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Volume 26, Issue 1
Displaying 1-50 of 59 articles from this issue
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MAMORU SUGIURA, MUTSUKO SUZUKI, TOKIKO SHIMOMURA, MASANORI SASAKI1978 Volume 26 Issue 1 Pages 1-8
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe enzymatic properties of crude β-galactosidases from M. phaseoli and S. tuliparum were studied from the standpoint on the pharmaceutical aspects in comparison with the properties of the enzyme from Aspergillus oryzae which is available on the market as a therapeutic agent for lactose intolerance. Optimum pH of Macrophomina and Sclerotium enzymes were 4.5 and 1.5, respectively. Stable pH ranges of the enzymes were 4 to 8.5 for Macrophomina and 3 to 6 for Sclerotium enzyme, and both enzymes were stable up to 60°and 55°for 30 min, respectively. These enzymes were not affected by addition of metal ions or reagents tested (excepting N-bromosuccinimide). The enzymes hydrolyzed lactose, and lactose in milk and dry milk with the same rate as Aspergillus enzyme. In a powder state, both enzymes were more stable than Aspergillus enzyme on standing at relative humidity (RH) of 92% and 30° and also stable to human gastric and intestinal juices in the presence of substrates. The enzymes were not affected by diluents tested. Furthermore, Macrophomina enzyme was stable for binders and disintegrators, whereas Sclerotium enzyme was completely inactivated by aerozol and sodium dodecyl sulfate (SDS) among the agents tested. Against wetting agents tested, Macrophomina enzyme was stable, but Sclerotium enzyme was stable to isopropanol and low concentration of ethanol and acetone. Both enzymes were more stable than Aspergillus enzyme under the pressure range of 0.5 to 2.0 ton. From these results, it is suggested that β-galactosidases from M. phaseoli and S. tuliparum can be effectively utilized as a therapeutic agent for lactose intolerance.View full abstractDownload PDF (830K) -
MINAKO TANAKA, HIDENORI FUKUDA, TSUNEJI NAGAI1978 Volume 26 Issue 1 Pages 9-13
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn investigation was done on the permeation of drug through the model membrane consisting of Millipore filter saturated with an oil, indicating that the method employed here might be satisfied for obtaining the permeation curve with an excellent reproducibility. The theoretical treatment of the data obtained by this method proved that the permeation of drug through the present system depended on the diffusion mechanism. The ionized molecules of salicylic acid and aminopyrine did not permeate through the membrane. The temperature dependence of the permeation was well expressed by Stokes-Einstein's equation concerning diffusion constant. The experiment using different oils showed that the permeability constant increased with the increase in distribution constant in oil and decreased with the increase in viscosity of oil. Actually, the apparent permeability constant increased proportionally with the increase in distribution constant in oil, and decreased with the increase in the viscosity of the oils used.View full abstractDownload PDF (542K) -
TERUYUKI MIYAMOTO, YOSHITAKA KIMURA, JUNICHI MATSUMOTO, SHINSAKU MINAM ...1978 Volume 26 Issue 1 Pages 14-18
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new and convenient synthetic method was presented for the derivatives of the pyrimido [4, 5-c] pyridazine. Reactions of α-diazo-β-oxo-5-(4-chloro-2-substituted pyrimidine) propionates (1a-c) with triphenyl phosphine afforded ethyl 1, 4-dihydro-4-oxo-7-substituted pyrimido [4, 5-c] pyridazine-3-carboxylates (3a-c) in good yields. α-Diazo-β-oxo-5-(4-methoxy-2-methylthiopyrimidine) propionate (5a), when treated with triphenyl phosphine in the same conditions, yielded {[1-ethoxycarbonyl-2-oxo-2-(4-methoxy-2-methylthio-5-pyrimidinyl) ethylidene] hydrazono} triphenyl phosphorane (6a) which was an intermediate for the 7-methylthio derivative (3a). The conversion of 6a into 3a was effected by treating with aqueous alcohol via ethyl α-hydrazono-β-oxo-5-(4-methoxy-2-methylthiopyrimidine) propionate (7a). The 2-phenyl derivative (5b) gave the 7-phenyl analog (3b). Reaction mechanisms for 1 leading to 3 were discussed.View full abstractDownload PDF (714K) -
KANJI TAKADA, HIROMI MIKAMI, SHOZO ASADA, SHOZO MURANISHI, KIYOSHI TAT ...1978 Volume 26 Issue 1 Pages 19-24
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSImprovement of the bioavailability of rifampicin (RFP) was attempted by dosage form design. As lipid vehicles, sesame oil, soybean oil, oleic acid and middle chain triglyceride (MCT) such as tricapriline, were employed. When sesame oil or MCT was used as a lipid vehicle, the percentage recovery of RFP into rat bile was significantly decreased and rat serum RFP level was increased. This improvement of the bioavailability of RFP was also occurred in a dog. The mechanism by which the bioavailability of RFP was improved by lipid vehicles was studied and it has been revealed that this improvement of the bioavailability of RFP is not due to its depressed hepatic uptake from the blood stream after absorption from the gastrointestinal tract but due to the depressed active biliary excretion from the hepatocytes into the bile.View full abstractDownload PDF (745K) -
SHOGO UEMATSU, YUKIO AKAHORI1978 Volume 26 Issue 1 Pages 25-32
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe tautomerism of 5-chlorobenzofuroxan, 5-bromobenzofuroxan, and 5-iodobenzofuroxan was studied by the proton magnetic resonance (PMR) at 60 MHz. The rate of intramolecular rearrangement between the tautomers was calculated from the PMR line shape, using the density matrix method of intramolecular nonmutual exchange. The activation parameters for the intramolecular rearrangement were found to be ⊿H≐̸=5∼24 kcal/mol, ⊿S≐̸=-34∼+33 cal/deg·mol. Structure of the transition state is discussed from electronic energies of the system and it was concluded that this reaction proceeds via a transition state of ψ-o-dinitrosobenzene produced by the electrocyclic ring opening reaction of benzofuroxan.View full abstractDownload PDF (706K) -
TSUYOSHI GOROMARU, KENJI MATSUYAMA, ATSUKO NODA, SADAO IGUCHI1978 Volume 26 Issue 1 Pages 33-37
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy means of mass fragmentography using the isotope dilution method, the measurement of the plasma concentration of aminopyrine (AM) and its metabolites was performed successfully. It was clarified from the plasma concentration-time curve that the individual differences were observed in two processes which are demethylation of AM to 4-monomethylaminoantipyrine (MAA) or MAA to 4-aminoantipyrine (AA) and acetylation of AA to 4-acetylaminoantipyrine. Furthermore, a quantitative correlation between the plasma concentration and the amount of urinary excretion was discussed.View full abstractDownload PDF (565K) -
MAMORU TANAKA, MITSURU KIMOTO, KANJI TOKUYAMA1978 Volume 26 Issue 1 Pages 38-47
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Dimethoxymethyl-3-methoxypropionitrile (I), an important compound for thiamine production, was obtained in good yield by the hydrogen chloride-catalyzed acetalation of 2-formyl-3-methoxypropionitrile (II) in methanol. The reaction was proved not to proceed through direct acetalation of the formyl group but via the pathway of II→allyl hydroxy-(V) and allyl ether-(VI) cations→2-dimethoxymethylacrylonitrile (III)⇌2-methoxymethylene-3-methoxypropionitrile (IV)⇌I. The reaction gave 2-oxopiperidines (VII, VIII) and pyrans (IX, X) as minor products which should be formed by the attack of the allyl cations to II or IV. Kinetic studies on the reaction pathway of III⇌IV⇌I revealed that the cis isomer of IV was more reactive than the trans counterpart. The same acetalation of methyl 2-formyl-3-methoxypropionate (XVI) was similarly investigated.View full abstractDownload PDF (1076K) -
MASATOSHI HARADA, YUKIHIRO OZAKI1978 Volume 26 Issue 1 Pages 48-52
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffect of 6 Gardneria alkaloids, namely, gardneramine, gardnerine, gardnutine, hydroxygardnutine, 18-demethylgardneramine, and Alkaloid I on ganglionic transmission was examined in the rabbit and rat superior cervical ganglionic in situ preparations. In general, no marked, if at all, difference between both preparations with respect to their maximal response to each of the first 4 compounds was observed. Among these compounds, the most potent ganglion blocking effect was found in gardneramine, gardnerine, and Alkaloid I. Their effect was short-acting compared with that of hexamethonium. The activity of gardneramine and gardnerine was about 1/2 (rabbit), and about 1/4 (rat), as potent as that of hexamethonium. On the other hand, the effect of hydroxygardnutine and 18-demethylgardneramine was very weak.View full abstractDownload PDF (1001K) -
TAKAYASU KITAGAWA, SATOSHI MIZUKAMI1978 Volume 26 Issue 1 Pages 53-58
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotometric titration was performed in MeOH using nitroaniline derivatives as an indicator and fluorosulfuric acid as titrant. 5-Substituted 4-hydroxy-2-methylpyrimidine and its three methyl derivatives were used as samples. Most of the samples could be determined using this method. Some samples, 5-carbethoxy-4-hydroxy-2-methylpyrimidine (1d) and its three methyl derivatives (2d, 3d and 4d) could not be determined successfully because of the appearance of large errors. These results show that the method is undesirable for determination of a very weak base with basicity less than pKa 2. A modification of the method was attempted in order to titrate such weaker base. The dissociation constant (pKBH) of the sample in MeOH was estimated from the slope of the straight line by Type II or the modified Type II plot. The basicity of the samples in MeOH generally increased by 10 to 100 times as compared with that in water. The degrees of the increase of the basicity were different among the compounds. Much larger increase of the basicity than the other compounds (about 100 times) was found for 5-substituted 1, 2-dimethyl-4 (1H)-pyrimidones.View full abstractDownload PDF (689K) -
TAKAYASU KITAGAWA1978 Volume 26 Issue 1 Pages 59-65
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid-base equilibria of the aniline derivatives in n-BuOH were investigated. The over-all dissociation constant (Kn-BuOHBH=KOBH/KBKBHX=[H+] [B] fH/[BH+] fBH) and the dissociation constant of ion pair (KBHX=[BH+] [X-] fBHfX/[BH+X-]) were estimated. The ion pair (BH+X-) existed to a considerable extent. The values of pKn-BuOHBH and pKBHX were respectively : 3.47, 2.83 for 4-methyl-3-nitroaniline ; 3.33, 2.66 for 4-carbethoxyaniline ; 2.94, 2.42 for 2-methoxy-5-nitroaniline ; 2.84, 2.74 for m-nitroaniline ; 2.79, 2.84 for 2-methyl-5-nitroaniline. The basicity of the anilines in n-BuOH increased as compared with that in water (ΔpK=pKn-BuOHBH-pKa=0.4-0.8).View full abstractDownload PDF (729K) -
TAKAYASU KITAGAWA1978 Volume 26 Issue 1 Pages 66-73
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotometric titration for 5-substituted 4-hydroxy-2-methylpyrimidine and its methyl derivatives was performed in n-BuOH. An equation for the titration was derived in consideration of ion pair formation in n-BuOH. [numerical formula] It was proved that Higuchi's Type II plot method was applicable only under a condition, KBHX=KIHX, from the analysis of the titration curves. The over-all dissociation constant of the pyrimidines (Kn-BuOHBH=KOHX/KBKBHX=[H+] [B]fH/[BH+] fBH) was estimated from the slope of the titration curve. The basicities of the compounds in n-BuOH generally increased as compared with those in water (ΔpK=pKn-BuOHBH-pKa=-0.1-2.3). The degrees of the increase differed largely among the compounds. Much larger increase of the basicity than the other compounds (ΔpK ; 2.1-2.3) was found for 5-substituted 1, 2-dimethyl-4(1H)-pyrimidones.View full abstractDownload PDF (790K) -
TADASHI ISHIMITSU, SHINGO HIROSE, HIROMU SAKURAI1978 Volume 26 Issue 1 Pages 74-78
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe acid dissociation equilibria in aqueous solution of dopamine were determined by potentiometry and complementary tristimulus colorimetry (CTS method), at 25°and μ=0.1 (NaClO4). From these data, microscopic equilibrium constants were calculated by the use of the substitution method. At physiological pH region (pH 7.2-7.4), dopamine is present as an ammonium species (I), and at pH 9.75 as zwitter-ionic species, (III) and (IV) in about 30% and 20%, respectively. The concentration of mono-phenolate anionic forms, (V) and (VI), are about 40% and 30%, respectively, at pH 11.0.View full abstractDownload PDF (597K) -
ISAO KITAGAWA, MINORU YOSHIHARA, TOSHIYUKI KAMIGAUCHI1978 Volume 26 Issue 1 Pages 79-87
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new diterpene named linarienone (2) was isolated from the ether-soluble portion of the fresh subterranean part of Linaria japonica MIQ. (Scrophulariaceae). Linarienone (2) is a monoacetyl-monoangeloyl derivative of a 5β-methyl-cis-clerodane-type diterpene and the stereostructure including the absolute configuration has been established as 2 on the basis of the chemical and physicochemical evidence and the unequivocal conversion starting from linarienone (2) and linaridial (1) leading to a common 5β-methyl-cis-clerodane-type hydrocarbon (18).View full abstractDownload PDF (1129K) -
HIROKO NAKAE, YASUYO IUCHI, SHOZO MURANISHI1978 Volume 26 Issue 1 Pages 88-95
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe liver/plasma (L/P) ratios of acetyl procainamide ethobromide (APAEB), procainamide ethobromide (PAEB) and quinine, which were transported from plasma into liver against a concentration gradient, were greatly decreased by infusing sulfhydryl reagents, p-chloromercuribenzoic acid (PCMB), p-chloromercury phenyl sulfonic acid (PCMBS) and iodoacetamide (IAA), into portal vein on account of the increase in the plasma level and the decrease in the liver level. The metabolism of PAEB and quinine was not affected by the infusion of the reagents. The binding of APAEB, PAEB and quinine was not depressed and that to plasma was not changed in the presence of the reagents. Consequently it was deduced that the hepatic uptake of the organic cations was blocked by the treatment with the sulfhydryl reagents, which acted on the plasma membrane involved in the concentrative uptake of the organic cations. In comparison with the previous results obtained by the intrabiliary retrograde infusion, PCMB and IAA were inhibitory only on the hepatic uptake process and N-ethylmaleimide (NEM) only on the excretory process, whereas PCMBS was effective on both steps. The finding of the specific reagents which are inhibitory only on one process would be of use in the study of the hepato-biliary transport of organic cations.View full abstractDownload PDF (879K) -
KOZO TAKAYAMA, SHIGEKI HASEGAWA, SUMIKO SASAGAWA, NAOKI NAMBU, TSUNEJI ...1978 Volume 26 Issue 1 Pages 96-100
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDissolution profiles of sulfamonomethoxine (SMM)/18-crown-6 (1, 4, 7, 10, 13, 16-hexaoxacyclooctadecane) complex, SMM anhydrate and SMM hydrate were investigated by dispersed amount method and stationary disk method, and also in vivo absorption study of these compounds in dogs was carried out in comparison with the data of the dissolution behaviors. According to the dispersed amount method, the concentration of SMM rose quickly and then decreased gradually when the complex was dispersed. On the other hand, a characteristic convex dissolution curve was observed in the case of the anhydrate. This result indicated that the dissolution rate of complex was extremely large, but its decomplexation accompanying the change to the hydrate form in water was also rapid compared with that of the anhydrate. The rate constant of phase change for the complex to the hydrate form, which was calculated by stationary disk method, was extremely large compared with that for the anhydrate. It was observed that the plasma levels of SMM increased extremely by the administration of the anhydrate form. An increase of plasma levels was also observed in the case of the complex.View full abstractDownload PDF (626K) -
MASAHIKO FUJINO, SUSUMU SHINAGAWA, MITSUHIRO WAKIMASU, CHIEKO KITADA, ...1978 Volume 26 Issue 1 Pages 101-107
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMotilin and [D-Phe1]-motilin were synthesized via the corresponding sulfoxide (Met13). The protected Met (O)13-motilin and [D-Phe1, Met (O)13]-motilin, in which Met residue was substituted by Met (O) residue, were constructed from three suitable subunits, respectively. The protected peptides were deblocked by methanesulfonic acid in the presence of anisole to obtain Met (O)13-motilin and its D-Phe1-derivative, and the resulting Met (O)-peptides were finally reduced by thiol to give the desired docosapeptides, motilin and D-Phe1-motilin.View full abstractDownload PDF (963K) -
YASUO KIKUGAWA1978 Volume 26 Issue 1 Pages 108-110
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral indole derivatives were reduced to the corresponding indolines in the combination of sodium borohydride with aluminium chloride in pyridine. N-Benzoyltryptamine (1f) was selectively reduced to the indoline derivative without reduction of the amide group.View full abstractDownload PDF (485K) -
MIKIO YAMAZAKI, HARUHIRO FUJIMOTO, EMI OKUYAMA1978 Volume 26 Issue 1 Pages 111-117
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of six new tryptoquivaline-related metabolites, tryptoquivaline E-J, isolated from Aspergillus fumigatus together with tryptoquivaline C and D were determined.View full abstractDownload PDF (894K) -
HITOSHI SEKIKAWA, MASAHIRO NAKANO, TAKAICHI ARITA1978 Volume 26 Issue 1 Pages 118-126
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to clarify the mechanism of coprecipitation of the drug with polyvinylpyrrolidone (PVP), the temperature of absolute ethanol solution saturated with various drugs, was lowered at a constant rate from 50°to 10°, and the inhibitory effect of PVP on the crystallization of drugs was examined. The interaction of these drugs with PVP in absolute ethanol was also investigated and compared with the effect of PVP on the crystallization of drugs. The crystallization of sulfamethizole and sulfisoxazole which interacted strongly with PVP were strongly inhibited and/or retarded over the temperature range studied. PVP retarded, but did not inhibit the crystallization of sulfamerazine. Crystallization of caffeine and nalidixic acid, which interacted poorly with PVP, was not affected by PVP. N-Vinyl-2-pyrrolidone, the monomer unit of PVP molecule, did not affect the crystallization of sulfisoxazole. PVP K-30 showed the strongest effect among K-15, K-30 and K-90. Polyethylene glycol and polysorbate 80 did not affect the crystallization of sulfisoxazole. Sulfamethizole and sulfisoxazole formed coprecipitates with PVP, whereas caffeine and nalidixic acid did not form coprecipitates with PVP. Sulfamerazine on the other hand did not form well-defined coprecipitate with equal weight ratio of PVP. The mechanism of coprecipitation of drug with PVP may be the inhibition of crystallization of drug by PVP, when the solution containing both drug and PVP is evaporated. The drug loses its crystal structure in PVP matrix. Coprecipitation does not occur when PVP does not inhibit the crystallization of drug.View full abstractDownload PDF (948K) -
NAOKI SHIMIDZU, TOYOZO UNO1978 Volume 26 Issue 1 Pages 127-134
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe coordination of the benzothiazole derivatives to divalent metal ions in solutions were examined by their absorption and resonance Raman spectra, and the comparison of the reactivities of the structurally related compounds with metal ions. In the solid state it was also investigated by the infrared spectrum and the magnetic susceptibility. Both in the solid state and in solutions, the benzothiazole derivatives behave as terdentate chelating agents with divalent metal ions and coordinate to the metal ions through the phenolic OH and the nitrogen atoms of the thiazole ring and the azo or azomethine group. The copper chelate has a plane structure in the molar ratio of 1 : 1 ligand-to-metal and an octahedron structure in 2 : 1, similarly to the nickel and the zinc chelates. The azohydrazone tautomerism of the benzothiazolylazo derivatives was also discussed.View full abstractDownload PDF (795K) -
TAKESHI KINOSHITA, TAMOTSU SAITOH, SHOJI SHIBATA1978 Volume 26 Issue 1 Pages 135-140
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of a new 3-arylcoumarin, glycyrin (I), isolated from the root of Glycyrrhiza spp. (Seihoku Kanzo) (Leguminosae) has been determined as 2', 4'-dihydroxy-5, 7-dimethoxy-6-γ, γ-dimethylallyl-3-arylcoumarin on the basis of spectroscopic and chemical studies.View full abstractDownload PDF (839K) -
TAKESHI KINOSHITA, TAMOTSU SAITOH, SHOJI SHIBATA1978 Volume 26 Issue 1 Pages 141-143
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new isoflavone, licoisoflavone A, was isolated from the root of Glycyrrhiza spp. (Leguminosae), and the structure I was formulated on the basis of chemical and spectroscopic studies.View full abstractDownload PDF (530K) -
TAMOTSU SAITOH, HIROSHI NOGUCHI, SHOJI SHIBATA1978 Volume 26 Issue 1 Pages 144-147
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs the constituents of Sinkiang licorice root (Glycyrrhiza spp., Leguminosae), two new isoflavonoid compounds, licoisoflavone B (V) and licoisoflavanone (XII), were isolated as acetates and their structures were determined by chemical and spectroscopic studies. Besides them, isoliquiritigenin, formononetin, 7, 4'-dihydroxyflavone, echinatin (III) and glabrol (IV) were also isolated.View full abstractDownload PDF (537K) -
HISAO TOMIDA, TOSHIHISA YOTSUYANAGI, KEN IKEDA1978 Volume 26 Issue 1 Pages 148-154
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe modifying effects of polyoxyethylene lauryl ether, sodium lauryl sulfate, cetyltrimethylammonium bromide and N-dodecyl betaine micelles on the rate of base-catalyzed hydrolysis of procaine were investigated. The retardation effect for the hydrolysis was observed in any surfactant solutions. Partition coefficients (K) to the micelles were calculated from kobs and the partial molar volume based on the phase separation model. The order of K was found to be SLS>CTAB>NDB>PLE for the free base. In the cationic surfactant system, the corresponding p-nitro substituted of procaine was also retarded in hydrolysis rate. These observations are contrary to the electrostatic theory. It could be considered that the effect of diethylaminoethyl moiety rather than p-substituents was predominant in the solubilization mechanism. The determination of partition coefficients by the potentiometric method was made for PLE and CTAB systems and a fairly good agreement with the values from kinetics data was obtained. Nuclear magnetic resonance studies suggested that in the case of SLS and PLE the solubilization of procaine was related as far as the center portion of the micelle whereas the drug molecule was located at the outer layer for CTAB and NDB micelles.View full abstractDownload PDF (845K) -
MASARU KIHARA, SHIGERU KOBAYASHI1978 Volume 26 Issue 1 Pages 155-160
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe apogalanthamine analogs, 10, 11-methylenedioxy- and 10, 11-dimethoxy-5, 6, 7, 8-tetrahydrodibenz [c, e] azocines (1 and 2, respectively) as α-adrenergic blocking agents were synthesized by photolysis of N-benzyl-2-iodo-4, 5-methylenedioxy- and N-benzyl-2-iodo-4, 5-dimethoxy-β-phenethylamine (20 and 21, respectively). 2, 3-Methylenedioxy-, and 2, 3-dimethoxy-5, 6, 7, 8-tetrahydrodibenz [c, e] azocine (9 and 10, respectively) were obtained similarly from N-(2-iodo-4, 5-methylenedioxybenzyl)- and N-(4, 5-dimethoxy-2-iodobenzyl)-β-phenethylamine (18 and 19, respectively). The yields of 9 and 10 from the iodo-amines (18 and 19) having an iodine atom in the benzyl group were found to be better than those of 1 and 2 from iodides 20 and 21 respectively having a halogen atom in the phenethyl group.View full abstractDownload PDF (704K) -
AKIO HOSHI, MASAAKI IIGO, ASAKO NAKAMURA, MOTOKO INOMATA, KAZUO KURETA ...1978 Volume 26 Issue 1 Pages 161-165
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRelationship between chemical structure and antitumor activity of various 1-alkylcarbamoyl derivatives of 5-fluorouracil by parenteral and oral administrations was examined in L1210 system. By intraperitoneal administration, in aliphatic derivatives, when carbon chain extended stepwisely, both antitumor activity and toxicity to host animals were reduced gradually, but ratios of reduction in activity and toxicity were different each other. tert-Butyl derivative showed the highest therapeutic ratio among the derivatives. However, it was lower than the therapeutic ratio of 5-fluorouracil. On the other hand, by oral administration, antitumor activity and toxicity to host animals were decreased along the extention of carbon chain in aliphatic derivatives and therapeutic ratios of the compounds having even carbons in their side chain were greater than those of the adjoining compounds having odd carbons. Among them, 1-hexylcarbamoyl-5-fluorouracil showed the highest therapeutic ratio. This compound was considered to be more suitable for treatment by oral administration than 5-fluorouracil, though the latter compound was superior than the former by parenteral administration.View full abstractDownload PDF (599K) -
HISASHI ISHII, TSUTOMU ISHIKAWA, KATSUHIRO HOSOYA, NARAO TAKAO1978 Volume 26 Issue 1 Pages 166-170
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of bocconoline, mp 232-233°, which was isolated from Macleaya cordata (WILLD.) R. Br. was established from its spectral data as the formula (1). Bocconoline was photochemically synthesized from chelerythrine (2) and methanol in 59.3% yield using acetone as a sensitizer with a low pressure mercury lamp in nitrogen stream.View full abstractDownload PDF (613K) -
TOSHIAKI MIURA, MICHIYA KIMURA1978 Volume 26 Issue 1 Pages 171-177
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe behavior of estrone methyl ether (V) in strong acid was studied, in order to elucidate the mechanism of the Kober color reaction. When V was dissolved into concentrated sulfuric acid, a maximum absorption gradually appeared at 465 nm which was then transferred to 452 nm with elapse of time. On the other hand, 3-methoxy-17α-methylestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIb) immediately gave the chromophoric cation χ-465 (VIIb) in concentrated sulfuric acid. Similarly, 3-methoxyestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIa) gave the cation χ-364 (XIVa) which changed in turn to χ-465 (VIIa). Sulfonation gradually occurred at C (2)s of VIIa and VIIb in the same acid to give the corresponding cations XIXa and XIXb ; the maximum absorption at 465 nm altered to 452 nm. The mechanism of the conversion of V into the C (2)-sulfonated χ-465 (XIXa) was elucidated from these behavior of XIIIa and XIIIb in concentrated sulfuric acid.View full abstractDownload PDF (858K) -
KENJI KOGA, TZUOHMIIN JUANG, SHUNICHI YAMADA1978 Volume 26 Issue 1 Pages 178-184
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt has become apparent that deaminative bromination of 3, 5-dichloro-L-tyrosine (L-4) to the corresponding α-bromo acid ((-)-5) occurs with retention of configuration, and that amination of this bromo acid to the starting amino acid (L-4) occurs also with retention of configuration. The unusual stereochemical course in this amination step was found to be due to the strong neighboring aryl group participation as a phenoxide form.View full abstractDownload PDF (912K) -
TOMOMICHI YANAGITA, TAKAYUKI MIKI, TATSUO SAKAI, ISAMU HORIKOSHI1978 Volume 26 Issue 1 Pages 185-190
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo forms of powdery sample for tabletting were prepared ; one was the mixture of Avicell (crystalline cellulose) and freeze-dried skim milk containing Escherichia coli cells and the other was a freeze-dried powder of skim milk solution containing E. coli cells together with Avicell. E. coli cells were killed by tabletting to some extent depending on the pressure applied. Different patterns of surviving fraction/pressure relation were obtained for the above two forms of samples. Effects of temperature and moisture content of samples were also examined. Large microbial cells, such as Rhodotorula glutinis, were much more sensitive to tabletting than smaller E. coli cells. Spores of Bacillus subtilis were highly sensitive to tabletting. From these observations the major cause of killing action in the process of tabletting was considered to be the shearing force.View full abstractDownload PDF (709K) -
NAOKI SHIMIDZU, TOYOZO UNO1978 Volume 26 Issue 1 Pages 191-198
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe relationship between the structure and the fluorescence of the benzothiazole derivatives and their metal chelates were investigated along with characteristics necessary for the fluorescence. By the chelation with zinc, N-salicylidene-4-aminobenzothiazole is held in plane and its electronic state was scarcely influenced, which induce fluorescence. In the fluorescent zinc chelates, the π electron distribution inclines towards the phenol portion from the thiazole portion in the transition from the ground state to the first excited state and the electron densities of the coordinate atoms to the central zinc ion do not almost change between both states. The fluorescence of the zinc chelates is due to π*-π transition. The effect of additional substituent groups on the fluorescence was also examined along with the correlation between the stability constant and the fluorescence intensity of the metal chelates.View full abstractDownload PDF (828K) -
YUICHI SUGIYAMA, TATSUJI IGA, SHOJI AWAZU, MANABU HANANO1978 Volume 26 Issue 1 Pages 199-208
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSpectrofluorometric studies using 1-anilino-8-naphthalenesulfonate (ANS) reveal that Z-fraction from rat liver has far the more hydrophobic binding sites than the other cytoplasmic binding fractions X and Y. Diagnostically important organic anions, such as sulfobromophthalein (BSP) and rose bengal (RB), are shown to displace ANS from Z-fraction by quenching the fluorescence of ANS and Z-fraction mixture without the change of quantum yield and emission maximum. The binding constants of these dyes to Z-fraction are determined by the competitive studies with ANS, and are coincident with those from other methods. Since the spectrophotometric technique reveals that the number of RB binding sites on Z-fraction is about twice as large as that of ANS binding sites, ANS and RB do not have necessarily the identical binding sites, though they must have partly common ones. The major binding force between organic anions and Z-fraction is supposed to be hydrophobic considering that the binding constant of Z-fraction for ANS is only about one-eight of that of bovine serum albumin (BSA) of which site is both hydrophobic and cationic. This property of sites accounts for the lower affinity for BSP of Z-fraction extracted from CCl4 chronically intoxicated rats, which our former study has made clear.View full abstractDownload PDF (1206K) -
TETSUZO KATO, MASAYUKI SATO, NOBUYA KATAGIRI, TOSHIKAZU AWAJI, JUN NAK ...1978 Volume 26 Issue 1 Pages 209-214
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMethylation of bikaverin (Ib) with diazomethane afforded monomethylbikaverin (Ic). Reductive acetylation of Ia, b, c with acetic anhydride and sodium acetate in the presence of zinc powder gave rise to benzoxanthene derivatives (IIc, d, e), respectively. Ib was hydrolyzed with aqueous sodium hydroxide to give everninic acid (III) and orcinol (IV). However, hydrolysis of Ic with alcoholic potassium hydroxide gave rise to cyclopentenoxanthene derivative (V). Ozonolysis of Ic gave xanthone derivative (XI).View full abstractDownload PDF (796K) -
TOMOJIRO HAYASHI, TAEKO NAKAYAMA, TERUMI NAKAJIMA, HIROFUMI SOKABE1978 Volume 26 Issue 1 Pages 215-219
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGoosefish angiotensin produced by incubation of the kidney extract with homologous plasma, was purified. The structure was identified as Asn1-Val5-His9-angiotensin (I) decapeptide by amino acid composition and fluorescent peptide mapping technique.View full abstractDownload PDF (640K) -
MAMORU SUGIURA, MASANARI AKATSUKA, KAZUYUKI HIRANO, SHUNJI SAWAKI, YUK ...1978 Volume 26 Issue 1 Pages 220-225
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSComparison of biological and immunological methods for determination of α1-antitrypsin showed that the amount of α1-antitrypsin determined in the presence of trypsin were not the same. From the result of the comparison of effect of heat on the amount of α1-antitrypsin found by biological and immunological methods, it is suggested that α1-antitrypsin and the α1-antitrypsin-trypsin complex are indistinguishable immunologically. The investigation of the trypsin inhibitory activity of α1-antitrypsin and molecular weight determination showed that α1-antitrypsin and trypsin formed a 1 : 1 stoichiometric complex. The results of immunoelectrophoresis and sodium dodecyl sulfate electrophoresis indicated that the α1-antitrypsin-trypsin complex was broken down with incubation and the breakdown products also had immunogenicity.View full abstractDownload PDF (734K) -
YOSHIO MATSUMOTO, TETSUYA SUGA1978 Volume 26 Issue 1 Pages 226-233
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn investigation has been in order to elucidate the mechanism of the elevation of serum enzyme activities and about the changes in subcellular distribution during development of experimentally produced hepatic damage in the rats. Two enzymes have been studied : acid phosphatase (Acid Pase) and N-acetyl-β-glucosaminidase (NAG). Three different methods of inducing hepatic damage have been used : administration of carbon tetrachloride (CCl4), dimethylnitrosamine (DMNA), and thioacetamide (TAA). In acute hepatic damage, an increase in soluble activity was found to occur for two enzymes studied. The extent of this increase was slightly much in the activity of NAG as compared with that of Acid Pase. The changes in serum NAG activity was remarkably much in the case of any drugs. During the development stages of chronic administration of CCl4, the subceliular distribution pattern of lysosomal enzymes after 4 weeks were similar to that of lysosomal enzymes after 12 weeks. At 4 weeks after the administration of CCl4, the changes of lysosomal enzymes activities in the plasma was similar to that of acute hepatic damage by the treatment with DMNA and TAA. Furthermore, in the plasma at 12 weeks after the administration of CCl4, the variation of lysosomal enzymes activities was clearly differed from that of acute hepatic damage. It is assumed that the changes in NAG activity is minor due to fibroblasts other than hepatic parenchymal cells for the origin of the increased serum NAG activity during the CCl4-chronic hepatic damage.View full abstractDownload PDF (1211K) -
MOTOKO KUNISHIMA, YUKIO SUGIURA, HISASHI TANAKA1978 Volume 26 Issue 1 Pages 234-239
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hydroxylation of acetanilide by iron-sulfur complexes produces p- and o-acetaminophenols as main products. The yield of p-acetaminophenol is 34.8 and 31.4% in the catalytic systems of dithiothreitol (DTT)-iron-inorganic sulfur (S) and glutathione (GSH)-Fe-S complexes, respectively. The turnover number of the acetanilide-hydroxylation is 3.9×10-2 and 3.5×10-2 (mol p-acetaminophenol/min/mol complex) in the DTT-Fe-S and GSH-Fe-S complex systems, respectively. The DTT-nickel complex incorporates inorganic sulfur to form unstable DTT-Ni-S complex. The DTT-Ni complexes have also high catalytic effect on the hydroxylation of acetanilide.View full abstractDownload PDF (637K) -
MORIO IKEHARA, TOKUMI MARUYAMA1978 Volume 26 Issue 1 Pages 240-244
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn antibiotic 2'-amino-2'-deoxyguanosine (I) was synthesized chemically from a guanine 8, 2'-O-cyclonucleoside (II), which could be obtained from guanosine. Compound (II) was converted to N2, 3', 5'-triacetyl derivative (III), which was subjected to opening of the anhydro linkage with liq. H2S in pyridine. Resulting 8-mercaptoarabinofuranosylguanine (IV) was dethiolated and mesylated to give N2, 3', 5'-triacetyl-2'-mesylarabinosylguanine (VI). Deprotection of VI and reprotection with tetrahydropyranyl groups gave compound VIII. Reaction of the compound VIII with sodium azide in acetamide at 210°for 10 min gave 2'-azido compound (IX). The compound IX was deprotected to give 2'-azido-2'-deoxyguanosine (X). Raney nickel catallyzed hydrogenolysis of X gave 2'-amino-2'-deoxyguanosine, which was proved to be identical with a sample of the antibiotic.View full abstractDownload PDF (724K) -
TAKASHI HIROTA, TAKAJI KOYAMA, TETSUTO NANBA, MASATOSHI YAMATO, TAKAFU ...1978 Volume 26 Issue 1 Pages 245-250
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of α-acyl-α-(m-chlorophenyl) acetonitrile (II) with formamide gave enamines (III) and 4-aminopyrimidines (IV). III could be converted to IV by the same treatment with formamide. 4-Acetamido-5-(3, 5-dimethylphenyl) pyrimidine (Ve) gave 1, 3, 10-triazaphenanthrene (VI) with polyphosphoric acid, although cyclization of m-chloro-(Va) and m-methyl-(Vd) phenyl derivatives were unsuccessful (Chart 1). Reactions of α-acyl-α-(3, 5-dimethoxyphenyl) acetonitrile (VII) with acetamide gave 6-alkyl-5-(3, 5-dimethoxyphenyl)-2-methyl-4 (3H)-pyrimidinone (VIII) which were converted to 4-chloro derivatives (X) with POCl3. Treatment of 3, 5-dimethoxybenzyl alkyl ketones (XI) with acetamide gave 3-alkyl-1-methylisoquinolines (XII) and analogous reaction of 3, 4-methylenedioxyphenylacetone (XIV) gave naphthalene derivative (XV) (Chart 2).View full abstractDownload PDF (839K) -
YASUHIRO YAMANE, KAZUO SAKAI, MASAAKI SHIBATA1978 Volume 26 Issue 1 Pages 251-255
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of copper and riboflavin on 4-dimethylaminoazobenzene (DAB) azo reductase activity and 1, 2-dimethyl-4-(p-carboxyphenylazo)-5-hydroxybenzene (CPA) azo reductase activity in rat liver were investigated. In the liver microsome both riboflavin content and DAB azo reductase activity were not significantly increased in the groups given the diet supplemented with 20 mg or 50 mg of riboflavin/100 g of diet as a riboflavin-excessive diet, but was significantly increased in the groups given the diet supplemented with copper. In the riboflavin-deficient diet group not only riboflavin but copper was also decreased. DAB azo reductase activity in the groups given the copper-supplemented diet was increased more than that in each group of the same concentration of riboflavin diet. The increase of CPA azo reductase activity was almost in parallel with that of DAB azo reductase activity in the groups given the diet supplemented with copper.View full abstractDownload PDF (689K) -
KEISUKE KITAMURA, TOMOKO TAKAHASHI, KEIICHIRO HOZUMI, TAKASHI SATO1978 Volume 26 Issue 1 Pages 256-259
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interaction of chlorpromazine hydrochloride with lecithin vesicles was investigated through proton magnetic resonance measurements. Sharp N (CH3)2 signal of the chlorpromazine hydrochloride in D2O was markedly broadened when the drug was added to a lecithin vesicle-D2O solution, whereas the broadening was not observed in a dextran-D2O solution of which viscosity was higher than the vesicle solution. Addition of Eu3+ to the vesicle solution induced an upfield shift of outward facing choline methyl signal, but the subsequent addition of the chlorpromazine hydrochloride reversed the induced shift. The vesicles prepared in the presence of Mn2+ did not show the PMR signal of choline methyl due to the presence of Mn2+ both inside and outside of the vesicles, but when the drug was added to the solution, choline methyl signal appeared again. The results confirmed that the chlorpromazine interacted with polar part of the lecithin vesicles displacing the trivalent ion Eu3+ and the divalent ion Mn2+ from the vesicle surfaces.View full abstractDownload PDF (498K) -
MITSURU FURUKAWA, TADASHI OKAWARA, YOSHIHIDE NOGUCHI, YURIKO TERAWAKI1978 Volume 26 Issue 1 Pages 260-263
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAsymmetric syntheses of β-amino acids and aspartic acid were achieved by the reaction of optically active Schiff bases prepared from aldehydes and optically active amines, R (+)- and S (-)-α-methylbenzylamines, with Reformatsky reagents in the range of 18-28% optical purities. When the Schiff bases having R (+)-amino component were used in the reaction, (S)-β-amino acids and (R)-aspartic acid were formed. The use of the Schiff bases involving S (-)-amino component gave (R)-β-amino acids and (S)-aspartic acid. The reaction of Schiff bases prepared from aldehydes and benzylamine with optically active Reformatsky reagents having l-menthyl ester gave (S)-β-amino acids and (R)-aspartic acid in the range of 2-5% optical purities. The steric course were also presumed.View full abstractDownload PDF (555K) -
EIICHI FUJITA, MASAHITO OCHIAI1978 Volume 26 Issue 1 Pages 264-274
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTotal synthesis of rac-kaur-16-ene-11α, 15α-diol (1) via a sequence of reactions including the Birch reduction of alcohol 4 and the Claisen rearrangement of vinyl ether 34 as the key steps is described.View full abstractDownload PDF (1463K) -
SEIGO SAWADA, TADASHI MIYASAKA, KIICHI ARAKAWA1978 Volume 26 Issue 1 Pages 275-287
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-(Substituted-phenyl)-2, 3-tetramethylenepyrrolo [2, 1-b] benzothiazoles (IV-2-IV-17) were synthesized from the correspoding 3-(substituted-phenyl) thiazolo [2, 3-b] benzothiazolium perchlorates (III) by the reaction of 1-morpholino-1-cyclohexene, an enamine. On reaction with cuprous cyanide p-substituted bromobenzene (IV-2) furnished benzonitrile (IV-23), which was converted into the corresponding 1-phenyl derivatives (IV) with various aliphatic functional groups at the para position of the phenyl moiety. On reaction with methylmagnesium iodide and subsequent acid hydrolysis IV-23 was converted into acetophenone (IV-24), which reacted with methyltriphenylphosphylene to give 2-phenylpropylene (IV-38). Hydroboration of IV-38 afforded 2-phenylpropanol (IV-39), which was oxidized into the corresponding propionic acid (IV-43), the sulfur atom being oxidized at the same time into sulfoxide. Deoxygenation of the ester (IV-44) was successfully carried out with PBr3 to obtain the desired α-phenyl substituted propionic acid ester (IV-45).View full abstractDownload PDF (1462K) -
TAKEFUMI MOMOSE, OSAMU MURAOKA1978 Volume 26 Issue 1 Pages 288-295
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe syntheses of the title bicyclic ketone (IV) are described. The Michael-aldol condensation of ethyl acetoacetate (VI) with 2-cyclohexen-1-one (V) afforded a bicyclic β-keto ester, the ketonic cleavage of which gave 1-hydroxybicyclo [3.3.1] nonan-3-one (IX). Removal of the bridgehead hydroxyl in IX via the bromide (X) gave the desired ketone (IV). Another route to IV starting with bromination of adamantane followed by alkaline cleavage was established. Ozonolysis and subsequent ketalization converted 7-methylenebicyclo [3.3.1] nonan-3-one (XVII) into 7-ethylenedioxybicyclo [3.3.1] nonan-3-one (XIX), which was reduced to the desired ketone (IV) by means of the Huang-Minlon reduction. In addition, ozonolysis of 3-methylenebicyclo [3.3.1] nonane (XXII) gained by the Huang-Minlon reduction of XVII as a minor product was also found to give IV in good yield.View full abstractDownload PDF (1000K) -
HISASHI ITO, KEIICHI OGAWA, TETSUO IIDA, IWAO ICHIKIZAKI1978 Volume 26 Issue 1 Pages 296-299
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral substituted phenylsulfenyl chlorides were synthesized for the investigation of the properties of sulfenyl N-protecting groups and new sulfenyl (o-nitrophenylsulfenyl and 2, 4-dinitrophenylsulfenyl) derivatives of some amino acids were obtained. The disubstituted phenylsulfenyl derivatives were far more stable than the monosubstituted ones in 80% acetic acid. Thus the sulfenyl derivatives of S-benzyl-L-cysteine was synthesized in pure state and used successfully to form cysteinyl peptides.View full abstractDownload PDF (611K) -
KUNIO NAKAGAWA, SATOSHI MINEO, SATOKO KAWAMURA1978 Volume 26 Issue 1 Pages 299-302
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNickel Peroxide (Ni-PO) was shown to be useful oxidizing agent for a preparation of substituted benzoic acids from the corresponding benzaldehydes in aqueous alkaline solution. Some kinds of aromatic carboxylic acids were also effectively obtained from the corresponding aldehydes in a similar way. The mechanism of these oxidations were discussed.View full abstractDownload PDF (554K) -
KAZUTAKA MOMOSE, YASUO GOMI1978 Volume 26 Issue 1 Pages 302-304
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSingle smooth muscle cells were isolated from vas deferens of guinea pig and effect of cocaine on calcium contraction of the individual cells under partially depolarized condition was examined. Among the isolated cells, a few cells were contracted by 20 mM calcium chloride in medium containing 60 mM potassium chloride. Cocaine increased the ratio of contracted cells. The result suggested that cocaine facilitated calcium contraction of individual cells in the tissue and induced larger contraction of the tissue.View full abstractDownload PDF (429K) -
SHIN MATSUURA, MUNEKAZU IINUMA, KIMIKO ISHIKAWA, KENGO KAGEI1978 Volume 26 Issue 1 Pages 305-306
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel procedure is described for the expedient preparation of flavone. Application of 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) in boiling dioxane as dehydrogenating agent to the several flavanones, e.g. 5, 6, 7-trimethoxy-, 4', 5, 7-trimethoxy-, 4', 5, 6, 7-tetramethoxy-, 4', 5, 6, 7, 8-pentamethoxy-, 4'-benzyloxy-5, 6, 7-trimethoxy-, 3', 4', 5, 6, 7-pentamethoxy-, 4'-benzyloxy-3', 5, 6, 7-tetramethoxy- and 3', 4'-dibenzyloxy-5, 6, 7-trimethoxyflavanone, furnishes a convenient and appropriate method for the preparation of the corresponding flavones, in excellent yields or without any contamination of undesired products.View full abstractDownload PDF (418K) -
YASUOKI MURAKAMI, KENJI KOGA, SHUNICHI YAMADA1978 Volume 26 Issue 1 Pages 307-308
Published: January 25, 1978
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStereochemical studies on the deaminative bromination of L-aspartic acid (1a) and its esters (1b, 1c, and 1d) have shown that α-carboxyl group almost completely holds the configuration in this substitution reaction, while β-carboxyl group has no ability to exhibit such neighboring group participation.View full abstractDownload PDF (363K)