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Volume 32, Issue 11
Displaying 1-50 of 69 articles from this issue
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MASAYUKI NAKAGAKI, MOTOKO SAKAI, TETSUROU HANDA1984 Volume 32 Issue 11 Pages 4241-4251
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotoelectron transfer from tris (hydroxymethyl) aminomethane (Tris) to methyl orange (MO) or methyl yellow (MY) as an electron acceptor was studied with α, β, γ, δ-tetraphenyl porphyrin (TPP) and α, β, γ, δ-tetraphenyl porphyrin trisulfonic acid (TPPS) as sensitizers. The reaction efficiency was reduced when the sensitizer was solubilized in heptaethyleneglycol dodecyl ether (HED) micelles. The partitioning of the sensitizers (TPP, TPPS) and the electron acceptors (MO, MY) was estimated by means of absorption spectral measurements in the micellar solution. At HED concentrations above 0.5 mM in aqueous solution, the sensitizers (TPP, TPPS) were completely solubilized in the micellar phase and thus the reaction environment was transferred from the aqueous phase to the micellar phase. The decrease of the reaction rate in the micellar environment can be explained in terms of the lower polarity in the micellar phase which inhibits charge separation in the sensitizer-acceptor excited complex (exciplex). The reaction rate of the TPPS-MO system was the highest and that of the TPP-MY system was the lowest in the micellar phase, because the former system was accommodated in a rather polar micellar environment, while the latter system was located in a less polar micellar environment. It was also observed that an increase in micellar concentration resulted in a decrease of the reaction rate. This was found to be caused by the decreases in the local concentrations of sensitizer and acceptor, not by a change of the reaction environment.View full abstractDownload PDF (894K) -
TAKASHI FUJII, MUTSUKO OHTA, KEIKI KOUNO, YUKIO ONO, YO UEDA1984 Volume 32 Issue 11 Pages 4252-4259
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVisible absorption spectra of 5, 10, 15, 20-tetra (p-methoxyphenyl) porphyrinatocobalt (II) [Co (II) (p-OCH3) TPP] and 5, 10, 15, 20-tetra (p-methoxyphenyl) porphyrinatocobalt (III) chloride [ClCo (III) (p-OCH3) TPP] were measured in toluene at room temperature in the absence or presence of O2. Changes of the spectra due to the presence of skatole and/or pyridine were investigated. The spectra of four-coordinate cobalt complexes of 5, 10, 15, 20-tetra (p-methoxyphenyl)-porphyrin were found to be practically indistinguishable from those of five-coordinate complexes, but clearly different from those of six-coordinate complexes, irrespective of the oxidation state of the central cobalt ion of complexes. The reaction medium for the oxygenation of skatole catalyzed by Co (II) (p-OCH3) TPP showed only the spectrum of a six-coordinate complex, (skatole) Co (II) (p-OCH3) TPP (O2). This result showed clearly that the oxygenation of skatole must proceed through a ternary complex of the type (skatole)-[Co (II) complex]-(O2). The addition of pyridine to the same reaction medium was found to produce a six-coordinate complex, (skatole) Co (II) (p-OCH3) TPP (pyridine), irreversibly. This explains why the oxygenation of skatole is remarkably repressed upon addition of a Lewis base such as pyridine to the reaction medium. The spectrum of the reaction medium for the oxygenation of skatole catalyzed by ClCo (III) (p-OCH3) TPP was found to consist of the superposed spectra of two six-coordinate complexes, ClCo (III) (p-OCH3) TPP (O2) and ClCo (III) (p-OCH3) TPP (skatole). Therefore, the oxygenation of skatole apparently proceeds through the interaction between these two six-coordinate complexes.View full abstractDownload PDF (817K) -
YOSHITAKA OHISHI, YOSHIO DOI, TERUO NAKANISHI1984 Volume 32 Issue 11 Pages 4260-4270
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious salicylaldehydes were treated with bromonitromethane in the presence of an inorganic base to give 2-nitrobenzo [b] furan derivatives, and the reaction mechanisms were investigated. The most remarkable feature of the reactions is that 3-hydroxysalicylaldehyde (1k) alone among various hydroxysalicylaldehydes (1b, k, n, r) gave 2-nitro-7-hydroxybenzo [b] furan in good yield. Bromonitromethane reacted with salicylaldehydes at the aldehyde group exclusively to give 1-(2-hydroxyphenyl)-2-bromo-2-nitroethanols (14), followed by cyclization to produce mixtures consisting of cis- and trans-2-nitro-3-hydroxy-2, 3-dihydrobenzo [b] furans (8a, b ; 9a, b ; 10a, b). The stereochemistry of these products is discussed on the basis of the spectral data and chemical reactivities. The intermediates, 2, 3-dihydrobenzo [b] furans, underwent dehydration smoothly to give 2-nitrobenzo [b] furans.View full abstractDownload PDF (1075K) -
YOSHIMOTO NAKASHIMA, YUTAKA KAWASHIMA, FUSAO AMANUMA, KAORU SOTA, AKIR ...1984 Volume 32 Issue 11 Pages 4271-4280
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-(3-Piperidinopropyl)-4, 6-disubstituted-furo [3, 2-b] indole-2-carboxamide derivatives were prepared and examined for analgesic and anti-inflammatory activities using the acetic acid writhing method in mice and the carrageenin edema method in rats. Some of the compounds were found to have potent and anti-inflammatory activities in the animal model.View full abstractDownload PDF (824K) -
EIICHI KOTANI, SHIGEKI KOBAYASHI, YOKO ISHII, SEISHO TOBINAGA1984 Volume 32 Issue 11 Pages 4281-4291
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe iron (III) complexes Fe (S)6(ClO4)3, S=solvent, were prepared from Fe (H2O)6(ClO4)3 in the donor solvents. Reactions of alkylbenzenes with Fe(AN)6(ClO4)3 (AN=acetonitrile) were explored because the AN complex has the highest formal redox potential, E°=1.73 V vs. SCE, among these complexes. Oxidation of the primary alkylbenzenes by the iron (III) AN complex gave the corresponding acetamides (Table II). Oxidation of the secondary alkylbenzenes, namely, cumene, 2-phenylbutane, and 2-exo-phenylnorborane, afforded the corresponding acetates and acetamides (Charts 2 and 3), consuming over 4 mol eq of reagent. Reactions of p-xylene and hexamethylbenzene with Fe (CH2=CHCN)6(ClO4)3 also yielded the amides 31a and 31b. These results demonstrate the applicability of the iron (III) AN complex as a powerful reagent to oxidize organic substrates which have onset potentials of anodic current of ca. 2.0 V vs. SCE.View full abstractDownload PDF (1029K) -
YUICHI YAMAMOTO, REIKO YODA, TOMOKO OKADA, YOSHIKAZU MATSUSHIMA1984 Volume 32 Issue 11 Pages 4292-4299
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 4-methyl-2-methylaminothiazole (1a) and N, N-dimethylthiocarbamoyl chloride (2a) in a nonpolar solvent gave four products, 4-methyl-2-methylimino-3-(N, N-dimethylthiocarbamoyl)-4-thiazoline (3a), 1, 1, 3-trimethyl-3-(4-methyl-2-thiazolyl) thiourea (4a), 4-methyl-2-methylamino-5-(N, N-dimethylthiocarbamoyl) thiazole (5a), and 1, 1-dimethyl-3-(3, 4-dimethyl-2 (3H)-thiazolyidene) thiourea (6a). The 2-phenylamino analog of 1a (1b) gave the corresponding phenyl compounds (3b-6b) on reaction with 2a. Compounds 3a and 3b were isomerized to 6a and 6b, respectively, in dioxane with a drop of hydrochloric acid. From studies with 15N-labeled compounds, a mechanism is proposed involving a proton-induced ring transformation of 3, via protonation of 3, cleavage of the 3, 4-bond, and bond formation between the imino nitrogen and 4-carbon atoms. A similar ring transformation took place with 3-N, N-dimethylcarbamoyl analogs of 3a and 3b, but not with a thiazolidine analog of 3b.View full abstractDownload PDF (609K) -
YUICHI HASHIMOTO, KOICHI SHUDO, TOSHIHIKO OKAMOTO1984 Volume 32 Issue 11 Pages 4300-4308
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Amino-1-methyl-5H-pyrido [4, 3-b] indole (Trp-P-2) is a mutagen/carcinogen isolated from a pyrolysate of L-tryptophan. The active metabolite of Trp-P-2, 3-hydroxyamino-1-methyl-5H-pyrido [4, 3-b] indole (N-OH-Trp-P-2), was synthesized and the chemical reactions of N-OH-Trp-P-2 with deoxyribonucleic acid were investigated. The structure of the nucleic acid base covalently bound with Trp-P-2 was elucidated as 3-(C8-guanyl) amino-1-methyl-5H-pyrido [4, 3-b] indole (Gua-Trp-P-2) by comparison with a synthetic sample. The initial chemical events in carcinogenesis caused by Trp-P-2 were established.View full abstractDownload PDF (954K) -
TAKAO MATSUNO, MASAHIRO OOKUBO, TOKUJI NISHIZAWA, ICHIRO SHIMIZU1984 Volume 32 Issue 11 Pages 4309-4315
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew marine carotenoids, halocynthiaxanthin (4) and mytiloxanthinone (5), were isolated from the sea squirt, Halocynthia roretzi ("Maboya" in Japanese). The structures of 4 and 5 were established to be (3S, 5R, 6S, 3'R)-5, 6-epoxy-3, 3'-dihydroxy-7', 8'-didehydro-5, 6, 7, 8-tetrahydro-β, β-caroten-8-one and 3, 8'-dihydroxy-7, 8-didehydro-β, κ-carotene-3', 6'-dione, respectively.View full abstractDownload PDF (726K) -
SHOJI IKEDA, FUMIO SAKAMOTO, HIROSATO KONDO, MASARU MORIYAMA, GORO TSU ...1984 Volume 32 Issue 11 Pages 4316-4322
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to prepare ampicillin prodrugs conveniently for practical use, a new synthetic method for 6β-aminopenicillanic acid (6-APA) esters as key intermediates of various ampicillin prodrugs has been developed. Acylation of 6-APA esters to ampicillin esters was achieved in good yields by using phenylglycyl chloride hydrochloride in dichloromethane in the presence of sodium bicarbonate and amide, or ammonium bicarbonate alone. KBT-1585, bacampicillin, talampicillin and pivampicillin have been obtained in good yields by this procedure.View full abstractDownload PDF (760K) -
HIROSHI TAKAHASHI, KOJI TANAHASHI, KIMIO HIGASHIYAMA1984 Volume 32 Issue 11 Pages 4323-4327
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChiral Mannich bases, (S)-3-oxazolidino-1-arylpropan-1-ones (3a, 3b), were obtained from acetophenone, (S)-valinol, and paraformaldehyde. The reaction of these 1-arylpropan-1-ones with organometallic reagents gave 3-oxazolidino- and 3-hydroxyethylamino-1-arylpropan-1-ols (5a, 5b, 6a-f) in good yields. These 1-arylpropan-1-ols consisted of two diastereomers and the ratios of major to minor products were estimated by proton nuclear magnetic resonance spectroscopy. The 1, 5-asymmetric induction of the chiral Mannich bases showed low stereoselectivity.View full abstractDownload PDF (628K) -
KATSUMI TAMOTO, SHIRO TERASHIMA1984 Volume 32 Issue 11 Pages 4328-4339
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMicrobial reduction of the racemic α-hydroxy ketones ((±)-3a, b) with fermenting baker's yeast was found to afford diastereomeric mixtures of the vicinal-diols ((-)-4a, b) and ((+)-5a, b) in 90 and 91% yields, respectively. Separation of these diastereomers was readily accomplished by fractional recrystallization, giving pure (-)-4a, b and mixtures of (-)-4a, b and (+)-5a, b. Oxidation of these samples furnished optically pure anthracyclinone intermediates ((R)-(-)-3a, b) and their partially optically active antipodes ((S)-(+)-3a, b). The undesired enantiomers ((S)-(+)-3a, b) and vicinal-diols ((+)-5a, b) could be recycled to (±)-3a, b and the prochiral ketones (6a, c) by racemization with p-toluenesulfonic acid and oxidative cleavage with sodium metaperiodate, respectively. Another important optically pure anthracyclinone intermediate ((R)-(-)-3c) was prepared from (R)-(-)-3a, b according to the reported method.View full abstractDownload PDF (1352K) -
KATSUMI TAMOTO, SHIRO TERASHIMA1984 Volume 32 Issue 11 Pages 4340-4349
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to discriminate the possible racemization mechanisms shown in Chart 1 (for (S)-(-)-1a) for the α-hydroxy ketone moiety (C9-position of the optically active anthracyclinones ((S)-(+)-1a-c), some plausible intermediates ((±)-2 and -3) and their equivalent ((R)-(-)-12) were first synthesized. Thus, the tertiary alcohol ((R)-(-)-12) was prepared from the 1'(S), 2 (R)-diol ((-)-10) according to the reaction scheme shown in Chart 2. The isomeric seven-membered α-hydroxy ketones ((±)-2 and -3) were elaborated from the 1, 4-dihydronaphthalene (13), following the synthetic scheme shown in Charts 3 and 4 based on Dieckmann condensation, dihydroxylation, regioselective enol acetate formation, and oxidation as key steps. By subjecting the plausible intermediates ((±)-2 and -3, 5, and (R)-(-)-12) to the racemization conditions, the facile loss of optical integrity observed for (S)-(+)-1a-c was found to proceed through the ring-expanded seven-membered α-hydroxy ketones ((±)-2 and -3 for (S)-(+)-1a, which might be produced by equilibrium C (Chart 1).View full abstractDownload PDF (1158K) -
KAZUHIKO OHTA, EIJI MIZUTA, HISAYOSHI OKAZAKI, TOYOKAZU KISHI1984 Volume 32 Issue 11 Pages 4350-4359
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe previous X-ray-crystallographic determination of the relative configuration of P-1894B, a potent prolyl hydroxylase inhibitor isolated from the culture broth of Streptomyces albogriseolus, was extended by means of chemical and spectral studies. The absolute configuration of P-1894B (1) was established from the absolute configuration of two constituent monosaccharides, L-aculose (3) and L-rhodinose (4), produced by chemical degradation of 1. The absolute configuration of the aglycone part (aquayamycin) was also established as 2. The stereostructure of the reduction product (11) obtained by the catalytic hydrogenation of 1 was also elucidated.View full abstractDownload PDF (1038K) -
HIROSHI SHIMIZU, KAZUNORI MATSUO, TADASHI KATAOKA, MIKIO HORI1984 Volume 32 Issue 11 Pages 4360-4371
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel cyclic sulfilimines (so-called azathiabenzenes), 2-methyl-1-aza-2-thianaphthalene (7) and 9-methyl-(14a) or 9-ethyl-10-aza-9-thiaphenanthrene (14b), were synthesized in high yields by deprotonation of the corresponding azasulfonium salts (6, 13a, 13b) with base. The ylidic properties of the azathiabenzenes were revealed by spectral and chemical evidence. The azathiabenzenes (14a, 14b) were easily oxidized with potassium permanganate to yield the corresponding azathiabenzene oxides (18a, 18b). Thermolysis of 14a in refluxing xylene afforded the ring-expanded product 7H-dibenzo [d, e] [1, 3] thiazepine (21), while 14b underwent β-elimination on refluxing in xylene to give 6H-dibenzo [c, e] [1, 2] thiazine (24). Reactions of the azathiabenzene derivatives with dimethyl acetylenedicarboxylate as an electrophile are also reported.View full abstractDownload PDF (1181K) -
YOSHINORI FUJIMOTO, MIKI KIMURA, NOBUO IKEKAWA, FATHYA.M. KHALIFA1984 Volume 32 Issue 11 Pages 4372-4381
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour C-24 epimeric pairs of 24-alkylsterols 1-8 were stereoselectively synthesized via orthoester Claisen rearrangement of the (22R) or (22S)-Δ23Z steroid derivatives (11 and 12). These compounds were tested on the silkworm larvae, Bombyx mori, in order to examine the relationship of the C-24 stereochemical arrangement and utilizability as a nutrient sterol. All of the tested sterols effectively supported the growth and development of the insect and were converted into cholesterol regardless of the C-24 configuration.View full abstractDownload PDF (1008K) -
YOSHIRO KOBAYASHI, TAKABUMI NAGAI, ITSUMARO KUMADAKI, MASAAKI TAKAHASH ...1984 Volume 32 Issue 11 Pages 4382-4387
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Friedel-Crafts reaction of 1, 1, 1-trifluoropropene with benzene and its derivatives was accomplished in the presence of fluorine-containing acid catalysts. The reaction proceeded at the terminal carbon atom of the olefin to give 3, 3, 3-trifluoropropylated aromatic compounds. The scope and limitations of this reaction were examined. This substituent was found to be ortho- and para-directing.View full abstractDownload PDF (717K) -
MASAHIRO TAGUCHI, NORIO AIKAWA, GORO TSUKAMOTO1984 Volume 32 Issue 11 Pages 4388-4395
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Formylrifamycin S (9) was found to react with secondary aliphatic amines to give 2, 3-dihydropyrimido [4, 5-b] rifamycin derivatives 4, in which the 2'-position was substituted with an alkyl group. When 7-, 8-, and 9-membered alicyclic amines were used, 2, 3-dihydropyrimido [4, 5-b] rifamycin derivatives 5, in which the 1'-and 2'-position were linked with a methylene chain, were obtained. The configuration of the 2'-position in 4 and 5 is discussed. The mechanism of formation of 4 and 5 is also discussed.View full abstractDownload PDF (796K) -
KAZUTAKE SHIMADA, KAZUO OHISHI, TOSHIO NAMBARA1984 Volume 32 Issue 11 Pages 4396-4401
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe occurrence of new bufotoxins, in which L-histidine, L-3-methylhistidine, or L-1-methylhistidine replaces the arginine residue of hitherto known "bufotoxin, " in the skin of the Formosan toad, Bufo melanostictus SCHNEIDER, is reported. Five novel bufotoxins, bufotalin 3-suberoyl-L-histidine, -3-methylhistidine and -1-methylhistidine esters and 19-hydroxybufalin 3-suberoyl-L-histidine and -3-methylhistidine esters, were separated by usual chromatographic methods including reversed phase high-performance liquid chromatography, and their structures were elucidated by degradative and synthetic means.View full abstractDownload PDF (716K) -
YOSHIRO KOBAYASHI, TOSHINORI YAMASHITA, KATSUHIRO TAKAHASHI, HISASHI K ...1984 Volume 32 Issue 11 Pages 4402-4409
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhenyltrifluoromethylacetylene (4a) was synthesized by the pyrolysis of triphenylphosphonium α-(trifluoroacetyl) benzylide (3a), which was easily derived from benzyl halide (1a). This method can be used for the synthesis of 4-substituted-phenyltrifluoromethylacetylenes (4). The 1, 3-dipolar reaction of 4 with diazomethane and phenyl azide proceeds readily to give trifluoromethylated pyrazoles and triazoles.View full abstractDownload PDF (845K) -
TAKUSHI KURIHARA, KEIKO NASU, SATOMI HAGINAGA, KYOKO MIHARA1984 Volume 32 Issue 11 Pages 4410-4418
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4, 7-Dihydro-4-methyl-7-(N-methyl-3-indolyl) pyrazolo [1, 5-α] pyrimidine (3) obtained from pyrazolo [1, 5-α] pyrimidine (1) was treated with indole in the presence of an excess of triethyloxonium fluoroborate to give a mixture of 1, 4-dihydro-3-(3-indolyl) cyclopent [b] indoles (5, 6, 7 and 8). The reaction of 6 with potassium hydroxide in ethanol at room temperature gave the 1-hydroxy derivative (10), while under reflux 6 gave 1, 4-dihydro-1-oxocyclopent [b] indole (11). Treatment of 6 with formaldehyde gave the 1-hydroxymethyl derivative (13). m-Chloroperbenzoic acid oxidation of 6 afforded the 3, 4-dihydrocyclopent [b] indole (14). Furthermore, the reaction of 6 with activated olefins, such as maleic anhydride, maleimide, acrylonitrile and ethyl acrylate under reflux in benzene or acetonitrile gave [4+2] cycloadducts, bicyclo [2.2.1] hept [2, 3-b] indoles (17, 18, 20 and 21), via the 2, 4-dihydrocyclopent [b] indole intermediate (6').View full abstractDownload PDF (938K) -
TETSURO FUJITA, YOSHIHISA TAKAISHI, YOSHIO TAKEDA, TETSUJI FUJIYAMA, T ...1984 Volume 32 Issue 11 Pages 4419-4425
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new minor metabolite, valinotricin (1), along with cyclonerodiol oxide (9) and epicyclonerodiol oxide (10) was isolated from Trichoderma polysporum. The structure of valinotricin was elucidated as 1 by chemical and spectral studies, and then confirmed by synthesis. Chemical and spectroscopic studies of cyclonerodiol oxide and epicyclonerodiol oxide led to the structures 9 and 10, respectively.View full abstractDownload PDF (756K) -
TZUOHMIIN JUANG, SHUNICHI YAMADA1984 Volume 32 Issue 11 Pages 4426-4430
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTrifluoroacetolysis of (S)-3-phenyllactic acid ester sulfonate ((S)-7), obtained from L-phenylalanine via nitrous acid deamination followed by ethanolysis, afforded (R)-tropic acid ester ((R)-8) in good yield by phenyl migration with inversion, while acetolysis followed by ethanolysis afforded (R)-phenyllactic acid ester ((R)-6b) in good yield by substitution with inversion. Mechanistic aspects of these reactions are discussed.View full abstractDownload PDF (532K) -
MIYOJI HANAOKA, MITSURU INOUE, MISAO TAKAHASHI, SHINGO YASUDA1984 Volume 32 Issue 11 Pages 4431-4436
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree methods were developed for the transformation of naturally occurring 9, 10-oxygenated protoberberines into non-naturally occurring 11, 12-oxygenated protoberberines through ring D inversion via spirobenzylisoquinolines. Berberine (14) was converted to the spirobenzylisoquinoline (18) through regioselective cleavage of the 8, 14-cycloberbine (17). Alkaline hydrolysis of the oxazolidinone (20) derived from 18 efficiently afforded the 11, 12-oxygenated protoberberine (23), which was also obtained from 8-methoxyberberinephenolbetaine (24) through treatment of the keto-hydroxy-spirobenzylisoquinoline (25) with alkali. The spirobenzylisoquinoline (26) derived from the 8, 14-cycloberbine (16) was subjected to hydrogenolysis and subsequent hydrolysis to give the amino-ketone (28), photolysis of which furnished the 11, 12-oxygenated protoberberine (29).View full abstractDownload PDF (698K) -
KENJI KAJI, HIROMU NAGASHIMA, SIGETO NAGAO, KEIZO TABASHI, HIROHISA OD ...1984 Volume 32 Issue 11 Pages 4437-4446
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclization of 2-substituted 5-[(α-bromobenzylidene) hydrazino)]-4-chloro-3 (2H)-pyridazinones (2) with potassium thioacetate, followed by deacetylation, provided new ring system derivatives, 7-substituted 2-phenyl-4H-pyridazino [4, 5-e] [1, 3, 4] thiadiazin-8 (7H)-ones (4). 8-Chloro and 8-amino derivatives (10) of the pyridazinothiadiazine ring were readily derived from 4-acetyl-2-phenyl-4H-pyridazino [4, 5-e] [1, 3, 4] thiadiazin-8 (7H)-one (3d) by chlorination and subsequent amination. Ring contraction of the 8-oxo derivatives (4) to 5-substituted 3-phenyl-1H-pyrazolo [3, 4-d] pyridazin-4 (5H)-ones (6), through extrusion of sulfur under basic or thermal conditions, was observed. A similar reaction occurred in the case of the 8-chloro and 8-amino derivatives (10). Probable mechanisms for these reactions and differences of reactivity between 4 and 10 are discussed.View full abstractDownload PDF (940K) -
JEAN-CHARLES LANCELOT, JEAN-MARIE GAZENGEL, SYLVAIN RAULT, NGUYEN HUY ...1984 Volume 32 Issue 11 Pages 4447-4454
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of pyrrolo [1', 2' : 1, 2] pyrazino [6, 5-c] and [5, 6-b] carbazole derivatives is described starting from 3-amino-4-nitrocarbazole and 3-amino-2-nitrocarbazole, respectively. A new route is proposed for the latter compounds. The pyrrole ring was obtained by using dimethoxytetrahydrofuran and then pyrazine ring formation was achieved by intramolecular cyclization after reduction of the nitro group. The 1H nuclear magnetic resonance spectra were analyzed.View full abstractDownload PDF (810K) -
TADATAKA NORO, AKIRA UENO, MASAKO MIZUTANI, TSUTOMU HASHIMOTO, TOSHIO ...1984 Volume 32 Issue 11 Pages 4455-4459
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSXanthine oxidase (XO) inhibitor was isolated from the aerial parts of Athylium mesosorum MAKINO (Aspidiaceae) and was identified as norathyriol (1, 3, 6, 7-tetrahydroxyxanthone) (1). The type of inhibition by 1 with respect to xanthine as a substrate was uncompetitive. The inhibitory activities of related xanthone derivatives towards XO were assayed.View full abstractDownload PDF (510K) -
TAKASHI SOHDA, KATSUTOSHI MIZUNO, YUTAKA KAWAMATSU1984 Volume 32 Issue 11 Pages 4460-4465
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOptical resolution of a new antidiabetic agent, (±)-5-[4-(1-methylcyclohexylmethoxy) benzyl]-2, 4-thiazolidinedione (1, ciglitazone) with (-)-and (+)-1-phenylethylamine (PEA) in ethyl acetate resulted in almost complete asymmetric transformation to give the salts, (-)-1·(-)-PEA and (+)-1·(+)-PEA, respectively, in up to quantitative yields. Optical purities of (-)-and (+)-1 obtained from the salts were determined by nuclear magnetic resonance and their absolute configurations were confirmed chemically. The optical isomers showed essentially the same antidiabetic and hypolipidemic activities.View full abstractDownload PDF (649K) -
TAKASHI YAEGASHI, SHIGEKI NUNOMURA, TOSHIYUKI OKUTOME, TOYOO NAKAYAMA, ...1984 Volume 32 Issue 11 Pages 4466-4477
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious amidinophenol derivatives (27-47) and their benzoates (4-26) were synthesized and evaluated for inhibitory activities against trypsin, plasmin, kallikrein, thrombin, Clr and Cls as well as in vitro complement-mediated hemolysis. 4-(β-Amidinoethenyl) phenyl 4-guanidinobenzoate (15) and 4-amidino-2-benzoylphenyl 4-guanidinobenzoate (26) were found to have potent inhibitory activities with IC50s of 9×10-8M (trypsin) and 2×10-7M (Cls) for the former and 3×10-8M (trypsin) and 2×10-7M (Cls) for the latter.View full abstractDownload PDF (1023K) -
TAKUO KOSUGE, HITOSHI ISHIDA, MASAMI YOKOTA, MASASHI YOSHIDA1984 Volume 32 Issue 11 Pages 4478-4481
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe antihemorrhagic principle in Sanguisorba officinallis L. was isolated by a combination of countercurrent distribution, column chromatography on silica gel and preparative thin layer chromatography on silica gel, and identified as 3, 3', 4-tri-O-methylellagic acid.View full abstractDownload PDF (492K) -
HIROKI TSUKAMOTO, SUEO HISADA, SANSEI NISHIBE1984 Volume 32 Issue 11 Pages 4482-4489
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new lignans, (+)-fraxiresinol [(1S, 2R, 5R, 6S)-1-hydroxy-2-(3, 5-dimethoxy-4-hydroxyphenyl)-6-(4-hydroxy-3-methoxyphenyl)-3, 7-dioxabicyclo [3.3.0] octane] (3), (+)-1-hydroxysyringaresinol (4) and (+)-1-hydroxypinoresinol-4'-β-D-glucoside (8), and five known lignans, (+)-pinoresinol (1), (+)-1-hydroxypinoresinol (2), (-)-olivil (5), (+)-cyclo-olivil (6) and (+)-pinoresinol-β-D-glucoside (7), were isolated from the bark of Fraxinus mandshurica RUPR. var. japonica MAXIM and the bark of F. japonica BLUME (Oleaceae). Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence.View full abstractDownload PDF (916K) -
TAKAKO YOKOZAWA, TAEKO KOBAYASHI, AKIKO KAWAI, HIKOKICHI OURA, YUJI KA ...1984 Volume 32 Issue 11 Pages 4490-4496
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to elucidate the effect of ginsenoside-Rb2 on lipid metabolism, a time course experiment was carried out in rats. The first phenomenon observed was a stimulation of glucose-6-phosphate dehydrogenase activity beginning 4h after the administration of ginsenoside-Rb2. At this time, a slight increase of acetyl-coenzyme A carboxylase activity was observed, and a significant increase was noted 16h after the treatment. The maximum increase in malic enzyme activity was observed at 12h. An increase in the lipolytic activity of lipoprotein lipase was observed 4h after the intraperitoneal administration of ginsenoside-Rb2, reaching a maximum (262%) 16h after the treatment, while a repressive effect was observed on hormone-sensitive lipase activity throughout the experimental period. Administration of ginsenoside-Rb2 to rats also increased the triglyceride content in adipose tissue. These results suggest that ginsenoside-Rb2 brings about the accumulation of triglyceride in adipose tissue as a result of its stimulating action on the lipogenic pathway.View full abstractDownload PDF (743K) -
TAKASHI ABIKO, HIROSHI SEKINO1984 Volume 32 Issue 11 Pages 4497-4505
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDeacetyl-thymosin β4 was synthesized by successive azide condensations of five peptide fragments, Boc-(1-4)-NHNH2, Boc-(5-12)-NHNH2, Boc-(13-20)-NHNH2, Boc-(21-27)-NHNH2 and Boc-(28-33)-NHNH2, with H-(34-43)-OBzl, followed by deprotection with hydrogen fluoride in the presence of anisole and thioanisole. Finally, the deprotected peptide was incubated with dithiothreitol to reduce sulfoxide on the methionine side chain. The synthetic deacetyl-thymosin β4 increased almost the entire peripheral T-cell population and a helper T-cell subset when incubated in vitro with uremic patient's blood but a suppressor T-cell subset was unaffected under these conditions.View full abstractDownload PDF (1026K) -
TAKAKO YOKOZAWA, NAOMI SUZUKI, PING DONG ZHENG, HIKOKICHI OURA, ITSUO ...1984 Volume 32 Issue 11 Pages 4506-4513
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of orally administered rhubarb extract was examined in rats with chronic renal failure induced by an adenine diet. On treatment of the rats with the rhubarb extract, the level of urea nitrogen and creatinine in the serum was dose-dependently decreased. The urea concentration in the liver was also decreased after the treatment. In addition, administration of the rhubarb extract to rats produced an increase in the serum calcium level, indicating an improvement of hypocalcemia. Improvement of hyperphosphatemia was also observed. Furthermore, rhubarb extract appeared to cause a gradual decrease of the taurocyamine, guanidinosuccinic acid, and methylguanidine levels in the serum with increasing dosage. Methylguanidine was not detectable in the serum or in the kidney of the rhubarb extract-treated group given 55 mg/rat/d. A marked decrease in the liver guanidinosuccinic acid concentration was also observed. Treatment of chronically uremic rats with the rhubarb extract resulted in a normal or nearly normal serum level of branched-chain amino acids. These results suggest that rhubarb extract may be useful as a conservative treatment for uremia.View full abstractDownload PDF (884K) -
KAZUTAKA TANIZAWA, YUICHI KANAOKA1984 Volume 32 Issue 11 Pages 4514-4517
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSImmobilized trypsin covalently attached to cross-linked dextran was prepared. In the presence of high concentrations of primary and secondary alcohols, the transesterification of L-lysine esters catalyzed by the immobilized trypsin was observed to be predominant. In contrast to this, no transesterified product was detected with tertiary butyl alcohol. These reactions were compared with the acid-catalyzed transesterification reactions and the characteristics of the enzymatic reaction are discussed.View full abstractDownload PDF (526K) -
TOSHIHIRO FUJII, YASUHIRO AKABANE, SATOMI ODORI, MICHIYO FUJII, YOSHIY ...1984 Volume 32 Issue 11 Pages 4518-4524
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA protein-bound polysaccharide (PS-K) suppressed glycerol-free microtubule polymerization in the same way as it suppressed the polymerization in a reassembly mixture containing glycerol. However, the extent of inhibition was enhanced in the absence of glycerol. Maximal inhibition reached about 85% (the extent of polymerization was 15% of the original level) in the standard assembly medium containing 100mM KCl. The addition of PS-K increased the critical concentration for microtubule polymerization. Electron microscopy indicated that PS-K did not change the ultrastructure of microtubules. During incubation with PS-K, microtubule proteins retained their ability to polymerize, because the addition of taxol largely restored the inhibition by PS-K and the presence of an excess amount of microtubule-associated proteins (MAPs) or tubulin dimers also sequestered the inhibition to some extent. The extent of cancellation was greater by MAPs than by tubulin dimers.View full abstractDownload PDF (859K) -
TAKEHIKO NOHMI, KUNIE YOSHIKAWA, MOTOI ISHIDATE, AKIRA HIRATSUKA, TADA ...1984 Volume 32 Issue 11 Pages 4525-4531
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism of species difference in N-hydroxyphenacetin mutagenicity was investigated by using the Salmonella/microsome mutagenicity test and high-performance liquid chromatographic (HPLC) analysis. Mutagenicity of N-hydroxyphenacetin in Salmonella typhimurium TA100 was about 10 times more efficiently detected with a liver 9000g supernatant fraction (S9) from hamsters than with the corresponding fraction from rats in the absence of a reduced nicotinamide adenine dinucleotide phosphate-generating system. Paraoxon and sodium fluoride, both inhibitors of microsomal amidase, not only inhibited the mutagenicity of N-hydroxyphenacetin, but also retarded the formation of the deacetylation product, p-nitrosophenetole, a strong intrinsic mutagen. The N-hydroxyphenacetin-deacetylation activity was about 20 times higher in liver microsomes from the hamster than in those from the rat.View full abstractDownload PDF (767K) -
YOSHIO INOUYE, YUKIE KAWAGUCHI, SHOSHIRO NAKAMURA1984 Volume 32 Issue 11 Pages 4532-4538
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA neutral metalloendopeptidase recovered from culture broth of Streptomyces griseoruber was purified by affinity chromatography on N-benzyloxycarbonylglycylleucylaminohexylamino-Sepharose (Z-Gly-Leu-AH-Sepharose) to electrophoretic homogeneity. The enzyme was adsorbed on this adsorbent from phosphate buffer (pH 5.6) and eluted with acetate buffer (pH 4.1) containing 2M urea. The enzyme was inactivated by ethylenediaminetetraacetate but not by sulfhydryl reagents or phenylmethanesulfonyl fluoride. The enzyme showed the maximum caseinolytic activity in the region of pH 6.0-7.0 and was stable within the pH range of 5.0-7.0. The molecular weight was estimated to be 52000. The enzyme preferentially hydrolyzed Z-Gly-Leu-NH2 and Z-Gly-Phe-NH2 among the synthetic substrates tested in this work. Based on taxonomic studies, the producing organism was identified as Streptomyces griseoruber.View full abstractDownload PDF (689K) -
HIROSHI UEKI, YUKO MATSUNAMI, AIICHIRO MOTOSHIMA, TAKAYUKI FUNAKOSHI, ...1984 Volume 32 Issue 11 Pages 4539-4544
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInsulin-like effects of N-succinyl-L-trialanine p-nitroanilide-hydrolyzing protease (STA-protease) purified from Pronase were investigated in rat epididymal adipose tissue. The enzyme stimulated the conversion of [3-3H] glucose into lipid and suppressed the epinephrine-stimulated lipolysis in the fat cells, like trypsin and insulin. When the fat pads were incubated with STA-protease in the presence of glucose, pyruvate dehydrogenase activity in the homogenate of the incubated fat pads was stimulated markedly. In the absence of glucose, STA-protease did not stimulate pyruvate dehydrogenase activity though trypsin and insulin showed a slight but significant stimulation. Further, the stimulatory effect of STA-protease in the presence of glucose was inhibited by the addition of 3-O-methylglucose or phlorizin to the incubation medium of the fat pads. Trypsin and insulin still showed a significant stimulation under similar conditions. When the homogenate of intact fat pads was incubated with STA-protease, no stimulation was observed throughout the range of effective concentrations. These results suggest that STA-protease also reacts with the cell surface and consequently mimics the actions of insulin, though a slight difference between STA-protease and trypsin may exist as regards the mechanism of stimulation of pyruvate dehydrogenase.View full abstractDownload PDF (674K) -
TOSHIAKI NISHIHATA, JUNKO KATO, KIHEUN KIM, MOTOMASA KOBAYASHI, ISAO K ...1984 Volume 32 Issue 11 Pages 4545-4550
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA mixture of sodium phenylalanine and ethyl acetoacetate in aqueous solution underwent enamine formation as determined by nuclear magnetic resonance- and ultraviolet-spectroscopic measurements. An equilibrium state was observed in the aqueous solution between the enamine and the starting materials. Although the observed equilibrium constant, Kobs, showed dependency on the pH value of the solution, the equilibrium constant, K, was not influenced by the pH value. The effect of pH values on Kobs was related to the pKa value of phenylalanine, suggesting that only the unionized form of the amino moiety of phenylalanine could take part in the enamine formation.View full abstractDownload PDF (553K) -
NOBUYOSHI KANENIWA, MAKOTO OTSUKA1984 Volume 32 Issue 11 Pages 4551-4559
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSolid cephalexin (CEX) has been obtained as crystals, the noncrystalline solid (NC) produced by freeze-drying and the noncrystalline solid (GNC) produced by grinding in a centrifugal mill for 4 h. Each product formed an anhydride, monohydrate and dihydrate. The interaction between water and CEX in the crystalline and noncrystalline states was studied by the infrared (IR) spectral method and the thermal kinetic analytical method (Criado method) using differential scanning calorimetry. In the IR spectrum of CEX, the hydroxyl vOH band was observed at 3400 cm-1, the amido vNH band at 3100 cm-1, the amine vNH3+ band at 2600 cm-1, the β-lactam vC=O band at 1760 cm-1, the amido vC=O band at 1680 cm-1, and the carboxylate vCO2- band at 1600 cm-1. The IR spectral intensity ratios were calculated from the peak heights of the bands with respect to the band at 1280 cm-1 as an internal standard peak. The changes of the IR spectral intensity ratios with increasing water content led us to the following conclusions. In the crystalline monohydrate (phase IV), the first water molecule interacted with the amine and carboxylate groups of different molecules in the crystal of CEX. In the crystalline dihydrate (phase II), the second water molecule interacted with NH and C=O of the amido group of CEX. In NC-H2O, the water molecule is adsorbed at the carboxylate group of CEX, while in NC-2H2O, the second water molecule is adsorbed at the amine group. The dehydrations of phase IV, GNC-H2O, GNC-2H2O and NC-2H2O followed first-order kinetics and the activation energies (E) were 15.67, 14.83, 14.58 and 12.50 kcal/mol, respectively, while that of NC-H2O followed three-dimensional diffusion kinetics and its E value was 15.81 kcal/mol. The E of phase II (second water molecule) was 11.74 kcal/mol as determined by the Kissinger method. These results suggest that the binding energies between the various forms of CEX and water reflect the characteristics of the groups of the CEX molecule to which water is actually bound in each case.View full abstractDownload PDF (878K) -
HISASHI ICHIBAGASE, YORISHIGE IMAMURA, TAKAFUMI MANAKO, KANETO UEKAMA, ...1984 Volume 32 Issue 11 Pages 4560-4565
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of oral and rectal administration of chloral hydrate (CH) on the gastrointestinal absorption of sulfisoxazole (SIX) were investigated in rabbits. The blood concentration data for SIX led us to conclude that the oral administration of CH causes an enhancement in SIX absorption, whereas the rectal administration of CH causes a reduction in SIX absorption. It is noteworthy that the route of administration plays an important role in the SIX-CH interaction involved in the gastrointestinal absorption. In addition, the factors determining the differential effects of oral and rectal administration of CH on the gastrointestinal absorption of SIX are discussed.View full abstractDownload PDF (619K) -
YOSHINOBU NAKAI, KEIJI YAMAMOTO, KATSUHIDE TERADA, JUNICHI ICHIKAWA1984 Volume 32 Issue 11 Pages 4566-4571
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe molecular properties of benzoic acid, ethyl p-aminobenzoate and benzophenone mixed with porous glass powder were investigated by differential scanning calorimetry (DSC), powder X-ray diffraction, and gas adsorption measurements. The mixtures had anomalous properties as compared with the mixtures with glass beads, that is, (1) a low concentration mixture (about 5%) did not show the melting heat and X-ray diffraction peaks associated with the medicinal crystals, (2) a high concentration mixture (about 20%) showed only a broad endothermic peak at a lower temperature than the melting point, and (3) a higher concentration mixture (more than 40%) showed an endothermic heat effect at the melting point together with the broad peak at a lower temperature. The peak area at the melting point increased with an increase of drug concentration while the broad peak area remained unchanged. Mixing with medicinals caused a decrease of surface area and a change of pore diameter distribution of the porous glass. From these results it was concluded that the medicinals took three phases in the mixture ; phase 1 (crystal structure), phase 2 (disordered structure) and phase 3 (probably adsorbed on the pore walls). The amounts of these phases were calculated from DSC curves.View full abstractDownload PDF (629K) -
SHIRO MORIMOTO, MAYUMI NAKAJIMA, YASUHISA MIZUNOYA, HIROFUMI OKAMURA, ...1984 Volume 32 Issue 11 Pages 4572-4579
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn enzyme which hydrolyzes dog plasma kininogen and prolyl-phenylalanyl-arginine-4-methylcoumaryl-7-amide (Pro-Phe-Arg-MCA) was separated from rat urinary kallikrein (RUK) by diethyl-aminoethyl-cellulose chromatography during the process of isolation of RUK. When some of the properties of this enzyme was examined, the enzyme was found to be a kinin-generating amidase with properties different from those of RUK, with respect to molecular weight and optimum pH for hydrolysis of Pro-Phe-Arg-MCA. Further, the kinin-generating amidase was activated with trypsin. The molecular weight of the kinin-generating amidase treated with or without trypsin was estimated to be 3.3×104 or 3.5×104, respectively, by gel filtration on a Sephadex G-100 column, these values being smaller than that of RUK (M.W. 3.8×104). These results indicate that rat urine contains a kinin-generating amidase of lower molecular weight than RUK, and that this kinin-generating amidase is activated with a reduction in molecular weight by trypsin treatment.View full abstractDownload PDF (885K) -
YUICHI YOKOYAMA, HIDEO NAKAMURA, MASANAO SHIMIZU1984 Volume 32 Issue 11 Pages 4580-4584
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe gastrointestinal (GI) ulcerogenicity of tolmetin sodium was compared with those of aspirin and indomethacin, as representative non-steroidal anti-inflammatory drugs, in rats. Ulcerogenic activity of tolmetin sodium administered orally was more potent in the stomach of the fasted rat than in the intestines of the fed rat, whereas indomethacin was more ulcerogenic in the intestines than in the stomach. Aspirin was ulcerogenic only in the stomach. In the gastric mucosa, tolmetin sodium, like aspirin but not indomethacin, produced far fewer lesions by the intravenous than by the oral route. However, tolmetin sodium, unlike aspirin, did not reduce the gastric acidity of the pylorus-ligated rat and was less ulcerogenic in the pylorus-ligated rat than in the intact rat. Consequently, the GI ulcerogenicity of tolmetin sodium appeared to be different in character from those of aspirin and indomethacin.View full abstractDownload PDF (582K) -
YOSHIO OKADA, NAOKI TENO, JUNKO MIYAO, YUMIKO MORI, MASACHIKA IRIE1984 Volume 32 Issue 11 Pages 4585-4592
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA decapeptide corresponding to the C-terminal sequence (residues 115-124) of bovine pancreatic ribonuclease A (RNase A) and four analogs in which Asp-121 is replaced by Asn, Glu, Gln and Ala were synthesized by the fragment condensation procedure, and their abilities to reactivate RNase A from which the last 4 residues, Asp-Ala-Ser-Val, had been removed were examined. Asp-decapeptide (I) and Glu-decapeptide (III) bound with inactivated RNase 1-120 non-covalently and exhibited hydrolytic activity towards cyclic 2', 3'-cytidylic acid. In contrast, Asn-decapeptide (II), Gln-decapeptide (IV) and Ala-decapeptide (V) did not show any ability to restore the activity of RNase A 1-120. Our systematic syntheses of the C-terminal decapeptide of RNase A and its analogs indicate a very important role of the free carboxyl group at position 121 of RNase A for manifestation of RNase activity.View full abstractDownload PDF (959K) -
YASUSHI OKAMOTO, KAZUHIKO SENOKUCHI, KEN KANEMATSU1984 Volume 32 Issue 11 Pages 4593-4599
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCookson's pentacyclic cage diketones substituted with an electron-donating group (1b-e) underwent a remarkably fast [2σ+2σ] cycloreversion reaction under various Lewis acid catalyzed conditions. The high reactivity of these cage ketones is discussed in terms of push-pull type interactions on the basis of large substituent effects and kinetic measurements.View full abstractDownload PDF (646K) -
HARUKI SASHIDA, TAKASHI TSUCHIYA1984 Volume 32 Issue 11 Pages 4600-4607
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe thermolysis of the N-imides (14, 15) of 6-ethynyl-1-methyl-1, 2, 5, 6-tetrahydropyridines (11) resulted in [2, 3]-sigmatropic rearrangement with either the triple bond or the double bond in the ring to give the dihydro-1, 2-diazonines (16) presumably via the allenic intermediates (19) and the tetrahydropyrazoles (17, 18). On the other hand, the N-ylides (26) of 11 gave the allenic compounds (27) and the Hofmann elimination products (28). Heating the N-oxides of 11 resulted in decomposition to give no characterizable products. The mechanisms, including stereochemistry, of these thermal reactions are discussed.View full abstractDownload PDF (863K) -
YOSHIO OKADA, SHIN IGUCHI, TAKAAKI HIRAI, YOSHITAKA GOTO, MASAMI YAGYU ...1984 Volume 32 Issue 11 Pages 4608-4615
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSZ-Gly-Val-Ser-Phe-Val-Leu-OMe and related peptides were synthesized by the conventional solution method and their attractant and repellent activities for Aedes aegypti (mosquito) and Blattella germanica (cockroach) were examined. Z-Val-Leu-OMe exhibited potent repellent activity against not only Aedes aegypti but also Blattella germanica.View full abstractDownload PDF (800K) -
YOSHIHISA ASADA, TSUTOMU FURUYA1984 Volume 32 Issue 11 Pages 4616-4619
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new pyrrolizidine alkaloid, senecicannabine (4) which was isolated from Senecio cannabifolius was derived from seneciphylline (1) by oxidation with performic acid. The transformation of jacozine (6) to 4 was also carried out with performic acid, and the configuration of the epoxide ring of 6 was chemically determined to be 15S and 20S.View full abstractDownload PDF (475K) -
TOSHIKO SATAKE, TAKAO MURAKAMI, YASUHISA SAIKI, CHIUMING CHEN, LUIS D. ...1984 Volume 32 Issue 11 Pages 4620-4624
Published: November 25, 1984
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe constituents of three Costa Rican ferns of Pteridaceae were investigated. From Jamesonia scammanae A. TRYON, a new pterosin-type compound (I), named jamesonin, along with two pterosin derivatives and six ent-kaurane-type diterpene derivatives were isolated, and I was established as (2R, 3R)-3-hydroxy-6-(2-hydroxyethyl)-2, 7-bishydroxymethyl-2, 5-dimethylindan-1-one by spectroscopic methods. From Dicksonia gigantea KARST., two known pterosin derivatives were isolated, and from Paesia anfractuosa C. CHR., two flavonol glycosides.View full abstractDownload PDF (617K)