YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
82 巻 , 5 号
選択された号の論文の35件中1~35を表示しています
  • 中垣 正幸, 砂田 久一
    1962 年 82 巻 5 号 p. 629-634
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Sedimentation volume of spherical particles attracted by cahesive force was theoretically calculated. It was found that there was a simple primary relationship between the sedimentation volume, Vs, and the ratio of range of attraction, δ, and radius of the sphere, γ, represented by ρ⋅Vs=5.6+14(δ/γ), where ρ is the specific gravity of the particle. Using this value, the value of (δ/γ) was calculated from the values of sedimentation volume reported in the past literature and it was found that the degree of sedimentation volume can be explained by the attraction between the particles. This attraction between the particles can be considered as a van der Waals force when the dielectric constant, D, of the medium is small, and is indicated by log (1+δ/γ)=B-(1/6)×logD.
  • 板谷 元一, 高井 義治
    1962 年 82 巻 5 号 p. 634-639
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Copeland synthesized about 10 kinds of 2-N-substituted carbamoylbenzimidazoles (I) as a compound of physiological interest but compounds with alkyl- or aryl-carbamoyl substituted in 5- or 6-position have not been reported. In order to prepare this compound reductive cyclization of 2′-nitro-4′-alkyl (or aryl) carbamoyl-acetanilide (III or IV) (Table I) with sodium dithionite was carried out and 2-methyl-5 (or 6)-alkyl (or aryl) carbamoylbenzimidazole (V or VI) (Table II) was obtained in a good yield. Isolation procedure was quite simple and a good result was obtained. (III) and (IV) are obtained by the application of amines to 3-nitro-4-acetamidobenzoyl chloride. Both (III) and (IV), and compounds derived from them, (V) and (VI), are new substances. The amines used in the foregoing reaction were primary amines, R-NH2 with R=CH3, C2H5, n-C3H7, iso-C3H7, n-C4H9, iso-C4H9, tert-C4H9, n-C5H11, n-C6H13, CH3(CH2)3CH(C2H5)CH2, n-C12H25, n-C18H37, C6H5, CH2(CH2)4CH, and C6H5CH2, and secondary amines, R2NH with R=CH3, C2H5, n-C3H7, iso-C3H7, n-C4H9, iso-C4H9, C6H5, CH2(CH2)4CH, C6H5CH, morpholine, and piperidine.
  • 新美 仁作, 仙福 健治, 大保 同
    1962 年 82 巻 5 号 p. 639-642
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    As the model substance of bis-benzyl-tetrahydroisoquinoline-type bases with biphenyl structure in the molecule, dl-2-methoxy-4′, 5-bis[2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydro-1-isoquinolyl)-1-methyl]biphenyl (XVI) was synthesized from 3, 4-dimethoxyphenethylamine and 2-methoxy-4′, 5′-biphenyldiacetic acid (XII) through the diacetamide (XIII) and bis (3, 4-dihydroisoquinoline) compound (XIV), by the route shown in Charts 1 and 2.
  • 谷口 卓見
    1962 年 82 巻 5 号 p. 643-648
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Examinations were made on the stabilizer for alkali proteinase of Bacillus subtilis. Effect of various kinds of alcohol, surfactant, antifungal agent, salt, and chelating agent was examined and it was found that the combined use of polyhydric alcohol and calcium acetate gave a stable solution.
  • 植木 寛, 林 清五郎
    1962 年 82 巻 5 号 p. 648-654
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Subcutaneous and oral administration of over 20 kinds of quinone derivatives, including quinone monoöxime methyl ether and p-benzoquinone, showed none of these derivatives had hypoglycemic activity. Concurrent or combined use of quinone monoöxime methyl ether with insulin extended the duration of action and the activity became stronger as the period after mixing increased.
    Similar extension of action time was observed by concurrent use with protamine-zinc-insulin but hypoglycemic effect was found to decrease by combined use, the effect becoming weaker as the period after mixing increased.
    Combined use of p-benzoquinone was found to weaken the hypoglycemic effect of both insulin and protamine-zinc-insulin. These facts suggest that there is a marked difference in the activity of quinone monooxime methyl ether and p-benzoquinone, and that these compounds have direct effect on the insulin molecule.
  • 植木 寛, 林 清五郎
    1962 年 82 巻 5 号 p. 654-659
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Hyperglycemic activity of extracted crude glucagon, glucagon contained in protamin-zinc-insulin, and amorphous pure glucagon was strongly inhibited by quinone monoöxime methyl ether, p-benzoquinone, toluquinone, xyloquinone, 2-methylnaphthoquinone, and xyloquinone-diaminoguanidone. The inhibition was stronger, the longer the period after mixing with glucagon. On the other hand, no such inhibition was effected by hydroquinone and BZ 55, the internal medicine for diabetes. These facts suggest that the quinones have a direct effect on the glucagon molecule.
  • 亀谷 富士夫, 久保田 晴寿
    1962 年 82 巻 5 号 p. 659-661
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    It had been believed that C-22 refractory brick is not desirable as a carrier for the analysis of organic bases by gas chromatography due to tailing but a good result was found to be obtained by the use of a suitable stationary liquid phase. For this purpose, analysis of a hydrous mixture of pyridine, 2-, 3-, and 4-picoline, and 2, 6-lutidine was carried out. A homogeneous mixture of 10% ethanolamine and 5% o-phenylphenol was coated on C-22 carrier to be used as a 2-m. column, and the foregoing five kinds of pyridine base were almost completely separated under the conditions of column temperature of 90° and Helium flow rate of 86 cc./min. In this case, water is eluted faster than pyridine that there is no need to dehydrate the sample or use a dehydration agent in the column.
  • 石館 守三, 松井 道夫
    1962 年 82 巻 5 号 p. 662-669
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Phenyl and p-nitrophenyl di-O-acetyl-β-D-glucofuranosiduronolactone, which are alkali-sensitive glycosides, were deacetylated in liquid ammonia at -76° to -78° and yielded phenyl and p-nitrophenyl β-D-glucofuranosiduronamide. Phenyl and p-nitrophenyl β-D-glucofuranosiduronolactone were obtained by hydrolysis of the above amides with nitrous acid-acetic acid mixture or with 0.2N hydrochloric acid.
    The stability of furanose- and pyranose-type glucuronides which have p-nitrophenol as an aglycone were compared by their hydrolysis with 0.1N sodium hydroxide solution at 0°, 40.8°, and 62.5°, and with 0.5N hydrochloric acid at 100°, and determining the liberated p-nitrophenol. It was found that their sensitivity to alkali was in the decreasing order of p-nitropheyl β-D-glucofuranosiduronolactone, β-D-glucofuranosiduronamide, β-D-glucopyranoside, and β-D-glucopyranosiduronamide, while their sensitivity to acid was in the decreasing order of p-nitrophenyl β-D-glucofuranosiduronamide, β-D-glucopyranoside, β-D-glucofuranosiduronolactone, and β-D-glucopyranosiduronamide.
  • 鈴木 信夫, 月田 潔
    1962 年 82 巻 5 号 p. 669-674
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    In order to confirm the structures of neo-luteochrome-U and -V, 9-cis-luteochrome (IV) and 9′-cis-luteochrome (V) were prepared by the following route: neo-β-carotene-U (II) converted from all-trans-β-carotene by the iodine catalysis in light was oxidized with monoperphthalic acid to give 9-cis-5, 6; 5′, 6′-diepoxy-β-carotene (III).
    Treatment of (III) with CHCl3 saturated with hydrogen chloride afforded (IV) and (V). Comparison of UV-, IR-spectra or other characteristics and mixed chromatogram test show that (III), (IV) and (V) are almost identical with diepoxy-neo-β-carotene-D, neo-luteochrome-U and -V respectively. Simillar attempt was made to elucidate the structure of neo-luteochrome-B.
  • 山中 正夫, 桜井 謙一, 西村 郁子
    1962 年 82 巻 5 号 p. 674-678
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    1) Solubility of sodium salicylate was measured by an analytical method and conditions for crystallization were examined by thermal analysis.
    2) Viscosity of saturated solution and dissociation vapor pressure of hydrates were measured, and transition point of the hydrates was determined from the break in the solubility curve, viscosity-temperature curve, and vapor pressure-temperature curve.
    3) Mutual solubility of the sodium salicylate-sodium hydroxide-water system at 0° was measured. It was thereby found that the compounds in the lower liquid phase were hexahydrate and anhydrate, the anhydrate being present when the concentration of sodium hydroxide in the solution is above 23% by weight and the hexahydrate at below this concentration. The anhydrate was found to be present in a metastable state at the concentration of sodium hydroxide below 23% by weight.
  • 山中 正夫, 藤井 守正, 西村 郁子
    1962 年 82 巻 5 号 p. 679-682
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Electroconductivity, viscosity, and specific gravity of the aqueous solution of sodium salicylate were measured in the range of temperatures above and below saturation temperature. It was thereby found that log κ-1/T, log η-1/T, and specific gravitytemperature relationship would be represented by two straight lines crossing at the point of saturation temperature. In supersaturated solution, activation energy for ion transfer was higher than that of ordinary solution so that the electroconductivity decreased and, with increase in the activation energy for molecular transferaccompanying flow, viscosity increases, together with increase in specific gravity.
  • 西海 枝東雄, 金岡 又雄
    1962 年 82 巻 5 号 p. 683-689
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Application of hydrazine hydrate to 2-chloro-5-R-1, 3, 4-thiadiazoles (IV:R=H, CH3, C2H5, C3H7, and iso-C4H9) and 2-amino-5-R-1, 3, 4-thiadiazoles (VII:R=H, CH3, C2H5, C3H7, iso-C4H9, C6H5, and (p) NO2C6H4) resulted in the so-called “Triazole conversion” to form 4H-1, 2, 4-triazole-3-thiols.
    1) Reaction of (IV) under drastic conditions afforded 4-amino-5-R-4H-1, 2, 4-triazole-3-thiols (VI), the amount formed decreasing with increasing number of carbon atoms in the alkyl chain at 5-position. Under mild conditions, (IV) formed 2-hydrazino-5-R-4H-1, 2, 4-triazoles, although 2-chloro-1, 3, 4-thiadiazole (IV:R=H) afforded 4-amino-4H-1, 2, 4-triazole-3-thiol even under this mild condition.
    2) Compounds of (VII) series tended to be affected greatly by the nature of a substituent present in 5-position, and only the compounds (VII) with R as H, CH3, and C2H5 formed (VI), giving 4-amino-5-hydrazino-4H-1, 2, 4-triazole-3-thiol (VIII) as a by-product. In the case of (VII) with R as nitrophenyl, the nitro group was reduced during the reaction to form 2-amino-5-p-aminophenyl-1, 3, 4-thiadiazole. The starting materials were recovered in the case of (VII) with R as propyl, isobutyl, and phenyl.
    3) In the case of 2-amino-5-chloro-1, 3, 4-thiadiazole and 1, 3, 4-thiadiazole-3-thiol, 4, 5-diamino-4H-1, 2, 4-triazole-3-thiol (VI:R=NH2) and (VIII) were produced, while (VIII) alone was formed from 2, 5-dichloro-1, 3, 4-thiadiazole and 1, 3, 4-thiadiazole-2, 5-dithiol.
  • 中村 勇蔵
    1962 年 82 巻 5 号 p. 689-695
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    It was reported in the previous paper that of the various amines examined for their effect on the anthrone reaction of sugars none except tryptophan had any effect. In the present series of experiment, several substances having structure similar to tryptophan were examined for their effect on the anthrone reaction. Coloration from the reaction between sugar and anthrone was examined in the presence of tryptophan and of other substances, and the color was found to be entirely different. The pigment assumed to have been formed by the reaction of a sugar and anthrone, that pigment added with triptophan, and a pigment formed in the presence of all these three were found to be all different. The color formed in the presence of these three substances at the same time must be a characteristic pigment and its isolation and purification were attempted. The substances thereby isolated was submitted to elemental analysis, molecular weight determination, and examination of properties. A molecular formula was proposed and some considerations were made on its structure.
  • 犬伏 康夫, 野村 敬一
    1962 年 82 巻 5 号 p. 696-703
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Fission of dibenzo-p-dioxin (I) with metallic sodium in liquid ammonia afforded two kinds of phenolic substance, 2-hydroxyphenyl phenyl ether (II) and o-aminophenyl o-hydroxyphenyl ether (III). The same fission of 2, 7-dimethyldibenzo-p-dioxin (VI) also afforded two kinds of phenolic substance, 2-hydroxy-5-methylphenyl p-tolyl ether (VII) and 2-amino-4-methylphenyl 2-hydroxy-5-methylphenyl ether (X). Further reaction of (I) and (VI) with metallic sodium in liquid ammonia in the presence of potassium amide resulted in increased yield of (III) from (I) and that of (X) from (VI). This fact indicates that addition of potassium amide increased the yield of aminophenyl hydroxyphenyl ether. However, reaction of (I) with potassium amide alone failed to cause fission of (I) and (I) was recovered entirely.
    Similar fission of 2, 7-dimethoxydibenzo-p-dioxin (XIV) afforded 2-hydroxy-5-methoxyphenyl p-methoxyphenyl ether (XV) and 2-hydroxy-4-methoxyphenyl m-methoxyphenyl ether (XVII), showing that there was no formation of an abnormal product.
  • 桑山 良像
    1962 年 82 巻 5 号 p. 703-705
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    The new method for synthesis of dihydrodictamnine, reported in the preceding paper, was applied to the synthesis of other alkaloids of the furoquinoline series and a satisfactory result was obtained. Condensation of 4-methoxy, 4, 5-dimethoxy, and 4, 5-methylenedioxy derivatives of 2-nitrobenzoic acid with α-acetylbutyrolactone in benzene with magnesium as a catalyst afforded α-(o-nitrobenzoyl) butyrolactone which was treated with diazomethane, forming three kinds of enol-methyl ether. Catalytic reduction of these ethers afforded the corresponding 2, 3-dihydroevolitrine, 2, 3-dihydrokokusaginine, and 2, 3-dihydromaculine in a fairly good yield. Bromination of dihydrokokusaginine and dihydromaculine with N-bromosuccinimide and subsequent dehydrobromination afforded kokusaginine and maculine.
  • 堀井 善一, 池田 正澄, 田村 恭光, 渡辺 利郎
    1962 年 82 巻 5 号 p. 706-710
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    A series of β-alanine methyl ester and 2-methyl-β-alanine methyl ester derivatives were prepared and their oxytocic activity was examined. Among the compounds tested, N-[2-(3-indolyl)ethyl]-2-methyl-β-alanine methyl ester possessed a high activity.
  • 堀井 善一, 村山 正雄, 渡辺 利郎
    1962 年 82 巻 5 号 p. 710-713
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    3-Methyl-1, 2, 3, 4, 5, 6-hexahydrobenzo [f] isoquinoline-1-carboxylic acid and its derivatives were synthesized and their oxytocic activity was examined. Only the amide (VI) was slightly active and others were entirely inactive.
  • 上田 伸一
    1962 年 82 巻 5 号 p. 714-718
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    In order to oxidize the methyl group in dibenzo-p-dioxin skeleton with potassium permanganate to obtain the corresponding carboxylic acid, oxidation of 2, 7-dimethyldibenzo-p-dioxin (I), 1, 6-dimethyldibenzo-p-dioxin (VI), and 2, 7-dimethyl-4, 9-dimethoxydibenzo-p-dioxin (XIV) was carried out with potassium permanganate in hydrous pyridine and the corresponding carboxylic acids were obtained in a good yield.
    Using 4, 9-dimethoxydibenzo-p-dioxin-2, 7-dicarboxylic acid (XV), obtained by the oxidation of (XIV), 2, 7-bis(2-aminoethyl)-4, 9-dimethoxydibenzo-p-dioxin (XX), an important intermediate for the synthesis of menisarine-type alkaloids, was synthesized by the route shown in Chart 1.
    During the course of synthesis of the starting materials in these experiments, Clemmensen reduction of 5-bromovanillin (IX) was found to produce 3, 3′-dimethoxy-5, 5′-dibromo-4, 4′-stilbenediol (XI) as a by-product besides the objective 2-bromo-6-methoxy-p-cresol (X).
    It was also found that 2, 7-dimethyl-4, 9-dimethoxydibenzo-p-dioxin (XIV) could be obtained in a comparatively good yield by refluxing 2-bromo-6-methoxy-p-cresol (X) in pyridine solution, with copper powder, instead of the Ullmann reaction of the potassium salt of (X) with copper powder as the catalyst.
  • 山添 寛, 岩科 六之助
    1962 年 82 巻 5 号 p. 719-725
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    In a search for antimicrobial substance among azo compounds, some examinations were made on compounds with p-phenylazophenol structure and in which vitro group had been introduced. In vitro growth-inhibitory tests were carried out on 33 compounds of p-(p-nitrophenylazo)phenol introduced with nitro, halogen, or other substituents, and 14 kinds of azophenol compounds containing a nitro group, using six kinds of fungi, Trichophyton asteroides, T. interdigitale, T. schoenleinii, Microsporum gypseum, Epidermophyton floccosum, and Candida albicans. It was found that 3-Chloro-and 3-bromo-4-(p-nitrophenylazo)phenol had growth-inhibitory action against all the fungi tested in a high dilution of 1:2, 560, 000 to 1:10, 240, 000.
  • 萩庭 丈寿, 原田 正敏
    1962 年 82 巻 5 号 p. 726-731
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Separatory determination of alkaloids was carried out on 10 kinds of extract of plants containing berberine-type alkaloids and comparative examinations were made on the action of each alkaloid on mouse uterus and intestine, antibacterial activity, and acute toxicity (LD50), observing individuality and similarity among these plants. Content of berberine was the maximum in Coptis japonica and that of the total crude tertiary bases was the greatest in Hydrastis canadensis. All the extracts had anticonvulsive action on intestines and uterus, except Jateorrhiza palmata and Coptis japonica which contracted the uterus. The total crude tertiary base also had anticonvulsive action. Berberine, palmatine, jatrorrhizine, several of tertiary bases, and the extract of Coptics japonica were effective against Staphylococcus aureus 209P in 1000-6000 dilution, berberine being the strogest. Acute toxicity (LD50) was the maximum in Coptis japonica, and lowest in Nandina domestica and Berberis Thunbergii. In evaluating the physiological action of these plants, the alkaloids contained in them have little specificity for comparing these plants as containing such alkaloids. It seems necessary to consider the specificity of each individual plant.
  • 亀谷 哲治, 加納 慎蔵
    1962 年 82 巻 5 号 p. 731-733
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Synthesis of isoquinoline derivatives with hydroxyls in 2, 4- and 3, 4-positions, out of the six kinds of compounds possessing two hydroxyls in 1-position of the isoquinoline ring, was already reported as part of work on the synthesis of water soluble, papaverine-like compounds. In the present series of work, a compound with hydroxyls in 2, 5-positions was synthesized. Gentisic acid dibenzyl ether was first prepared, derived to acid chloride, and condensed with α-methyl-β-methoxy 3, 4-methylenedioxyphenethylamine to form the amide, and submitted to isoquinoline cyclization with phosphoryl chloride. Debenzylation of its product with ethanolic hydrochloric acid afforded the objective 1-(2, 5-dihydroxyphenyl)-3-methyl-6, 7-methylenedioxyisoquinoline.
  • 富田 真雄, 国友 順一
    1962 年 82 巻 5 号 p. 734-741
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    The so-called biscoclaurine-type alkaloids among the bases contained mostly in the Menispermaceae plants and also in allied families of Magnoliaceae and Berberidaceae, have been studied extensively and their structures have been established almost fully. This type of alkaloids submit to cleavage reaction with metallic alkali in liquid ammonia and form two kinds of coclaurine-type bases, the direction of rotation of their asymmetric center being revealed. However, nothing has been done on the absolute configuration of the two asymmetric centers in these biscoclaurine-type bases.
    In the present series of experiments, D-(-)-laudanosine (VIII), whose absolute configuration has already been established, was submitted to cleavage reaction with metallic sodium in liquid ammonia and D-(-)-laudanidine (IX) thereby obtained was submitted to the Ullmann reaction with bromobenzene. D-(-)-Laudanidine phenyl ether (X) thereby obtained was again submitted to cleavage reaction with metallic sodium in liquid ammonia and derived to l-O, O, N-trimethylcoclaurine (II). This proved that D-(-)-laudanosine (VIII) and l-O, O, N-trimethylcoclaurine (II) have the same steric configuration and are D type, Its antipodal L-(+)-laudanosine (VIII a) was similarly derived to d-O, O, N-trimethylcoclaurine (II a).
    It follows, therefore, that the optically active coclaurine-type bases, l-armepavine would be presented by (XI), d-coclanoline-A by (III), and l-magnocurarine by (XII). It also became possible to establish the absolute configuration of this type of bases obtained by the cleavage reaction of biscoclaurine-type bases with metallic sodium in liquid ammonia. l-N-Methylcoclaurine, would therefore be represeted by (XIII a), l-O, N-dimethylcoclaurine by (XIII b), and l-N, O-dimethylisococlaurine by (XIII c), and they are all D types, while d-N, O-dimethylcoclaurine would be represented by (XIV a), d-armepavine by (XIV b), and d-N-methylisococlaurine by (XIV c), and these are all L types.
  • 富田 真雄, 国友 順一
    1962 年 82 巻 5 号 p. 741-748
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Absolute configuration of the coclaurine-type bases (IV to VI), obtained by cleavage reaction of biscoclaurine-type alkaloids with metallic sodium in liquid ammonia, was established by their derivation from laudanosine (I or Ia), whose absolute configuration is already known. It was found that levorotatory bases of coclaurine type have the D-system configuration and, inversely, dextrorotatory bases have the L-system configuration.
    In the present series of work, examinations were made on the absolute configuration of the two asymmetric centers in biscoclaurine-type bases, with coclaurine-type bases, whose absolute configuration had been establised, as the standard. As shown in Tables I to V, the absolute configuration was established in majority of the biscoclaurine-type bases.
  • 谷 千秋, 高尾 楢雄, 高尾 佐知子
    1962 年 82 巻 5 号 p. 748-750
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Tetrahydrocorysanine was prepared by the methylation of acetonylcoptisine, followed by reduction. Good agreement was found between this synthesized product and the one isolated from a natural source.
  • 谷 千秋, 高尾 楢雄, 高尾 佐知子, 田ケ原 清
    1962 年 82 巻 5 号 p. 751-755
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    In order to determine the position of C-methyl group in corysamine, tetrahydrocorysamine was derived to dl-corydaline and identified with that derived from dl-thalictricavine. Hofmann and Emde degradation and ozonolysis of dl-thalictricanine afforded 2′-methyl-3′, 4′-dimethoxyacetophenone which was identified with that product obtained by the Friedel-Crafts reaction of 2, 3-dimethoxytoluene and acetyl chloride. This has proved the position of the C-methyl group in dl-thalictricavine and consequently that of corysamine to be at 6.
  • 谷 千秋, 高尾 楢雄
    1962 年 82 巻 5 号 p. 755-759
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    As the tertiary bases of Bocconia cordata (Maclea cordata), protopine and α-allocryptopine have been isolated and identified but no quaternary base has been isolated, although its presence had been presumed. For the purpose of isolating a quaternary base, extraction of the plant was carried out and chelerythrine and sanguinarine were isolated and identified, and oxysanguinarine was obtained. Three kinds of bases (A, B, and C), which had never been found from this plant, were also obtained.
  • 宇野 豊三, 上田 道広
    1962 年 82 巻 5 号 p. 759-762
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Excretion of sulfathiazole, N4-acetylsulfathiazole, sulfathiazole-N4-sulfonate, sulfathiazole-N4-glucuronide, and sulfathiazole-glucuronic acid conjugates into human urine was separatory determined by paper chromatography by the following method.
    Urine obtained after oral administration of sulfathiazole was adjusted to pH 7.6 with N sodium hydroxide, 1ml. of this urine was spotted on a filter paper (Toyo Roshi No. 51, 40×40cm.) in several portions and developed ascendingly with a solvent system of butanol-methanol 0.1N ammonium hydroxide (3:1:1) for 24hours. The paper was dried in air, portions corresponding to the products were cut out, and eluted descendingly with 0.2N sodium carbonate for sulfathiazole and N4-acetylsulfathiazole, and with 0.02N sodium carbonate for others. Each of these substances was hydrolyzed with hydrochloric acid or sodium hydroxide by the usual process to form sulfathiazole and determined by the Bratton-Marshall method. The content was calculated from a calibration curve prepared before-hand.
    The amount excreted 43hours after oral administration of 1g. of the sulfa drug was 970.7mg. calculated as sulfathiazole, including 626mg. of sulfathiazole, 294mg. of N4-acetylsulfathiazole, 38mg. of sulfathiazole-glucuronic acid conjugate, 4.8mg. of sulfathiazole-N4-sulfonate, and 7.9mg. of sulfathiazole-N4-glucuronide.
  • 松本 郁男, 中川 寛治
    1962 年 82 巻 5 号 p. 763-765
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Metalation reacton of 1, 3-dimethoxybenzene (I) with phenylsodium is completed approximately in about 1 hour at 30-35° to produce organosodium compound, 2, 6-dimethoxyphenylsodium (II-Na). The yield (82%) of 2, 6-dimethoxybenzoic acid (IV) from (II-Na) by its carbonation with Dry Ice is better than that from the corresponding organolithium compound (II-Li). Treatment of (II-Na) with N-methylformanilide or alkylation with dimethyl sulfate gives 2, 6-dimethoxybenzaldehyde (V) in 79% yield or 2, 6-dimethoxytoluene (VI) in 80% yield.
  • 尾関 昭二
    1962 年 82 巻 5 号 p. 766-768
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Examinations were made on the glucoside (colorless crystalline powder, m.p. 300-301°, [α]D30-26° (pyridine)), obtained from the nonsaponifiable matter of the crude oil of Pinellia ternata BREIT. (Japanese name “Hange”). Analytical values of this glucoside correspond to the formula of C35H60O6 and its hydrolysis with ethanolic hydrochloric acid afforded β-sitosterol as the aglycone and d-glucose as the sugar, which were identified with authentic samples. β-Glucoside tetraacetate was prepared from acetobromoglucose and β-sitosterol and identified with the tetraacetate obtained from the plant product. These experiments have proved that the glucoside obtained from the plant is β-(β-sitosteryl)-D-glucoside.
  • 岡本 喜八郎, 鉄尾 又一
    1962 年 82 巻 5 号 p. 769-771
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    1-(2-Pyridyl) amino-3-o-tolyloxy-2-propanol, synthesized to obtain an analgesic, was reported by Beasley and others as melting at 138°, the compound synthesized melted at 109-110°. Reaction of 1, 2-epoxy-3-o-tolyloxypropane and 2-aminopyridine in methanol-water mixture afforded a compound of m.p. 134.5-135.5o, which undergoes hydrolysis with alkali but the compound of m.p. 109-110° obtained by its reaction with sodium amide in anhyd. ether no longer undergoes hydrolysis. From these facts and from infrared spectral measurement of the two compounds, it was assumed that the former took the imine form and the latter, the amine form. Consequently, the compound reported by Beasley and others was probably a compound of the imine form, i.e. α-o-tolyloxymethyl-2-imino-1, 2-dihydro-1-pyridineethanol.
  • 有富 正和
    1962 年 82 巻 5 号 p. 771-773
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Astragalin was isolated and identified from the flower petals of Rosa multiflora THUNB. Astragalin and trifolin were separated and identified from the flower petals of Rubus hirsutus THUMB.
  • 三橋 監物, 塩谷 俊作
    1962 年 82 巻 5 号 p. 773-777
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Nitration of 7-tosyloxy-, 7-methoxy-, 5-methoxy-, and 5-tosyloxy-quinoline 1-oxides with 1mole of benzoyl chloride and silver nitrate gave the corresponding 3-nitro derivatives. Further reaction of the resulting 3-nitro derivatives of 7- and 5-tosyloxyquinoline 1-oxides with 2moles of benzoyl chloride afforded 1-benzoyloxycarbostyrils. In this case, nitration of the benzene ring did no take place, probably due to the steric hindrance of the tosyloxyl group. In a similar case, 3-nitro-7-methoxyquinoline 1-oxide was nitrated at 6-position and 3-nitro-5-methoxyquinoline 1-oxide in 8-position, by the polar effect of the methoxyl group. The structure of these nitrated quinolines were established by the ultraviolet and infrared absorption spectra, and by synthetic method.
  • 柴田 承二, 村田 忠一, 藤田 路一
    1962 年 82 巻 5 号 p. 777-779
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    The constitutents of rhizome and roots of Podophyllum pleianthum HANCE, a Chinese drug (_??__??__??_), have been investigated to isolate podophyllotoxin, desoxypodophyllotoxin, astragalin (kaempferol-3-D-glucoside), quercetin-3-D-galactoside, quercetin, kaempferol, and β-sitosterol.
  • 富永 敏夫, 住田 導彦
    1962 年 82 巻 5 号 p. 780-781
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
    Application of hot ethanolic sodium acetate solution to 2′-hydroxy-α, 4, 4′, 6′-tetramethoxychalcone (I) afforded a cyclized product which was identified with (±)-dihydrokaempferol tetramethyl ether (II).
  • 荒田 義雄, 大橋 力, 奥村 二郎, 和田 豊, 石川 道子
    1962 年 82 巻 5 号 p. 782
    発行日: 1962/05/25
    公開日: 2010/02/19
    ジャーナル フリー
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