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IKUO MORIGUCHI
1975 Volume 23 Issue 2 Pages
247-257
Published: February 25, 1975
Released on J-STAGE: March 31, 2008
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The logarithm of partition coefficient between octanol and water, log P, widely used in structure-activity studies as a hydrophobic parameter was factored into two intrinsic components, free molecular volume and hydrophilic effect of polar group. Among those additive parameters relating to molecular volume as parachor, molar refraction, diamagnetic susceptibility, molar attraction constant, and Exner's molar volume, Quayle's atomic parachor, Pr, showed the best correlation with observed log P for apolar compounds. The hydrophilic group effect, Ew, was estimated as a correction term in the evaluation of log P for polar compounds by using a linear relation of log P to Pr obtained for apolar molecules. The parameters Pr and Ew could be satisfactorily applied to the regression analysis of water-solubility of 156 organic liquids and frog muscle narcosis of 39 drugs. These artificial parameters have a great advantage in drug design because they can be evaluated for a wide variety of classes of compounds before the molecules are even synthesized.
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MITSUAKI WATANABE, TOSHIO KINOSHITA, SUNAO FURUKAWA
1975 Volume 23 Issue 2 Pages
258-263
Published: February 25, 1975
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Treatment of dimethyloxosulfonium 1-benzoyl-3, 3-diacylallylides (Ia-b) with sodium ethoxide in ethanol or sodium methoxide in methanol gave several thiabenzene 1-oxide derivatives (IIa-b, IIIa-d). Similar treatment of dimethyloxosulfonium 1-benzoyl-3-acetylallylide (Ic) afforded 1, 5-dimethyl-2-benzoylthiabenzene 1-oxide (IIIe) in a good yield. On the other hand, treatment of dimethyl-and tetramethylene-sulfonium 1-benzoyl-3, 3-diacylallylides (Va-c) with sodium ethoxide in ethanol gave biphenyl derivatives (VIa-c).
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YOSHISUKE TSUDA, KIMIAKI ISOBE, TAKEHIRO SANO
1975 Volume 23 Issue 2 Pages
264-271
Published: February 25, 1975
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New triterpenoid-tetra-ols, lycocryptol, 21-epilycocryptol, and diepilycocryptol, isolated from various Lycopodium plants were shown to be serrat-14-en-3β, 21α, 24, 30-tetraol (1a), serrat-14-en-3β, 21β, 24, 30-tetraol (2a), and serrat-14-en-3α, 21β, 24, 30-tetraol (3a) respectively, by spectral and chemical means. Two new acids, lycernuic acid-A and -B which were isolated from L. cernuum were settled to be 3β, 21β-dihydroxyserrat-14-en-24-oic acid (14a) and 3β, 21β, 30-trihydroxyserrat-14-en-24-oic acid (15a) by correlating them to 21-episerratriol and 21-epilycocryptol respectively.
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MASAKATSU SHIBASAKI, SHIRO TERASHIMA, SHUNICHI YAMADA
1975 Volume 23 Issue 2 Pages
272-278
Published: February 25, 1975
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Aminig to develop a new biogenetic-type cyclization of acyclic terpene derivatives which is applicable to the asymmetric synthesis of optically active terpenes, a novel acidcatalyzed cyclization of the dienamines (7) easily prepared with citral (1) and several kinds of secondary amines, was studied. Treatment of citral-pyrrolidine enamine (7a) with a mixture of concd. sulfuric acid and water, followed by hydrolysis, was found to exclusively afford α-cyclocitral (2) in 41% yield. Detailed studies on the structure of 7 and the reaction mechanism for the new cyclization reaction were also carried out.
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MASAKATSU SHIBASAKI, SHIRO TERASHIMA, SHUNICHI YAMADA
1975 Volume 23 Issue 2 Pages
279-284
Published: February 25, 1975
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Application of the biogenetic-type cyclization of citral (2) via its enamine, which was developed by us as described in the preceding paper, to the asymmetric synthesis, has been found to give (R) (+)-α-cyclocitral ((R) (+)-4) in at most 33% optical yield. (R) (+)-4 thus prepared was successfully converted to (R) (+)-trans-α-damascone ((R) (+)-6), a famous perfume which has fragrant odor, without racemization.
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ISAMU MURAKOSHI, FUMIO IKEGAMI, JOJU HAGINIWA, KAZUO TOMITA, MASAYUKI ...
1975 Volume 23 Issue 2 Pages
285-288
Published: February 25, 1975
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Enzyme preparations obtained from Citrullus, Pisum and Leucaena seedlings catalyzed the glucosylation of 3-hydroxy-5-phenylisoxazole (II) by UDP-glucose to yield 3-β-D-gluco-pyranosyloxy-5-phenylisoxazole (III) and 2-β-D-glucopyranosyl-5-phenyl-4-isoxazolin-3-one (IV). Some other properties of the enzyme (s) are described. The enzyme preparations also catalyzed the hydrolysis of III into II and D-glucose, but an analogous reaction for the hydrolysis of IV could not be demonstrated at pH values in the range 4.5 to 6.5.
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KUNIO KAWAI, SHIGEO BABA
1975 Volume 23 Issue 2 Pages
289-293
Published: February 25, 1975
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As part of problems on the applicability of a drug labeled with deuterium to metabolic studies in man, an analytical method for urinary metabolites by deuterium-tracer technique was investigated and its reliability was compared with that of
14C-tracer technique. l-Ephedrine [arom.-
2H
5] or l-ephedrine [α-
14C] was subcutaneously injected to rabbits and the main urinary metabolites (1-phenyl-1, 2-propanediol and hippuric acid) excreted for 24 hr after dosing were analyzed. A deuterated metabolite such as the diol absent in normal urine was submitted to the inverse isotope dilution analysis using the unlabeled compound both as an internal standard and as a carrier. The molar ratio of the unlabeled to the deuterated compound was determined by mass spectrometry. The amount of deuterated hippuric acid diluted with the endogenous material present in urine was determined by using both the direct isotope dilution analysis and the inverse isotope dilution analysis. It was found that reliability of the deuterium-tracer technique was comparable with that of the
14C-tracer technique on the basis of data obtained from both techniques.
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GENICHIRO NONAKA, ITSUO NISHIOKA
1975 Volume 23 Issue 2 Pages
294-298
Published: February 25, 1975
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Two new alkaloids, corydalispirone, C
20H
17O
6N, mp 196-198°, [α] D 0°, and corydalisol, C
20H
21O
5N, mp 160-161°, [α] D +21.4°, were isolated from Corydalis incisa PERS. (Papaveraceae). The structure of corydalispirone was established to be I by the spectroscopic examinations and chemical correlation with bicucullinediol and adlumidinediol, and the structure of corydalisol was determined as VIII by the conversion to d-tetra-hydrocoptisine. Corydalispirone and corydalisol are noted as a new series of isoquinoline-type alkaloids having one more carbon atom at the benzyl moiety, and probably are metabolites of coptisine.
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NORIO TAKAMURA, TOMISHIGE MIZOGUCHI, SHUNICHI YAMADA
1975 Volume 23 Issue 2 Pages
299-303
Published: February 25, 1975
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α-Diazo-β-phenyl-propionic acid esters (II) prepared from the phenylalanine derivatives (I) were readily decomposed by the alkoxide in tetrahydrofuran to give trans-cinnamic acid esters (III) stereoselectively, while the decomposition of II in the presence of boron trifluoride etherate and dicyclohexylcarbodiimide in methylene chloride afforded ciscinnamic acid esters (IV) as sole reaction products.
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MASAKO NAKAGAWA, MIDORI KIUCHI, MICHIKO OBI, MASAKATSU TONOZUKA, KAZUM ...
1975 Volume 23 Issue 2 Pages
304-312
Published: February 25, 1975
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The reaction of tryptamine with δ-valerolactone in tetralin gave δ-hydroxyamide (3) as the main product and the lactam (4) as the minor product. However, the reaction of 5, 6-dihydro-2-pyrone with tryptamine or aniline afforded a mixture of the corresponding αβ- and βγ-unsaturated lactams, whereas, 2-pyrone did not react with either tryptamine or aniline to give the corresponding pyridone. Cyclization of 3 or 4 by Bischler-Napieralski reaction and followed NaBH
4 reduction provided a convement synthesis of 1, 2, 3, 4, 6, 7, 12, 12b-octahydroindolo [2, 3-α] quinolizine (23).
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CHIAKI TANI, NAOTAKA NAGAKURA, SHIN HATTORI
1975 Volume 23 Issue 2 Pages
313-319
Published: February 25, 1975
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The structure of corydalidzine isolated from Corydalis koidzumiana OHWI collected in Taiwan was established to be 2, 9-dimethoxy-13α-methyl-13aβ-berbine-3, 10-diol by the spectroscopic methods and synthesis of dl-base.
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TOSHIO NAMBARA, TOSHIHIRO KUDO, HIROSHI HOSODA, YOICHI IITAKA, NORIHIS ...
1975 Volume 23 Issue 2 Pages
320-325
Published: February 25, 1975
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The crystal structure of the titled compound (IVb) has been determined by threedimensional X-ray analysis from the diffractometer data. Crystals are monoclinic, a=14.494 (10), b=6.586 (3), c=12.420 (8) Å, β=111.89 (2)°, U=1100.1 Å
3, Z=2, space group P2
1. Conformation of ring C has proved to be somewhat distorted boat from. The relative ease with which 16, 17-diketo-C/D-cis steroids do enolize has been interpreted in terms of conformational change.
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JUTARO OKADA, YOSHINOBU FUKUMORI
1975 Volume 23 Issue 2 Pages
326-332
Published: February 25, 1975
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Various powders are compressed at the constant rate of displacement of upper punch equal to 0.332 mm/sec for the comparison of the results to those in the cases of potassium chloride and lactose powder reported in the previous paper. Consequently, from the patterns of changes of pressure-transmission-ratio with the increase of upper punch pressure, the powders are divided into three classes, as followings ; (1) KCl type, for which the pressure-transmission-ratio takes the maximum value at the almost constant porosity (about 32%) without reference to material and net volume, (2) lactose type, for which the values of the ratio decrease monotonously, and (3) the powders not belonging to KCl and lactose type, for which the values of the ratio do not decrease. Besides, the comfirmity of the results to the Janssen's equation is checked up. Furthermore, the powders are compressed continuously under the constant pressure of upper punch for the hours for the purpose of examining the creep properties.
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YOSHIO ARATA, TADASHI AOKI, MIYOJI HANAOKA, MICHIE KAMEI
1975 Volume 23 Issue 2 Pages
333-339
Published: February 25, 1975
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The stereochemistry of a number of the 9a-substituted quinolizidine methiodides was established, and confirmed from their
13C-nuclear magnetic resonance (NMR) spectra. The N
+-methyl signals of the trans 9a-substituted quinolizidine methiodides were found to appear at lower field than those of the corresponding cis methiodides except for the 9a-cyano methiodides in their NMR spectra. On quaternization of the 9a-substituted quinolizidines with methyliodide, the formation of the cis methiodide vs. the corresponding trans methiodide increased according to the order of the bulkiness of the 9a-substituents as CH
2NO
2>CH
2OH>CH
2>CN>H.
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YUKIHISA KURONO, KEN IKEDA, KANETO UEKAMA
1975 Volume 23 Issue 2 Pages
340-345
Published: February 25, 1975
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Formation and hydrolysis rates for methanesulfonic acid derivatives (MSD) of anilines including o-, m-, and p-carboxyaniline and various ortho-substituted anilines were studies as compared with those of the other substituted anilines. For o-, m-, and p-carboxyaniline, a practical pK
a was discussed on the relationship between logarithm of formation or hydrolysis rate constant and pK
a of the corresponding anilinium ion. Formation rates for the reaction of intramolecular H-bonding aniline with hydroxymethanesulfonate were about half to those for the other substituted anilines, which supported the assumption that the reactive H in NH
2 group became half owing to the intramolecular H-bonding. In the cases of anilines substituted by negatively charged group, formation and hydrolysis rates were fairly correlated to Hammett σ value of negative group and both the rates were slower than those of the other anilines. Hammett σ values of NHCH
2SO
3-group were determined and the values of σ
m and σ
p were -0.10 and -0.57 respectively. From these observations the structure of intermediate of the reversible MSD reaction was proposed.
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MASATOMO HAMANA, KAZUHISA FUNAKOSHI, HIROMICHI SHIGYO, YOSHIYUKI KUCHI ...
1975 Volume 23 Issue 2 Pages
346-350
Published: February 25, 1975
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The 1, 3-dipolar cycloaddition between quinoline N-oxide (I) and methyl propiolate progressed in the presence of acetic anhydride or hydroquinone to afford methyl α-formyl-2-quinolineacetate (IIa). The reaction with ethyl propiolate in the presence of hydroquinone gave the corresponding ethyl ester (IIb). The reaction of I with methacrylonitrile in the presence of hydroquinone produced cyanohydrin of 2-acetonylquinoline (VIII) or 2-acetonylquinoline (IX) and 2-cyanoquinoline (X). Isoquinoline N-oxide (XI) was less reactive and resisted the reaction with propiolates, but reacted with methacrylonitrile in the presence of hydroquinone to give 1-acetonyl-isoquinoline (XII), 1-cyanoisoquinoline (XIII) and isoquinoline.
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TAKASHI TATSUNO, NORIKO KOBAYASHI, KAORU OKUBO, HIROSHI TSUNODA
1975 Volume 23 Issue 2 Pages
351-354
Published: February 25, 1975
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The toxicological research of the metabolites of Penicillium tardum was carried out. The cytotoxic metabolic substances of P. tardum have been confirmed as endocrocin and emodin. In addition, the known metabolites of this fungus, rugulosin and skyrin were isolated.
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ISAO KITAGAWA, HIDEYO SUZUKI, KIYOSHI KITAZAWA, NOBUKO YAMAO, ITIRO YO ...
1975 Volume 23 Issue 2 Pages
355-364
Published: February 25, 1975
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The structure of spergulagenin A, a new genuine sapogenol isolated (second major) from the root of Mollugo spergula L. (Molluginaceae) along with oleanolic acid and methyl spergulagenate (1a) (major), has been established as 3 on the basis of chemical investigations and X-ray structure evidence. The full account of chemical evidence is described. Spergulagenin A (3) possesses a new migrated-hopane skeleton, in which 22-CH
3 in the ordinary hopane framework is migrated to C-21, and the probable biogenetic pathway of spergulagenin A has been presumed.
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TETSUZO KATO, MASAYUKI SATO, YOSHINORI KITAGAWA
1975 Volume 23 Issue 2 Pages
365-370
Published: February 25, 1975
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Photoreaction of diketene with benzophenone gave 5, 5-diphenyl-1, 6-dioxaspiro [3.3]-heptan-2-one (IV), 2, 5-dihydro-4-hydroxydiphenylmethylfuran-2-one (V), 2, 2, 5, 5-tetraphenyl-1, 6-dioxaspiro [3.3] heptane (VI), and 2, 2-diphenyl-4-diphenylmethyleneoxetane (VII). Similar reaction of benzaldehyde gave trans (XVI) and cis (XVII) isomer of 5-phenyl-1, 6-dioxaspiro [3.3] heptan-2-one.
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HARUAKI YAJIMA, HIROSHI OGAWA, HIDEHIKO WATANABE, NOBUTAKA FUJII, MASA ...
1975 Volume 23 Issue 2 Pages
371-374
Published: February 25, 1975
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Trifluoromethanesulphonic acid removed all protecting groups from Z-Thr-Lys (Z)-Pro-Arg (Tos)-OH to give the phagocytosis-stimulating tetrapeptide, H-Thr-Lys-Pro-Arg-OH, named tuftsin. To this synthesis, the 5-chloro-8-quinolyl ester procedure was applied. With this connection, a number of analogous active esters was prepared.
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HIDEHIKO WATANABE, HIROSHI OGAWA, HARUAKI YAJIMA
1975 Volume 23 Issue 2 Pages
375-383
Published: February 25, 1975
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The octadecapeptide corresponding to the entire amino acid sequence of porcine β-MSH was synthesized by assembling four peptide subunits ; Z (OMe)-Asp (OBzl)-Glu-(OBzl)-Gly-OH (I), Z (OMe)-Pro-Tyr-Lys (Z)-Met-NHNH
2 (II), Z (OMe)-Glu (OBzl)-His-Phe-Arg (Tos)-Trp-Gly-OH (III) and Z (OMe)-Ser-Pro-Pro-Lys (Z)-Asp (OBzl)
2, followed by deblocking of all protecting groups with hydrogen fluoride. The synthetic porcine β-MSH was 3.16 times active than our synthetic human β-MSH (6.2×10
9 MSH unit/g).
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HIROYUKI INOUYE, TAKUO OKUDA, TOSHIMITSU HAYASHI
1975 Volume 23 Issue 2 Pages
384-391
Published: February 25, 1975
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As the naphthoquinones and a derivative relating to the already reported catalpalactone (1), the following seven substances have been isolated from Catalpa ovata wood : α-lapachone (3), α-dihydrocaryopterone (=9-hydroxy-α-lapachone) (4), 9-methoxy-α-lapachone (5), 4-hydroxy-α-lapachone (6), 4, 9-dihydroxy-α-lapachone (7), 4-oxo-α-lapachone (8) and catalponol (9). Their sturctures, except catalponol (9) have been clarified.
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HIROYUKI INOUYE, TOSHIMITSU HAYASHI, TETSURO SHINGU
1975 Volume 23 Issue 2 Pages
392-399
Published: February 25, 1975
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Absolute structure of catalponol, a naphthoquinone congener of Catalpa ovata has been established as 1. Examination of the reaction of 1 and its oxidation product, catalponone (2) with BF
3 giving several derivatives including natural products such as 2, 2-dimethylnaph-thochroman (12), nordihydrolapachenole (14) and tetrahydrotectol (15), has offered interesting materials for considering the biosynthetic pathway of these substances.
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TETSUO KOMURO, SHIKIFUMI KITAZAWA, HITOSHI SEZAKI
1975 Volume 23 Issue 2 Pages
400-408
Published: February 25, 1975
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Relation between diminution of intestinal tissues brought about by fasting and/or by treatment with antineoplastic agents and intestinal absorption of drugs was investigated. Both in fasted and antineoplastic agent pretreated rats, intestinal absorption was markedly decreased in a similar manner. In the latter case, a remarkable loss in the weight of small intestine with a little decrease in the body weight was noted. These phenomena are closely resembled the results observed in fasted rats which showed a severe atrophy in intestine rather than in body. In all cases, there exists a close relation between drug absorption and intestinal weight. The loss of the latter seemed to be partly due to a decrease in mucosal tissues, thus resulting in the reduction of surface area. From these results, it is concluded that a reduction in the absorptive surface area of intestine seems to be one of the predominant factors which induced the apparent fall in intestinal drug absorption observed in fasted and antineoplastic agent pretreated rats under the experimental conditions.
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YUKIHISA KURONO, KEN IKEDA, KANETO UEKAMA
1975 Volume 23 Issue 2 Pages
409-415
Published: February 25, 1975
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Reaction of substituted aniline liberation from its methanesulfonic acid derivative (MSD) was studied in acid region. From the ultraviolet spectral changes, the extraction of liberated parental anilines by 1, 2-dichloroethane, and thin-layer chromatography, it was suggested that a consecutive reaction other than direct hydrolysis of MSD occurs in acid range. Reaction scheme for the liberation of free amine was proposed and the analytical method of kinetic data was presented. The pH-profile of total decreasing rate of p-chloroaniline MSD had a slope of -1 below pH 3.5 and it was pH-independent above pH 5.0. The pH-profile of the direct hydrolysis around pH 2.0-1.0 had a slope steeper than -1 and it was -1 below pH 1.0, while the estimated profile of the indirect pathway had a slope of -1 and it became pH-independent below pH 1.0. For the explanation of these pH-profiles the protonation of MSD was considered and its dissociation constant was estimated.
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TOHRU KIKUCHI, TOSHINARI NISHINAGA, MITSURU INAGAKI, MINEO(nee NIWA, K ...
1975 Volume 23 Issue 2 Pages
416-429
Published: February 25, 1975
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The structure of spiropachysine, a major alkaloid of the leaves of Pachysandra terminalis SIEB. et ZUCC. (Buxaceae), was investigated and assigned to the formula I, including absolute configuration, on the basis of chemical and spectroscopic evidences. The stereochemistry at the C
3-position was clarified by the circular dichroism study in comparison with the compounds having analogous aromatic chromophores and the known absolute stereochemistry. This alkaloid is unique in the structural feature possessing a five-membered spiro-lactam system.
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MASASHI TOMODA, SACHIKO KANEKO, SATOMI NAKATSUKA
1975 Volume 23 Issue 2 Pages
430-436
Published: February 25, 1975
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A mucous polysaccharide, named Lilium-A-glucomannan, has been isolated from the bulbs of Lilium auratum LINDL. It was homogeneous on glass-fiber paper electro-phoresis and by ultracentrifugal analysis. It was composed of D-mannose and D-glucose in the molar ratio of 8 : 3, and its molecular weight was estimated at 35700. The O-acetyl groups in it were identified and the content was 5.1%. The O-acetyl groups were located in both positions 3 and 6 of a part of D-mannose units. Methylation, periodate oxidation and partial acid hydrolysis studies suggested that the polysaccharide is mainly composed of β-1→4 linked aldohexopyranose residues having a small degree of branching at position 2 of D-mannose residues and the non-reducing ends were terminated by D-mannose units.
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MASAFUMI YOSHIMOTO, CORWIN HANSCH, PRISCILLA Y.C.JOW
1975 Volume 23 Issue 2 Pages
437-444
Published: February 25, 1975
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A quantitative structure-activity relationship for benzyl pyridinium ions inhibiting complement has been formulated. The best equation describing the relationship is log 1/C=0.18π-1+0.46π-2+1.01σ
+-1+0.72D-1+2.50 where C is the molar concentration causing 50% inhibition of complement, π-1 is the hydrophobic constant for substituents on the pyridine moiety and π-2 for substituents on the benzyl moiety, σ
+-1 refers to the electronic effects of substituents on the pyridine ring, and the indicator variable D-1 refers to the SO
2F function in the 2-position of the benzene ring. This expression correlates 69 derivatives with a correlation coefficient of 0.939 and a standard deviation of 0.198. The implications of this relationship for the design of inhibitors is discussed.
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JUNKO NODA, HIROKO SAKAMOTO, TSUNEJI NAGAI
1975 Volume 23 Issue 2 Pages
445-449
Published: February 25, 1975
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In the course of investigating the adsorption of non-steroid anti-inflammatory drugs at carbon black (CB)/water interface, it was found that the degradation of some of these drugs was accelerated. It was also found that this acceleration was observed in the existense of graphite in the place of CB, but not observed in a simple aqueous solution nor in the presence of such hydrophilic powder as silica gel. The results obtained from solutions of different pH and temperature showed that the Rf values of thin-layer chromatography of the degradation products of the respective drugs were coincident to both cases of the presence of CB at 30°and the absence of CB at 60°, while the rate of degradation was observed greater in the presence of CB than in the absence of CB.
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HITOSHI UNO, AKIRA IRIE, KATSUHIKO HINO
1975 Volume 23 Issue 2 Pages
450-451
Published: February 25, 1975
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Thiazolo [2, 3-f] guanines were synthesized by the cyclization of 8-acylmethylthioguanines. Structure of these compounds were determined by desulfurization with Raney Ni.
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TETSUZO KATO, SHINICHI MASUDA
1975 Volume 23 Issue 2 Pages
452-455
Published: February 25, 1975
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1-Iminopyridinium ylide reacted with diketene to give 1-(N-acetoacetylimino)-pyridinium ylide (VI), which, on treatment with sodium ethoxide, was transformed to 3-acetyl-2-hydroxypyrazolo [1, 5-a] pyridine (XI). On the other hand, reaction of diketene with 1-(N-methylimino) pyridinium ylide afforded directly 3-acetyl-1-methylpyrazolo [1, 5-a] pyridin-2-one (VIII). Reaction of diketene with 1-iminoquinolinium ylide (XIII) and 2-iminoisoquinolinium ylide (XVI) gave rise to 3-acetyl-2-hydroxypyrazolo [1, 5-a] quinoline (XV) and 3-acetyl-2-hydroxypyrazolo [1, 5-a] isoquinoline (XVII), respectively.
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TETSUZO KATO, MASAYUKI SATO, KATSUMI TABEI, ETSUKO KAWASHIMA
1975 Volume 23 Issue 2 Pages
456-459
Published: February 25, 1975
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Reaction of hydrazobenzene (Ia) with diketene in the presence of triethylamine gave 1, 2-diphenyl-5-methyl-3-pyrazolone (IIIa) in 80% yield. Similarly, twelve kinds of symmetrical substituted hydrazobenzene derivatives, such as dimethylhydrazobenzenes (Ib, c, d), dichlorohydrazobenzenes (Ie, f, g), dimethoxyhydrazobenzenes (Ih, i, j), and diethoxyhydrazobenzenes (Ik, l, m) afforded the corresponding 1, 2-diaryl-5-methyl-3-pyrazolone derivatives (IIIb-m).
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JINSAKU SAKAKIBARA, YOSHIHIRO HOTTA, MASAITI YASUE
1975 Volume 23 Issue 2 Pages
460-462
Published: February 25, 1975
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Correlation of protolyofoligenic acid (II) with cycloartenol (III) was established to certify the stereostructure of II. Protolyofoligenic acid (II) was derived to 24, 25-di-O-isopropylidene-9 (10)-cyclolanostane-3α-ol (VIII) through protolyofoligenol (VI) and the corresponding aldehyde (VII). Cycloartenol (III) was acetylated, epoxidized, and benzoylated. The product, dibenzoate, was separated into 24R and 24S isomers by column and preparative thin-layer chromatography. Hydrolyzed product of 24R isomer, which has 3β-hydroxyl group, was derived to isopropylidene derivative, oxidized to 3-oxo compound and reduced by Meerwein-Ponndorf method to yield 3α-hydroxyl compound. The final product was identified with (VIII), which was derived from protolyofoligenic acid.
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EIICHI YOSHII, TAMOTSU MIWA, TORU KOIZUMI, EITARO KITATSUJI
1975 Volume 23 Issue 2 Pages
462-464
Published: February 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A practical synthetic method of 21-dimethoxypregn-14-en-20-ones which are key intermediates in bufadienolide syntheses is described. It involves 21-thiomethylation of pregn-14-en-20-ones followed by oxidation with N-chlorosuccinimide in methanol.
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KAZUNOBU MIURA, TSUGUO KASAI, TOHRU UEDA
1975 Volume 23 Issue 2 Pages
464-466
Published: February 25, 1975
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
A versatile chemical conversion of adenosine to guanosine is described. Treatment of adenosine-1-oxide with cyanogen bromide afforded hydrobromide salt of 2-imino-6-β-D-ribofuranosyl-(1, 2, 4-oxadiazolo [2, 3-f] purine), which existed as N
6-cyanoadenosine-1-oxide on neutralization. Methylation of the latter followed by treatment with alkali afforded N
6-methoxy-2-aminoadenosine. The solvolysis of the product with liquid hydrogen sulfide gave 6-thioguanosine in high yield. Thioguanosine can be oxidatively hydrolyzed to guanosine by the known procedure. Catalytic hydrogenation of the oxadiazolopurine riboside in the presence of acetic acid gave 6-ureidopurine riboside.
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