All issues
Volume 23, Issue 9
Displaying 1-50 of 58 articles from this issue
-
YOSHIO SASAKI, HIDEKO KAWAKI, YUKO OKAZAKI1975 Volume 23 Issue 9 Pages 1899-1904
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTris (dipivalomethanato) europium induced paramagnetic shifts of aliphatic amines and alcohols were examined with respect to sterio, electronic and solvent effects. The paramagnetic shifts are an exponential function of the three effects, and can be expressed by the following type of equation : S=A·e-B×k where k=parameters of the steric, electronic and solvent effects The intercepts A, referred to the unperturbed state, decrease regulary from α to γ, whereas the slopes B, referred to the perturbed state, decrease in a zig-zag manner.View full abstractDownload PDF (485K) -
YOSHIO SASAKI, HIDEKO KAWAKI, YUKO OKAZAKI1975 Volume 23 Issue 9 Pages 1905-1909
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe induced paramagnetic shift parameters, S values, due to tris (dipivalomethanato)-europium were examined in alkyl pyridine derivatives from the view points of steric, electronic and solvent effects. 1. The log S values are linearly related with ΔΔ ER, σ* and 1-1/ε, and expressed by the following type of equation. S=A.e-B×k, k=ΔΔ ER, σ* or 1-1/ε 2. The three kinds of intercepts are linearly related with each other and decrease regularly from α to γ, whereas a plot of three kinds of slopes, referring to the perturbed state is zig-zag. 3. The S values are expressed by the sum of the contributions of Δ Esteric, Δ Eelect, and Δ Esolv.View full abstractDownload PDF (448K) -
TAKUZO HISANO, MASATAKA ICHIKAWA, AKIRA NAKAGAWA, MASAYOSHI TSUJI1975 Volume 23 Issue 9 Pages 1910-1916
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour useful procedures for preparing a series of new 2-pyridyl-4(3H)-quinazolinones were investigated and twelve quinazolinones were evaluated for hypnotic activity. Some of them showed a definite hypnotic effect in intraperitoneal doses above 100 mg/kg, whose structure-activity relationship demonstrated that 3-pyridyl and 4-pyridyl substitution at 2-position of 4 (3H)-quinazolinone ring and ο-fluorophenyl and ο-chlorophenyl at 3-position are appropriate for the manifestation of hypnotic activity. A maximum hypnotic effect was observed in 2-(4-pyridyl)-3-(ο-fluorophenyl)-4(3H)-quinazolinone (1), the potency of which was equal to methaqualone in mice.View full abstractDownload PDF (769K) -
YOICHI SAWA, TAKESHI KATO, TORU MASUDA, MIKIO HORI, HAJIME FUJIMURA1975 Volume 23 Issue 9 Pages 1917-1927
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to examine more advantageous syntheses and the structure activity relationship, derivatives of 1, 2, 3, 4-tetrahydro-5H-benzazepine were synthesized via two routes from 3, 4-dihydro-1(2H)-naphthalenone. First, these compounds were synthesized via Beckmann rearrangement of 3, 4-dihydro-1(2H)-naphthalenone oximes and second, via 2-(2-cyano-1, 1-dimethylethyl)-4-methoxybenzoic acid. The synthesized compounds were tested for analgesic activity in mice.View full abstractDownload PDF (1232K) -
ISAO NEGISHI, YOSHIO AIZAWA1975 Volume 23 Issue 9 Pages 1928-1931
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe content of liver lipids and protein, and serum beta-lipoprotein were determined in control and orotic acid-fed rats. Further, the effect of phosphatidylcholine on the release of beta-lipoprotein from liver slices into the incubation medium was examined in both groups. Results are summarized as follows : 1. The amount of liver glycerides increased significantly by ingestion of orotic acid, but liver phospholipid and protein decreased. 2. A 50 per cent depression of the content of serum beta-lipoprotein was observed in rats fed orotic acid. 3. The release of beta-lipoprotein from liver slices decreased when orotic acid was added to the diet. This decrease was partly restored by the addition of phosphatidylcholine. 4. When liver slices were pre-treated with phospholipase C, the amount of released beta-lipoprotein increased in both control and orotic acid-fed rats. The treated liver slices from orotic acid-fed rats released the same amount of lipoprotein as the control by the addition of phosphatidylcholine. From these observations, phosphatidylcholine appears to take part in the release of beta-lipoprotein. Accordingly, it was concluded that fatty liver induced by orotic acid resulted from the impaired phosphatidylcholine synthesis in the liver.View full abstractDownload PDF (588K) -
YOICHI SAWA, TAKESHI KATO, TORU MASUDA, MIKIO HORI, HAJIME FUJIMURA1975 Volume 23 Issue 9 Pages 1932-1937
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSContinuing our study of new types of non-narcotic analgesics, we synthesized several 1, 2, 3, 4, 5, 6-hexahydro-6, 6-dimethyl-1, 5-methano-3-benzazocine derivatives from ethyl 4-methoxyphenylacetate via the ring closure reaction of 5-(1-hydroxy-1-methylethyl)-3-(4-methoxyphenyl)-2-piperidinone (V). The by-product which was produced by the ring closure reaction of V, was presumed to be 1, 2, 3, 4, 5, 6-hexahydro-8-methoxy-6, 6-dimethyl-9-sulfo-1, 5-methano-3-benzazocine (VII). The synthesized compounds were tested for analgesic activity in mice.View full abstractDownload PDF (781K) -
ISAO NEGISHI, YOSHIO AIZAWA1975 Volume 23 Issue 9 Pages 1938-1942
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffect of phospholipid on fatty liver induced by orotic acid, carbon tetrachloride, or ethionine has been studied. Results are summarized as follows : 1. Orotic acid induced a marked accumulation of liver glycerides, and a decreased concentration of liver phospholipid and protein, and of serum beta-lipoprotein. These lesions were restored by administration of phospholipid. 2. In rats given carbon tetrachloride or ethionine, liver lipid accumulation and a decreased concentration of serum beta-lipoprotein were partially restored by administration of phospholipid, but a decreased protein content in the liver was unaffected. These results indicate that administration of phospholipid is effective in counteracting the depression of serum beta-lipoprotein and liver lipid accumulation by orotic acid, carbon tetrachloride, or ethionine. Phospholipid appears to have an important role in normal release of beta-lipoprotein.View full abstractDownload PDF (708K) -
TETSUYA TAJIMA1975 Volume 23 Issue 9 Pages 1943-1948
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe prothrombin activity in plasma was highly correlated with that in liver in normal rats, bishydroxycoumarin (dicumarol)-treated rats and CCl4-treated rats. Menaquinone-4(K2(20)) significantly increased the prothrombin activities in plasma and in liver of rats which had hypoprothrombinemia induced by administration of dicumarol or CCl4. K2(20) significantly promoted the prothrombin synthesis in liver homogenate in the rats treated with dicumarol or CCl4. Furthermore, it was observed that K2(20) exerted a promoting effect on prothrombin synthesis in the microsomal fraction of liver. However, when plasma was incubated with K2(20), the prothrombin time of the plasma was not shortened. The effects of K2(20) on the prothrombin activity and on the prothrombin synthesis of liver were more rapid and stronger than those of vitamin K1. It is concluded that K2(20) promotes prothrombin synthesis in liver parenchymal cells and improves hypoprothrombinemia caused by dicumarol or CCl4 in rats.View full abstractDownload PDF (783K) -
SHIGEO BABA, SHINICHI MORISHITA1975 Volume 23 Issue 9 Pages 1949-1954
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSpecies differences in the metabolism of 1-butyryl-4-cinnamyl [γ-14C] piperazine (I-14C) hydrochloride in mice, rabbits, guinea pigs, and rats were studied by a tracer technique in an attempt to select the most appropriate species of animals for the evaluation of safety use of this drug in man. After the administration of a single dose of 20 mg/kg I-14C, radioactive metabolites excreted in urine were analyzed. The excretion of I-14C and its metabolites in mice and rabbits was mostly in the urine (69.3%, 89.6%), while in rats and guinea pigs approximately a half of the total radioactivity appeared in the feces (57.1%, 41.7%). In these experimental animals, the main metabolic route of compound I was through p-hydroxylation, but the ratio of the p-hydroxylated metabolites to the total metabolites identified was differed considerably among these species (mice 95.4%, rabbits 97.7%, guinea pigs 68.7%, rats 74.2%). In guinea pigs and rats, 5-12% (percentage of the 14C-activity in the urine) of unchanged I-14C was detected in the urine, but in mice and rabbits, the amount of the unchanged compound was rather small (0.2-0.9%). The amount of benzoic acid, hippuric acid and their hydroxylated metabolites varied and were found to be 1-17% in guinea pigs and rats. In rabbits, a larger part of metabolites of I-14C were excreted as its conjugated form.View full abstractDownload PDF (755K) -
KAYOKO FUKUDA, TAKAYOSHI UEMATSU, AKIRA HAMADA, SHICHIRO AKIYA, NOBUHI ...1975 Volume 23 Issue 9 Pages 1955-1959
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom Lampteromyces japonicus, a polysaccharide was extracted with hot water and purified by deproteinization, removal of nucleic acid and DEAE cellulose column chromatography. The purified neutral polysaccharide, [α]34D+218.3° (c=0.93, H2O), was white powder and constituted of mannose, glucose and galactose in the molar ratio of 1 : 0.66 : 0.54. The tumor inhibition ratio of the polysaccharide against the implanted sarcoma 180 in mice was 55.1% in the doses of 40 mg/kg/day for 5 days, and the tumors in 3 of 8 mice completely regressed.View full abstractDownload PDF (632K) -
HIROSHI TERADA, TOSHIO INAGI1975 Volume 23 Issue 9 Pages 1960-1968
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe partition mechanism of tetracycline in an n-octanol/H2O system was studied by mathematical treatment of the changes in the apparent partition coefficient determined by Colaizzi and Klink (J. Pharm. Sci., 58, 1184 (1969)) and by us, and by measuring the spectral properties of tetracycline in organic solvents. Tetracycline exists in a neutral molecular form in n-octanol, so it could be concluded that transfer of tetracycline from an aqueous to an organic phase is governed not by the amount of the zwitterionic form, but by the amount of the neutral molecular form in the aqueous phase. Results showed that the tetracycline molecule itself is hydrophobic, but that the concentration of the neutral molecular species in the aqueous phase is very small. The relationship between the apparent partition coefficient and the three macroscopic ionization constants of tetracycline at a certain pH was also clarified. From this the macroscopic ionization constants were evaluated. The values agreed very well with those determined by potentiometric titration.View full abstractDownload PDF (879K) -
MAMORU SUGIURA, MASANORI SASAKI, CHIAKI MORIWAKI, KEIKO YAMAGUCHI1975 Volume 23 Issue 9 Pages 1969-1975
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo clarify the multiplicity of proteinases, i.e. Ficins A, B, C, D, and S (EC 3.4.4.12) from Ficus carica var. HORAISHI, immunochemical properties of the enzymes were examined. Each enzyme used was proved to be homogeneous with immunoelectrophoresis. Antibodies were purified from rabbit antisera by ammonium sulfate fractionation, the use of Ficins immunoadsorbents and Sephadex G-200 gel-filtration. The relation of the enzymes was examined with Ouchterlony's double immunodiffusion, immunoelectrophoresis, cross-reaction among the enzymes on an immunoadsorbent column and inhibition of the caseinolytic activity of the enzymes by the antibodies. The results from the experiments are as follows : (a) Ficins A and S were immunochemically identical and also Ficins B and C resembled to each other. (b) Ficins A and S, Ficin B, Ficin C, and Ficin D possessed common antigenic determinants at the rate of more than 38%, but the enzymes could be distinguished, in case that the relation of Ficin A and Ficin S be excepted. From these results, it is suggested that the immunochemical similarity of the enzymes to Ficin A is in the order of Ficin A=Ficin S>Ficin B>Ficin C>Ficin D.View full abstractDownload PDF (1100K) -
AKIRA TAHARA, HIROYUKI AKITA1975 Volume 23 Issue 9 Pages 1976-1983
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of methyl dehydroabietate derivatives having electron-donating group at aromatic C-ring with aluminum chloride were examined. It became clear that the reaction proceeded through isomerisation of 9, 10-bond and/or deisopropylation and the direction of the reaction is affected by the substituent at the aromatic C-ring. For instance, the reaction of 12-hydroxy ester (7) proceeded through both routes while 14-hydroxy ester (19) was selectively deisopropylated. Interconversion between cis- and trans-stereoisomers of deisopropyl ester (e.g., 10↔9) was observed and the former is predominant in the equilibrium.View full abstractDownload PDF (997K) -
AKIRA TAHATA, HIROYUKI AKITA1975 Volume 23 Issue 9 Pages 1984-1988
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 12-acetyl ester (5) with aluminum chloride gave predominant trans-isomer (6) in company with the cis (7). trans-Isomer had not been observed as major product in the reactions of methyl dehydroabietate having electron-donating group at aromatic ring as described previously. In the other cases of reactions of methyl dehydroabietate derivatives having electron-withdrawing group, 7-oxo ester (20) did not react even under the drastic condition. But 7-oxo ester having a hydroxyl or a methoxyl group at 12-or 14-position was deisopropylated to give only the respective trans deisopropyl isomer.View full abstractDownload PDF (652K) -
AKIRA TAHARA, YOSHIHIRO HARIGAYA, MASAYUKI ONDA1975 Volume 23 Issue 9 Pages 1989-1995
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConversion of dehydroabietic acid (1) to a steroid skeleton was attempted. Synthesis of the 3-oxo compound (25) having a steroid-type A ring was successfully completed from starting material (9) via the intermediates (18) and (19).View full abstractDownload PDF (850K) -
AKIRA TAHARA, YOSHIHIRO HARIGAYA, MASAYUKI ONDA1975 Volume 23 Issue 9 Pages 1996-2000
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConversion of dehydroabietic acid (1) to a steroid skeleton was attempted. The oxo ester (3), an important intermediate in the synthesis of 4, was synthesized from 7 having a double bond in the A ring. It was confirmed that the oxo ester (3) has the α configuration at the 5-position.View full abstractDownload PDF (682K) -
FUMIO YONEDA, TOMOHISA NAGAMATSU1975 Volume 23 Issue 9 Pages 2001-2009
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA convenient synthesis of toxoflavins and toxoflavin 4-oxides, which consists of the nitrosative cyclization of the aldehyde hydrazones of 3-methyl-6-(1-methylhydrazino) uracil, is described. Both toxoflavins and toxoflavin 4-oxides gave the corresponding 1-demethyltoxoflavins (8-demethylfervenulins) by treatment with nucleophiles such as dimethylformamide, dimethylacetamide and acetic acid. The preparation of some 4, 8-dihydrotoxoflavin derivatives is described.View full abstractDownload PDF (791K) -
TETSUJI KAMETANI, SHYHPYNG HUANG, MASATAKA IHARA, KEIICHIRO FUKUMOTO1975 Volume 23 Issue 9 Pages 2010-2014
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPentazocine (1) was synthesized from L-tyrosine (2). N-Benzylation of methyl ester (3), obtained from L-tyrosine, followed by Schotten-Baumann reaction of the amine (4), gave the amide (5). Dieckmann reaction of 5 gave the racemic β-ketoester (6), whose methylation followed by decarboxylation afforded the ketoamide (8). Grignard reaction gave the carbinol (9), which was cyclized with hydrobromic acid to afford the amide (10) in good yield. Reduction of 10 with sodium bis-(2-methoxyethoxy) aluminum hydride or lithium aluminum hydride gave the amine (11), which had already been converted into pentazocine.View full abstractDownload PDF (684K) -
TAKAJI KOYAMA, HIDEKI HARA, TAKASHI HIROTA, SHINJI OHMORI, MASATOSHI Y ...1975 Volume 23 Issue 9 Pages 2015-2018
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS11, 13, 15-Triazasteroidal compounds, that is, 1, 2, 4, 5-tetrahydrobenz [h] imidazo [1, 2-c]-quinazolines (IV) were synthesized by the new route. Its intermediates (VII, VIII) were compared with the previous intermediates (II, III). II and III were corrected to II'and III'respectively.View full abstractDownload PDF (582K) -
MAMORU SUGIURA, KAZUYUKI HIRANO, SHIRO IINO, HIROSHI SUZUKI, TOSHITSUG ...1975 Volume 23 Issue 9 Pages 2019-2024
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHuman biliary alkaline phosphatase was purified by butanol treatment, protamine sulfate treatment, diethylaminoethyl (DEAE)-cellulose, carboxymethyl (CM)-cellulose, Sephadex G-200 and DEAE-Sephadex A-50. The purified enzyme exhibited a single protein band by disc electrophoresis. It was found that the properties of the purified biliary alkaline phosphatase was similar to those of human placental and intestinal alkaline phosphatases in relation to the influence of chemicals, optimum pH, pH stability and isoelectric point but the biliary enzyme was less stable against heat than the placental enzyme.View full abstractDownload PDF (646K) -
TETSUJI KAMETANI, YASUO FUJIMOTO, MASAKATSU MIZUSHIMA1975 Volume 23 Issue 9 Pages 2025-2028
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReductive cyclization of 1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-1-(4, 5-dimethoxy-2-nitrophenethyl)-2-methylisoquinoline (11) with triethyl phosphite afforded 2, 3, 9, 10-tetramethoxybenz [c] acridine (12), the structure of which was identical with the sample, which was synthesized in a different route, in spectral comparisons.View full abstractDownload PDF (509K) -
TAKAJI KOYAMA, TAKASHI HIROTA, YURIE SHINOHARA, SACHIKO MATSUMOTO, SHI ...1975 Volume 23 Issue 9 Pages 2029-2032
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn heating phenylacetone (III) with formamide in the presence of phosphoryl chloride (called the modified Vilsmeier reaction) afforded 4-methyl-5-phenylpyrimidine (IV), 5-phenyl-4-(5-pyrimidinyl) pyrimidine (V), and 3-methyl-2, 4-diphenylaniline (VI). The modified Vilsmeier reaction of 3-methoxyphenylacetone (VII) gave 6-methoxy-3-methylisoquinoline (VIII), 4-β-formylaminovinyl-5-m-methoxyphenylpyrimidine (IX), 9-methoxybenzo [f] quinazoline (X), and 7-methoxybenzo [f] quinazoline (XI). The same reaction of 2-phenylcyclohexanone (XII) gave 8-phenyl-5, 6, 7, 8-tetrahydroquinazoline (XIII) and 4-formylamino-4, 4a, 5, 6, 7, 8-hexahydroquinazoline (XIV).View full abstractDownload PDF (602K) -
SHIGERU KOBAYASHI, SUSUMU SHINAGAWA, MIKIHIKO OBAYASHI, TSUNEHIKO FUKU ...1975 Volume 23 Issue 9 Pages 2033-2038
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight new di- and tri-substituted luteinizing hormone releasing hormone (LH-RH) analogs, i.e., des-Gly10-[Thr4]-LH-RH-ethylamide, des-Gly10-[Phe5]-LH-RH-ethylamide, des-Gly10-[Phe5, Ile7]-LH-RH-ethylamide, des-Gly10-[Nle7]-LH-RH-ethylamide, des-Gly10-[Met7]-LH-RH-ethylamide, des-Gly10-[Orn8]-LH-RH-ethylamide, des-Gly10-[Lys8]-LH-RH-ethylamide and des-Gly10-[Gly9]-LH-RH-ethylamide, were synthesized by the solution method, and tested in vitro for the ability to induce secretion of luteinizing hormone. On the basis of structure-activity relations of these analogs, it is concluded that the effect of several structural changes in the LH-RH-molecule on its hormonal activity is"additive".View full abstractDownload PDF (805K) -
MASASHI OKADA, TAKAKO ANJYO1975 Volume 23 Issue 9 Pages 2039-2043
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Oxo-12β, 14-dihydroxy-14β-carda-4, 20(22)-dienolide (VII) derivable from digoxigenin (V) was treated with lithium borohydride in pyridine to give 5α-digoxigenin (VIa), which was demonstrated to be identical with the natural cardenolide aglycone, syriogenin. The structure of syriogenin was thus firmly established as 3β, 12β, 14-trihydroxy-5α, 14β-card-20(22)-enolide.View full abstractDownload PDF (677K) -
YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, YUJI HANZAWA, MASATAKA MIMURA1975 Volume 23 Issue 9 Pages 2044-2047
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism for a novel reaction of a trifluoromethyl group as a leaving group is confirmed. Reaction of 2-(heptafluoro-n-propyl) quinoline with sodium amide gave 2-aminoquinoline, which shows that a perfluoroalkyl group could behave as a leaving group in some SNAr reactions. Tris (trifluoromethyl)-s-triazine gave a 1, 4-ammonia adduct, which shows that the reaction passed through addition-elimination mechanism.View full abstractDownload PDF (497K) -
OSAMU HOSHINO, HIROSHI HARA, NOBUAKI SERIZAWA, BUNSUKE UMEZAWA1975 Volume 23 Issue 9 Pages 2048-2053
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid (conc. H2SO4-Ac2O) treatment of the p-quinol acetate derived from (±)-1, 2, 3, 4-tetrahydro-7-hydroxy-6-methoxy-2-methyl-1-(3', 4'-methylenedioxy-benzyl or -phenethyl)-isoquinoline (VIII or IX) gave the corresponding 1-monoacetoxy-and 1, 4-diacetoxy-aporphine (XIX, XXa, and XXb) or-homoaporphine (XXIII and XXIV), respectively. Hydrolysis of XIX afforded (±)-domesticine (VI).View full abstractDownload PDF (897K) -
TAMOTSU YASHIRO, KYOKO YAMADA, HIDEAKI SHIRAI1975 Volume 23 Issue 9 Pages 2054-2057
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the purpose of testing the biological activity, spiro-[4-hydroxycyclohexane-1, 4'-2', 3'-dihydro-6'-methoxy-2'-methyl-1'H-isoquinoline] (IV) was synthesized by cyclization of 1-(m-methoxyphenyl)-4-hydroxycyclohexanemethylamine (XIII), which was obtained from the trans-acetoxy-amide (XII), in the presence of excess formic acid and formaldehyde under the conditions of Eschweiler-Clarke reaction. 4-Dimethylaminomethyl-4-(m-methoxyphenyl) cyclohexanol (V) was synthesized by reduction of 1-(m-methoxyphenyl)-4-acetoxycyclohexanecarbonyl dimethylamide (XIV), which was obtained from the trans-acetoxy-acid chloride (XI), with lithium aluminum hydride.View full abstractDownload PDF (591K) -
SHINZO KANO, EIJI KOMIYAMA, TOSHIHISA OGAWA, YOUKO TAKAHAGI, TSUTOMU Y ...1975 Volume 23 Issue 9 Pages 2058-2063
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe benzyne reaction of 1-(2-bromo-4, 5-dimethoxyphenethyl)-1, 2, 3, 4-tetrahydro-6-hydroxy-7-methoxy-2-methylisoquinoline (13) was examined by using sodium methylsulfinylmethanide and the dibenzo [b, g] azecine (16) was obtained. The 1-halogenophenethylisoquinoline (14) also yielded the corresponding dibenzo [b, g] azecine (17) under the similar conditions. The reductive deoxygenation of (16) and (17), followed by desulfurization of 14-(methylthio) methyl derivative (18) and (19) gave the corresponding 14-methyl derivative (20) and (21), respectively. The similar ring expansion occurred also in the case of 1-halogenobenzylisoquinoline (15) to give the dibenzo [b, f] azonine (29), which was converted to the 13-methyl derivative (31).View full abstractDownload PDF (844K) -
KAZUNOBU MIURA, TOHRU UEDA1975 Volume 23 Issue 9 Pages 2064-2069
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSynthesis of thiopurine nucleosides (and nucleotides) by the application of aminothiono exchange reaction (sulfhydrolysis) was described. 1-Methyl-6-thioinosine and 2', 3'-O-isopropylidene-5'-deoxy-3, 5'-cyclo-2-thioxanthosine were obtained from 1-methyladenosine and cycloguanosine, respectively. Sulfhydrolysis of a 3, 5'-cycloadenosine gave a 5-amino-N5, 5'-cycloimidazole-4-thiocarboxamide riboside in high yield. Synthesis of 6-thioinosine and 6-thioxanthosine by sulfhydrolysis of N6-methoxyadenosine and crotonoside, respectively, was also performed.View full abstractDownload PDF (798K) -
KUK HYUN SHIN, HIDEO NAKAGAWA, SUSUMU TSURUFUJI1975 Volume 23 Issue 9 Pages 2070-2074
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTime course of the effects of a single local injection of glucocorticoid on synthesis of collagen, non-collagen protein and deoxyribonucleic acid (DNA), and on vascular permeability of pre-formed carrageenin granuloma in the rat has been investigated. Maximum inhibitions for the synthetic activity of collagen and non-collagen protein were attained at 4 hr after the administration of a single dose (3 mg/kg) of hydrocortisone acetate. The synthetic activity of collagen had recovered quickly to the control level at around 18 hr after the injection of the steroid, while non-collagen protein showed a recovery reaching the control level at 32 hr. The inhibitory effect of the steroid on the synthetic activity of DNA was greater than those on proteins and a significant inhibition was still noted at 32 hr (34.7% inhibition). Vascular permeability measured with the aid of radioiodinated human serum albumin was also inhibited markedly by the steroid treatment and preserved the level of 48% inhibition continuously from 8 hr upto the end of the experimental period. Possible differences in the mechanism of action of anti-inflammatory steroid between a single acute and repeated chronic treatments are discussed.View full abstractDownload PDF (642K) -
HIKARU OZAWA, KAZUNOBU SUGAWARA, MARI KOOI, TETSUZO KATO1975 Volume 23 Issue 9 Pages 2075-2086
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe general pharmacological actions of N-acetoacetyl-3-hydroxytyrosine (L-DOPA acetoacetate) were investigated and compared with those of L-3, 4-dihydroxypenylalanine (L-DOPA). The following results were obtained. 1) L-DOPA acetoacetate and L-DOPA suppressed slightly the spontaneous motor activity in mice. 2) L-DOPA acetoacetate and L-DOPA showed no effect on the sleeping time induced by hexobarbital and on maximal electroshock-, pentetrazol- and strychnine-convulsions in mice, but maximal electroshock convulsion was inhibited by the combined administration of L-DOPA and a monoamine oxidase inhibitor, pargyline. 3) L-DOPA acetoacetate and L-DOPA suppressed the squirming induced by acetic acid in mice. 4) L-DOPA acetoacetate did not have a hypothermic action in mice although L-DOPA did slightly. 5) In anaesthetized rats, L-DOPA acetoacetate and L-DOPA produced a slight temporary rise in the blood pressure and potentiated the pressor actions of norepinephrine and tyramine. The tyramine-induced tachyphylaxis and the abolishment of the response of tyramine induced with reserpine pretreatment were restored by both compounds. 6) On the isolated smooth muscle preparations such as guinea-pig vas deferens, intestine, aorta, rabbit aorta and rat uterus, the contractions induced by several agonists were almost unaffected by L-DOPA acetoacetate and L-DOPA. On guinea-pig vas deferens, aorta and rabbit aorta preparations, however, the tyramine-induced tachyphylaxis and the abolishment of the response of tyramine induced with reserpine pretreatment were restored by both compounds. These restorations were not observed by the treatment of a peripheral DOPA decarboxylase inhibitor, Ro4-4602. These actions were also found on guinea-pig atria preparations. Furthermore, on rat uterus preparations, both compounds increased the spontaneous motility. 7) On the gastrointestinal propulsion in mice and on the isolated skeletal muscle preparations in frog, L-DOPA acetoacetate and L-DOPA showed no effect. From the results mentioned above, it could be assumed that L-DOPA acetoacetate possessed only peripheral without central action though L-DOPA possessed both of central and peripheral actions, and that the activities would be due to their metabolites.View full abstractDownload PDF (1166K) -
ISAO KITAGAWA, HIDEYO SUZUKI, ITIRO YOSIOKA1975 Volume 23 Issue 9 Pages 2087-2093
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical correlation of spergulagenin A (1), which is a new migrated hopane-type sapogenol elucidated previously from the root of Mollugo spergula L., with hydroxyhopane (2) has been accomplished through the conversion of both to the common derivative 4a (=7a). The Meerwein-Ponndorf type reduction of the methylcarbonyl moiety in spergulagenin A (1), which occurs on prolonged treatment with ethanolic alkali, has been described.View full abstractDownload PDF (768K) -
TOZO FUJII, SHIGEYUKI YOSHIFUJI, MASARU TAI1975 Volume 23 Issue 9 Pages 2094-2103
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stereochemistry of pairs of isomers found for 5-ethyl-2-oxo-4-piperidineacetic acid (I) and its derivatives [methyl ester (II), ethyl ester (III), and 1-benzyl derivative (IX)] has been established by interrelation of I with cincholoipon ethyl ester [(+)-VIIb], derived from the alkaloid cinchonine, through 3-ethyl-4-piperidineethanol (IV). trans-Acid IXa has been prepared by benzylation of trans-lactam ester IIIa and subsequent alkaline hydrolysis of the N-benzylated product (XIa) ; cis-acid IXb, by the alkaline hydrolysis of lactam ester Xb obtained from lactim ether VIIIb by the reaction with benzyl bromide. The lactim ether (VIIIb) has been synthesized from cis-lactam ester IIb the methylation with dimethyl sulfate in boiling benzene. It has been found that on thermal treatment at 180° either cis-acid IXb or trans-acid IXa is partially isomerized to give an equilibrated 67 : 33 mixture of IXa and IXb in 50 min. Under the same conditions the N-unsubstituted trans-acid (Ia) attains to an equilibrium faster than IXa, resulting in 33% conversion into Ib in 8 min. At 210° cis-acid Ib undergoes isomerization very rapidly to produce an equilibrated mixture of the same composition. In boiling 6 N hydrochloric acid either IXa or IXb gives an equilibrated 57 : 28 : 15 mixture of IXa, IXb, and the ring-opened product (XIII, R=C6H5CH2) within 28 hr. In contrast, the methyl esters (IIa, b, Xa, b) of these acids have been found not to suffer such a cis-trans isomerization at 180° over a period of at least 1 hr. On the basis of these findings, mechanisms of the observed isomerizations are discussed.View full abstractDownload PDF (1305K) -
ISOO ITO, NORIICHI ODA, TETSUO KATO, KAZUO OTA1975 Volume 23 Issue 9 Pages 2104-2108
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 4-Diamino-6-methylpyrimidine (II) was synthesized from acetoacetonitrile (III) and guanidine which was then converted to 5-amino-7-methyloxazolo [4, 5-d] pyrimidin-2(3H)-one(IX). Several nucleoside type compounds were synthesized by the condensation of IX with some halogenoacetyl and halogenobenzoyl sugars in the presence of metal salts as a halogen acceptor. The antitumor activity of the compounds was tested and found to be inactive.View full abstractDownload PDF (581K) -
KAYOKO KAKEMI, HARUKO KAMEDA, MASAWO KAKEMI, MICHIHIRO UEDA, TAMOTSU K ...1975 Volume 23 Issue 9 Pages 2109-2113
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMathematical models were defined that simulate the percutaneous absorption of drug and its transport in the ointment. Ointment and skin were, respectively, assumed as homogeneous phases through which drug diffuses according to Fick's law. Blood compartment and drug disposition were also taken into account.View full abstractDownload PDF (514K) -
KAYOKO KAKEMI, HARUKO KAMEDA, MASAWO KAKEMI, MICHIHIRO UEDA, TAMOTSU K ...1975 Volume 23 Issue 9 Pages 2114-2117
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to verify the applicability of the mathematical models that were proposed in the preceeding paper to simulate the percutaneous absorption of drug and its transport in the ointment, experiments on release and percutaneous absorption of NaI from hydrophilic ointment were carried out. Agreement of calculated and observed values was reasonable.View full abstractDownload PDF (498K) -
HIROSHI HOSODA, KOUWA YAMASHITA, HIROMITSU SAGAE, TOSHIO NAMBARA1975 Volume 23 Issue 9 Pages 2118-2122
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to obtain the more precise knowledge on the nature of the dimethyl-tert-butylsilyloxy linkage, several steroid silyl ethers were prepared. The rate of acid-catalyzed hydrolysis was determined with the typical steroid derivatives. Convenient syntheses of 3β-hydroxy-4-androsten-17-one have also been described.View full abstractDownload PDF (695K) -
TSUNEHIRO KITAGAWA, TAKAKO MIURA, MISAKO TAKAISHI, HYOZO TANIYAMA1975 Volume 23 Issue 9 Pages 2123-2127
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to determine which amino function of N-terminal two amino groups is important factor for the exhibition of antimicrobial activity of viomycin, selective acetylations for both amino functions were performed. The limited acetylation gave III exclusively while, the limited benzyloxycarbonylation followed by acetylation and debenzyloxycarbonylation yielded VI. Antimicrobial activities of III and VI showed almost the same reduced activities than I but somewhat stronger activities than II. From these results both of the terminal amino functions are deduced to be important factors for the exhibition of the activities of I.View full abstractDownload PDF (645K) -
SHIKIFUMI KITAZAWA, HAJIME ITO, MASAAKI IINUMA1975 Volume 23 Issue 9 Pages 2128-2133
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAttempts confirming the effect of the transmucosal fluid movement and the glucose effect on the intestinal drug absorption, those of which had been revealed in the previous studies of in situ experiment, in the in vivo studies were undertaken using an intraduodenal administration method to mice. These effects were reflected amply on the indices of the lethality and the survival time after the administration of ephedrine hydrochloride. From the results obtained in the present study, it was able to be concluded that the effects of the transmucosal fluid movement and the glucose are observed realistically in the in vivo experiment. In the course of the studies, calcium chloride was appeared to affect similar in nature to the glucose effect on the drug absorption from the small intestine.View full abstractDownload PDF (761K) -
YUICHI YAMAMOTO, REIKO YODA, MAKIKO MATSUMURA1975 Volume 23 Issue 9 Pages 2134-2139
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe compounds synthesized through the route (a) and the route (b) as shown in Chart 1 have been assigned by S. Gabriel in the past and by E. Cherbuliez, et al. recently to Type A, N-alkyl-N'-alkyl-N'-(2-thiazolin-2-yl) thiourea (5). We had some doubt in the structure of the above compounds synthesized through the route (a) and (b), so they were hydrolyzed with 15% H2SO4 to give Type B, 3-N-alkylthiocarbamoyl-2-oxothiazolidine (6) which was assigned with infrared spectrum (IR), Mass Spectra and nuclear magnetic resonance (NMR) data and confirmed by synthesis of 6 through the route (c). Thus, it was confirmed that the compounds obtained by our synthesis through the route (a) and (b) possessed the Type B structure ; 3-N-alkylthiocarbamoyl-2-alkyliminothiazolidine (4), instead of the Type A structure. The data for ultraviolet spectrum (UV), IR, MS and NMR are shown in Table I, II and III.View full abstractDownload PDF (644K) -
MIYOJI HANAOKA, NOBUO OGAWA, YOSHIO ARATA1975 Volume 23 Issue 9 Pages 2140-2144
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first stereoselective total synthesis of one of Lythraceae alkaloids, decaline, was described. The Mannich condensation of isopelletierine (III) with 6-bromoisovanillin (IV) afforded stereoselectively the trans quinolizidine (V) which was converted to the methyl ether (VI). Stereoselective reduction of VI with the Henbest catalyst gave the axial alcohol (VII) along with the equatorial alcohol (VIII). The Ullmann condensation of the acetyl derivative (IX) from VII with the ester (XI) furnished the biphenyl ether (XII). Hydrolysis of XII and lactonization of the resulting hydroxy-acid (XIV) provided (±)-decaline (II).View full abstractDownload PDF (743K) -
HIDEOMI FUKUDA, JUNICHI ISHIKO1975 Volume 23 Issue 9 Pages 2145-2147
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAfferent activity from baroreceptors in the isolated heart of the bullfrog was recorded. Two types of volley were observed during the period of the cardiac cycle : a lasting volley of discharges accompanying the QRS complexes in electrocardiogram and a short volley of discharges following immediately after the P wave. Epinephrine, veratridine and ouabain caused an increase in the rate of afferent discharges from baroreceptors in the heart, whereas acetylcholine and ajmaline caused a reduction in the rate. Thus this method allowed a simple measurement of the effect of drugs on the cardiac afferent activities.View full abstractDownload PDF (469K) -
TETSURO IKEKAWA, MITSUAKI SANO, MIDORI OKABE, FUMIKO FUKUOKA1975 Volume 23 Issue 9 Pages 2148-2150
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRelationship between the host-mediated antitumor effect and biogenic amines was investigated. Histamine and serotonin values in solid tumor of sarcoma 180 were periodically determined by fluorometric method. When treated with the antitumor active polysaccharide (EA5), significantly high histamine values were detected at the end of 2 weeks after tumor transplantation. Although some increase of the histamine value was also found at 2 and 3 weeks by treatment with the antitumor inactive polysaccharide (EA505) and/or cyclic adenosine monophosphate it was not significant in comparison with the remarkable increase in the antitumor active polysaccharide (EA5) treatment. Any remarkable increase of serotonin values in tumor tissues was not found.View full abstractDownload PDF (464K) -
SHOZO MIYAZAKI, MASAHIRO NAKANO, TAKAICHI ARITA1975 Volume 23 Issue 9 Pages 2151-2155
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGastrointestinal absorption of the free base and the hydrochloride of chlortetracycline (CTC) was studied in rats and human subjects. Following oral administration, the free base produced higher CTC levels in the body fluids than the hydrochloride. The difference between the bioavailability of the free base and that of the hydrochloride was due to the difference in the solubility characteristics at the gastric pH. Similar investigations were carried out with demethylchlortetracycline (DMCT) and methacycline (MOTC). The results indicated that plasma level after oral administration of MOTC base to rats was slightly higher than that of the hydrochloride and plasma levels of DMCT base and the hydrochloride were essentially identical. In the study comparing the cumulative amounts of MOTC base and the hydrochloride after oral administration to human subjects, the free base gave greater cumulative amounts than the hydrochloride in two of the three subjects.View full abstractDownload PDF (653K) -
TAKEMI YOSHIDA, KEIKO HOMMA, YASUO SUZUKI, MITSURU UCHIYAMA1975 Volume 23 Issue 9 Pages 2155-2157
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo examine the mechanisms of the inhibition of drug metabolizing enzyme activity by organophosphate insecticides, microsomal components of drug metabolizing system were determined after treatment with fenitrothion. Mice given intraperitoneal dose of fenitrothion exhibited the rapid decrease in cytochrome P-450 content and slight inhibition of NADPH-cytochrome c reductase activity. Administration of fenitrothion to phenobarbital-treated mice decreased in N-demethylation of aminopyrine as well as cytochrome P-450 content. The actual decrease in cytochrome P-450 content caused by fenitrothion in phenobarbital-treated mice was greater than non-treated mice. The results presented here strongly suggest that the inhibition of drug metabolizing enzyme by fenitrothion was due to the decrease in cytochrome P-450.View full abstractDownload PDF (425K) -
TAKAJI KOYAMA, TAKASHI HIROTA, CHIZUKO BASHOU, YOSHIKO SATOH, YASUKO W ...1975 Volume 23 Issue 9 Pages 2158-2161
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of ketones with trisformylaminomethane were described. Except pyrimidine derivatives reported by Bredereck, et al., few by-products were obtained. Thus methyl ethyl ketone (I) gave 4-ethylpyrimidine (III) and 5-methyl-4-(5-pyrimidinyl) pyrimidine (IV), diethyl ketone (V) gave 4-amino-3, 5-dimethylpyridine (VII), cyclohexanone (VIII) gave bis (5, 6, 7, 8-tetrahydro-8-quinazolinylidenemethyl) amine (X). 4-Methyl-5-phenylpyrimidine (XII) and 8-phenyl-5, 6, 7, 8-tetrahydroquinazoline (XIV) were obtained from phenylacetone (XI) and 2-phenylcyclohexanone (XIII) respectively. Dehydrogenation of (XIV) with sulfur afforded 8-phenylquinazoline (XV).View full abstractDownload PDF (535K) -
KENJI ISHII, YUKIO ANDO, YOSHIO UENO1975 Volume 23 Issue 9 Pages 2162-2164
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sample of moldy corn infected with Fusarium species was analyzed both chemically and biologically to elucidate the vomiting factor. With the aid of rabbit reticulocyte and ducking bioassays, 26 mg of deoxynivalenol, one of trichothecene mycotoxin, was isolated from 3.5 kg of the corn sample. The toxin was extracted with aqueous methanol and purified using solvent partitions and chromatographic separations.View full abstractDownload PDF (417K) -
TOSHIO NAMBARA, SHIGEO IKEGAWA, MOTOHIKO KATO1975 Volume 23 Issue 9 Pages 2164-2166
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (415K) -
YOSHIKAZU KONDO, KEIKO HOSOYAMA, TSUNEMATSU TAKEMOTO1975 Volume 23 Issue 9 Pages 2167-2168
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe steroidal toluene-p-sulfonyl esters have been cleaved rapidly to the corresponding alcohols by the photolysis in the presence of sodium borohydride. In this method, even cholesteryl toluene-p-sulfonate was converted into cholesterol without isosterol rearrangement.View full abstractDownload PDF (374K) -
KIKUO ISHIZUMI, KAZUO MORI, SHIGEHO INABA, HISAO YAMAMOTO1975 Volume 23 Issue 9 Pages 2169-2173
Published: September 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy ultraviolet (UV) irradiation in dimethyl sulfoxide (DMSO) or acetone tetrahydro-1, 4-benzodiazepines of type 1 and 6-chloro-1-cyclopropylmethyl-4-phenyl-1, 2, 3, 4-tetrahydroquinazolin-2-one (3) were oxidized to the corresponding dihydro compounds (2 and 4). 7-Chloro-1-methyl-5-phenyl-1, 3, 4, 5-tetrahydro-2H-1, 4-benzodiazepin-2-one (1b) was prepared from 4-acetyl-7-chloro-1-methyl-2, 3, 4, 5-tetrahydro-5-phenyl-1H-1, 4-benzodiazepine (5) by oxidation with potassium permanganate followed by acid hydrolysis. Oxidation of other types of 4-acylbenzodiazepine derivatives was also examined.View full abstractDownload PDF (714K)