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Volume 31, Issue 6
Displaying 1-50 of 53 articles from this issue
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KIYOKO TAKAMURA, SATOSHI INOUE, FUMIYO KUSU, MASAKI OTAGIRI, KANETO UE ...1983 Volume 31 Issue 6 Pages 1821-1826
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe electrochemical oxidation mechanism of chlorpromazine hydrochloride (CPZ-HCI) was examined in aqueous buffers in the pH range from 2 to 7. Three anodic waves were observed on the cyclic voltammogram of CPZ. The peak potential of the second wave was highly dependent on the properties of the supporting electrolyte, but the first peak was independent of these properties. At a higher pH or higher concentration of electrolyte, both peak currents increased. The final oxidation product was found to be chlorpromazine sulfoxide by comparison of its ultraviolet (UV) absorption spectrum and Rf value of thin layer chromatography (TLC) with those of an authentic sample. The experimental results suggest that the first wave is a catalytic wave and depends on the pH and the concentration of the supporting electrolyte, but that the second is an oxidation wave of CPZ-buffer anion adducts.View full abstractDownload PDF (605K) -
MUHAMMAD ISHAQ ALI KHAN, YOSHIHISA MIWA, SHUSHI MORITA, JUTARO OKADA1983 Volume 31 Issue 6 Pages 1827-1832
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCatalytic oxidation of ethylene glycol in an alkaline aqueous solution over a Pt/C catalyst by oxygen was studied in a slurry reactor at 40°C and ambient pressure. Under our experimental conditions, the interphase and intraparticle mass transfer resistances were found to be insignificant. The catalyst deactivation observed during the course of experiments can be ascribed to the formation of some oxidized species of platinum and/or to the adsorption of some by-products on the catalyst surface, and the decay of catalyst activity is consistent with a first order consecutive process, as described in the previous paper. The rate of reaction can be expressed by a power-law model under the conditions used. The orders of reaction with respect to ethylene glycol, sodium hydroxide and oxygen were estimated to be 0.20, 0.34 and zero, respectively. The mechanism of this reaction is discussed.View full abstractDownload PDF (668K) -
NOBUYA KATAGIRI, RYUJI NIWA, YOICHI FURUYA, TETSUZO KATO1983 Volume 31 Issue 6 Pages 1833-1841
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of dichloroketene with pyridine 1-oxide (1) gave four products, namely, 2-dichloromethylpyridine (2), 4-dichloromethylpyridine (3), 3, 3, 7-trichloro-6-dichloroacetyl-2-oxo-2, 3, 3a, 6, 7, 7a-hexahydrofuro [2, 3-c] pyridine (4), and 3, 3-dichloro-6-dichloroacetyl-7-hydroxy-2-oxo-2, 3, 3a, 6, 7, 7a-hexahydrofuro [2, 3-c] pyridine (5). Reaction of dichloroketene with 1, followed by treatment with abs. methanol gave 3, methyl 2, 2-dichloro-2-(2-pyridyl) acetate (6), and methyl 2, 2-dichloro-2-(4-pyridyl) acetate (7). Similar reaction of dichloroketene with methylpyridine 1-oxides gave the corresponding 2-dichloro and 4-dichloro methylpyridines. On the other hand, reaction of dichloroketene with 2, 6-dimethylpyridine 1-oxide (18), followed by treatment with abs. methanol gave 4-dichloromethyl-2, 6-dimethylpyridine (19) and bis (2, 6-dimethyl-4-pyridyl) dichloromethane (21). Dichloroketene also reacted with quinoline 1-oxide (24) and isoquinoline 2-oxide (29) to give the corresponding dichloromethyl derivatives (25 and 26, and 30, respectively).View full abstractDownload PDF (905K) -
KIYOFUMI FUKUKAWA, TOHRU UEDA, TAKAO HIRANO1983 Volume 31 Issue 6 Pages 1842-1847
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2'(R)-Halogeno-2'-deoxyneplanocin A's were hydrogenated with tri-n-butyltin hydride to yield 2'-deoxyneplanocin A. The same compound was obtained by reduction of the 2'-O-(1-imidazolyl) thiocarbonyl derivative of neplanocin A. This procedure was also applicable to the synthesis of 2'-deoxyadenosine and-guanosine from the corresponding ribosides. Treatment of a neplanocin 2', 3'-O-cyclic thiocarbonate with tri-n-butyltin hydride gave 3'-deoxyneplanocin selectively in high yield.View full abstractDownload PDF (711K) -
MASARU KOBAYASHI, TAKAAKI HAYASHI, KOJI HAYASHI, MASATO TANABE, TAKASH ...1983 Volume 31 Issue 6 Pages 1848-1855
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(24S)-24-Methylcholest-5-ene-3β, 25-diol (ergost-5-ene-3β, 25-diol, 3), (24S)-24-methyl-5α-cholestane-1β, 3β, 5, 6β-tetrol (5α-ergostane-1β, 3β, 5, 6β-tetrol, 2a), and a new sterol, 5α-cholestane-1β, 3β, 5, 6β-tetrol (1), were isolated from the soft coral Sarcophyton gluacum. The structure of 1 was confirmed by the spectroscopic data and by synthesis starting from ruscogenin. The configurations at C-24 of the known C28-polyhydroxysterols (2-5) were shown to be (S) by proton nuclear magnetic resonance (1H-NMR) analysis or by correlation to 22, 23-dihydrobrassicasterol (16a).View full abstractDownload PDF (856K) -
MIKIO TANIGUCHI, AKINORI GONSHO, MASAKO NAKAGAWA, TOHRU HINO1983 Volume 31 Issue 6 Pages 1856-1865
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSelective Na-alkylation, 5-chlorination, 5-bromination, and 5-nitration of tryptophan derivatives were achieved. The alkylation of the cyclic tautomer 2 of Nb-methoxycarbonyl-DL-tryptophan methyl ester (1) with alkyl halides in acetone-K2CO3 gave the Na-alkyl derivatives (3a and 4) in excellent yields. The chlorination of the cyclic tautomer 3b with NCS-AcOH gave the 5-chloro derivative (5b) in 89% yield, and this was readily converted to the 5-chlorotryptophan derivatives (7a, 7b, 9). The similar chlorination of 12 gave the 5-chloro derivatives (13a, 15a) and the 3a-chloropyrroloindole derivative (17). On the other hand the bromination of 12 with NBS-AcOH gave the 5-bromo derivative (13b) in good yield, and this was readily converted to 15d and further to 15c. The nitration of 3b and 12 with fuming nitric acid also gave the 5-nitro derivatives (5c, 7c, 13c, 15e) in excellent yields.View full abstractDownload PDF (1131K) -
MATAO KANAOKA, SABURO YANO, HIROMI KATO, NAOKO NAKANO, EIKO KINOSHITA1983 Volume 31 Issue 6 Pages 1866-1873
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to develop an enzyme immunoassay of glycyrrhizin (GL), N-(glycyrrhizinyl)-ε-aminohexanoic acid and -trans-4-aminomethylcyclohexanecarboxylic acid were synthesized as haptens from GL via 6', 6"-di-tert-butyl GL (VI) as a key intermediate, which was obtained by the selective tert-butylation of GL with O-tert-butyl-N, N'-dicyclohexylisourea or by the hydrogenolysis of 6', 6"-di-tert-butyl-30-benzyl GL (V) over palladium carbon. Coupling of the hapten with bovine serum albumin (BSA) (carrier protein) and β-galactosidase (labelled enzyme) was carried out by the N-hydroxysuccinimide ester method. Anti-GL serum was elicited in rabbits by immunization with N-(glycyrrhizinyl)-ε-aminohexanoic acid-BSA conjugate (XIV). Separation of bound and free fractions was performed by a double antibody method using a goat antiserum to rabbit IgG. 7-β-D-Galactopyranosyl-4-methylcoumarin was used as the substrate for the fluorometric assay of β-galactosidase activity. A satisfactory standard curve for GL was obtained in the range of 0.2-20 ng/ml.View full abstractDownload PDF (921K) -
TAISUKE MATSUO, TOHRU SUGAWARA, HIROTOMO MASUYA, YASUHIKO KAWANO, NORI ...1983 Volume 31 Issue 6 Pages 1874-1884
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSulfazecin (1) is a monocyclic β-lactam antibiotic isolated from strain G-6302, Pseudomonas acidophila. As a key intermediate for the synthesis of sulfazecin derivatives, 3-amino-2-azetidinone (16) was synthesized from penicillins, and various new compounds were synthesized by acylation and sulfonation of 16. Some of these new compounds showed potent antibacterial activity.View full abstractDownload PDF (1242K) -
NORIYA OHTA, YOSHIO OKADA, KEIICHI TANAKA1983 Volume 31 Issue 6 Pages 1885-1895
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA C-terminal hexacosapeptide corresponding to residues 36-61 of human liver metallothionein (hMT II) was synthesized by the fragment condensation method using the azide procedure. Protecting groups were removed by the methanesulfonic acid (MSA) method or hydrogen fluoride (HF) method to give the desired peptide. The binding ability of this peptide with Cd and Zn was examined by measuring the absorbance in the ultraviolet region (200-260 nm) as a function of heavy metal concentration and by the gel-filtration method. The heavy metal-binding behavior of this peptide is quite similar to that of thionein.View full abstractDownload PDF (1288K) -
MASAYUKI SATO, HIROMICHI OGASAWARA, KEIICHI OI, TETSUZO KATO1983 Volume 31 Issue 6 Pages 1896-1901
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA facile and general synthesis of 2, 2-dimethyl-1, 3-dioxin-4-one derivatives (1) is reported. Treatment of β-keto acids with a mixture of acetone, acetic anhydride, and conc. sulfuric acid or with a mixture of isopropenyl acetate and conc. sulfuric acid gave 2, 2-dimethyl-1, 3-dioxin-4-ones (1). Similar treatment of tert-butyl esters of β-keto acids also gave 1.View full abstractDownload PDF (679K) -
MASAYUKI SATO, HIROMICHI OGASAWARA, ERIKO YOSHIZUMI, TETSUZO KATO1983 Volume 31 Issue 6 Pages 1902-1909
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 2, 2, 6-trimethyl-1, 3-dioxin-4-one (diketene-acetone adduct) (1) with imines was investigated. Heating of the adduct 1 with N-(1-phenylethylidene) aniline (6a) gave 6-methyl-1, 2-diphenyl-4-(1H)-pyridone 7a. Similar treatment of N-benzylideneaniline (3a) gave 3, 4-dihydro-6-methyl-2, 3-diphenyl-2H-1, 3-oxazin-4-one (4a). N-Benzylidenealkylamines likewise reacted with the adduct 1 to give the corresponding 1, 3-oxazine derivative 4. Reaction of diketene with N-benzylidenealkylamines in the presence of triethylamine gave the corresponding 1, 3-oxazine along with 3-acetyl-1-alkyl-4-phenylazetidin-2-one (8).View full abstractDownload PDF (756K) -
EIKO OHTSUKA, MITSURU OHKUBO, AKIO YAMANE, MORIO IKEHARA1983 Volume 31 Issue 6 Pages 1910-1916
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2'-O-Tetrahydrofuranyl nucleosides were prepared by an improved procedure via 3', 5'-tetraisopropyldisiloxanylnucleosides. A large scale synthesis of the anticodon heptanucleotide C-U-C-A-U-A-A of E. coli formylmethionine tRNA was performed by the phosphotriester method involving condensation of oligonucleotides having 2'-O-tetrahydrofuranyl protecting groups.View full abstractDownload PDF (910K) -
MASAYOSHI KUBO, MASAHIRO NAGAI, TAKAO INOUE1983 Volume 31 Issue 6 Pages 1917-1922
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe assignment of chemical shifts in the carbon-13 nuclear magnetic resonance (13C NMR) spectra of acerogenin A (1), acerogenin B (2), rhododendrol (5) and related compounds was carried out on the basis of signal multiplicity in the off-resonance spectra, the results of proton selective decoupling, the effect of O-methylation of ortho-monosubstituted phenols on the aryl carbon shielding, and comparison with NMR data for some known compounds, including the effect of oxidation of sec-alcohols to the corresponding ketones on the neighboring carbon shielding. The results offer a useful means for structure elucidation of diarylheptanoids and arylbutanols analogous to 1 and 5. The 13C NMR spectrum of aceroside IV (6), C25H30O8, mp 153°C, [α]D-39.5°, isolated from the stem bark of Acer nikoense (Aceraceae) suggested that 6 is a β-D-glucopyranoside of a new diarylheptanoid, acerogenin C (17), C19H20O3, mp 116°C [the ketonic derivative of acerogenin A (1)]. The structure of 6 was finally confirmed by chemical means.View full abstractDownload PDF (720K) -
MASAHIRO NAGAI, MASAYOSHI KUBO, KUNIO TAKAHASHI, MASAO FUJITA, TAKAO I ...1983 Volume 31 Issue 6 Pages 1923-1928
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the stem bark of Acer nikoense MAXIM. (Aceraceae), three glycosides were isolated, namely aceroside III (1), C30H40O12, mp 138-141°C, [α]D-98.4°, aceroside VI (2), C25H32O8·1/2H2O, mp 124-125°C, [α]D-69.3°, and apiosylepirhododendrin (3), amorphous film (C21H32O11), [α]D-59.5°. On acid hydrolysis, 1 yielded acerogenin A (4), apiose, glucose, and a partially hydrolyzed product 2, while 3 afforded (+)-rhododendrol (11), apiose, and glucose. Inspection of the carbon-13 nuclear magnetic resonance (13C NMR) and the PRFT-NMR spectra of 1 and 3 disclosed that they are apiosyl-(1→6)-glucosides. The proton nuclear magnetic resonance (1H NMR) spectral data of their permethylates (6 and 12) and the analytical data of methanolysis products of 6 and 12 established the structures of 1, 2 and 3 as acerogenin A 11-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, acerogenin A 11-O-β-D-glucopyranoside and (+)-rhododendrol 2-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, respectively.View full abstractDownload PDF (764K) -
YUTAKA YAMAMOTO, SHUHEI OHNISHI, YUTAKA AZUMA1983 Volume 31 Issue 6 Pages 1929-1935
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious of 2, 6-disubstituted 4H-1, 3-thiazin-4-ones (5) were synthesized by successive treatment of N-acylacetylcarboxamides with acid (such as 70% perchloric acid or fluorosulfonic acid) and hydrogen sulfide. Reactions of 5 were investigated ; ammonolysis with ethanolic ammonia gave the corresponding pyrimidin-4-ones; hydrolysis of 2-alkyl-1, 3-thiazine derivatives yielded ring-opened N-acyl-β-mercaptocrotonamides ; reduction with NaBH4 or LiAlH4 afforded 3, 4-dihydro-2H-1, 3-thiazin-4-one derivatives.View full abstractDownload PDF (695K) -
YUTAKA YAMAMOTO, SHUHEI OHNISHI, REIMEI MOROI, ATOMI YOSHIDA1983 Volume 31 Issue 6 Pages 1936-1942
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Alkyl-4H-1, 3-thiazin-4-one derivatives (1) were readily dimerized on being allowed to stand at room temperature, leading to linearly combined dimers. In addition, the 1, 3-thiazines (1) were found to be converted into another type of dimer, having a novel spiro structure, by the action of an acid such as CF3CO2H, ClSO3H, or FSO3H. The structures of the dimers were elucidated.View full abstractDownload PDF (643K) -
KIYOSHI TANAKA, FUMIAKI UCHIYAMA, ATAE ASADA, YASUHIDE FURUSAWA, YASUO ...1983 Volume 31 Issue 6 Pages 1943-1957
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 6-Addition of 2-methyl-1, 3-cyclopentanedione (8) to protoanemonin (7) gave 5-(2-methyl-1, 3-dioxo-2-cyclopentyl) methyl-2, 5H-furanone (6). The Grignard reaction of 6 with isopropenylmagnesium bromide-cuprous iodide provided two kinds of lactones, (10) and (11), in excellent yield through 1, 4-addition of the Grignard reagent to 6 and the subsequent internal aldol cyclization. These lactones, however, possessed the undesired stereostructures for the present synthesis and conversion of the lactone (10) into the desired lactone (4) was performed by retroaldol cleavage and subsequent internal aldol recyclization as shown in Chart 6.View full abstractDownload PDF (1618K) -
KIYOSHI TANAKA, FUMIAKI UCHIYAMA, TAKAHARU IKEDA, YASUO INUBUSHI1983 Volume 31 Issue 6 Pages 1958-1971
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe picrotoxane skeleton (5) except for a C1 unit at the C9 position was effectively synthesized starting from protoanemonin and 2-methyl-1, 3-cyclopentanedione through five steps. The key reaction of this synthesis was the Grignard reaction of the ester (6) with isopropenylmagnesium bromide. A synthetic approach for completing the total synthesis of coriamyrtin (4) by functionalization of the five-membered ring of the lactone (5) was also examined.View full abstractDownload PDF (1604K) -
KIYOSHI TANAKA, FUMIAKI UCHIYAMA, KIYOSHI SAKAMOTO, YASUO INUBUSHI1983 Volume 31 Issue 6 Pages 1972-1979
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stereocontrolled total synthesis of (±)-coriamyrtin (1) has now been completed, starting from protoanemonin and 2-methyl-1, 3-cyclopentanedione, through fifteen steps. The Wittig reaction of the ditetrahydrofuranyl ether (3) with triphenylphosphonium methylide gave the exo-methylenic compound (4), which was derived to the lactone (6) by consecutive hydrolysis, alkaline hydrolysis, and lactonization. The lactone (6) was transformed into the bromoether (8), which was subjected to allylic hydroxylation to give the allyl alcohol (10). Epoxidation of the allyl alcohol (10) provided selectively the epoxy-alcohol (11), which was derived to the mesylate (16). Elimination of the O-mesyl group gave the olefin (17). Epoxidation of 17 with m-chloroperbenzoic acid gave (±)-bromocoriamyrtin (18) and finally, reductive debromination of 18 furnished (±)-coriamyrtin (1).View full abstractDownload PDF (984K) -
YOSHIAKI WATANABE, SHUICHI SANADA, YOSHITERU IDA, JUNZO SHOJI1983 Volume 31 Issue 6 Pages 1980-1990
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight steroidal glycosides, tentatively named glycosides A (1), B (2), C (3), D (4), E (5), F (6), G (7) and H (8), were isolated from the methanol extract of the subterranean part of Liriope platyphylla WANG et TANG (Liliaceae). The structures of these glycosides were established as ruscogenin 3-O-α-L-rhamnopyranoside (1), 25 (S)-ruscogenin 1-O-β-D-fucopyranosido-3-O-α-L-rhamnopyranoside (2), 25 (S)-ruscogenin 1-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside (3), ruscogenin 3-O-β-D-glucopyranosyl (1→3)-α-L-rhamnopyranoside (4), a mixture of 3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl (1→3)]-β-D-glucopyranosides of diosgenin and yamogenin (=a mixture of ophiopogonin D' and its 25 (S)-isomer, 5), a mixture of 3-O-β-chacotriosides of diosgenin and yamogenin (=a mixture of dioscin and its 25(S)-isomer, 6), ruscogenin 1-sulfate 3-O-α-L-rhamnopyranoside (7), and 26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β, 26-diol 3-O-β-chacotrioside (=methyl proto-dioscin, 8).View full abstractDownload PDF (1337K) -
HIDEJI ITOKAWA, HIROSHI NAKANISHI, SUSUMU MIHASHI1983 Volume 31 Issue 6 Pages 1991-1997
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid-catalyzed rearrangement of hinesol α-epoxide (5a) gave 1α-hydroxyeudesmols (9, 10, 11) together with other spirane-type products (6, 8, 14). The same reaction of α-and β-epoxides of hinesol acetate also provided eudesmane derivatives. These results and mechanistic considerations led us to re-examine the formic acid dehydration reaction of hinesol and it was found that the main product does not have the structure 3 or 4 as assumed by Marshall et al., but is identical with (+)-δ-selinene (21).View full abstractDownload PDF (854K) -
HIROKO KIMATA, TAEKO NAKASHIMA, SETSUKO KOKUBUN, KEISO NAKAYAMA, YOHKO ...1983 Volume 31 Issue 6 Pages 1998-2005
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom pericarps of Sapindus mukurossi (Japanese name : Enmei-hi), saponins of hederagenin (1), 2-7, 9, 11 and 12 were isolated along with sapindosides A (10) and B (8), both of which have already been isolated from this crude drug. Saponins 7 and 9 were identified as α-L-arabinopyranosyl (1→3)-α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoside and α-L-arabinofuranosyl (1→3)-α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoside of 1, respectively, both of which were recently isolated from Lecaniodiscus cupanoides by Sandberg et al. New saponins named mukurozi-saponins E1 (11) and G (12) were proved to be the mono-acetate of 8 and the di-acetate of 7, respectively. By means of mass and 13C nuclear magnetic resonance (NMR) spectroscopy, the locations of the acetyl groups of 11 and 12 were established to be at the 4-hydroxyl group of the xylosyl unit of 8 and at the 3, 4-hydroxyl groups of the terminal arabinosyl unit of 7, respectively. The other new saponins, named mukurozi-saponins X (6), Y1 (5) and Y2 (4), were revealed to be β-sophorosyl esters of 10, 8 and 7, respectively, by comparison of the mass and 13C NMR spectra with those of the β-sophorosyl ester of 1 (13), which was synthesized from 1 as a reference compound for the study of the anomalous glycosylation shifts. Studies on the structures of the remaining saponins, 2 and 3, are in progress. The water solubilities of the monodesmosides, 7-9, which cause remarkable enhancement of the absorption of sodium ampicillin from rat intestine and rectum, were greatly increased by the bisdesmosides, 4-6.View full abstractDownload PDF (930K) -
KATSUMI ITOH, AKIO MIYAKE, MASAO TANABE, MINORU HIRATA, YOSHIKAZU OKA1983 Volume 31 Issue 6 Pages 2006-2015
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 3-aminomethyl-1, 2-dihydronaphthalene derivatives (6-22) was prepared from the corresponding 3, 4-dihydro-1 (2H)-naphthalenone derivatives (24a-q) in three steps, namely the Mannich reaction, reduction of the carbonyl group with sodium borohydride, and dehydration with ethanolic hydrogen chloride. Compounds 6-22 and several related analogs (23, 27-30) were tested for vasodilating and antihypertensive activities. Potent cerebral vasodilating and antihypertensive activities were exhibited by 1-benzhydryl-4-(7-disubstituted amino-1, 2-dihydro-3-naphthyl) methylpiperazines (16, 18 and 19).View full abstractDownload PDF (1049K) -
KATSUMI ITOH, YOSHIKAZU OKA1983 Volume 31 Issue 6 Pages 2016-2022
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-(N-Substituted amino)-3-arylcyclohex-2-enol (7) was designed as a new type of β-adrenergic blocker on the basis of the X-ray crystallographic data for propranolol. Eight such compounds (7) were prepared by a six-step sequence of reactions from 3-arylcyclohex-2-enone (8), and tested for β-blocking activity in vitro. A weak β-blocking activity was exhibited by 6-(1-methyl-3-phenylpropyl) amino-3-phenylcyclohex-2-enol (7e).View full abstractDownload PDF (720K) -
SHUNSUKE NARUTO, HIROYUKI MIZUTA, TOYOKICHI YOSHIDA, HITOSHI UNO, KATS ...1983 Volume 31 Issue 6 Pages 2023-2032
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral analogs of (Z)-2-(1, 2-benzisoxazol-3-yl)-3-[2-(2-piperidinoethoxy) phenyl]-acrylonitrile (1a), such as (Z)-2-(1, 2-benzisothiazol-3-yl)-, (Z)-2-(1H-indol-3-yl)-, (E)-2-(2-thienyl)-and (E)-2-benzoyl-3-(ω-dialkylaminoalkoxyphenyl) acrylonitriles (2-5), were synthesized by means of the Knoevenagel condensation. The descyano analog (6) was prepared by means of the Wittig reaction. Triethylammonium formate reduction of 1 afforded the dihydro analog (7). The spasmolytic activities of these analogs were examined. Among these compounds, (Z)-2-(1, 2-benzisothiazol-3-yl)-3-[2-(2-piperidinoethoxy) phenyl]-acrylonitrile (2a) and (Z)-2-(1, 2-benzisothiazol-3-yl)-3-[2-(2-morpholinoethoxy) phenyl]-acrylonitrile (2b) showed potent antispasmodic activities in vitro and in vivo (in mice).View full abstractDownload PDF (1011K) -
YASUHIKO MATSUKI, TOMIHARU ITO, MAKOTO KOJIMA, HIDEO KATSUMURA, HIROSH ...1983 Volume 31 Issue 6 Pages 2033-2038
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe administration of a deuterium-labeled drug together with a prodrug made it possible to determine the bioconversion rate of the prodrug into the parent compound accurately in dogs. Deuterated indomethacins were prepared from acetaldehyde p-methoxyphenylhydrazone in four steps. Indomethacin in blood plasma was derivatized into the hexafluoroisopropyl ester and determined by means of selected ion monitoring employing indomethacin-d9 as an internal standard. When a single dose of indomethacin or oxametacin was orally given to dogs, the time courses of plasma level of indomethacin were remarkably different from one another. This result implied that the bioconversion rate of oxametacin into indomethacin could not be directly estimated from the area under the drug concentration-time curve (AUC) value. When a mixture of indomethacin-d4 and oxametacin was administered to three dogs, the ratios of the AUC value of the nonlabeled indomethacin derived from oxametacin to that of the labeled indomethacin in the dogs were found to be almost equal. This approach was also applicable to the estimation of acemetacin. It has been demonstrated that the bioavailabilities of oxametacin and acemetacin can be fairly accurately evaluated with a small number of animals by the combined use of labeled indomethacin and selected ion monitoring.View full abstractDownload PDF (681K) -
SHIGEO NAKAJO, KAZUYASU NAKAYA, YASUHARU NAKAMURA1983 Volume 31 Issue 6 Pages 2039-2044
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe major plasma memebrane glycoproteins of AH-66 cells were radiolabeled by three methods which are known to label cell surface carbohydrates. The labeled components were separated by polyacrylamide gel electrophoresis and detected by fluorography. The AH-66 cells were found to be unusual because a single major glycoprotein with an apparent molecular weight of 165000 was almost exclusively labeled by both neuraminidase-galactose oxidase-NaB3H4 and dilute periodate-NaB3H4 treatments. The major glycoprotein was not labeled by galactose oxidase-NaB3H4 treatment. When the major glycoprotein labeled by the neuraminidase-galactose oxidase-NaB3H4 procedure was solubilized with Triton X-100 and then subjected to affinity chromatography on Sepharoseconjugated Ricinus communis agglutinin II, the 3H-labeled major glycoprotein bound to Sepharose-conjugated Ricinus communis agglutinin II lectin and was eluted with lactose. These results indicated that the major glycoprotein contained sialyl-galactosyl or sialyl-N-acetylgalactosaminyl terminal groups, which are exposed on the external surface of the plasma membranes of AH-66 cells.View full abstractDownload PDF (889K) -
TOSHIAKI ANDO, HIROSHI YUASA, YOSHIO KANAYA, KIKUO ASAHINA1983 Volume 31 Issue 6 Pages 2045-2054
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of different granulation methods on the anisotropy, the pore size and the crushing strength of tablets were studied. Calcium phosphate dibasic was granulated by three methods-(A) extruding granulation, (B) disintegrating granulation and (C) tumbling granulation. Five and 10% ethanol solutions of hydroxypropyl cellulose were used as binders. The degree of anisotropy of tablets was assessed in terms of the difference of the apparent compliance values between the compressive axial direction and the radial direction, which were obtained from the strain recovery at the ejection of tablets. The measurements of pore size in tablets were carried out with a mercury porosimeter. For both concentrations of the binder, the degree of anisotropy was in the order tablets (C) (tumbling granulation) > tablets (B) (disintegrating granulation) > tablets (A) (extruding granulation). It is presumed that the structure, bulk density and strength of the granules are important factors. At the same porosity, the mean pore diameters of the tablets were in the order tablets (C) > tablets (B) > tablets (A). The crushing strengths of the tablets were in the order tablets (A) > tablets (B) > tablets (C) for both concentrations of the binder. The larger the degree of anisotropy was, the larger the strain recovery was. Thus, it is presumed that large pores are formed by large strain recovery in the tablets, and consequently the strength of the tablets becomes low.View full abstractDownload PDF (1386K) -
MITSURU HASHIDA, YOSHINOBU TAKAKURA, SATOSHI MATSUMOTO, HITOSHI SASAKI ...1983 Volume 31 Issue 6 Pages 2055-2063
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe regeneration characteristics and biological activities of mitomycin C-dextran conjugate (MMC-D) were investigated in comparison with those of free mitomycin C (MMC), and the following results were obtained. (1) MMC is coupled at the 1a-nitrogen position via an amide linkage to a carboxyl group of ε-aminocaproic acid (6-aminohexanoic acid) which was introduced onto dextran as a spacer. (2) MMC-D was stabler than MMC against acid-catalyzed and metabolic degradation. (3) MMC was liberated from MMC-D with a half-life of about 24 h under physiological conditions (pH 7.4, 37°C) and more rapidly at higher pH. (4) Liver homogenate did not accelerate the liberation of MMC from MMC-D. (5) Antimicrobial activity of MMC-D against Escherichia coli B was less than one-eighteenth of that of MMC. (6) MMC-D showed about one-tenth of the antitumor activity of MMC in vitro in contact with L1210 leukemia cells, but showed almost equal efficiency in the i. p.-i. p. system in vivo, suggesting that MMC-D exhibited activity after being regenerated to the parent drug in the body.View full abstractDownload PDF (940K) -
Dissolution Properties and Bioavailability of Phenytoin from Ground Mixtures with Chitin or ChitosanYOICHI SAWAYANAGI, NAOKI NAMBU, TSUNEJI NAGAI1983 Volume 31 Issue 6 Pages 2064-2068
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith a view to application of chitin and chitosan to pharmaceutical preparations, the dissolution and bioavailability of ground mixtures of phenytoin with chitin or chitosan were investigated. Ground mixtures of phenytoin with chitin, chitosan and crystalline cellulose in 1 : 2 weight ratio were prepared by co-grinding in a ball mill. The X-ray diffraction patterns suggested that the size of crystals of phenytoin was decreased in the ground mixtures. The dissolution rate of phenytoin from the ground mixtures was significantly greater than that from physical mixtures or intact phenytoin powder. The ground mixture with chitosan showed fastest dissolution, followed by that with chitin and then that with crystalline cellulose. The dissolution of phenytoin from tablets of the ground mixture with chitin or chitosan was greater than that from tablets of the physical mixture, while that from tablets of the ground mixture with crystalline cellulose was significantly smaller than that from tablets of the physical mixture. It was confirmed that the ground mixture of phenytoin-chitosan gave enhanced bioavailability of phenytoin in beagle dogs.View full abstractDownload PDF (595K) -
YOSHIAKI KAWASHIMA, TERUYOSHI NASU, SUMIO WATANABE, YASUO MIYAKE, HIDE ...1983 Volume 31 Issue 6 Pages 2069-2078
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiffusion coefficients of theophylline and aminophylline in carrageenan gels of various concentrations at 37°C were measured by means of drug sorption and permeation tests using a diffusion cell. The permeation data were analyzed by Rogers' method and a lag time method. The diffusion coefficients determined by Rogers' method coincided reasonably well with those determined by means of the drug sorption test. They were 0.54 to 0.81×10-5 cm2/s and 0.43 to 0.86×10-5 cm2/s for theophylline and aminophylline, respectively. The diffusion coefficients determined by the lag time method were larger than those determined by the other methods. The diffusion coefficient of aminophylline was slightly larger than that of theophylline at the same initial concentration, e. g. 5.0×10-3 (g/ml). Ethylenediamine might loosen the carrageenan network, thus enhancing the diffusion of the drug. The diffusion coefficient was dependent upon the carrageenan concentration in the gel. The gel thickness bad a less important effect on the diffusion coefficient, although the lag time greatly depended on it. The diffusion coefficients were also determined by means of drug release tests using the same diffusion cell. When the drug was dispersed in the gel as a solution, the diffusion coefficient agreed fairly well with that determined in the sorption test. In carrageenan with dispersed solid particles, the drug transfer rate was enhanced by hydrodynamic flow from the voids left after dissolution of the particles in the gel.View full abstractDownload PDF (960K) -
AYAKA SUENAGA, TERUMI WADA, HISASHI ICHIBAGASE1983 Volume 31 Issue 6 Pages 2079-2084
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDicyclohexylamine (DCHA), a metabolite of sodium cyclamate (CHS-Na), was identified by gas liquid chromatography (GLC) and thin-layer chromatography (TLC) from the urine of rabbits and rats following repeated oral administration of CHS-Na. The urinary excretions (% of the dose) of DCHA in rabbits and rats receiving CHS-Na were 0.041×10-3 and 0.143×10-3%, respectively. Moreover, the metabolic fate of DCHA was investigated in rabbits and rats. The urinary and fecal excretions of unchanged DCHA were relatively small in both rabbits and rats receiving oral or intravenous administration of DCHA. In addition, DCHA was suggested to be primarily metabolized by oxidative reaction in the hepatic 10000×g supernatant. Thus, it may be due to further metabolism of the produced DCHA that only a small amount of DCHA is excreted in the urine after repeated oral administration of CHS-Na to rabbits and rats.View full abstractDownload PDF (651K) -
KENICHI SHIROTANI, ETSUKO SUZUKI, KEIJI SEKIGUCHI1983 Volume 31 Issue 6 Pages 2085-2093
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSolvates of sulfathiazole with acetone, 2-butanone, 2-pentanone and dioxane were isolated, and their physico-chemical properties were investigated by infrared spectroscopy, X-ray powder diffractometry, differential scanning calorimetry (DSC), thermogravimetry and scanning electron microscopy. The process of desolvation was observed thermo-microscopically and the specific surface areas of the desolvated products were measured by the BET method. The combining ratios of all the solvates were determined to be 1 : 1 from the weight descrease in the thermogravimetric curves. The DSC measurements and the visual observations revealed that these solvates belong to the class of compounds with incongruent melting points. The kinetic analysis of the isothermal desolvation showed that the desolvation proceeded in accordance with the mechanism of random nucleation and two-dimensional crystal growth as represented by the Avrami-Erofeev equation. The effects of desolvating conditions and the molecular volume of the solvent on the particle size and the surface appearance of recovered sulfathiazole were examined in detail.View full abstractDownload PDF (1771K) -
KIMIO KATSUURA, KEMMOTSU MITSUHASHI1983 Volume 31 Issue 6 Pages 2094-2102
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSyntheses of 4, 5, 6, 7, 8, 9-hexahydro-4, 8-methano-5-methylthiazolo [4, 5-c] azocine (III) and 4, 5, 6, 7, 8, 9-hexahydro-4, 8-methano-5-methylthiazolo [5, 4-c] azocine (IV) are described. Thiazolization of 2-azabicyclo [3. 3. 1] nonan-8-one (V) gave the 2-aminothiazole (VII), which was converted into III by deamination, hydrolysis of the benzoyl group and Esch-weiler-Clarke N-methylation. The 2-hydroxyl derivative (XIII) was also synthesized. On the other hand, compound (IV) was synthesized by cyclization of the olefinic urethane (XXI) with phenylselenenyl chloride, as a key step. Deselenation of XXII with triphenyltin hydride followed by LiAlH4 reduction gave IV. The urethane (XXI) was prepared from the 2-aminothiazole (XVIIa), which was obtained by condensation of the bromodiketone (XVI) and thiourea.View full abstractDownload PDF (1072K) -
TOSHIO FUJITA, YUKIKO HARIMA, AKIRA KOSHIRO1983 Volume 31 Issue 6 Pages 2103-2109
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetics of the degradation of cefotiam in aqueous solution was studied at 25°C and an ionic strength of 0.6 over the pH range of 2 to 12. The degradation was a pseudo first order reaction in this pH range. The rate-pH profile showed a characteristic maximum near the isoelectric point of cefotiam (pH 5.8). The optimal pH of an aqueous solution of cefotiam dihydrochloride for stability was calculated to be 8.0. The degradation pathways were shown to involve spontaneous hydrolysis of four ion species and hydroxide ion-catalyzed hydrolysis of the monoanion. Aminoglycosides accelerated the degradation of cefotiam by a pseudo second order reaction. From analysis of the rate-pH profile of the second order rate constants of these aminoglycosides, it appeared that the reaction was substantially a third order reaction with regards to cefotiam, aminoglycoside and hydroxide ion. Therefore, the combined use of cefotiam and aminoglycosides should be avoided at alkaline pH and/or at high concentration.View full abstractDownload PDF (711K) -
TOSHIHIKO OZAWA, AKIRA HANAKI1983 Volume 31 Issue 6 Pages 2110-2113
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of axial ligation to meso-tetraphenylporphinatocadmium (CdTPP) were studied in dimethyl sulfoxide (DMSO) or dichloromethane (CH2Cl2). Addition of neutral (L) or anionic ligands (X-) to CdTPP caused red shifts in the absorption spectrum. The magnitude of the red shift depended on the charge but not on the strength of the Cdligand bond. Further, a relationship between the ratio εα/εβ and the wavenumber of the Soret band was observed.View full abstractDownload PDF (440K) -
YOSHIHISA OKAMOTO, TAKEO UEDA, KANAME TAKAGI1983 Volume 31 Issue 6 Pages 2114-2119
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHydrazines readily reacted with 4-amino-1H-1, 5-benzodiazepine-3-carbonitrile (1) to afford ring-opened hydrazine adducts (2) which were recyclized to compounds 3, 4 and 9 by treatment with aqueous sodium hydroxide solution. Compound 4 was converted to 5 by loss of ammonia in good yield. All the reactions described here were carried out in water.View full abstractDownload PDF (617K) -
RYOJI KASAI, HIROMICHI BESSO, OSAMU TANAKA, YUHICHIRO SARUWATARI, TOHR ...1983 Volume 31 Issue 6 Pages 2120-2125
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom Red Ginseng, all of the known saponins of White Ginseng were isolated in yields similar to those obtained from White Ginseng. Two additional minor saponins, notoginsenoside-R1 (19) (the saponin of roots of Panax notoginseng) and quinquenoside-R1 (20) (the saponin of roots of P. quinquefolium), were also isolated and identified. Besides these known saponins, two new minor saponins named ginsenosides-Rs1 (17) and -Rs2 (18) were also isolated. Compounds 17 and 18 were established to be monoacetates at the 6-hydroxyl group of the terminal glucosyl moiety of the sophorosyl unit of ginsenosides-Rb2 (5) and-Rc (7), respectively.View full abstractDownload PDF (644K) -
TAKUSHI KURIHARA, ATSUTOSHI OTA, HIROFUMI HAYASHI, HIDEHITO URATA, MAS ...1983 Volume 31 Issue 6 Pages 2126-2129
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn improved synthesis of 5'-deoxy-5'-adenosineacetic acid (5), which is useful as a model nucleotide of adenosine-5'-monophosphate, is presented.View full abstractDownload PDF (544K) -
MASAICHIRO MASUI, TAKAHIRO UESHIMA, TOMOKO YAMAZAKI, SHIGEKO OZAKI1983 Volume 31 Issue 6 Pages 2130-2133
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe electrochemical acylation of amines and alcohols is described. The yield of products from the electrochemical reaction is markedly improved by the use of N-phenyl derivatives of hydroxamic acids in place of the N-hydrogen counterparts.View full abstractDownload PDF (548K) -
OSAMU FUJISHITA, SHUN HIGUCHI, MANABU YOSHIKAWA, TOSHINOBU AOYAMA, MAS ...1983 Volume 31 Issue 6 Pages 2134-2138
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA correlative equation relating the molecular weight of ions to the relative step height in an isotachopherogram was derived : hR=a+b M/|Z|, in which hR, M, |Z|, a and b are the relative step height with chloride ion as a standard, the molecular weight, the electric charge of ions and two constants, respectively. Therefore, the molecular weight of ions may be estimated from the relative step height in an isotachopherogram, when the electric charge is known. The equation for carboxylic acids was : hR=0.65+0.01 M/|Z|. The optimum pH of electrolytes for the estimation of molecular weight or for the separation of ions may be determined from the relative step height-pH curves obtained on the basis of this equation.View full abstractDownload PDF (590K) -
KEIJI SEKIGUCHI, ETSUKO SUZUKI, YASUYUKI TSUDA, YUTAKA MORITA1983 Volume 31 Issue 6 Pages 2139-2141
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermal analysis of the griseofulvin-chloroform system was done by differential scanning calorimetry with special pressure-resistant sample containers. Thus, the complete phase diagram in a condensed state could be constructed successfully. From the diagram, it was confirmed that a single one-to-one solvate having an incongruent melting point of 147°C was formed between the two components.View full abstractDownload PDF (379K) -
Toshihiko Ozawa, Akira Hanaki1983 Volume 31 Issue 6 Pages 2142-2145
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of superoxide ion, O2-, with chloro-5, 10, 15, 20-tetra-p-tolylporphinatocobalt (III), [Co (III) (TTP) Cl], was investigated by spectroscopic methods (UV/vis and ESR) in dimethyl sulfoxide (DMSO). Spectral data show that O2- does not bind to Co (III) (TTP) Cl to give the O2- complex, but reduces it directly to Co (II) (TTP) at room temperature.View full abstractDownload PDF (409K) -
Atsushi Numata, Tsuruko Takemura, Hideyuki Ohbayashi, Takako Katsuno, ...1983 Volume 31 Issue 6 Pages 2146-2149
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn addition to the eight known compounds two new constituents were isolated as antifeedants for the larvae of the yellow butterfly, Eurema hecabe mandarina de 1' Orza, from the methanol extract of Lycoris radiata Herb. Their structures were established to be (-)-3'-hydroxy-4'-methoxy-7-hydroxy-8-methylflavan (I) and O-methyl-lycorenine (III) on the basis of spectral evidence. Final evidence for the structure of I came from the synthesis of the racemate. Two of the known compounds, galanthamine and lycoramine, were isolated as carbonate. In addition to I and demethylhomolycorine (IV), lycoricidinol (VII) and lycoricidine (VIII), reported as plant growth inhibitors, were main antifeedants in L. radiata.View full abstractDownload PDF (412K) -
Makoto Nishizawa, Takashi Yamagishi, Tohru Ohyama1983 Volume 31 Issue 6 Pages 2150-2152
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInhibitory effects of galloylglucoses having 3 to 10 galloyl groups isolated from crude drugs were examined on the State 3 respiration of rat liver mitochondria. The degree of the inhibition of respiration by these gallotannins depended on the number of galloyl groups per glucose.View full abstractDownload PDF (375K) -
Masanori Somei, Shoichi Tokutake, Chikara Kaneko1983 Volume 31 Issue 6 Pages 2153-2156
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first syntheses of 6, 6a, 7, 8, 9, 9a-hexahydro-and 6, 6a, 9, 9a-tetrahydro-2H-isoindolo [4, 5, 6-cd] indoles are described. The preparation of 1, 3, 4, 5-tetrahydrobenz [cd] indole derivatives is also included.View full abstractDownload PDF (528K) -
Hiroshi Takaku, Kazuo Kamaike, Hisashi Mori, Yoshiaru Ishido1983 Volume 31 Issue 6 Pages 2157-2159
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe phosphoric acids were smoothly alkylated with alkyl halides in the presence of cesium fluoride.View full abstractDownload PDF (356K) -
Motomasa Kobayashi, ByengWha Son, Masaru Kido, Yoshimasa Kyogoku, Isao ...1983 Volume 31 Issue 6 Pages 2160-2163
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new trinor-guaiane sesquiterpene named clavukerin A (1) was isolated from the Okinawan soft coral Clavularia koellikeri (stolonifer) and the absolute stereostructure was elucidated by the chemical and physicochemical evidence and the X-ray crystallographic analysis.View full abstractDownload PDF (450K) -
Hiromichi Tanaka, Akira Matsuda, Shuji Iijima, Hiroyuki Hayakawa, Tada ...1983 Volume 31 Issue 6 Pages 2164-2167
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new class of 5, 6-disubstituted uridines, in which the C-6 position was occupied by phenylthio group or iodine, were synthesized via lithiation of the corresponding 5-substituted 2', 3'-O-isopropylidene-5'-O-methoxymethyluridines and subsequent electrophilic reactions. These newly-synthesized uridine derivatives exhibited antileukemic activities against mouse leukemia L5178Y cells in culture.View full abstractDownload PDF (399K) -
Chikara Kaneko, Toshihiko Naito, Yu Momose, Naoyuki Shimomura, Tetsuo ...1983 Volume 31 Issue 6 Pages 2168-2171
Published: June 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclopentane ring annelation methods for 2-pyridone derivatives are provided by cyclobutane ring expansion of 1, 2-dihydrocyclobuta [c] pyridin-3 (4H)-ones having an appropriate function at the l-position. Since the latter compounds are readily accessible from 4-alkoxy-2-pyridones via our two-step procedure (Kaneko-Naito method), the methods seem to have wide applicability for the synthesis of cyclopenta [c] pyridines.View full abstractDownload PDF (446K)