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Volume 26, Issue 8
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KIYOKO TAKAMURA, MIZUHO SAKAMOTO1978 Volume 26 Issue 8 Pages 2291-2297
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSComplex formation of flavonoids (rutin, quercetin, flavocummelin and flavonol) with copper (II) was studied by spectrophotometry. These flavonoids have some possible chelating sites (such as 3-hydroxy-4-keto, 5-hydroxy-4-keto and 3, 4-o-dihydroxy groups denoted as site a, b, and c, respectively) depending on the number and position of hydroxyl substituents in their molecules. Absorption spectra of the flavonoid-copper (II) systems with the changes of Cu2+ concentrations were observed, and the molar ratio and continuous variation plots indicated the existence of only 1 : 1 complex in the flavonol-, flavocummelin-, and rutin-copper (II) systems, and both 1 : 1 and 1 : 2 types in the quercetin-copper (II) system. A comparison of the magnitudes of bathochromic shift was compared to consider the sites used for the complex formation. The 1 : 1 complex formation in the flavonol-copper (II) system appears to take place at site a whereas that of the flavocummelin-and the rutin-copper (II) systems at site b. In the case of quercetin, the initial complex formation seems to occur at site a and the subsequent complex formation at site c. In order to compare the relative stability of the flavonoid-copper (II) complexes, the free Cu2+ concentrations equilibrated in the mixed solutions of each flavonoid and copper (II) were determined by polarography. The relative stability decreased in the order of quercetin, flavonol, rutin, and flavocummelin.View full abstractDownload PDF (734K) -
SHIGERU GOTO, YOKIKO ODAWARA, MISAO NAKANO, YASUNORI ARAKI1978 Volume 26 Issue 8 Pages 2298-2304
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe binding of seven commercial diuretics with bovine serum albumin (BSA) was investigated at three different temperatures, 5°, 30° and 37°, by the equilibrium dialysis method and at 37° by the dynamic dialysis method. The binding data of diuretics were described on the basis that the sites per BSA molecule can be divided into two classes, except that of hydrochlorothiazide, and each class characterized by the binding constants, K1, n1, and K2, n2. The thermodynamic values, ⊿G°, ⊿H°, and ⊿S°for the primary site of binding were determined, and were discussed on the basis of the fact that a hydrophobic interaction is formed between diuretics and BSA. It was also shown that there are sizable negative entropy and enthalpy changes in the binding of ethacrynic acid and BSA, and that hydrochlorothiazide is bound very weakly with BSA and has a remarkable diffusion pattern through cellulose membrane in the dynamic dialysis.View full abstractDownload PDF (782K) -
KYUYA OKAMURA, SHUNICHI YAMADA1978 Volume 26 Issue 8 Pages 2305-2311
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe asymmetric synthesis of (3S 15S 20R)-(-)-yohimbone (III) was accomplished. The key reactions in the process are : (i) the asymmetric Pictet-Spengler reaction of L-tryptophan (IV) with sodium 3-(m-methoxyphenyl) glycidate (V) (1, 3-asymmetric induction), and (ii) the elimination of the chiral center derived from IV (1, 3-transfer of asymmetry). The latter was conveniently achieved by converting the cyclic α-amino acid amide (XIIIa) to the pentacyclic α-amino nitrile (XIV), followed by reductive decyanization with sodium borohydride. Thus, the indole alkaloids, natural yohimbol (XX) and natural corynantheine (XXI), may be synthesized from L-tryptophan.View full abstractDownload PDF (831K) -
HIROSHI TOMISAWA, HIROSHI HONGO, HIDEKI KATO, REIKO FUJITA, AKIRA SATO1978 Volume 26 Issue 8 Pages 2312-2315
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStudies on the Diels-Alder reaction of 1-methyl-2 (1H)-pyridone (I) with fumaric acid and its ester were carried out. Reaction of I with dimethyl fumarate in toluene gave dimethyl 2-methyl-3-oxo-2-azabicyclo [2. 2. 2] oct-7-ene-5-endo-6-exo-dicarboxylate (IV) in about 4% yield. Boiling of I and fumaric acid in water afforded 6-methyl-7-oxo-6-azabicyclo [3. 2. 1] oct-2-ene-2, 8-endo-dicarboxylic acid (VII) in about 20% yield.View full abstractDownload PDF (499K) -
AKIRA AKAHORI, MASAO MASUI, MASANORI ANDO1978 Volume 26 Issue 8 Pages 2316-2320
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCarbon tetrachloride (CCl4) was orally administered to female C57BL mice (0.02, 0.1, 0.5, 1.0 or 1.5 ml/kg). Activities of serum glutamic oxaloacetic transaminase (SGOT) were recorded at 15, 24, 39, 48, 63, 72 and 87 hr after administration. SGOT levels rose more slowly but reached higher maximum levels later in mice given higher doses of CCl4. Therefore, an inverse dose response was observed at earlier times after drug administration. This phenomenon was observed also in female C3H mice and male and adrenalectomized female C57BL mice.View full abstractDownload PDF (682K) -
MASATOSHI YAMATO, KUNIKO HASHIGAKI, KUMIKO MITO, TAKAJI KOYAMA1978 Volume 26 Issue 8 Pages 2321-2327
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn the basis of the information from our previous studies on structure-sweetness relationships of phyllodulcin and related 3, 4-dihydroisocoumarins, syntheses of sweet flavanones and dihydrochalcones are designed. 5-Hydroxyflavanones, VII, IX, and X, and dihydrochlacone XIII has a sweet taste and the others are tasteless. The structuresweetness relationships of these compounds are discussed. It is considered that the mode of interaction of 5-hydroxyflavanones and Dihydrochalcone (DHC) lacking glycoside group with a sweet receptor seems to be similar to that of 3, 4-dihydroisocoumarins.View full abstractDownload PDF (701K) -
KOICHI MIYANO, TAKEJI SAKASAI, HIROAKI HAMANO1978 Volume 26 Issue 8 Pages 2328-2333
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe improved synthesis of 5-(4-chlorobutyl) picolinic acid (II), the potent dopamine β-hydroxylase inhibitor, was reported. The key intermediate, 2-cyclopropyl-5-cyclopropylcarbonylpyridine (IV) was converted to 5-(4-chlorobutyl)-2-cyclopropylpyridine (VII), which was directly oxidized with nitric acid to give II. Similarly, fusaric acid (I) was synthesized from 2-cyclopropyl-5-(cyclopropylhydroxy) methylpyridine (V).View full abstractDownload PDF (778K) -
TETSUO MIYADERA, HARUMITSU KUWANO, YOICHI KAWANO, RYUJI TACHIKAWA1978 Volume 26 Issue 8 Pages 2334-2339
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBenzo [c]-and benzo [α] quinolizinium bromides (X and XIII) were reacted with phenylmagnesium bromide in order to examine their chemical reactivities. Ring opening reactions occurred with preferential attack of the nucleophile at C-1 for X and C-4 for XIII to give phenylbutadienylquinoline (XII) and isoquinoline (XV), respectively. In connection with the structural determination of XII and XV, the nuclear magnetic resonance spectra of phenylbutadienylpyridine derivatives (VII and its derivatives) were compared with calculated spectra. The calculated band positions and intensities of the olefinic protons are in accord with the observed values.View full abstractDownload PDF (677K) -
AKIRA MATSUDA, HIDEO INOUE, TOHRU UEDA1978 Volume 26 Issue 8 Pages 2340-2345
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 5-bromocytidine or its 2', 3', 5'-tri-O-acetate, and 2', 3'-O-isopropylidene derivative with sodium cyanide gave the respective 6-cyanocytidine. Methoxide treatment of the 6-cyano compound gave methyl cytidine-6-carboximidate which was converted to cytidine-6-carboxylic acid. Treatment of 2', 3'-O-isopropylidene-N4-acetyl-5-bromocytidine with sodium cyanide afforded the O6, 5'-cyclo-N4-acetylcytidine through the 6-cyanocytidine as the intermediate.View full abstractDownload PDF (775K) -
KUNITOSHI YOSHIHIRA, MASAMICHI FUKUOKA, MASANORI KUROYANAGI, SHINSAKU ...1978 Volume 26 Issue 8 Pages 2346-2364
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSToxicity tests to experimental animals and cultured HeLa cells were performed on the extracts of young fronds of bracken, Pteridium aquilinum var. latiusculum, aiming the isolation and characterization of the carcinogen (s) and the cattle poison (s). The separation of the extracts monitored by cytotoxicity tests resulted in the isolation of more than twenty kinds of sesquiterpenes having 1-indanone nucleus, named pterosins, and their glucosides, pterosides, and several known phenolics and steroids. Although the dried fronds and rhizomes of the fern exhibited carcinogenicity by feeding to rats, none of the extracts and the fractions along with pterosin B and pteroside B, major indanones, induced tumors under the employed conditions.View full abstractDownload PDF (1633K) -
MASAMICHI FUKUOKA, MASANORI KUROYANAGI, KUNITOSHI YOSHIHIRA, SHINSAKU ...1978 Volume 26 Issue 8 Pages 2365-2385
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of twenty-four sesquiterpenes isolated from the young fronds were disclosed by chemical and physical methods. The stereostructures were established as 1-22 by degradation and correlation reactions and physical data.View full abstractDownload PDF (2430K) -
KIYOSHIGE OCHI, ISAO MATSUNAGA, MINORU SHINDO, CHIKARA KANEKO1978 Volume 26 Issue 8 Pages 2386-2390
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom 5α-cholestane-3α, 24 (R)- or -3α, 24 (S)-diol (2a and 2b) obtained from lithocholic acid in the previous work, both 24-epimers of 1α, 24-dihydroxycholesterol (6a and 6b) were synthesized. Thus, syntheses of these compounds were accomplished by dehydrogenation of the diols with dichlorodicyanobenzoquinone followed by the 1α-hydroxylation of the resulted 1, 4-dien-3-ones (3a and 3b) by the three-step procedure originally uncovered by one of the present authors (C. K.). The last step in the above transformation, the modified procedure reported recently by Ikekawa's group : oxymercuration-demercuration, was used. An alternative preparation of 1α, 24ξ-dihydroxycholesterol (6) either from lithocholic acid or from hyodeoxycholic acid was also described.View full abstractDownload PDF (688K) -
NOBUYUKI YAMAJI, KYOKO TAHARA, MOTOHIKO KATO1978 Volume 26 Issue 8 Pages 2391-2395
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBecause of the presence of etheno group, the reactivity of mercapto residue at 2 position in purine skeleton is so high that 2-chloro-1, N6-etheno adenosine 3', 5'-cyclic phosphate (2-chloro-1, N6-etheno c-AMP) and 2-iodo-1, N6-etheno c-AMP were easily synthesized from 2-mercapto-1, N6-etheno c-AMP. The deblocking reaction of the etheno group from these two halogenated products with N-bromosuccinimide (NBS) gave 2-chloro-c-AMP and 2-iodo-c-AMP. When 2-amino-c-AMP, which was synthesized from 2-amino-1, N6-etheno c-AMP by the same deblocking reaction, was diazotized with sodium nitrite in 42% fluoroboric acid (HBF4) at -10--20°, 2-fluoro-c-AMP was obtained in a yield of 17.8%. Since 2-bromo-c-AMP has been similarly obtained in previous work, the deblocking reaction of etheno group offers an excellent new route to synthesis of 2-halogeno-c-AMPs from c-AMP.View full abstractDownload PDF (733K) -
SEIICHI UESUGI, SHOJI TANAKA, EIKO OHTSUKA, MORIO IKEHARA1978 Volume 26 Issue 8 Pages 2396-2406
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPolymerization of tri (adenylic acid) bearing a 2'-O-(o-nitrobenzyl) group and a 3'-phosphate group at the 3'-end (A-A-A-NBD) was attempted in the presence of poly (uridylic acid), poly (U), using water-soluble carbodiimide. The nitrobenzyl group can be removed photochemically under mild conditions. A reaction containing the trimer and poly (U) in 1 : 2 ration at 0°for 15 days gave polymerized products (up to the 9-mer) in 14% yield and was proved to be dependent on the template. Raising the reaction temperature to 15°accelerated the polymerization rate. Reaction with a doubled trimer concentration at 0°did not improve the polymerization yield. Although the newly formed phosphodiester linkage was exclusively 3'-5', some isomerization (7%) to 2'-5' linkages seems to occur at bonds adjacent to free 2'-hydroxyl groups. As a side product, cyclic tri-(adenylic acid), which was formed by intramolecular condensation, was obtained in these reactions and in control reactions without template.View full abstractDownload PDF (1248K) -
AKIRA UENO, KIYOSHI HIRAKAWA, SEIGO FUKUSHIMA, TADATAKA NORO, KUNIO MO ...1978 Volume 26 Issue 8 Pages 2407-2410
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew 2-alkylchromone derivatives were isolated from the epigeal part of Sophora flavescens AITON. These compounds were obtained as a mixture of 2-n-heneicosyl-5, 7-dihydroxy-6, 8-dimethylchromone, 2-n-tricosyl-5, 7-dihydroxy-6, 8-dimethoxychromone and the homologous compounds, in which 2-alkyl groups are n-undecyl, n-tridecyl, n-pentadecyl, n-heptadecyl and n-tricosyl. Their structures were clarified by the spectral and chemical data, and the synthesis of 2-n-heptadecyl-5, 7-dihydroxy-6, 8-dimethylchromone.View full abstractDownload PDF (585K) -
AKIRA UENO, YUKINOBU IKEYA, SEIGO FUKUSHIMA, TADATAKA NORO, KUNIO MORI ...1978 Volume 26 Issue 8 Pages 2411-2416
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new flavone derivative named desmodol was isolated together with N, N-dimethyltryptamine, bufotenine and bufotenine N-oxide from the roots and stems of Desmodium caudatum DC. The structure of desmodol was presented to be 5-hydroxy-6-methyl-8, 8-dimethyl-2-(3, 4-dihydroxyphenyl)-4H, 8H-benzo [1, 2-b : 3, 4-b'] dipyran-4-one (5, 3', 4'-trihydroxy-6-methyl-8, 8-dimethylpyrano (2, 3-h)-flavone) by the spectral and chemical data.View full abstractDownload PDF (763K) -
MICHINAO MIZUGAKI, HARU FUKUYAMA, TAKAO SAKAMOTO, HIROSHI YAMANAKA1978 Volume 26 Issue 8 Pages 2417-2421
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-Hydroxydodec-cis-3-enoic acid was synthesized to identify a metabolite of ricinoleic acid by Escherichia coli and to use it as substrate in the investigation on unsaturated fatty acid metabolism. In a total synthesis of the 6-hydroxy acid, the key step involved the reaction of the trialkynylborane with ethyl diazoacetate. Dec-1-yn-4-ol was lithiated after protection of the hydroxyl group with dihydropyran, and was transformed into the trialkynylborane by treating with boron trifluoride etherate. The subsequent reaction with ethyl diazoacetate afforded the 6-hydroxy-3-ynoate, which was hydrogenated over Lindlar catalyst to yield 6-hydroxydodec-3-cis-enoic acid. The results obtained by gas chromatography-mass spectrometry (GC-MS) showed that the final metabolite of ricinoleic acid by E. coli was identical with the synthetic 6-hydroxy acid.View full abstractDownload PDF (628K) -
HIROAKI TAKAYAMA, TOSHIHIKO OKAMOTO1978 Volume 26 Issue 8 Pages 2422-2427
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of N-methoxypyridinium iodide with nitromethane, nitroethane, and 1-nitropropane in the presence of sodium ethoxide in anhydrous ethanol afforded 1-methoxyimino-6-nitrohexa-2, 4-diene, 1-methoxyimino-6-aci-nitrohepta-2, 4-diene, and 1-methoxyimini-6-aci-nitroocta-2, 4-diene, respectively. The spectral behaviors of these products were discussed in relation to the nitro-acinitro prototropy and the assumed reaction mechanism was also offered.View full abstractDownload PDF (683K) -
AKIO OHSAWA, TOMIO UEZU, HIROSHI IGETA1978 Volume 26 Issue 8 Pages 2428-2434
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSide-chain lithiation with lithium diisopropylamide and subsequent alkylation of various alkylpyridazines have been investigated. The lithiated side chains of alkylpyridazines were alkylated efficiently with alkyl halides.View full abstractDownload PDF (807K) -
HIROAKI TAKAYAMA, TOSHIHIKO OKAMOTO1978 Volume 26 Issue 8 Pages 2435-2441
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of N-methoxy quinolinium methosulfate with malononitrile in dimethylsulfoxide afforded 2-and 4-dicyanomethylene-quinoline (II and III), N-methoxy-2- and 4-dicyanomethylene-quinoline (IV and V) in addition to quinoline and quinoline-1-oxide. The reaction at the higher temperature (100-110°) gave anomalous products (VI and VII). The assumed reaction mechanism was offered.View full abstractDownload PDF (789K) -
TOSHIRO IBUKA, YUJI MORI, YASUO INUBUSHI1978 Volume 26 Issue 8 Pages 2442-2448
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSdl-Pumiliotoxin C (1) was stereoselectively synthesized via 5β-methyl-cis-decahydroquinoline-2, 7-dione (5) which was prepared in two routes. The Diels-Alder reaction of 1, 3-bis (trimethylsiloxy)-5-methylcyclohexa-1, 3-diene (6) with acrylonitrile gave the cycloadducts (7) from which anti-8-methyl-exo-2-cyanobicyclo [2. 2. 2] oct-5-en-1-ol (2) was obtained in four steps. Treatment of the compound (2) with acid gave the keto-lactam (5). The Diels-Alder reaction of 1, 3-bis (trimethylsiloxy)-1, 3-butadiene (11) with ethyl crotonate furnished the adduct (12) from which the keto-lactam (5) was obtained via the compound (19) in seven steps. Reduction of the carbonyl group at the C7 position and introduction of the n-propyl group at the C2 position of the keto-lactam (5) gave dl-pumiliotoxin C.View full abstractDownload PDF (996K) -
MORIO IKEHARA, HIROKO MIKI1978 Volume 26 Issue 8 Pages 2449-2453
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS9-(2'-O-Methanesulfonyl- or trifluoromethanesulfonyl-3', 5'-di-O-tetrahydropyranyl-β-D-arabinofuranosyl) adenine (Ia, b) were reacted with lithium chloride or tetrabutylammonium halide to yield 2'-halogeno-2'-deoxy compounds (IIa-d). These halogeno compounds were deprotected with 80% acetic acid to give 2'-chloro-, 2'-bromo-, 2'-fluoro and 2'-iodo-2'-deoxyadenosine (IVa-d) in overall yields of 12-25% from the compound I. Ultraviolet absorption properties, 1H and 13C-nuclear magnetic resonance spectral properties were recorded on the compounds IVa-d.View full abstractDownload PDF (676K) -
KOHKI TAKASHIMA, TETSUJI MORI, KAZUAKI OHYAMA, SYUJI NITTA, SHIGEYUKI ...1978 Volume 26 Issue 8 Pages 2454-2457
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hypocholesterolemic activities of LK-903 (α-methyl-p-myristyloxycinnamic acid-1-monoglyceride) and clofibrate were examined in miniature pigs (OHMINI-875) and beagle dogs. When administered in the diet for one week, LK-903 and clofibrate were active in the miniature pig at doses of 5 and 10 mg/kg/day, respectively, whereas the two drugs showed no hypocholesterolemic activity in the beagle dog. In cynomolgus monkeys, LK-903 showed a hypocholesterolemic effect, but serum cholesterol depression was less marked than in the miniature pig.View full abstractDownload PDF (530K) -
HARUJI OSHIO, YOSHITOMO NARUSE, MAKOTO TSUKUI1978 Volume 26 Issue 8 Pages 2458-2464
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA study on the estimation of sennosides and derivatives of oxyanthraquinones in rhubarb and senna is described. After extracing a ground crude drug with the mixture of calcium acetate buffer and tetrahydrofuran (THF), the extract was fractionated to aqueous and THF phases. Both fractions were heated with sulfuric acid to hydrolyze the glycosides contained, and the resulting aglycones were extracted with ether. The aqueous fraction containing sennidins and rhein was analyzed by spectrophotometry. The THF fraction containing only oxyanthraquinones was analyzed by densitometry on a thin-layer plate. It was suggested that sennosides were the main purgative principles of rhubarb or senna, and that oxyanthraquinones had little contribution to the activities of crude drugs. The qualities of rhubarbs varied more markedly than those of sennas. It was clarified that the activities of crude drugs in mice correlated closely to the contents of sennosides. One can, therefore, estimate the purgative activity roughly from the contents of sennosides.View full abstractDownload PDF (758K) -
HIROSHI SAKAGUCHI, HIROSHI ANZAI, KIMIO FURUHATA, HARUO OGURA, YOICHI ...1978 Volume 26 Issue 8 Pages 2465-2474
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal structure of fac-[bis-(adeninato)(dien) copper (II)] monohydrate has been determined from three-dimensional X-ray diffractometer data by heavy atom Fourier methods. Crystals of fac-[Cu (Ade)2 (dien)]·H2O are monoclinic with unit cell dimensions a=16.015 (2), b=14.577 (2), c=7.959 (1) A, β=90.11 (1)°, space group P21/n, and Z=4. Block-diagonal least-squares refinement using 2695 independent reflexions yielded the R value of 0.068. The copper ion assumes a distorted square pyramidal coordination with five coordination sites of which four square planar sites are occupied by the nitrogen N (9) atoms of two unidentate adenine monoanions and the two (terminal and central) nitrogen atoms of tridentate dien, and the axial site (apical position) is occupied by another terminal nitrogen atom of dien. Therefore, the present dien-copper (II) complex takes a bent form (facial coordination). The propensity of adenine to occupy the cis position in equatorial plane of the copper (II) coordination is much stronger than that of dien to take a planar coordination form.View full abstractDownload PDF (949K) -
TETSUYA AONO, MASAYUKI IMANISHI, YASUHIKO KAWANO, SHOJI KISHIMOTO, SHU ...1978 Volume 26 Issue 8 Pages 2475-2482
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhenoxy-1-indancarboxylic acids (II and III) and (2-thienylcarbonyl)-1-indancarboxylic acids (V, VI and VII) were synthesized via the corresponding phenoxy- and (2-thienylcarbonyl)-1-indancarbonitriles (XII, XVII and XXIII). The relationship between the antiinflammatory activity and the stereochemical features of the substituents of the compounds synthesized was also discussed.View full abstractDownload PDF (967K) -
KUNIO MORINAGA, AKIRA UENO, SEIGO FUKUSHIMA, MICHIO NAMIKOSHI, YOICHI ...1978 Volume 26 Issue 8 Pages 2483-2488
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new stereoisomer (I) of (-)-sophocarpine (II) was isolated from epigeal part of Sophora flavescens. The relative configuration and stereochemistry were determined by X-ray diffraction studies with monohydrate of free base. The absolute configuration was elucidated by chemical interrelation of I with (+)-matrine (III) and (+)-allomatrine (IV) of known absolute configuration.View full abstractDownload PDF (710K) -
HITOSHI SEKIKAWA, RYOHEI HORI, TAKAICHI ARITA, KEIJI ITO, MASAHIRO NAK ...1978 Volume 26 Issue 8 Pages 2489-2496
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPolyvinylpyrrolidone (PVP) aqueous solution exhibited coacervation by addition of some inorganic salts and organic compounds. The cloud point of PVP K-90 solution appeared by addition of the least amount of ammonium sulfate, among PVP K-15, K-30 and K-90. Effect of some aromatic compounds on the cloud point of PVP aqueous solution containing ammonium sulfate was investigated. The extent of the aromatic compounds to lower the cloud point of PVP solution differed depending upon their functional groups, number of their substituents, and mutual position of the substituents. Urea derivatives elevated the cloud point, its extent being increased with the number of substituted methyl groups. Thiourea derivatives, on the other hand, lowered the cloud point. The order of the compounds to lower the cloud point was in parallel with the order of extent of interaction studied by the equilibrium dialysis method.View full abstractDownload PDF (933K) -
SADAO NISHIGAKI, YUKAKO KANAMORI, KEITARO SENGA1978 Volume 26 Issue 8 Pages 2497-2501
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 6-hydroxyamino-1, 3-dimethyluracil (1) with Vilsmeier reagent (phosphorus oxychloride and dimethylformamide) or arylaldehydes afforded 5, 7-dimethyl-isoxazolo [3, 4-d] pyrimidine-4, 6 (5H, 7H)-dione (2) and its 3-aryl derivatives (10-17), respectively. The 3-arylisoxazolo [3, 4-d] pyrimidines (9, 10) underwent photorearrangement to yield the corresponding 2-aryloxazolo [4, 5-d] pyrimidines (19-20). Some reactions on 2 are also reported.View full abstractDownload PDF (550K) -
KIKUO SASAJIMA, KEIICHI ONO, JUNKI KATSUBE, HISAO YAMAMOTO1978 Volume 26 Issue 8 Pages 2502-2507
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new synthesis of 2'-amino-4'-fluoro-4-[4-hydroxy-4-(α, α, α-trifluoro-m-tolyl) piperidino] butyrophenone using a selective ortho-amination as a key step was described. The solvents and temperature effects on the selectivity for this ortho-amination of 2', 4'-difluoro-4-[4-hydroxy-4-(α, α, α-trifluoro-m-tolyl) piperidino] butyrophenone were investigated.View full abstractDownload PDF (687K) -
CHIKARA KANEKO, REIKO HAYASHI, MASAMI YAMAMORI, KUNIHIRO TOKUMURA, MIC ...1978 Volume 26 Issue 8 Pages 2508-2514
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photolysis of 6-cyanophenanthridine 5-oxide (1) in various solvents was reported. In addition to the expected 6-cyanodibenz [d, f] [1, 3] oxazepine (2), two new types of rearrangement products : 5-alkoxyphenanthridin-6 (5H)-one (3), as a byproduct in the photolyses using an aprotic solvent, were obtained in the present experiments. In order to account for the formation of these products (3 and 9), reasonable assumptions that the oxygen walk process from the oxaziridine species (11) leading to the oxazepine (2) is relatively inhibited to occur and thus 11 has a longer life time as compared to the related oxaziridines derived from α-cyanated bicyclic amine N-oxides were proposed. A mechanistic rationalization and characteristic features in the photochemical rearrangement reactions of 1 are discussed in detail, together with the structure determinations of the photoproducts.View full abstractDownload PDF (832K) -
KAORU FUJI, TOSHIHIDE YAMADA, EIICHI FUJITA, HIROYUKI MURATA1978 Volume 26 Issue 8 Pages 2515-2521
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe basic components of Lagerstroemia subcostata collected on Amami-ohshima Island and two slightly different types of Lagerstroemia fauriei collected on Tanegashima Island were investigated. We distinguished the two types by calling them L. fauriei and L. fauriei (Tanegashima-type). Four new alkaloids, lasubine-I (12), -II (14), subcosine-I (15), and -II (16), all of which belong to type E, were isolated from the former. From the latter two, however, lythrine (3), cryogenine (17), and lythridine (18), all of which belong to type C, were isolated. L. fauriei has been classified as L. subcostata var. fauriei by S. Hatusima, but from the chemotaxonomical aspect, it shows prominent differences from L. subcostata. Thus their classification under species would be more appropriate.View full abstractDownload PDF (845K) -
MASANORI SOMEI, MARI MATSUBARA, YOSHIHIRO KANDA, MITSUTAKA NATSUME1978 Volume 26 Issue 8 Pages 2522-2534
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel N-amination method was investigated under various conditions and optimum reaction condition was established. The method was successfully applied for the synthesis of 1-aminoindoles, 1-aminobenzimidazole, and 9-aminopurines. Some chemical reactivity of 9-aminopurines was investigated.View full abstractDownload PDF (1541K) -
TAKASHI YOSHIDA, JUNKO NOBUHARA, MICHIKO UCHIDA, TAKUO OKUDA1978 Volume 26 Issue 8 Pages 2535-2542
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new piscicidal sesquiterpenes, buddledin A (1) and B (2), have been isolated from the root bark of Buddleja davidii FRANCH. These structures have been deduced on the basis of spectroscopic and chemical evidences, and confirmed by X-ray analysis of the bromohydrin (8). The absolute configuration was determined by the applications of benzoate rule and dibenzoate chirality rule. Buddledin A and B are the first examples of toxic compounds possessing the caryophyllene skeleton.View full abstractDownload PDF (1032K) -
TAKASHI YOSHIDA, JUNKO NOBUHARA, NATSUKO FUJII, TAKUO OKUDA1978 Volume 26 Issue 8 Pages 2543-2549
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFurther toxic principle, buddledin C, and two additional sesquiterpenes, buddledin D and E, have been isolated from the root bark of Buddleja davidii FRANCH. The structures of buddledin C and D have been determined to be 3 and 4 by chemical transformation of buddledin A into buddledin D and dihydrobuddledin C (6), and by comparisons of their spectral data with those of buddledin A and its cis-isomer (8), which was obtained by the photoisomerization of 1. Structure 5 has been assigned for buddledin E by its spectral data and deuteration experiment.View full abstractDownload PDF (772K) -
AKIO OHSAWA, YOSHIHITO ABE, HIROSHI IGETA1978 Volume 26 Issue 8 Pages 2550-2554
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlkyl- and arylpyridazines have been prepared by cross-coupling reaction between chloropyridazines and Grignard reagents in the presence of nickel-phosphine complexes (as catalysts). Hitherto unaccessible naphthyl- and thienylpyridazines have been obtained.View full abstractDownload PDF (618K) -
MAKIKO SUGIURA, NARAO TAKAO, HIDEAKI FUJIWARA, YOSHIO SASAKI1978 Volume 26 Issue 8 Pages 2555-2561
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe nitrogen inversion rate of 1, 2, 3, 4, 6, 7-hexahydro-11bH-benzo [α] quinolizine (I) is determined by means of line broadening of 13C FT nuclear magnetic resonance under the successive alteration of pD. The ktrans thus obtained was confirmed to be reasonable but kcis was presumed to be smaller than the actual one, which is responsible to the difference of pKa between trans- and cis "a"-conformer. Actually, it was realized for benzo [α]-quinolizidines that trans-conformer takes lower pKa than that of cis "a"-conformer because of the steric effect.View full abstractDownload PDF (740K) -
YOSHIAKI KISO, HIROKO ISAWA, KOUKI KITAGAWA, TADASHI AKITA1978 Volume 26 Issue 8 Pages 2562-2564
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe use of thioanisole as a scavenger was found to suppress a side reaction when the O-protecting groups of tyrosine were deblocked under the acidic conditions. This good result gives a promising outlook for the synthesis of tyrosine-containing peptides by solid-phase method.View full abstractDownload PDF (503K) -
KOJI KURODA, TERUYOSHI YOKOYAMA, TSUNEO UMEDA, YASUSHI TAKAGISHI1978 Volume 26 Issue 8 Pages 2565-2568
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSForm I, form II, and CHCl3-II type of acetohexamide are obtained by recrystallization from different solvents. X-ray diffraction patterns, infrared spectra, and differential scanning calorimeter curves of the CHCl3-II type are identical with those of form II, but CHCl3-II type contains a chloroform molecule, which cannot be removed by normal drying condition, and CHCl3-II type seems unsuitable for medical use. The solubility of form II is 1.2 times that of form I.View full abstractDownload PDF (524K) -
MASAYOSHI YAMAGUCHI, TAKEO YAMAMOTO1978 Volume 26 Issue 8 Pages 2568-2571
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe change of calcium concentrations in the serum, liver, and bile of rats was investigated after a single oral administration of calcium chloride. The administration of calcium produced a corresponding increase of calcium concentration in the serum and liver, and this increase was dose dependent. A remarkable elevation of calcium content in the bile was caused by the administration of calcium. By the ligation of bile duct, the calcium concentration in the serum was markedly enhanced after the administration of calcium (10 and 50 mg/100g) when compared with that of the sham-operated rats. These results suggest that the excretion of calcium into the bile prevents the elevation of calcium concentration in the serum after the absorption of calcium from the intestine.View full abstractDownload PDF (540K) -
TOSHIHIKO OZAWA, AKIRA HANAKI1978 Volume 26 Issue 8 Pages 2572-2575
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe spin trap, 5, 5-dimethyl-1-pyrroline-1-oxide has been used to detect the OH radical produced by the Haber-Weiss reaction between superoxide ion and hydrogen peroxide. In the presence of a small amount of H2O2, the OH radical adduct can be detected by electron spin resonance spectroscopy, while, H2O2 being added excessively, the HO2 radical adduct can be detected.View full abstractDownload PDF (530K) -
HIROAKI TAKAYAMA1978 Volume 26 Issue 8 Pages 2575-2578
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical transformations of 1-methoxyimino-6-nitrohexa-2, 4-diene (II), resulted from the reaction of N-methoxypyridinium iodide (I) with nitromethane, were examined in relation to the nitro-aci-nitro prototropy. II reacted with diazomethane to afford methyl 1-methoxyimino-hexa-2, 4-diene-6-acinitronate (III), with acetic anhydride and with benzoyl chloride to give O-acetate and O-benzoate of 1-methoxyimino-hexa-2, 4-diene-6-hydroxamic acid (VI) respectively. The ultraviolet spectra of them were correlated to their structures.View full abstractDownload PDF (567K) -
NORIICHI ODA, KAZUHIRO KOBAYASHI, TAISEI UEDA, ISOO ITO1978 Volume 26 Issue 8 Pages 2578-2581
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiels-Alder reaction of 5-nitro-1, 4-naphthoquinone (1) and unsymmetrical butadienes was carried out. Reaction of 1 and 2-methyl-1, 3-butadiene gave 1, 4, 4a, 9a-tetrahydro-2-methyl-5-nitro-anthraquinone (2) and its 3-methyl analogue (3) at the ratio of 9.2 : 1. Reaction of 1 and 1, 3-pentadiene gave 1, 4, 4a, 9a-tetrahydro-1-methyl-8-nitroanthraquinone (8) and its 5-nitro analogue (9) at the ratio of 10 : 7. Their structures have been determined by aromatization to methyl-nitroanthraquinones.View full abstractDownload PDF (578K) -
MOTOICHI MIYAZAKI, HIROMI FUKUMOTO, SUGAKO YAMADA, NOBORU OKUBO1978 Volume 26 Issue 8 Pages 2582-2585
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSpectrophotometric studies on the complex formation between Fe2+ ion and three kinds of aryl β-ketoimines derived from 2, 4-pentanedione and anilin were reported. Spectra of these Fe (III)-ketoimine complexes revealed similar features to that of tris (2, 4-pentanedionato) iron (III) in 80% EtOH. The composition, equilibrium constant and stability constant were also determined for the complexes.View full abstractDownload PDF (577K) -
YASUNORI MORIMOTO, TOKIKO IZUMI, TAKAICHI ARITA1978 Volume 26 Issue 8 Pages 2585-2588
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffect of pyrazolone derivatives on the critical micelle concentration (cmc) of surfactants was investigated by using ionic surfactants which were sodium dodecyl sulfate (SDS) and dodecyl N-dimethylethylammonium bromide (DDAB). It is shown that antipyrine and 4-aminoantipyrine which are very water soluble is in breaking up micelles of SDS and DDAB. However, addition of phenylbutazone which is very slightly soluble in water results in increase in stability of the micelles. It is presumed from these results that the affinity of these additive for water plays an important role in stability of the micelles.View full abstractDownload PDF (536K) -
TAKEFUMI MOMOSE, OSAMU MURAOKA1978 Volume 26 Issue 8 Pages 2589-2593
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Baeyer-Villiger oxidation of 3β-benzoylbicyclo [3. 3. 1] nonane (1), 8β-benzoylbicyclo [4. 3. 1] decane (2), and 3β-benzoylbicyclo [3. 2. 1] octane (3) is described. The ratio of the main product bicycloalkyl benzoate to its isomeric product phenyl bicycloalkanecarboxylate was determined to be ca. 10 : 1 by the 1H-NMR measurement of the crude mixture. The Baeyer-Villiger reaction of cyclohexyl phenyl ketone (11) was also carried out and was found to give a similar result in its isomer ratio of the products. The high selectivity in this oxidation enabled the practicable preparation of bicyclo [3. n. 1] alkan-3-ones via bicyclo [3. n. 1] alk-3β-yl phenyl ketones to be achieved.View full abstractDownload PDF (645K) -
TOSHIO IMANARI, YUKO ISHIDA, KAZUICHI HAYAKAWA, MOTOICHI MIYAZAKI1978 Volume 26 Issue 8 Pages 2594-2595
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSuperoxide dismutase (SOD)-like activity was found in rabbit plasma and the active substance was separated. Its properties were similar to those of copper-zinc SOD in cyanide and azide sensitivity and heat-stability, but its molecular weight was presumed to be 140000 by Sephadex G-150 column.View full abstractDownload PDF (339K) -
SHINICHIRO SAKAI, NOBUO SHINMA1978 Volume 26 Issue 8 Pages 2596-2598
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHeteroyohimbine alkaloids, akuammigine and 3-isorauniticine, were synthesized using a modified Polonovski reaction followed by NaCNBH3 reduction from desmethylhirsuteine N-oxide, which was derived from the indole alkaloid hirsuteine. Corynanthe alkaloid, corynantheidine was also synthesized using the same method from hirsuteine N-oxide.View full abstractDownload PDF (457K) -
ISHII HISASHI, TSUTOMU ISHIKAWA1978 Volume 26 Issue 8 Pages 2598-2600
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew coumarins, arnocoumarin (1) and arnottiacoumarin (2), were isolated from X. arnottianum MAXIM. The structures of these coumarins were established by chemical transformation from marmesin (7) and rutaretin methyl ether (10) respectively.View full abstractDownload PDF (496K) -
TOSHIKO SATAKE, TAKAO MURAKAMI, YASUHISA SAIKI, CHIUMING CHEN1978 Volume 26 Issue 8 Pages 2600-2602
Published: August 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDie oberirdischen Teilen von Lindsaea ensifolia Sw. enthalten neben einem bereits bekannten Flavon-C-Glykosid, Vitexin ein neuartiges Chromen-Derivat, Lindsaeasaure (I), deren Struktur durch spektroskopische Methoden aufgeklart wird.View full abstractDownload PDF (485K)
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