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Volume 27, Issue 6
Displaying 1-33 of 33 articles from this issue
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HIROYASU OGATA, TOSHIO SHIBAZAKI, TETSUO INOUE, AKIRA EJIMA1979 Volume 27 Issue 6 Pages 1281-1286
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe relation of absorption sites of sulfonamides administered orally in uncoated tablets to their solubilities and dissolution rates was studied. Eight sulfonamides, sulfisomidine, sulfamethoxypyridazine, sulfamethizole, sulfamethoxazole, sulfisoxazole, sulfamonomethoxine, sulfaphenazole and sulfadimethoxine, were tested to determine their solubilities, dissolution rates and absorption rates following oral administration to humans. As a marker of gastric emptying time, the lag time of the urinary excretion of total salicylate was determined after the concurrent administration of enteric tablets of aspirin. A new parameter, RAAS (Relative Amount Absorbed in the Stomach) is proposed in order to represent the relative amount absorbed in the stomach region. RAAS values showed good correlations with the solubilities and dissolution rates of sulfonamides determined by means of the Sartorius solubility simulator with continuous pH change under non-sink conditions. It was concluded that : 1) The critical value of the solubility which distinguishes drugs according to their absorption sites, stomach or intestine, is about 3 mg/ml in 0.1 N HCl at 37° when 1 g of the drug is administered to humans orally with 200 ml of water after overnight fasting. 2) A drug having a solubility larger than the critical value can reasonably be tested for dissolution rate in an acidic medium, and a drug having a solubility less than the critical value should be tested under neutral conditions after pretreatment in acidic conditions.View full abstractDownload PDF (644K) -
HIROYUKI ASAKAWA, MITSUO MATANO1979 Volume 27 Issue 6 Pages 1287-1298
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome derivatives of 6-chloro-5-sulfamoyl-and 6-chloro-3-sulfamoylanthranilic acids, which have a chlorine atom and a sulfamoyl group ortho and meta to the carboxy group, respectively, were synthesized and the diuretic activities of the two positional isomers were compared. The presence of a chlorine atom ortho to the carboxy group, which enhanced the hypoglycemic activity of anthranilic acid derivatives, had no effect on the diuretic activity of sulfamoylanthranilic acid derivatives. The diuretic activity of the 6-chloro-3-sulfamoylanthranilic acid derivatives was greater than that of the 6-chloro-5-sulfamoyl ones.View full abstractDownload PDF (1297K) -
YUTAKA HIGASHI, NOBORU YATA, AKIRA KAMADA1979 Volume 27 Issue 6 Pages 1299-1306
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of concomitant administration of salicylate on the pharmacokinetics of five sulfonamides in rats was studied. Changes in the bolld concentration profiles of sulfonamides at the elimination phase due to salicylate treatment were classified into three types : Type I-little change was observed (sulfanilamide) ; Type II-the blood concentration was decreased, but the disposition rate constant, kβ, was hardly influenced (sulfadiazine and sulfisoxazole) ; Type III-the value of kβ decreased (sulfamethoxazole and sulfathiazole). An intravenous administration of salicylate after administration of sulfamethoxazole brought about a sudden decrease in the blood concentration of sulfamethoxazole. The effects of salicylate treatment on the distribution of sulfamethoxazole and sulfadiazine were studied employing a two-compartment open model. Their distribution to the tissue compartment of the model was increased by the salicylate treatment. The effect of salicylate was interpreted on the basis of a redistributional interaction of sulfonamides with salicylate.View full abstractDownload PDF (798K) -
HIROSHI IWASE, YOKO TAKEUCHI, ASAO MURAI1979 Volume 27 Issue 6 Pages 1307-1315
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe fragmentation of 58 N-trimethylsilyl amino acid trimethylsilyl esters, including those of α-, β-, γ-, and α-methyl-amino acids and related compounds, upon electron impact was investigated to provide a spectral basis for further studies of physiological samples, and to look into the possibility of selective identification and ultramicrodetermination of amino acids by mass fragmentography. It was found that the ion at m/e 73 or m/e (M-117) is the base peak common to most of the amino acids. The results obtained in this study suggest that this derivative can be used for the ultramicrodetermination and selective identification of amino acids by mass fragmentography because this derivative produces characteristic ions such as m/e (M-117), (M-15), 174, 218 and 232. The fragmentations of N-trimethylsilyl n-butyl esters and N-trimethylsiyl l-methyl esters of six amino acids were also studied.View full abstractDownload PDF (943K) -
AKIHIRO OHTA, YASUO AKITA, AKIKO IZUMIDA, IKUKO SUZUKI1979 Volume 27 Issue 6 Pages 1316-1320
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSdl-Neohydroxyaspergillic acid (I), the l-isomer of which has been isolated from Aspergillus flavus, was synthesized from DL-leucine anhydride. By treatment of 2-chloro-3, 6-diisobutylpyrazine 4-oxide (II) with acetic anhydride, an acetoxyl group was introduced into the isobutyl group. Deoxygenation of the N-oxide group at the 4-position of a 2-hydroxypyrazine 1, 4-dioxide derivative (XII), prepared by hydrolysis of a 2-chloro-pyrazine 1, 4-dioxide derivative (XI), was achieved using titanium (III) chloride to afford I.View full abstractDownload PDF (630K) -
RYOHEI HORI, HISAHIRO YOSHIDA, KATSUHIKO OKUMURA1979 Volume 27 Issue 6 Pages 1321-1327
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe lung accumulation and permeation of some antibiotics were studied using an isolated blood-perfused rat lung preparation with artificial ventilation and the intact lung of anesthetized rats in vivo. Leucomycin A3 and erythromycin, which have been widely used for the treatment of pulmonary infections, were accumulated well in the lung, while tetracycline and chloramphenicol did not show specific accumulation. The specific accumulation of leucomycin A3 and erythromycin is probably due to the fact that both drugs have an amino group and a strongly lipophilic group. In the case of intratracheal administration in the perfused lung, the transport of these antibiotics from alveoli to the blood was shown to be dependent on their lipid solubility, and the drug distribution in the lung was found to be similar to that from the perfusate in the equilibrium state. However, in the in vivo distribution study, marked accumulation of erythromycin after intratracheal administration was observed as compared with intravenous administration, whereas, the distribution of leucomycin A3 was not greatly affected by the route of administration. On the basis of these experimental findings, drug delivery systems are discussed in relation to the effective distribution of drugs in the lung.View full abstractDownload PDF (741K) -
TAKEHIKO NAKA, YOSHIYASU FURUKAWA1979 Volume 27 Issue 6 Pages 1328-1334
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 3-Dialkyl-6-hydrazinouracils (I) reacted with alkyl and acyl isothiocyanates to yield 5, 7-dialkyl-3-alkyl (or acyl) aminopyrazolo [3, 4-d] pyrimidine-4, 6 (5H, 7H)-diones (II). This reaction was investigated in detail and it was found that the first product was a 6-[4-alkyl (or acyl) thiosemicarbazido] uracil (IV), which cyclized to II through two pathways. Acylation of II afforded the corresponding 2-acyl derivatives. Treatment of 1, 3-diethyl-6-hydrazinouracil (Ia) with phosgeneimmonium chloride afforded 5, 7-diethyl-3-dimethylamino [3, 4-d] pyrimidine-4, 6 (5H, 7H)-dione (X).View full abstractDownload PDF (704K) -
YOSHIHARU KANEO, ATSUKO NISHIKAWA, YURIKO KATO, SETSUO KIRYU1979 Volume 27 Issue 6 Pages 1335-1342
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of six nonsteroidal anti-inflammatory drugs, phenylbutazone, flufenamic acid, salicylic acid, indomethacin, flurbiprofen, and naproxen, on the binding of sulfonamides to bovine serum albumin were examined using the equilibrium dialysis method at pH 7.4 and 37°. Lineweaver-Burk plots suggested that these anti-inflammatory drugs inhibit the binding of sulfonamides competitively. Anti-inflammatory drugs could be ranked in the following order of diminishing ability to inhibit the binding of sulfonamides to bovine serum albumin : phenylbutazone, flufenamic acid, salicylic acid, indomethacin, flurbiprofen, and naproxen ; the inhibitory activities of the first three drugs were especially high. Furthermore, the competitive binding of sulfisoxazole and salicylic acid was studied in detail on the basis of a theoretical equation. The data for the inhibition of the binding of sulfisoxazole by salicylic acid satisfied the equation well, confirming that this theoretical equation is suitable to describe such competitive binding phenomena.View full abstractDownload PDF (705K) -
MIYOKO SUZUKI, YOSHIO SASAKI1979 Volume 27 Issue 6 Pages 1343-1351
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAzo dyes with a hydroxylated α-naphthyl group form 1 : 1 complexes with cyclodextrin. The nature of the substituent, the bulkiness of the molecule, the change of the 1H nuclear magnetic resonance (NMR) spectral pattern of cyclodextrin and the signs of the maxima in circular dicroism (CD) spectra indicate the specific orientation and freedom of motion in the cavity of the guest molecules after inclusion. For example, in orange II-β-cyclodextrin complex, the 1H NMR spectrum of β-cyclodextrin rules out inclusion from the benzenesulfonate side of orange II. The CD spectrum suggests inclusion from the short molecular axis side and tight fitting with β-cyclodextrin. The azo dyes investigated are longer than the depth of the cavity of cyclodextrin. Nevertheless, the inclusion shifts of the guest molecules are not localized at one side of the molecule. The whole H2O structure around the azo dye is probably broken down upon inclusion, or the included azo group produces inclusion shifts at all the ring protons.View full abstractDownload PDF (862K) -
MIKIHIKO OBAYASHI, SEIJI KUZUNA, SHUNSAKU NOGUCHI1979 Volume 27 Issue 6 Pages 1352-1359
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Willgerodt-Kindler reaction of 21-chloro-20-ketosteroids (5) or sodium 21-thiosulfate derivatives of 20-ketosteroids (6) with sulfur in secondary amines gave the corresponding steroidal α-oxothiocarboxamides (3) in good yields. Among these compounds (3), 11β, 17α-dihydroxy-21-morpholinopregna-1, 4-diene-3, 20-dione-21-thione (3a) and 11β, 17α-dihydroxy-21-morpholinopregn-4-ene-3, 20-dione-21-thione (3b) showed potent anti-inflammatory activities comparable to or a little less than those of the parent compounds, prednisolone and hydrocortisone, respectively, in the carrageenin edema test in rats. 3a also showed potent activity in the granuloma pouch test in rats but much less activity in the cotton pellet test in rats. These results suggest that 3a might be more active against acute or subacute inflammation than against chronic inflammation.View full abstractDownload PDF (807K) -
YOSHIO OKADA, CHIE KAWASAKI, MIYUKI OKINAKA, KOICHI KAWASAKI1979 Volume 27 Issue 6 Pages 1360-1365
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo heptapeptides, Z-Leu-Ala-Cys (Bzl)-Ser-Thr-Cys (Bzl)-His-OH (A) and Z-Leu-Gly-Cys (Bzl)-Gln-Ile-Cys (Bzl)-Leu-OH (B), corresponding to sequences 50-56 and 90-96 of adrenodoxin from bovine adrenal cortex, respectively, were synthesized. The deblocked peptides from A and B formed iron-sulfur complexes, both of which gave absorption maxima at 415 nm.View full abstractDownload PDF (808K) -
YOKO SAKIYA, YOSHIKO MIYAUCHI1979 Volume 27 Issue 6 Pages 1366-1372
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe contribution of the stationary layer to the absorption of benzoic acid, salicylic acid, phenol and p-aminoethylbenzoate from the gills of goldfish was estimated by kinetic analysis of the relationship between perfused flow to the gills and the drug absorption rate. The changes in the absorption rate constant increased as the perfusion velocity increased. A double combination model consisting of an aqueous diffusion layer in the perfusing solution and the diffusion layer on the gill membranes was used to analyze drug absorption from the membranes. Even though the molecular weights of these drugs are similar, there were variations in the permeability coefficients of the drugs through the aqueous diffusion layers, suggesting that drug absorption from the gills cannot be explained simply in terms of a static diffusion layer in the perfusing solution.View full abstractDownload PDF (763K) -
KENICHI NUNAMI, MAMORU SUZUKI, KAZUO MATSUMOTO, MUNEJI MIYOSHI, NAOTO ...1979 Volume 27 Issue 6 Pages 1373-1377
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNitro-1, 2-dihydro-1-oxoisoquinoline-3-carboxylate compounds (5a, b and 9a, b) were synthesized by the reaction of methyl isocyanoacetate with nitrophthalic anhydrides in the presence of 1, 8-diazabicyclo [5. 4. 0] undec-7-ene (DBU), followed by esterification with diazomethane and hydrolysis with HCl. In these reactions, the methylidenephthalide compound (10) was also obtained by hydrolysis of the oxazole-4-carboxylate compound (8b) due to the presence of the bulky ortho nitro group. Moreover, 1, 2-dihydro-4-hydroxy-1-oxoisoquinoline-3-carboxylic acid (16) was prepared via the oxazole dicarboxylic acid compound (15) in good yield.View full abstractDownload PDF (669K) -
AKIHIRO OHTA, TOSHIKO OHWADA, CHIKAKO UENO, MARIKO SUMITA, SAWAKO MASA ...1979 Volume 27 Issue 6 Pages 1378-1382
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDeoxyneo-β-hydroxyaspergillic acid (I), originally isolated from Aspergillus ochraceus WILH., was synthesized from 2-chloro-3, 6-diisolbutylpyrazine (III) through several steps. Methylmagnesium iodide was used for cleavage of the ether bond on the last step.View full abstractDownload PDF (628K) -
YUKINOBU IKEYA, HEIHACHIRO TAGUCHI, ITIRO YOSIOKA, HIROSHI KOBAYASHI1979 Volume 27 Issue 6 Pages 1383-1394
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new dibenzocyclooctadiene lignans, named gomisin A (2), B (3), C (4), F (5) and G (6), were isolated from the petroleum ether extract of fruits of Schizandra chinensis BAILL. (Schizandraceae) and their absolute structures were elucidated by chemical and spectral techniques. The absolute structure of schizandrin (1), the plane structure of which had already been elucidated by Kochetkov et al., was also elucidated on the basis of spectroscopic results.View full abstractDownload PDF (1163K) -
YUKINOBU IKEYA, HEIHACHIRO TAGUCHI, ITIRO YOSIOKA, YOICHI IITAKA, HIRO ...1979 Volume 27 Issue 6 Pages 1395-1401
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new dibenzocyclooctadiene lignan, named gomisin D (1), was isolated from the petroleum ether extract of the fruits of Schizandra chinensis BAILL. (Schizandraceae), and its structure was elucidated on the basis of chemical and spectral evidence. The absolute structure of gomisin D was determined by X-ray analysis of its 4, 11-dibromo-derivative (4).View full abstractDownload PDF (751K) -
JUNICHI GOTO, HIROAKI KATO, FUSAE HASEGAWA, TOSHIO NAMBARA1979 Volume 27 Issue 6 Pages 1402-1411
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 3-, 7- and 12-monosulfates of unconjugated, and glycine- and taurine-conjugated bile acids have been prepared. Bile acid derivatives protected by appropriate groups were sulfated in the usual manner with chlorosulfonic acid in pyridine. Subsequent removal of the protecting groups provided the desired sulfates of bile acids in satisfactory yields. The nuclear magnetic resonance spectral properties of sulfated bile acids and related compounds are briefly discussed.View full abstractDownload PDF (997K) -
ISAMU MIYATA, HIROSHI KISHIMOTO1979 Volume 27 Issue 6 Pages 1412-1421
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTransition temperatures between coexisting (solid-smectic, solid-cholesteric, smectic-cholesteric and cholesteric-isotropic liquid phases) of cholesteryl myristate (ChM) and cholesteryl palmitate (ChP) were studied by differential scanning calorimetry (DSC) as well as polarized light microscopy, in the presence and absence of n-heptane, n-octane and n-nonane as solutes. The polymorphism of ChM and ChP was maintained in spite of the addition of ca. 0.06 molar ratio of alkanes, although the distinction between coexisting phases decreased in enthalpy and entropy terms, resulting in the disappearance of liquid crystal phases (smectic and cholesteric phases). The addition of alkanes markedly depressed the transition temperatures ; this could be described quantitatively by thermodynamic analysis, taking into consideration the partition of alkanes between coexisting phases. The partition coefficients and the molar transition excess enthalpies of alkanes on mixing with ChM and ChP were calculated by simulation. The partition coefficients obtained from the DSC study agreed reasonably well with those previously determined by gas-liquid chromatography.View full abstractDownload PDF (846K) -
MASAKO TAKANI, KAZUE OHYA, KOTARO TAKAHASHI1979 Volume 27 Issue 6 Pages 1422-1425
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAndrosin, β-sitosteryl glucoside and a new lignan glycoside named schizandriside were isolated from the woody part of Schizandra nigra MAX., in addition to schizandronic acid, schizandrolic acid, schizandronol, oplodiol and (+)-catechin-7-β-D-glucopyranoside. Schizandriside (I) was shown to be (+)-isolariciresinol-2α-β-D-xylopyranoside on the basis of spectral and chemical data.View full abstractDownload PDF (573K) -
MASARU IWANAMI, TADAO SHIBANUMA, MASAHARU FUJIMOTO, RYUTARO KAWAI, KAZ ...1979 Volume 27 Issue 6 Pages 1426-1440
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral kinds of water-soluble dihydropyridine vasodilators were prepared and their vasodilating activities were evaluated. Among them, 2-(N-benzyl-N-methylamino)-ethyl methyl 2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylate hydrochloride (YC-93) was found to have outstanding activity and bioavailability. Various synthetic routes for this compound were examined.View full abstractDownload PDF (1274K) -
SHOZO MIYAZAKI, HITOMI INOUE, TANEKAZU NADAI, TAKAICHI ARITA, MASAHIRO ...1979 Volume 27 Issue 6 Pages 1441-1447
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe pH-solubility profiles of four basic drugs were studied at 37°. The solubility of papaverine hydrochloride in acetate buffer showed a typical pH-profile, which increased with decrease in pH. On the other hand, the pH-solubility profile of the hydrochloride in HCl-sodium acetate buffer was not as simple as that in acetate buffer, showing as solubility maximum at approximately 3.7. Similar pH-profiles of solubility were observed for trihexyphenidyl hydrochloride, isoxsuprine hydrochloride, and oxyphencyclimine hydrochloride. The decrease in the solubility of these drugs at more acidic pH values could be rationalized on the basis of the common ion effect. The dissolution behavior of the free bases and that of the hydrochloride salts of papaverine, trihexyphenidyl, and isoxsuprine were compared in dilute hydrochloric acid solutions, in the pH range from 1.0 to 1.8. It was confirmed that a much higher solution concentration and dissolution rate could be obtained using the free bases than from the hydrochloride salts in the pH range of the stomach (pH 1.0-1.2 for papaverine, and pH 1.2-1.4 for trihexyphenidyl and isoxsuprine) due to the common ion effect. It is suggested that salt formation does not always result in an enhancement of solubility characteristics.View full abstractDownload PDF (686K) -
TAKEFUMI MOMOSE, TETSUAKI TANAKA, TAKASHI YOKOTA, NORIO NAGAMOTO, KAZU ...1979 Volume 27 Issue 6 Pages 1448-1453
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSyntheses of 3-hydroxypyrroles (4-oxo-2-pyrrolines) (1b-1d) bearing no substituents on the ring carbon and of 3-hydroxypyrrole-4-carboxylates (2-4) with no substituents at C-5 were accomplished ; the former by hydrogenolysis of the benzyl esters (6b and 6c) or by acid cleavage of the tert-butyl ester (7), and the latter by acid cleavage of the diesters (15 and 16) or of the pyrrolinone (17). On the basis of spectral evidence, compounds 1c and 1d exist in the keto form while compounds 2-4 exist in the enol form. Only 1b was shown to be at equilibrium between the two tautomers. New information concerning the factors governing the tautomerism of 3-hydroxypyrroles was obtained.View full abstractDownload PDF (722K) -
EIICHI KOSHINAKA, NOBUO OGAWA, SAKAE KURATA, KAGARI YAMAGISHI, SHINJI ...1979 Volume 27 Issue 6 Pages 1454-1463
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of a search for new antispasmodic agents, we have synthesized 1-, 2-, and 3-diarylmethylenequinolizidine quaternary ammonium salts (4-15), which can be regarded as conformationally rigid derivatives of diphemanil methylsulfate (1) or timepidium bromide (2). The Grignard reaction of ethoxycarbonylquinolizidines (16, 21, and 30) with phenyllithium or 2-thienylmagnesiumbromide, followed by dehydration, afforded diarylmethylenequinolizidines (19, 20, 24, 25, 33, and 34). Quaternization of the 1-substituted derivatives (19 and 20) with methyl bromide afforded only the cis methobromides (4 and 6). On similar treatment, the 2-substituted derivatives (24 and 25) each afforded two isomeric methobromides, the trans (8a and 9a) and cis (8b and 9b), and the 3-substituted derivatives also afforded trans (12a and 13a) and cis methobromides (12b and 13b). The stereochemistry of these methobromides was confirmed by thermal isomerization experiments and the chemical shifts of N+-methyl signals in the 1H-and 13C-nuclear magnetic resonance spectra. The quaternary ammonium salts (4-15) exhibited more potent anticholinergic activity than 1 and 2, and the activities of several compounds (8, 9, and 13) were equal to or greater than that of atropine. The structure-activity relationships of these compounds are discussed.View full abstractDownload PDF (1136K) -
JOHJI YAMAHARA, YUKO TAKAGI, TOKUNOSUKE SAWADA, HAJIME FUJIMURA, KIYOH ...1979 Volume 27 Issue 6 Pages 1464-1468
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSScreening tests of crude drugs was carried out using a model system of congestive edema in rats. Some crude drugs containing saponin, i.e., Akebiae Caulis, Platycodi Radix, Polygalae Radix, and Mi-saponin (which resembles senega saponin in chemical structure) showed anti-edmatous and diuretic actions. Concomitant use of phenylbutazone with Mi-saponin resulted in an increase in urine volume and anti-edmatous action.View full abstractDownload PDF (984K) -
HIROYUKI ASAKAWA, EIKO IMAMIYA, YUKIHIKO HAMURO1979 Volume 27 Issue 6 Pages 1468-1472
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hypoglycemic activities of O-substituted salicylic acids (1-11), N-substituted anthranilic acids (18-27) and related compounds (12-17, 28-30) were investigated. It was concluded that the presence of a chlorine atom ortho to the carboxy group in salicylic and anthranilic acid derivatives might enhance the hypoglycemic activity.View full abstractDownload PDF (599K) -
YOSHIAKI KISO, KAORU ITO, SHIZUO NAKAMURA, KOUKI KITAGAWA, TADASHI AKI ...1979 Volume 27 Issue 6 Pages 1472-1475
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThioanisole-trifluoromethanesulfonic acid and thioanisole-methanesulfonic acid systems were found to be useful as deblocking methods in the synthesis of a methionine-containing peptide, Met-enkephalin, without any side reaction.View full abstractDownload PDF (561K) -
TERUYOSHI YOKOYAMA, TSUNEO UMEDA, KOJI KURODA, KOJI SATO, YASUSHI TAKA ...1979 Volume 27 Issue 6 Pages 1476-1478
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe thermodynamic values of two polymorphic forms of acetohexamide (form I and form II) were calculated from solubility measurements. The transition temperature and the heat of transition were estimated to be 154°, and 230 cal./mol, respectively. In vivo absorption studies of these polymorphs were carried out in four beagle dogs, and bioavailability parameters were determined from the blood concentration versus time curves. The polymorphic form of acetohexamide did not affect the bioavailability.View full abstractDownload PDF (400K) -
NORIHIDE UMINO, TAKEO IWAKUMA, NOBUO ITOH1979 Volume 27 Issue 6 Pages 1479-1481
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe sodium salts of amino acid borane complexes (1) produced from equimolar amount of NaBH4 and optically active α-amino acids in tetrahydrofuran at room temperature reduced various ketones to the corresponding optically active alcohols (2-62% optical yield). Sodium prolinate borane complex (2) gave the best results. Asymmetric reduction of (3) with sodium L-prolinate borane complex (2) followed by catalytic hydrogenolysis of benzyl and carbobenzoxy groups gave (4), a cardiotonic agent, in 62% optical yield.View full abstractDownload PDF (422K) -
MASAICHIRO MASUI, SHIGEKO OZAKI1979 Volume 27 Issue 6 Pages 1482-1485
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnodic oxidation of cycloserine and its acetylderivatives was studied at a glassycarbon electrode in alkaline aqueous buffer solution. On electrolysis, cycloserine consumed one Faraday per mol and yielded about 50% serine, 10% ammonia and a small amount of resinous products. A possible reaction scheme for the anodic oxidation of cycloserine is proposed.View full abstractDownload PDF (483K) -
TOZO FUJII, SHIGEYUKI YOSHIFUJI1979 Volume 27 Issue 6 Pages 1486-1490
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA formal synthesis of the Ipecac alkaloid emetine has been achieved in terms of the synthesis of the lactam ester 12 from ethyl dl-trans-5-ethyl-2-oxo-4-piperidineacetate (4). The steps involved are conversion of 4 into the lactim ether 5 or 6, N-alkylation of 5 or 6 with 3, 4-dimethoxyphenacyl bromide, and NaBH4 reduction of the resulting lactam ketone 7, followed by catalytic hydrogenolysis.View full abstractDownload PDF (682K) -
NORIO MINAMI, SHIZUMASA KIJIMA1979 Volume 27 Issue 6 Pages 1490-1494
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was found that the ethoxycarbonyl derivatives of o-acylphenols were reduced to the corresponding o-alkylphenols by sodium borohydride under mild conditions ; the use of 3 molar equivalents of sodium borohydride was sufficient for this reduction. Various kinds of o-acylphenols (1, 3, 5, 7, 9, 11, 13, 15, 17, 19, 21, 23, 25 and 27) were reduced to the corresponding o-alkylphenols (2, 4, 6, 8, 10, 12, 14, 16, 18, 20, 24, 26 and 28, respectively) in high yield by this method. o-acetylphenyl acetate (29) afforded o-ethylphenol (8) in better yield with sodium borohydride than ethyl o-acetylphenylcarbonate, but o-acetyl-phenyl p-toluenesulfonate (30) did not give 8.View full abstractDownload PDF (618K) -
TADATAKA NORO, SEIGO FUKUSHIMA, AKIRA UENO, TOSHIO MIYASE, YOICHI IITA ...1979 Volume 27 Issue 6 Pages 1495-1497
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new main alkaloid, croomine (I), was isolated from the roots and rhizomes of Croomia heterosepala OKUYAMA (Stemonaceae). The structure was established by chemical and spectral evidences and X-ray analysis.View full abstractDownload PDF (440K) -
TSUKASA TAKAMURA, TAKU CHIBA, HIDEKO ISHIHARA, SETSUZO TEJIMA1979 Volume 27 Issue 6 Pages 1497-1499
Published: June 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe protected tetrasaccharide (6) was synthesized in 77% yield by condensation of 1, 6-anhydro-2, 2', 3, 4', 6'-penta-O-benzyl-β-lactose (4) with the oxazoline derivative of lacto-N-biose I (5). The protecting groups of 6 were removed by the following series of reaction to provide lacto-N-tetraose (10) : debenzylation, acetylation, acetolysis, and de-O-acetylation. The synthetic product (10) was crystallized from aqueols ethanol as white needles, mp 225-228°, [α]21D+27° (4 min)→+21.3° (3 hr) (c=0.45, H2O). The homogeneity and the mobility of 10 were confirmed by the gel permeation chromatography using Bio-Gel P-4 column. The specific rotation and IR spectrum of 10 were similar to those of the natural material reported by Kuhn, Gauhe, and Baer [Chem. Ber., 86, 827 (1953)].View full abstractDownload PDF (389K)
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