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Volume 20, Issue 7
Displaying 1-44 of 44 articles from this issue
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KEN-ICHIRO MINEGISHI, MASATO ASAHINA, TSUTOMU YAMAHA1972 Volume 20 Issue 7 Pages 1351-1356
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolism of 35S-labeled saccharin, o-, p-toluenesulfonamide (TSA), o-and p-sulfamoylbenzoic acid (SBA) was investigated in rats and guinea pigs. Saccharin was rapidly excreted unchanged ; almost in urine in guinea pigs, while about 70% in urine and the remainder in feces in rats. It was suggested that such a difference of excretion patterns in the both animals might be due to the different absorption rate in stomach presumed from the observation of distinct pH values of their gastric juice. The urinary excretion of o-and p-TSA in rats was approximately 80% of those compounds administered, halves of which were oxidized to o-and p-SBA respectively by the oxidation of the methyl group. More than 90% of o-and p-SBA were excreted unchanged in rats, but the excretion ratios shared in urine and feces were considerably variable in individual animals.View full abstractDownload PDF (642K) -
AYAKA SUENAGA, SHOJI KOJIMA, HISASHI ICHIBAGASE1972 Volume 20 Issue 7 Pages 1357-1361
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the purpose of elucidating the metabolic sites of sodium cyclamate (CHS-Na), the influences of neomycin and sulfaguanidine on the metabolism of CHS-Na were investigated in rabbits, rats, and mice. Neomycin and sulfaguanidine caused a conspicuous decrease in the urinary excretion of CHS-Na metabolites in rats and mice. However the excretion of CHS-Na metabolites in rabbits did not decrease by administration of neomycin or sulfaguanidine. Also, CHS-Na metabolites were found in the urine of rabbits and rats following intravenous dose of CHS-Na. These results demonstrate that the metabolism of CHS-Na in the rat and mouse is predominantly carried out in the intestines, probably by the microbial flora, and that CHS-Na metabolism in the rabbit takes place mainly in the liver.View full abstractDownload PDF (639K) -
YUKIO SUGIURA, YASUSHI HOJO, HISASHI TANAKA1972 Volume 20 Issue 7 Pages 1362-1367
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chelating agents containing sulfhydryl group, such as penicillamine and cysteine, formed stable chromium (III) complexes by the reductive chelate formation with sodium chromate. The sulfur-containing ligands coordinated with chromium (III) ion through their sulfur atom, and the nephelauxetic effect in chromium (III) complexes occured to a larger extent with sulfur-containing ligands than the other ligands. The effects of the chelating agents containing sulfhydryl group on the removal of chromium bound to hemoglobin were compared with those of ascorbic acid and EDTA, and the sulfur-containing ligands were superior to ascorbic acid and EDTA, in the rate and the amount of the removal of chromium.View full abstractDownload PDF (707K) -
TETSUZO KATO, NOBUYA KATAGIRI, NOBUYOSHI MINAMI1972 Volume 20 Issue 7 Pages 1368-1373
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of diketene with hydroxylamine was reinvestigated. Hydroxylamine, O-methylhydroxylamine and O-benzylhydroxylamine reacted with two equimolar amounts of diketene in the presence of triethylamine to give the corresponding 1-substituted 5-acetyl-6-hydroxy-4-methyl-2 (1H)-pyridones ; i.e., 1-hydroxy (VI), 1-methoxy (XIII), and 1-benzyloxy (XVI) derivatives. Treatment of O-benzylhydroxylamine with an equimolar amount of diketene in the absence of triethylamine yielded O-benzylacetoacetohydroxamic acid (XVII) in good yield. Catalytic reduction of XVII with palladium charcoal afforded an oily substance (XVIII), which was treated with dry hydrogen chloride to give 3-hydroxy-5-methylisoxazole (XIX).View full abstractDownload PDF (717K) -
MASASHI HASHIMOTO, YOSHIHISA SAITO, HIDEO SEKI, TAKASHI KAMIYA1972 Volume 20 Issue 7 Pages 1374-1379
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis three stereoisomers of eritadenine (I) ; D-threo-(II), L-threo-(III) and L-eritadenine (IV), described. D-threo-Eritadenine (II) was derived from eritadenine by utilizing a novel ■thro-threo epimerization. L-threo-Eritadenine (II) was synthesized, starting from L-threonolactone dibenzoate (IX), through the route involving an imidazole ring closure. The synthesis of L-eritadenine (IV) was achieved conveniently by direct condensation of adenine and L-erythronolactone acetonide (XX).View full abstractDownload PDF (815K) -
SHIGEO SENDA, KOSAKU HIROTA, JIYOJI NOTANI1972 Volume 20 Issue 7 Pages 1380-1388
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRing closure reactions for synthesizing 1-substituted 5-cyanouracils, 3-substituted 5-cyanouracils, 1-substituted 5-carboxyuracils and 1-substituted 5-acetyluracils were investigated where substitutents were methyl, butyl, phenyl, and cyclohexyl. These compounds were then methylated in 1-or 3-position to give 1, 3-disubstituted uracil derivatives which were useful as intermediates for drugs.View full abstractDownload PDF (895K) -
SHIGEO SENDA, KOSAKU HIROTA, JIYOJI NOTANI1972 Volume 20 Issue 7 Pages 1389-1396
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen 1-substituted 5-cyanouracils, 3-substituted 5-cyanouracils or 1, 3-disubstituted 5-cyanouracils (substituents : phenyl, cyclohexyl, methyl) were heated to reflux in conc. HBr, the cyano group in the 5-position was removed and 1-substituted, 3-substituted or 1, 3-disubstituted uracils were obtained, respectively. When warmed with conc. H2SO4, they gave 5-carbamoyluracil derivatives. Refluxing of the 5-carbamoyluracil derivatives with conc. HCl in AcOH, produced 5-carboxyuracil derivatives. Detailed consideration was made on mechanism of hydrolysis and decarboxylation of 5-cyanouracil derivatives under acidic conditions. Furthermore, hydrolysis of 5-cyanouracils under alkaline conditions was investigated.View full abstractDownload PDF (848K) -
YOSHIHIRO ENDO, MITSURU UCHIYAMA1972 Volume 20 Issue 7 Pages 1397-1406
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyrithioxine (pyridoxine 5-disulfide) increased the pentobarbital-induced sleeping time in mice. This potentiation was divided into two phases ; one appeared immediately after the administration of pyrithioxine and reached a maximum within 20 min. The other appeared 8-10 hr later and corresponded to the inhibition of hepatic drug-metabolizing enzymes. When the potentiation without relation to the inhibition of hepatic drug-metabolizing enzymes occurred, the pentobarbital concentration increased in the brain and liver, but was unchanged in the serum. Pyrithioxine stimulated the transport of 14C-labeled fatty acids, glucose, amino acids, acetic acid, and inulin into the brain and liver, same as pentobarbital. Since [Na++K+]-ATPase, K+-phosphatase, and [Mg2++Ca2+]-ATPase activities were not influenced by pyrithioxine, this stimulation was not dependent on the increase of active transport, but depended on the increase of passive transport. However, the uptake of radioiodinated human serum albumin into the brain and liver of mice and the water content of these tissues were not affected by pyrithioxine treatment. The brain was not stained by Trypan Blue in pyrithioxine-treated and in control mice, but the liver, kidneys, intestines, skin, abdominal wall, and tail were stained deeper in pyrithioxine-treated mice. Increase in radioactivity from octanoate-1-14C was detected only in the free fatty acid fraction in the brain, but the radioactivity in the liver increased in the free fatty acid and the triglyceride fractions. This shows that pyrithioxine affects not only the histo-hematic barrier but also the fatty acid metabolism in the liver. Brain pentobarbital concentration at the time of awakening was lower in pyrithioxine-treated mice than the control. This result suggests that pyrithioxine increases the susceptibility of central nervous system to barbiturates. In addition, increased uptake of 45Ca in the brain indicates the disturbance of ion transport regulation which is necessary to preserve the central nervous excitability. These results suggest that pyrithioxine increases the pentobarbital sleeping time by three mechanisms of (1) inhibition of hepatic drug-metabolizing enzymes, (2) increase in brain pentobarbital concentration, and (3) decrease of excitability of the central nervous system.View full abstractDownload PDF (1381K) -
MIKIO SUZUKI, YOSHIFUMI MAKI1972 Volume 20 Issue 7 Pages 1407-1411
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolysis of simple primary alcohols in the presence of 2-aminothiophenol (I) and cyclohexene afforded 2-methyl-2-alkylbenzothiazolines (II : R1=CH3, R2=alkyl) having the methyl group arising from a carbon of cyclohexene. Similar irradiation of secondary alcohols resulted in the fromation of 2, 2-dialkyl-benzothiazolines (II) in which the R1R2C parts correspond to the carbon skeleton of the parent alcohols. The concurrent formation of 2-cyclohexylthioaniline (III) and 2, 2-pentamethylene-benzothiazoline (IV) in these reactions was also observed. Mechanisms for the formation of these photochemical products have been discussed.View full abstractDownload PDF (627K) -
KAZUYUKI HIRANO, KAZUMI MORI, NOBUKO TSUBOI, SATOSHI KAWAI, TAKEO OHNO1972 Volume 20 Issue 7 Pages 1412-1416
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple procedure has been developed for the simultaneous determination of the urinary anthranilic and 3-hydroxyanthranilic acids by gas chromatography. The method is based on extracting from urine with chloroform or ether at pH 3.0, followed by converting to their trifluoroacetyl derivatives. A clear separation of anthranilic and 3-hydroxyanthraniclic acids was achieved by using 3% OV-17 column at 110°. Compared with the recovery values of anthranilic acid, those of 3-hydroxyanthranilic acid are considerably low, which is due to the decomposition of 3-hydroxyanthranilic acid in the extraction procedure.View full abstractDownload PDF (551K) -
ITSUO YOSHIZAWA, MICHIYA KIMURA1972 Volume 20 Issue 7 Pages 1417-1423
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOf the two hydroxyl groups of catechol estrogen, C-2 phenolic functional is six times more reactive as the adjacent one at C-3 position toward the Smiles rearrangement of 2-benzoyl-4-nitrophenyl group. The reasons for this result are discussed.View full abstractDownload PDF (879K) -
TOSHIO NAMBARA, KAZUTAKE SHIMADA, YOUICHI FUJII1972 Volume 20 Issue 7 Pages 1424-1427
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to examine the physiological activity the suberoylamino acid esters of digitoxigenin (VIIa-h) as the bufotoxin analogs have been synthesized. Digitoxigenin 3-(hydrogen suberate) (Ib) was transformed into the p-nitrophenyl ester (IVb), which in turn was condensed with a variety of amino acids to yield the desired compounds. The results of the model experiment employing digitoxigenin 3-(hydrogen succinate) (Ia) were also described.View full abstractDownload PDF (631K) -
FUMIO YONEDA, SHINOBU FUKAZAWA, SADAO NISHIGAKI1972 Volume 20 Issue 7 Pages 1428-1431
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 17β-hydroxy-5α-androstan-3-one morpholine or pyrrolidine enamine with 6-amino-5-nitrosopyrimidines or 6-amino-5-phenylazopyrimidines led to the formation of the corresponding androstano [2, 3-g] pteridines. These steroidal pteridines were also prepared by the Isay's pteridine synthesis from 17β-hydroxy-5α-androstan-2, 3-dione and the corresponding 5, 6-diaminopyrimidines.View full abstractDownload PDF (551K) -
HYOZO TANIYAMA, YOSUKE SAWADA, KUNIHIRO MIYAZEKI, SHIGEO TANAKA, FUMIH ...1972 Volume 20 Issue 7 Pages 1432-1437
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSβ-Lysine dipeptide was isolated from the acid hydrolysate of Racemomycin-C and identified with a synthetic sample of ε-N-(L-β-lysyl)-L-β-lysine. Similarly, β-N-dinitro-phenyl-L-β-lysine and β-N, N-dimethyl-L-β-lysine were respectively isolated from the acid hydrolysate of dinitrophenylated Racemomycin-C and hexa-N-methyl Racemomycin-C and identified with authentic samples. These results confirm that β-lysine peptide sequence of Racemomycin-C is ε-peptide bond.View full abstractDownload PDF (782K) -
MASAO TANIGUCHI, KENJI KOGA, SHUNICHI YAMADA1972 Volume 20 Issue 7 Pages 1438-1444
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDetailed examinations were made of nitrous acid deaminations of L-valine and its benzyl ester in acetic acid. These showed that while the substitution product is the only detectable compound in the deamination of L-valine, various migration and elimination products are obtained along with the substitution product in the deamination of L-valine benzyl ester.View full abstractDownload PDF (865K) -
AKITADA NAKAMURA, SHOZO KAMIYA1972 Volume 20 Issue 7 Pages 1445-1450
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe alkaline decomposition of quaternary fused hydrazines containing 2, 3, 5, 10-tetrahydro-1H-pyrazolo [1, 2-b] phthalazine methiodide (III) and 1, 2, 3, 4, 6, 11-hexahydro-pyridazo [1, 2-b] phthalazine methiodide (VI) was examined. While compound VI having 6/6 ring system gave a Hofmann-type elimination product, 2-methyl-1, 2, 3, 4, 5, 6-hexahydro-benzo [c] [1, 6] diazacyclodecine (XII), compound III having 6/5 ring system gave a rearranged quaternary salt, 5-methyl-1, 2, 3, 4, 6, 10b-hexahydropyrimido [2, 1-α] isoindolium iodide (X) together with an elimination product, 6-methyl-4, 5, 6, 7-tetrahydro-3H-2, 6-benzodiazonine (VII).View full abstractDownload PDF (763K) -
TOZO FUJII, SHIGEYUKI YOSHIFUJI1972 Volume 20 Issue 7 Pages 1451-1456
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mercuric acetate-(ethylenedinitrilo) tetraacetic acid oxidation of aminoalcohol III furnished lactamalcohol V in 73% yield and its O-acetyl derivative (VI) as a minor product. Treatment of V with phosphoryl chloride gave tetrahydrobenzo [α] quinolizinium salt X in 87% yield, whereas hydrogenolysis of V in the presence of perchloric acid and ring-closure of the resulting lactam VIII afforded hexahydrobenzo [α] quinolizinium salt IX, which produced benzo [α] quinolizidine Ia on hydrogenation. When treated with perchlo-ric acid, lactamalcohol V yielded oxazolinium salt VIIa in a good yield. The facile hydrogenolysis of VIIa to VIII has suggested the possibility that the perchloric acid-accelerated, direct hydrogenolysis of V may proceed through VIIa. The starting aminoalcohol III was synthesized either by the sodium borohydride reduction of aminoketone II obtained from piperidine and 3, 4-dimethoxyphenacyl bromide or by reduction of quaternary salt IV from pyridine and 3, 4-dimethoxyphenacyl bromide.View full abstractDownload PDF (893K) -
RICHARDA. RUNKEL, KRAFTS. KARL, GERHARD BOOST, HILLI SEVELIUS, ENRICO ...1972 Volume 20 Issue 7 Pages 1457-1466
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOral doses of 2.5 mg/kg of naproxen in beagle dogs were found to be rapidly and completely absorbed. In the dog, the sodium and calcium salts of naproxen were absorbed significantly faster than the non-micronized form of naproxen, while the micronized drug could not be distinguished from either the salts or the macro from. Area responses to intravenous and oral doses of naproxen in two human subjects showed that oral doses of 200 and 250 mg were apparently one hundred percent absorbed. In a comparison of the amount and rate of absorption of naproxen form capsules and tablet formulation variants, no significant difference in either of the parameters could be detected. These results indicated that capsules and tablets were identical in absorption characteristics and furthermore that neither increasing the concentration of magnesium stearate nor changing the tablet lubricant to stearic acid had any effect on availability. Similarly, the tablet formulation with an extraordinarily long disintegration time and the tablet formulated with an alkalinizing agent were not significantly different from the other tablets or the capsules. A comparison of the results obtained from oral administration of 200 mg of naproxen taken by volunteer subjects in three forms, suspensions, capsules and tablets, revealed an apparent rise in the absorption rate constant with the suspension from but no difference in the amount of drug absorbed. It was suggested that more rapid dissolution of the drug in the wetted and well dispersed form explained the faster appearance of naproxen in the plasma. In a second tablet formulation study where the relative amounts of naproxen and lactose were altered, the drug was absorbed to the same extent, and at the same rate regardless of the fraction of total tablet weight that was naproxen. Finally, although differences in absorption rate constants were not statistically significant, naproxen appeared to be more rapidly absorbed in fasted subjects than in those who took the drug with food. However, there was no diminution in the amount absorbed in the non-fasted subjects.View full abstractDownload PDF (1032K) -
MASAYUKI ONDA, ATSUKO AZUMA1972 Volume 20 Issue 7 Pages 1467-1472
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOne step formation of 6-acetoximino-3β-acetoxycholestan-5α-ol nitrite (I) from 3β-acetoxycholest-4-ene has been carried out in a fairly good yield. Catalytic reduction of I affords the 6-keto compounds with 5α-OAc in dioxane and the 6β-amino compounds with 5α-OAc in acetic acid, respectively.View full abstractDownload PDF (707K) -
KEITARO SENGA, SADAO NISHIGAKI, MASATSUGU HIGUCHI, FUMIO YONEDA1972 Volume 20 Issue 7 Pages 1473-1478
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 8-phenyl-7-deazatheophyllines (I) with phosphorus oxychloride gave 6-chloro-6-deoxy-8-phenyl-7-deazatheophyllines (II) in high yields. Compounds II served as useful starting materials for several nucleophilic reactions. The reaction of I with phosphorus oxychloride in the presence of amines has been carried out to succeed in obtaining the corresponding 6-amino-derivatives in a single step. The reaction of 8-phenyl-theophylline (III) with phosphrous oxychloride gave 6-chloro-6-deoxy-8-phenyltheophylline (IV) in good yield. 6-Substituted 6-deoxy-8-phenyltheophyllines were prepared by the reaction of III with phosphorus oxychloride in the presence of amines in a single step. The reaction of I (or III) with phosphorus oxychloride essentially involves the conversion of aminoenketone (or aminoazadienketone) to iminoenchloride (or iminoazadienchloride).View full abstractDownload PDF (690K) -
FUJIO KAMETANI, YASUKO SUMI1972 Volume 20 Issue 7 Pages 1479-1483
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGeometrical isomers of 2, 4-dimethyl-, 4, 5-dimethyl-, 2, 4, 5-trimethyl-and 2-ethyl-4-methyl-1, 3-dioxolane were prepared and separated by preparative gas liquid chromatography. These isomers were identified by analysis of the nuclear magnetic resonance spectra of the protons at position 2 in the 1, 3-dioxolane ring and their retention volumes on gas chromatography. The deshielding effect of the γ-methyl group on the proton at the position 2 was estimated.View full abstractDownload PDF (598K) -
MASAYUKI ONDA, KENSHIRO KAWAKAMI1972 Volume 20 Issue 7 Pages 1484-1487
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSl-α-Narcotine is easily converted into dihydroprotoberberine methiodide. The Hofmann degradation of this methiodide gives methine base which is transformed to benzo [c] phenanthridine derivative by photocyclization and dehydrogenation.View full abstractDownload PDF (517K) -
TETSUJI KAMETANI, TETSUYA KOHNO, RAMAMURTY CHARUBALA, SHIROSHI SHIBUYA ...1972 Volume 20 Issue 7 Pages 1488-1491
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolytic intramolecular cyclization of N-(4-hydroxyphenethyl)-2-bromo-4, 5-methylenedioxybenzylamine (Va) gave (±)-oxocrinine (VI). Meerwein-Ponndorf reaction of VI resulted in the exclusive formation of (±)-epicrinine (I), similar to the reduction of VI, employing lithium aluminum hydride. The same reaction of N-(2-hydroxy-3-methoxyphenethyl)-2-bromo-4, 5-methylenedioxybenzylamine (Vb) was also examined.View full abstractDownload PDF (588K) -
GEN-ICHIRO OSHIMA, KINZO NAGASAWA1972 Volume 20 Issue 7 Pages 1492-1498
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1. Fluorescence characteristics of benzidine was examined. Benzidine had an emission maximum at 387 nm under excitation at 295 nm in 90% ethanol. The fluorescence intensity increased the most in 70% ethanol. The concentration of HCl in 70% ethanol also influenced the fluorescence intensity. 2. The nature of fluorescence of benzidine was changed by the treatment with nitrite. The wavelengths for both excitation and emission maxima shifted to 275 and 348 nm, respectively, and its fluorescence intensity decreased to about one-third that of benzidine. 3. For the determination of nitrite, a fluorescence measurement was carried out at 326 and 387 nm for excitation and emission, respectively. The best results was obtained from the following procedure. Benzidine is treated with nitrite at 98°for 1 min in 0.1 NHCl and the mixture is diluted 10-fold with ethanol, then the fluorescence intensity is measured. Under these conditions, 0.25 to 1.25×10-6M nitrite was successfully determined by the use of 10-6M benzidine. 4. Among cations tested, Cu2+, Sn2+, Fe2+, and Al3+ interfered seriously with the determination of nitrite at a concentration of 5×10-4M. Among the anions, citrate, malonate, thiocyanate, molybdate, and tungstate also interfered at a level of 10-4M. Oxidants and reductants had also a serious effect on the determination of nitrite at a level of 5×10-5M.View full abstractDownload PDF (790K) -
ITIRO YOSIOKA, KATSUHIKO HINO, AKIKO MATSUDA, ISAO KITAGAWA1972 Volume 20 Issue 7 Pages 1499-1506
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe sapogenol constituents of leaves of Pittosporum tobira AIT. (Pittosporaceae) have been examined. On the basis of chemical and physicochemical evidences, three sapogenols obtained by acid hydrolysis of crude saponin have been shown to be R1-barrigenol (II), 21β-angeloyloxy-3β, 15α, 16α, 22α, 28-pentahydroxyolean-12-ene (=21-O-angeloyl-R1-barri-genol) (IV), 21β-angeloyloxy-3β, 16α, 22α, 28-tetrahydroxy-olean-12-ene (=21-O-angeloyl-barringtogenol C) (V) respectively. A1-barrigenol (I) has not been detected in the total acid hydrolysate of saponin.View full abstractDownload PDF (980K) -
TETSUJI KAMETANI, TAKUO NAKANO, CHIZUKO SEINO, SHIROSHI SHIBUYA, KEIIC ...1972 Volume 20 Issue 7 Pages 1507-1512
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolysis of the diazonium salt derived from 1-(2-amino-4-hydroxy-5-methoxy-phenethyl)-7-hydroxy-1, 2, 3, 4-tetrahydro-6-methoxy-2-methylisoquinoline (V) gave, 1, 11-dihydroxy-2, 10-dimethoxyhomoaporphine (IX), which was identical with the rearranged product of kreysiginone (VII) by acid. The same reaction of 1-(2-aminophenyl)-1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-2-methylisoquinoline (XXI) gave an abnormal product, 3, 4-dihydro-6, 7-dimethoxy-1-phenylisoquinoline (XXV), in addition to the deamination product (XXII) and the phenolic isoquinoline (XXIII).View full abstractDownload PDF (714K) -
SHOJIRO YURUGI, MASARU HIEDA, TOMIYOSHI FUSHIMI, YUTAKA KAWAMATSU, HIR ...1972 Volume 20 Issue 7 Pages 1513-1521
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Substituted-5, 6, 7, 8-tetrahydropyrimido [4, 5-d] pyridazine-5, 8-diones (6) having a variety of substituents at 2-position were synthesized. Chlorination reaction of 6 were carried out, and it was found that only the compound which have aryl substituent at 2-position could be converted to 2-aryl-5, 8-dichloropyrimido [4, 5-d] pyridazine (14), while other derivatives gave no corresponding dichlorides (14). 2, 4-Diphenyl-5, 6, 7, 8-tetra-hydropyrimido [4, 5-d] pyridazine-5, 8-dione (9) was not obtained because of its structural unstability caused by steric interference of phenyl group at 4-position.View full abstractDownload PDF (908K) -
SHOJIRO YURUGI, MASARU HIEDA1972 Volume 20 Issue 7 Pages 1522-1527
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 2-phenyl-5, 8-dichloropyrimido [4, 5-d] pyridazine (1) with a variety of primary and secondary amines afforded the corresponding mono-substituted compounds which were mixtures of two isomers, 5-substituted compound (5) and 8-substituted compound (6). Both isomers were separated and their structures were determined. Only one isomer was obtained by the reaction of 1 with morpholine or aniline under milder condition and its structure was proved to be 8-substituted compound. The reactivity of chlorine atoms at 5-and 8-position in 1 was discussed.View full abstractDownload PDF (736K) -
SHOJIRO YURUGI, MASARU HIEDA, TOMIYOSHI FUSHIMI, YUTAKA KAWAMATSU, HIR ...1972 Volume 20 Issue 7 Pages 1528-1535
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen 2-aryl-5, 8-dichloropyrimido [4, 5-d] pyridazine (1) was reacted with a variety of nucleophiles, such as amines, sodium methoxide, sodium azide, sodium sulfide etc., 5, 8-disubstituted compounds (5) were obtained. Treatment of 2-phenyl-5-chloro-8-morpholinopyrimido [4, 5-d] pyridazine (9, [chemical formula] : morpholino) or 2-phenyl-5-morpholino-8-chloropyrimido [4, 55-d] pyridazine (10, [chemical formula] : morpholino) with nucleophiles gave the corresponding products with a different kind of substituents at 5-and 8-position (12 and 13). The phenyl group at 2-position seems to accelerate the substitution at position 5 and 8. The reaction of 2-phenyl-5, 8-bis (substituted thio) pyrimido [4, 5-d] pyridazine (5) with chlorine afforded the dichloride (1, Ar : phenyl). Among the synthesized disbstituted compounds, 5v, 5h, 5i, 5j, 5k, 5m, 5C, 5E, 5F, 5K, 5M and 5O showed diuretic activity.View full abstractDownload PDF (829K) -
Influence of Ball-Milling Atmosphere on Decrease of Molecular Weight of Polyvinylpyrrolidone PowdersNOBUYOSHI KANENIWA, AKIKO IKEKAWA1972 Volume 20 Issue 7 Pages 1536-1543
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe rate of a decrease of mean molecular weight and molecular weight distribution of polyvinylpyrrolidone (PVP) powders changed by ball-milling in nitrogen, air or oxygen were investigated, and influence of a ball-milling atmosphere on the probability in which a PVP molecule was broken in a unit time and molecular size distribution of the polymers formed by the break of a PVP molecule in a unit time was discussed. If the function representing the probability in which a PVP molecule was cut off in a unit time, S (M), was proportional to (M-M∞)α, α was considered to be between 1.0 and 1.5, and to be 1.0 for the case of ball-milling in nitrogen of air and to be larger than 1.0 for the case of ball-milling in oxygen. It was considered to be much probable that a PVP molecule with molecular weight of 1.6×106 was broken both at the center and at the molecular weight between 6×103 and 1.1×104 from the end of a main chain by ball-milling in nitrogen, and at the molecular weight of 3.6×104 from the end by ball-milling in air or oxygen. It seemed to be possible that a PVP molecule with molecular weight of 1.6×106 was broken at the molecular weight between 5.0×104 and 3.7×105 from the end by ball-milling in oxygen.View full abstractDownload PDF (727K) -
TAKEO HIGASHINO, HIROYUKI ITO, EISAKU HAYASHI1972 Volume 20 Issue 7 Pages 1544-1550
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of quinazoline (I) with active methylene compound in the presence of sodium amide were carried out and resulted in the formation of 4, 4'-biquinazoline (III) and 4-substituted quinazoline. Thus reaction with phenylacetonitrile gave III and α-phenyl-4-quinazolineacetonitrile (IV), with ethyl cyanoacetate, III and methyl α-cyano-4-quinazolineacetate (V), with nitromethane, III and 4-(nitromethyl) quinazoline (VI), respectively. But in the case of the reaction with malononitrile, it gave III, 2-amino-3-quinolinecarbonitrile (VII) and 2-amino-6-methoxy-3, 5-pyridinedicarbonitrile (VIII). The reaction of I with active methylene compound without a base catalyst was also carried out and succeeded in finding the transformation of I into quinoline derivatives. Thus, the reaction with malononitrile gave VII, with ethyl cyanoacetate, ethyl 2-amino-3-quinolinecarboxylate (XV) and 2-hydroxy-3-quinolinecarbonitrile (XVI), with phenyl-acetonitrile, 2-amino-3-phenylquinoline, respectively. But in the case of the reaction with diethyl malonate, ethyl 4-quinazolineacetate (XVIII) was obtained.View full abstractDownload PDF (830K) -
YUKIO KAMEDA, KATSUHIKO MATSUI, HISATO KATO, TOMOKO YAMADA, HITOSHI SA ...1972 Volume 20 Issue 7 Pages 1551-1557
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThere were at least two kind of cytolytic substances on Ehrlich ascites carcinoma cells in the culture medium of Bacillus natto KMD 1126. One was adsorbed on carbon, eluted with EtOH, and large molecule by Sephadex G 25 gel filtration, but the other was not adsorbed on carbon and small molecule by Sephadex G 25 gel filtration. The former was stable on wide range of pH and temperature. This cytolytic substance was isolated and its chemical structure was examined by elementary analysis, infrared spectrum, nuclear magnetic resonance, and mass spectroscopy and study of decomposed products. As the results, the cytolytic substance was proved to be identical with surfactin which was potent coltting inhibitor in the thrombin fibrinogen system obtained from culture medium of Bacillus subtilis by Kakinuma, et al.View full abstractDownload PDF (897K) -
TERUO KUTSUMA, KAZUO FUJIYAMA, YASUO SEKINE, YOSHIRO KOBAYASHI1972 Volume 20 Issue 7 Pages 1558-1566
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTetramethyl 3, 10b-dihydropyrrolo [2, 1-α] isoquinoline-1, 2, 3, 3-tetracarboxylate (VI) was isolated for the first time as the primary addition product of a reaction between isoquinolinlium bis (methoxycarbonyl) methylide (V) and dimethyl acetylenedicarboxylate (IV). Treatment of VI with hydrogen chloride and then with potassium carbonate resulted in its isomerization into 2, 3-dihydropyrrolo [2, 1-α] isoquinoline derivative (VII). In the reaction of isoquinolinium dicyanomethylide (XI) with IV, the isomerized 2, 3-dihydro compound (XIII) and the eliminated product (XIV) were produced, instead of their primary adduct (XII). The relation between a substituent group in the 2, 3-dihydrotype compounds and their reactivity was examined. On the other hand, in the reaction of disubstituted pyridinium methylides with acetylenic compounds, only aromatized products were obtained.View full abstractDownload PDF (953K) -
MASARU KOBAYASHI, HIROSHI MITSUHASHI1972 Volume 20 Issue 7 Pages 1567-1569
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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KIYOMI KIKUGAWA, KAZUHIRO IIZUKA, MOTONOBU ICHINO1972 Volume 20 Issue 7 Pages 1569-1571
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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AKIRA HANAKI1972 Volume 20 Issue 7 Pages 1572-1574
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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TETSUZO KATO, TOYOHARU HOZUMI1972 Volume 20 Issue 7 Pages 1574-1578
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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TAEKO NAKAYAMA, TERUMI NAKAJIMA, HIROFUMI SOKABE1972 Volume 20 Issue 7 Pages 1579-1581
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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KAICHEONG CHAN, L.E. TEO1972 Volume 20 Issue 7 Pages 1582-1584
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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TETSUJI KAMETANI, MASATAKA IHARA, KEIICHI TAKAHASHI1972 Volume 20 Issue 7 Pages 1587-1588
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (353K) -
SEIJI MIYANO, NOBUHIRO ABE1972 Volume 20 Issue 7 Pages 1588-1589
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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MITSUTAKA NATSUME, MORITAKA WADA1972 Volume 20 Issue 7 Pages 1589-1592
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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MITSUTAKA NATSUME, SETSUKO KUMADAKI, KAZUKO KIUCHI1972 Volume 20 Issue 7 Pages 1592-1595
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
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MITSUTAKA NATSUME, IWAO UTSUNOMIYA1972 Volume 20 Issue 7 Pages 1595-1598
Published: July 25, 1972
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (482K)
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