Showing papers in "Chemical & Pharmaceutical Bulletin in 1960"
TL;DR: In this paper, a substrate for β-glucuronidase was proposed for the assay of the hydrolytic activity of α-Dglucosiduronic acid.
Abstract: 1. ρ-Nitrophenyl β-D-glucosiduronic acid is proposed as a substrate for the assay of the hydrolytic activity of β-glucuronidase. The liberated p-nitrophenol is measured photocolorimetrically in alkaline solution. 2. The chemical synthesis of p-nitropenyl β-D-glucopyranosiduronic acid was accomplished by alkaline hydrolysis of methyl (p-nitrophenyl 2, 3, 4-tri-O-acetyl-β-D-glucopyranosid) uronate which was prepared by the condensation of methyl 1-bromo-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate and p-nitrophenol using acetonitrile and freshly prepared silver oxide. 3. The kinetics of the hydrolysis of p-nitrophenyl β-D-glucopyranosiduronic acid by β-glucuronidase were investigated. The optimum pH is 3.8 in 0.2M acetate buffer at 38°. The reaction velocity is constant with time and varies linearly with enzyme concentrations in the presence of excess substrate. The Michaelis-Menten constant is 2×10-4M.
116 citations
TL;DR: In this article, the authors attempted to isolate active principles in the ligusticum root (Hokkai-Toki) by tracing anticholinergic principles with rat intestine using the Magnus method.
Abstract: Isolation of active principles in the ligusticum root (Hokkai-Toki) was attempted. Anticholinergic principles were traced by the Magnus method with rat intestine. Ligustilide, which is a new and the most active constituent was isolated. It is an isomer of butylphthalide. It was marked bluish fluorescence and decomposes rapidly on exposure to air.
32 citations
TL;DR: In this paper, the infrared spectra of pyrazine, its eight mono-substituted derivatives, and their ten N-oxide derivatives were analyzed and correlated to the nature of a substituent present.
Abstract: The infrared spectra of pyrazine, its eight mono-substituted derivatives, and their ten N-oxide derivatives were analyzed. Their characteristic N-O streching frequencies (a strong absorption in the region of 1250 and 1350 cm-1) were found to be correlated to the nature of a substituent present and the linear relationship between the N-O frequency and the σ-value of a substituent in substituted pyridine N-oxides could be extended to that in substituted pyrazine N-oxides by applying the σ-value of ring nitrogen (0.93) and the N-oxide group (0.25) toward 4-position of pyridine for mono- and di-N-oxides, respectively. The considerably higher frequency shift of the N-O frequency was shown to be characteristic for the methyl group at β-position with respect to the N-oxide group. Ring and ring CH vibrations were discussed on the basis of the correlations found in the pyridine ring system. The splitting of the carbonyl stretching frequency of ester group adjacent to ring nitrogen was pointed out and discussed. The infrared spectra of pyrimidine N-oxide and its eight derivatives were also examined and discussed in comparison with the above results.
30 citations
TL;DR: In this article, pyridine lactones were prepared from 2-methylnicotinic acid using 2-hydroxymethylnaphthyridine derivatives, which were then reduced with lithium aluminium hydride, yielding pyrrolopyridine and 1, 7 naphthiridine derivatives with a fair degree of hypotensive action.
Abstract: New type 2, 3-disubstituted pyridine lactones were prepared from 2-methylnicotinic acid The lactones, 2-hydroxymethylnicotinic acid lactone and 2-hydroxymethylpyridine-3-acetic acid lactone, were reacted with various amines to form the corresponding lactams, and the lactams were reduced with lithium aluminium hydride, yielding pyrrolopyridine and 1, 7-naphthyridine derivatives which possessed a fair degree of hypotensive action
28 citations
TL;DR: In this article, the replacement reaction at C-1 position of N, N-phthaloyl derivatives of D-glucosamine gave β-anomers and there was some steric hinderance for the formation of αanomers.
Abstract: N, N-Phthaloyl-1-bromo-3, 4, 6-tri-O-acetyl-1-deoxy-β-D-glucosamine (III) reported in Part IV1) of this series is the first example of 1, 2-trans-acetobromo-sugar obtained in glucose and glucosamine series. Several replacement reactions at C-1 position of (III) as well as properties of several new N, N-phthaloyl derivatives of D-glucosamine were described in the present paper. From the results of these reactions, it was concluded that the replacement reaction at C-1 position of N, N-phthaloyl derivatives of D-glucosamine gave β-anomers and there was some steric hinderance for the formation of α-anomers.
28 citations
25 citations
TL;DR: Puerarin, C21H20O9 m.p. 187°(decomp), and the substance f, which were isolated from Pueraria root were studied to establish their structure as mentioned in this paper.
Abstract: Puerarin, C21H20O9 m.p. 187°(decomp.), and the substance f, which were isolated from Pueraria root were studied to establish their structure. puerarin was proved to be 8-D-glucopyranosyl-4', 7-dihydroxyisoflavone (=8-D-glucopyranosyldaidzein) by oxidation of its dimethyl ether with sodium iodate to 8-formyl-4', 7-dimethoxyisoflavone and by ozonolysis of puerarin to D-glucose and D-arabinose. On hydrolysis with sulfuric acid, the substance f yielded puerarin and D-xylose.
24 citations
TL;DR: In this paper, the spectral properties of 20 kinds of monosubstituted quinolines, quinoline 1-oxides, and isoquinoline 2-oxide were determined.
Abstract: Infrared spectra of 20 kinds of monosubstituted quinolines, quinoline 1-oxides, and isoquinoline 2-oxides, and 18 kinds of monosubstituted quinoline 1-oxides were determined By comparison with the spectra of corresponding quinolines, two strong absorptions in the regions of 1280∼1340 cm-1 and 1210∼1260 cm-1 of the N-oxide compounds were assigned to the characteristic N-O absorptions By examining the solvation effect of methanol and water, however, it was clarified that the N-O stretching vibration contributes to two or more absorptions in the region of 1150 and 1350 cm-1 due to complex coupling with the vibrations originating in the quinoline ring and ring hydrogens, and there was not found any correlation between these frequencies and the structure Ring CH out-of-plane bending frequencies were assigned and interpreted by considering the number of adjacent free hydrogens on heterocyclic and carbocyclic rings, and it was found that all the frequencies of monosubstituted quinoline 1-oxides, except the band near 770 cm-1 in 4-substituted derivatives, show an appreciable shift to a lower frequency than those of the corresponding quinolines
24 citations
TL;DR: In this paper, the synthesis of 5-substituted uridines and their 5'-phosphates was described, and 5-Bromo-UMP was isolated by ion exchange chromatography.
Abstract: The syntheses of 5-substituted uridines and their 5'-phosphates were described. 5-Bromo-2', 3'-isopropylideneuridine was phosphorylated with phosphoryl chloride and from the mixture of 5-Bromo-UMP, -UDP, and -UTP obtained, 5-Bromo-UMP was isolated by ion exchange chromatography. Phosphorylation of 5-bromo-2', 3'-isopropylideneuridine with polyphosphoric acid afforded 5-Bromo-UMP in a good yield. 5-Hydroxyuridine and its 5'-phosphate were synthesized by the addition of bromine to uridine or UMP and successive treatment with pyridine. 5-Morpholinouridine and its isopropylidene derivative were obtained from corresponding 5-bromo derivatives and morpholine, and 5-Morpholino-UMP was obtained by phosphorylation of 5-morpholino-2', 3'-isopropylideneuridine with polyphos phoric acid.
22 citations
22 citations
TL;DR: The Sterin-Gehalt der grunen Meeres-Algen was kleiner als derjenige der roten bzw. braunen Alge.
Abstract: Im Zusammenhang mit den fruheren Untersuchungen uber Algen-Sterine wurden diesmal die Sterin-Bestandteile der grunen Meeres-Algen untersucht. Aus Monostroma nitidum WITTROCK wurden namlich das Triterpenoid, Friedelin und ein Sterin, das vermutlich das Haliclonasterin was, isoliert. Bei der Aufarbeitung des Sterin-Bestandteils von Enteromorfa linza L. ergab sich ein Stigmastadienol, dessen Eigenschaften mit denjenigen des △5-Avenasterins identisch waren. Der Sterin-Gehalt der grunen Alge war kleiner als derjenige der roten bzw. braunen Alge.
TL;DR: In this article, the authors measured the infrared absorption spectra of over 500 pieces of gallstones and established the best method now known for the analyses of gall stones by infrared spectra.
Abstract: Infrared absorption spectra of over 500 pieces of gall stone were measured and analysis of gall stones by infrared spectra was established. This is the best method now known for the analyses of gall stones. Spectra were newly obtained for a group of calculi containing stearic acid, calcium stearate, triglyceride, and polysaccharide. Almost all of the gall stones are composed of a combination of such substances and cholesterol, calcium salt of bilirubin, calcium carbonate, calcium phosphate, and proteins, in various ratios and in variety of modes. A new classification has been proposed based on these chief components. It was also found that there is a vast difference in gall-stone components between urban and rural areas. Cholesterol, which is found in metropolitan area, is rare in rural villages and in its stead ratio of calcium stearate to calcium salt of bilirubin increases.
TL;DR: The chemical structure of the compounds found by the reaction of cyanogen bromide and acylhydrazines was determined as 2-alkyl-5-amino-1, 3, 4-oxadiazoles (I), 3-Alkyl-5, 6, 7, 8-tetrahydro-s-triazolo [4, 3-b] [1, 2, 4] triazine-6, 7-diones (III), which are listed in Table III, were prepared from 4, 5-diamino
Abstract: The chemical structure of the compounds found by the reaction of cyanogen bromide and acylhydrazines was determined as 2-alkyl-5-amino-1, 3, 4-oxadiazoles (I). 3-Alkyl-5, 6, 7, 8-tetrahydro-s-triazolo [4, 3-b] [1, 2, 4] triazine-6, 7-diones (III), which are listed in Table III, were prepared from 4, 5-diamino-1, 2, 4-triazoles (II) and diethyl oxalate. Several unreported intermediates of these compounds - 2-alkyl-5-amino-1, 3, 4-oxadiazoles (I) and 4, 5-diamino-1, 2, 4-triazoles (II)-were also prepared and are listed in Tables I and II.
TL;DR: In this article, the steric structure of dihydrolycorine was considered, in view of the sequence of reactions used in this transformation, to be that of the ring-system.
Abstract: Treatment of dihydrolycorine (I) with phosphoryl chloride under mild conditions yielded a chlorohydrin (V). Reduction of this hydrin with zinc in acetic acid followed by reduction with hydrogen and platinum oxide afforded (-)-α-lycorane (VII), the steric structure of which was considered, in view of the sequence of reactions used in this transformation, to be that of the ring-system of dihydrolycorine.
TL;DR: Sixty-eight substituted azaindolizines were tested for their activity on Lactobacillus casei and Streptococcus faecalis and compounds which have amino or closely related groups were antagonized by folic acid, leucovorin, and thymine but not by purines.
Abstract: Sixty-eight substituted azaindolizines were tested for their activity on Lactobacillus casei and Streptococcus faecalis. These azaindolizines could be divided into three classes according to the pattern of growth inhibition, substituent present, and the position of the substituent in azaindolizine molecule. Compounds in Group 1 and 2 which have sulfurcontaining substituents and halogen groups, respectively, were not affected appreciably by folic acid, leucovorin, thymine, or purines, while Group 2 compounds which have amino or closely related groups were antagonized by folic acid, leucovorin, and thymine but not by purines.
TL;DR: In this paper, 13 kinds of aldehyde and ketone, including some basic and/or alicyclic carbonyl compounds, were subjected to Wittig reaction, using ethoxycarbonylmethyl-triphenyl-phosphonium bromide and sodium ethoxide in dehyd. ethanol at room temperature in nitrogen atmosphere.
Abstract: Thirteen kinds of aldehyde and ketone, including some basic and/or alicyclic carbonyl compounds, were subjected to Wittig reaction, using ethoxycarbonylmethyl-triphenyl-phosphonium bromide and sodium ethoxide in dehyd. ethanol at room temperature in nitrogen atmosphere, and corresponding α, β-unsaturated ethyl esters were formed as expected.
TL;DR: In this article, the Ultraviolet and infrared absorption spectra of 3, 4, 4-dihydroisoquinoline and its homologs are described, which have been very useful in the interpretation of the absorptions of 2'-acyl-5, 11b-dehydroemetines.
Abstract: The Ultraviolet and infrared absorption spectra of 3, 4-dihydroisoquinoline and its homologs are described which have been very useful in the interpretation of the absorptions of 2'-acyl-5, 11b-dehydroemetines
TL;DR: A flavonoid isolated from the leaves of sesame (Sesamum indicum L. ), was determined as 5, 3', 4'-trihydroxy-6methoxyflavone 7-glucoside as discussed by the authors.
Abstract: A flavonoid, isolated from the leaves of sesame (Sesamum indicum L. ), was determined as 5, 3', 4'-trihydroxy-6-methoxyflavone 7-glucoside.
TL;DR: Chlorination reactions of 1, 3, 4, 6-tetra-O-acetyl-N-acyl-β-D-glucosamines at C-1 position were studied and it was found that these reactions suffered remarkable electronic effect of N-acyls groups.
Abstract: Chlorination reactions of 1, 3, 4, 6-tetra-O-acetyl-N-acyl-β-D-glucosamines at C-1 position were studied and it was found that these reactions suffered remarkable electronic effect of N-acyl groups The mechanism of these reactions is discussed
TL;DR: In this paper, the spectral properties of a number of indole compounds have been examined and the characteristic frequencies of the indole group are given, and the CH out-of-plane bending vibration of the pyrrole moiety of the Indole ring and related methylpyrroles are discussed.
Abstract: Infrared Spectra of a number of indole compounds have been examined and the characteristic frequencies of indole group are given. The CH out-of plane bending vibration of the pyrrole moiety of the indole ring and related methylpyrroles are discussed.
TL;DR: In this paper, it was shown that 1-alkyl-1, 2, 3, 4-tetrahydroisoquinoline derivatives are dehydrogenated with the same reagent to afford 3-4-dihydro compounds, but the corresponding 2-acyl compounds resisted similar dehydrogenation.
Abstract: Mercuric acetate dehydrogenation of (-)-2'-acylemetines, which have the same configuration as (-)-emetine, was found to afford 5, 11b-dehydro-2'-acylemetines. In preliminary experiments, it was shown that 1-alkyl-1, 2, 3, 4-tetrahydroisoquinoline derivatives are dehydrogenated with the same reagent to afford 3, 4-dihydro compounds, but the corresponding 2-acyl compounds resisted similar dehydrogenation. These results seem to strongly support Openshaw's view about the structure of tetradehydroemetine.