodic AcidShichiro Akiya, Setsuzo Tejima1952 Volume 72 Issue 12 Pages 1577-1579
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSPhenyl(1)-alkylphenyl(2)-glucosazones in which the alkyl was ethyl, allyl, and butyl, were prepared. These compounds required 3 moles of periodic acid to form 2 moles of formic acid and precipitated corresponding mesoxaldehyde-phenyl(1)-alkylphenyl(2)-osazones. The color of these crystals also changed by sunlight, that of ethyl derivative from yellow to orange yellow, that of allyl and butyl from yellow to red, without any change in their melting points. These changes were also found to be reversible, the original yellow crystals being obtained on recrystallization, and vice versa.View full abstractDownload PDF (567K) -
Preparation of Glucosone-methylphenylhydrazone-(2)Shichiro Akiya, Setsuzo Tejima1952 Volume 72 Issue 12 Pages 1580-1582
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOfner reported (Ber. 37, 4400 (1904)) that the application of methylphenylhydrazine to D-glucose in 50% acetic acid solution yielded D -glucose methylphenylhydrazone. Reëxamination of this experiment failed to furnish the hydrazone but glucosone methylphenylhydrazone-(2) as pale yellow needles, m.p. 170°, was obtained.View full abstractDownload PDF (489K) -
Akira Ito, Wataru Hamanaka1952 Volume 72 Issue 12 Pages 1583-1584
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSElectrochemical studies were made on the acyl rearrangement from oxygen to nitrogen in compounds of chloramphenicol series. As a means of dynamic study of this rearrangement, potential titration was found to be suitable, through which it was learned that the acetyl group easily underwent rearrangement in the presence of sodium hydroxide, but that the dichloroacetyl group refused to undergo such arrangement and finally decomposed as dichloroacetic acid.View full abstractDownload PDF (473K) -
Synthesis of 3-[2′-β-Hydroxyethyl-4′-aminopyrimidyl-(5′)]-methyl-4-methyl-5-β-hydroxyethylthiazolium CompoundTaizo Matsukawa, Shojiro Yurugi1952 Volume 72 Issue 12 Pages 1585-1588
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS2-β-Hydroxyethyl-4-amino-5-cyanopyrimidine (III) was prepared from β-hydroxypropionitrile by deriving it first to β-hydroxypropioimidoether by the application of the alcohol and hydrogen chloride, then to β-hydroxypropioamidine by the application of ammonia to the ether, and by the condensation of ethoxymethylenemalonitrile. (III) forms 2-β-chloroethyl derivative (IV) by the action of phosphoryl chloride, and 2-β-acetoxyethyl derivative (V) by acetylation with acetic anhydride in pyridine. Heating of (III) with acetic anhydride alone results in the formation of 2-vinyl derivative (VI) with (V). Electrolytic reduction of (III) in hydrochloric acid, with palladium-black as the cathode, yields 2-β-hydroxyethyl-4-amino-5-aminomethylpyrimidine (VII) hydrochloride. Application of carbon disulfide and γ-aceto-γ-chloropropyl acetate to (VII), in the presence of ammonia, results in the formation of α-aceto-γ-acetoxypropyl N-[2-β-hydroxyethyl-4-aminopyrimidyl(5)]-methyldithiocarbamate (VIII), whose heating with diluted hydrochloric acid yields 3-[2′-β-hydroxyethyl-4′-aminopyrimidyl(5′)]-methyl-4-methyl-5-β-hydroxyethylthiazol-2-thione (IX) The treatment of (VIII) with alkali yields 2-thio-7-β-hydroxyethyl-1, 2, 3, 4-tetrahydropyrimido-(4, 5-d)-pyrimidine (X). Application of ethyl iodide to (IX) yields 2, 9-di(β-hydroxyethyl)-3-methylthiochromine (XI), and application of hydrogen peroxide to the dil. hydrochloric acid solution of (IX) results in the formation of 3-[2′-β-hydroxyethyl-4′-aminopyrimidyl(5′)]-methyl-4-methyl-5-β-hydroxyethylthiazolium compound (II). The hydrochloride of (II) was found to possess one-third to one-quarter the effect of thiamine, tested with rice birds. (IX) was found to be totally ineffective.View full abstractDownload PDF (838K) -
Kenji Kaji, Hiromu Nagashima1952 Volume 72 Issue 12 Pages 1589-1591
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAs ethylenediamine compounds of indole series assumed to possess antihistaminic properties, two kinds of N-(β-diethylaminoethyl)-α-methylindoles and four kinds of N-(β-diethylaminoethyl)-α-arylindoles were prepared by heating sodium salts of α-substituted indoles and β-diethylaminoethyl chloride in anhydrous toluene or xylene in the presence of sodium amide.View full abstractDownload PDF (592K) -
Synthesis of γ-DiphenylalkanolaminesKeijiro Takagi, Yutaka Kasuya, Kazuo Hattori1952 Volume 72 Issue 12 Pages 1592-1594
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFive kinds of diphenylbutanolamines and two kinds of diphenylpropanolamines were prepared to examine their antispasmodic actions. The butanolamines are all new compounds and were prepared by the Grignard reaction of β-aminobutyric esters. The anticholinergic activity of these compounds was found to be the strongest in 1, 1-diphenyl-3-piperidylbutanol, being one-third to one-half of the action of atropine sulfate when tested with excised small intestines of guinea pigs.View full abstractDownload PDF (586K) -
Morphology of Japanese SenegaMiti-iti Fujita, Kazumitu Nishimoto1952 Volume 72 Issue 12 Pages 1595-1598
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe morphology of Japanese senega, said to originate from Polygala Senega L. var. latifolia Torr. et Gray, was studied. The Japanese senega was found to be similar to the Northern senega, generally used as drugs, in that it possessed many branched lateral roots and fine rootlets, especially with strong tendency of lateral roots to bend, and showing keel and abnormal growth of internal structure. These facts probably indicate that the botanical origin of the two drugs are quite closely related. It was also found that the characteristics of Japanese senega were almost identical with those of Southern senega.View full abstractDownload PDF (1619K) -
Chemical Change of Vitamin B1 in SolutionsTaizo Matsukawa, Shojiro Yurugi1952 Volume 72 Issue 12 Pages 1599-1601
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe change of vitamin B1 when it was heated in an aqueous solution of pH 8 at 60° for 2.5 hours was examined by paper partition chromatography, and it was found that thiochrome (IV), SB1 (VII), B1 disulfide (V), and B1 thiazolone (VI) had been formed. However, a large amount of vitamin B1 was found to be still intact. The same procedure carried out in alcohol, instead of water, showed that almost none of vitamin B1 remained, and that the formation of SB1 (VII) was larger than in the case of aqueous solutions, SB1 being obtained as crystals. Other compounds formed were (IV), (V), and (VI), as in the case of aqueous solutionsView full abstractDownload PDF (573K) -
Isolation of AllithiamineTaizo Matsukawa, Shojiro Yurugi1952 Volume 72 Issue 12 Pages 1602-1604
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAllithiamine, a compound formed by the reaction of vitamin B1 and the component of garlic (Allium sativum L. var. japonicum Kitamura), was isolated in crystals of m.p. 132-133° (decomp.) as recrystallized from benzene, or of m.p. 141-142° (decomp.) as recrystallized from water. Molecular weight determination by the Barger method and analytical values suggest the empirical formula of C15H22O2N4S2. It was assumed from absorption spectra and other properties that it possessed a structure similar to “Aneurindisulfid.”View full abstractDownload PDF (1072K) -
On the Alkaloids of Aconitum tasiromontanum NakaiEiji Ochiai, Toshihiko Okamoto, Tsutomu Sugasawa, Hidewo Tani1952 Volume 72 Issue 12 Pages 1605-1607
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSAconitum tasiromontanum Nakai roots (Tashiroyamabushi) were collected in the forests around Nasu-Sandogoya, in central Japan, and their alkaloid content was examined. Crude base was obtained in approximately 0.1% yield as against fresh root. Of the crude base, 64% precipitate out from the hydrochloric acid solution upon the addition of ammonia water, and 9.8% are obtained by extraction of its mother liquor with chloroform. Purification of the former by chromatography yielded hypaconitine, mesaconitine, aconitine, and ignavine, as crystalline bases. The characteristics of this plant are that its alkaloid contains a very large amount of mesaconitine, a small amount of hypaconitine and aconitine, and that it contains, although in a small amount, the newly found ignavine.View full abstractDownload PDF (333K) -
Tomoyoshi Komai, Sawako Irie, Nobuyuki Utsugi, Den-ichi Mizuno1952 Volume 72 Issue 12 Pages 1608-1610
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS1) Dried B. C. G. Vaccine and Dried Normal Human Serum are marked as lyophilized product sealed in hermetic ampuls. In such a country as Japan where atmospheric moisture is very high, the moisture content of air in the room where ampuls are opened for examination of moisture content gives a great deal of effect on the determined values. For this reason, the relationship between the moisture content of air and the time spent in weighing was examined. Both preparations were found to absorb approximately 1-5% of moisture during 3 minutes of weighing in the air containing 50% or more moisture. When the relative moisture was below 30%, there were almost no increase in the weight of a sample by weighing during 3 minutes.
2) The moisture content of Dried B. C. G. Vaccine and Dried Serum is carried out by the weight method. Comparison of this method with that using the Karl Fischer reagent (time of contact with the reagent: 45 minutes) showed that both preparations gave a larger value by the Karl Fischer method, but with penicillin and streptomycin, there were no difference between the values by the two methods.View full abstractDownload PDF (611K) -
“White-lime”Syun Iseda1952 Volume 72 Issue 12 Pages 1611-1613
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSWhite bird-lime was purified with ether from which 48% of purified bird-lime was obtained. Its hydrolysis yielded 42.8% of fatty acids, 41.4% of crystalline unsaponifiable matter, and 4.3% of non-crystalline unsaponifiable matter. Acetylation of the crystalline unsaponifiable matter, followed by recrystallization from ethyl acetate yielded a new triterpene alcohol in 1.61% yield, designated as ilexol, of m.p. 205-206°, [α]D28: -16.81°(CHCl3), which gives an acetate of m.p. 282-283°, [α]D28: +22.29°(CHCl3), and a benzoate of m.p. 242-243°. α-Amyrin and lupeol were detected in the residue, with a larger amount of α-amyrin. No evidence was obtained for the presence of β-amyrin.View full abstractDownload PDF (555K) -
Tsutomu Momose, Munemitsu Tomoeda1952 Volume 72 Issue 12 Pages 1614-1616
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBiological changes of p-(α-aminoethyl)-phenylsulfonamide (I), p-(α-aminoethyl)-phenyl methyl sulfone (II), p-(β-aminoethyl)-phenylsulfonamide (III), and p-(β-aminoethyl)-phenyl methyl sulfone (IV) in rabbit were observed by the direct injection of the aqueous solution of the hydrochlorides of these compounds into rabbit stomach by Nela-ton's catheter. The urine was collected about 40 hours after injection, and extracted with ether or ethyl acetate at an optimum pH. Unchanged, free bases of (I) and (II) were obtained in 57% and 26% yield, respectively, and a very small amount of the acetylated compound of (I). (III) and (IV) yielded oxidation products, p-(carboxymethyl)-phenylsulfonamide and p-(carboxymethyl)-phenyl methyl sulfone in 58% and 55% yield, respectively. The free bases of these compounds were not recovered These results led to the conclusion that the oxidation of aminomethyl group was interfered by the introduction of a methyl group into the α-position of the amino radical.View full abstractDownload PDF (581K) -
Structure of AllithiamineTaizo Matsukawa, Shojiro Yurugi1952 Volume 72 Issue 12 Pages 1616-1619
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSHydrolysis of allithiamine with hydrochloric acid was found to yield formic acid, 2-methyl-4-amino-5-aminomethylpyrimidine (I), and α-aceto-γ-hydroxypropyl allyl disulfide (II). Reduction of (II) in acetic acid solution with zinc dust yielded allylmercaptan (IV) and γ-aceto-γ-mercaptopropyl alcohol (III). Reduction of allithiamine in alcoholic hydrochloric acid with zinc dust resulted in the formation of allyimercaptan (IV) and vitamin B1 (VI). From these results, the structure of 2-[2′-methyl-4′-amino-pyrimidyl(5′)]-methylformamino-5-hydroxy-Δ2-pentenyl(3) allyl disulfide (VII) can be given to allithiamine. Further examinations were made to find which of the component of garlic bulbs reacted with vitamin B1 to form allithiamine and it was found that the latter was formed by the reaction of allicin (IX) and vitamin B1.View full abstractDownload PDF (740K) -
Reactions of N, N-Dichlorobenzenesulfonamide on Cholesterol and Cholesterol AcetateYoshio Ueno1952 Volume 72 Issue 12 Pages 1620-1622
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe reaction of cholesteryl acetate with N, N-dichlorobenzenesulfonamide (Dichloramine-B) under the conditions used by Fieser in his oxidative reaction with N-bromosuccinimide (NBS) produced two hypochlorous acid adducts, (A) C29H49O3Cl, m.p. 195-196° (yield, 48%), and (B) C29H49O3Cl, m.p. 186-187° (yield, 7%). The melting point of (A) coincides with that of 5α-chlorocholestane -3β, 6β-diol 3-acetate. When (A) is heated with alcoholic NaOH, it undergoes saponiicatron and at the same time an oxide ring is formed to give the known cholesterol β-oxide, m.p. 131-132.5°. The acetylation of (A) results in the formation of 5α-cholestane-3β, 6β-diol 3, 6-diacetate. (B) is in complete agreement with 6β-chlorocholestane -3β, 5α-diol 3-acetate.
The reaction of cholesterol with Dichloramine-B under the same conditions as in the case of cholesteryl acetate produced only one hypochlorous acid adduct, C27H47O2Cl, m.p. 165-166° (decomp.), in 23% yield, which corresponded with the compound representable by 5α-chlorocholestane-3β, 6β-diol. In this case the isomer having C5-OH and C6-Cl could not be isolated, probably due to the formation of this compound in a small quantity and the coexistence of several other compounds. In accordance with the inference by Urushibara, Mori, Fürst, and the others, these compounds are believed to have the above-mentioned structural arrangements.View full abstractDownload PDF (642K) -
Reactions of N, N-Dibromobenzenesulfonamide on Cholesteryl AcetateYoshio Ueno1952 Volume 72 Issue 12 Pages 1622-1625
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSReaction of cholesteryl acetate with N, N-dibromobenzenesulfonamide (Dibrornamine-B) in dilute acetone containing some acetic acid gave two compounds, (A) and (B). (A), C29H49O3Br, m.p. 175° (decomp.), [α]D20=-33.8° (yield, 37%), was established as 5α-bromocholestane-3β, 6β-diol 3-acetate from its acetyl derivative, oxidation product, debrominated product of the oxidation product, and the formation of a β-oxide compound by treating with alcoholic KOH. (B), C29H49O3Br, m.p. 188° (decomp.), [α]D32=-34.7° (yield, 6%), was found to be 6β-bromocholestane-3β, 5α-diol 3-acetate from the properties of the α-oxide compound obtained by treating with alcoholic KOH. Cholesteryl acetate was reacted with NBS according to the Fieser's report. In this case two compounds, (C) and (D), corresponding to the above (A) and (B) were obtained, but the 6-one compound reported by Fieser could not be isolated.View full abstractDownload PDF (820K) -
Reaction of N, N-Dibromobenzenesulfonamide on Cholesterol and Cholestane-triolYoshio Ueno1952 Volume 72 Issue 12 Pages 1626-1628
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSReaction of cholesterol with Dibromamine-B produced two compounds, (A) and (B). (A), C27H48O3, m.p. 236-238° (yield, 61%), was identical with cholestane-3β, 5α, 6β-triol, and (B), C27H48O2Br, m.p. 154-155° (decomp.), [α]D32=+21.1°, seemed to be the HOBr adduct of cholesterol, but this product could not be thoroughly investigated owing to its poor yield. Reaction of the triol compound (A) with Dibromamine-B or with Dichloramine-B in dioxane containing some water yielded cholestane-3β, 5α-diol-6-one, C27H46O3, m.p. 232-234°, in a good yield.View full abstractDownload PDF (521K) -
On Condensation Agents in Syntheses of Cyanine Dyes from Orthoformic EsterHisanao Zenno1952 Volume 72 Issue 12 Pages 1628-1630
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSCarbocyanine dyes were prepared from orthoformate and quinaldine methiodide or ethiodide or 2-methylbenzothiazole ethiodide, using 2-aminothiazole hydrochloride, formamide, p-nitrotoluene, 2-am ino-4-methylthiazole, acetamide, acetanilide, propionitrile, ammonium chloride, ethylene glycol, pyrocatechol, or dimethylaniline as an addition agent.View full abstractDownload PDF (528K) -
On Syntheses of Merocarbocyanine Dyes by Using Compounds Containing Active Methylene Radicals as Condensation AgentsHisanao Zenno1952 Volume 72 Issue 12 Pages 1630-1633
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSMerocarbocyanine dyes, similar to the dyes obtained from dye intermediates and ethoxymethylene cyanoacetate, cyanoacetamide or acetoacetate, were prepared by the reaction of orthoformate and quinaldine methiodide or 2-methylbenzothiazole ethiodide, using a large amount of cyanoacetate, cyanoacetamide, cyanoacetanilide, acetoacetate, or benzoylacetonitrile as an addition agent.View full abstractDownload PDF (688K) -
Syntheses of Merocarbo and Polymethine Cyanine Dyes from Sodium Salts of Formyl CompoundsHisanao Zenno1952 Volume 72 Issue 12 Pages 1633-1636
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSMerocarbocyanine dyes were prepared by reacting quinaldine methiodide or ethiodide, 2-methylbenzothiazole ethiodide, or 2-methyloxazole ethiodide, with several kinds of formyl compounds, formylcyanoacetate, formylacetate, or 2-formyl-3(2H)-thionaphthe-none, or several kinds of sodium salts of formyl compounds, formylacetone, formylacetophenone, or the sodium salt of 4-formyl-1, 3-indandione. Pentamethine cyanine dyes possessing phenyl or methyl substituents in the β-position were prepared by reacting one-half molar equivalent of the sodium salt of formylacetophenone or formylacetone to quinaldine methiodide.View full abstractDownload PDF (742K) -
Synthesis of 2-Amino-5-substituted DerivativesMasaki Ohta1952 Volume 72 Issue 12 Pages 1636-1639
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBy heating the hydrochloric acid solution of the hydrazides of acetic, hippuric, benzoic, phenylacetic, salicylic, p-hydroxybenzoic, and o- and p-nitrobenzoic acids with potassium thiocyanate, corresponding acylthiosemicarbazides are obtained. Treatment of these acylthiosemicarbazides with conc. sulfuric acid at a room temperature resulted in the formation of the following 5-substituted 2-amino-1, 3, 4-thiadiazoles: 5-Phenyl compound, m.p. 225°; 5-benzyl compound, m.p. 203°; 5-(o-hydroxyphenyl) compound, m.p. 223°; 5-(p-hydroxyphenyl) compound, m.p. 216°; 5-(o-nitrophenyl) compound, m.p. 232-234°; 5-(p-nitrophenyl) compound, m.p. 260°; and 5-benzoylarninomethyl compound, m.p. 218°. Hydrolysis of the 5-benzoylaminomethyl derivative yielded 2-amino-5-aminomethylthiadiazole hydrochloride. 5-Aminomethyl- and 5-aminoethyl derivatives were prepared from phthaliminoacetyl- and β-phthaliminopropionylthiosemicarbazides, respectively.View full abstractDownload PDF (648K) -
Masao Shimizu, Takeo Naito, Genkichi Ohta, Kikuji Suzuki, Akira Kasaha ...1952 Volume 72 Issue 12 Pages 1639-1642
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSNumber of acid hydrazide derivatives, as given in the accompanying Table, were prepared and their antibacterial activity, in vitro, was examined in Lockemann-Bloch medium, using the so-called “Mycobacterium tuberculosis A. T. C. C. No. 607, ” with isonicotinic acid hydrazide (INAH) as the control. The compounds which possessed activities equal to or almost equal to INAH were those in which carbonyl compounds such as acetone (No. 7 in Table) or glucose (No. 8) were bonded to the amino group in INAH, or the one (No. 9) in which sodium hdyroxymethane sulfonate was bonded. The compounds marked with asterisks in the Table are new compounds prepared for the first time.View full abstractDownload PDF (873K) -
Masao Shimizu, Renzo Dohmori1952 Volume 72 Issue 12 Pages 1643-1644
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSPyridine N-oxide and its homologs undergo deoxidation when heated to 200-210° with selenium and sulfuric acid. Increase of this temperature to 290-300° results in the oxidation of the alkyl group.View full abstractDownload PDF (325K) -
Mitiiti Fujita, Kazumitu Nishimoto1952 Volume 72 Issue 12 Pages 1645-1646
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSExisting literature on the hemolytic methods for potency determination of saponinbearing drugs was examined. In the activity determination of Japanese senega, hemolytic index was obtained by using rabbit blood in a phosphate buffer solution of pH 7.4, Merck's pure Saponin as the standard. As a result, it was found that the domestic product possessed a potency equal to the drug of S. B. Penick & Co., which is assumed to be the Northern senega (cf. Table I)View full abstractDownload PDF (411K) -
Antibacterial Activity of Salicylic Acid Hydrazide and Related CompoundsShichiro Kakimoto, Isao Sekikawa, Ken-ichi Yamamoto1952 Volume 72 Issue 12 Pages 1646-1648
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSSeveral kinds of acid hydrazides were prepared and their antibacterial action in vitro was examined. As shown in Table III, p-aminosalicylic acid hydrazide was found to be far more effective than isonicotinic acid hydrazide against Mycobacterium tuberculosis. It was also pointed out that, in order for acid hydrazide to show any effective antitubercular action, the presence of a double bond in the α-position of the carbonyl would be one of the requisites.View full abstractDownload PDF (562K) -
Constituents of the Essential OilTakeshi Shimano, Shintaro Nomura1952 Volume 72 Issue 12 Pages 1648-1649
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe essential oil obtained from Thymus Serpyllum L. var. Przewalskii Komarow by steam distillation was fractionally distilled under a reduced pressure by which the chief component was found to be thymol, comprising about 35%. Other components found were linalool, p-cymene, α-pinene, and a trace of d-borneol. The oil did not contain carvacrol but it could be used in place of thymus oil.View full abstractDownload PDF (375K) -
Yasuo Inubushi1952 Volume 72 Issue 12 Pages 1650
Published: December 25, 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (74K) -
1952 Volume 72 Issue 12 Pages e6af
Published: 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (115K) -
1952 Volume 72 Issue 12 Pages e6ag
Published: 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (115K) -
1952 Volume 72 Issue 12 Pages e6b-e7
Published: 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (203K) -
1952 Volume 72 Issue 12 Pages e7aa
Published: 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (105K) -
1952 Volume 72 Issue 12 Pages e7ab
Published: 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (105K) -
1952 Volume 72 Issue 12 Pages e7ac
Published: 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (105K) -
1952 Volume 72 Issue 12 Pages e7ad
Published: 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (105K) -
1952 Volume 72 Issue 12 Pages e7ae
Published: 1952
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDownload PDF (105K)