Chemical and Pharmaceutical Bulletin

Alkylsulfonyltoluene Derivatives (Diuretics. I.)

Hiroshi Kugita, Mikio Takeda, Toyonari Oine, Ko Higaki

1962 Volume 10 Issue 11 Pages 1001-1008
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1001

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Alkylsulfonyltoluenesulfonamides and their derivatives bearing a chlorine and an amino group on the benzene rings, or a variety of substituents on the nitrogen atom were synthesized. All compounds were evaluated for diuretic activity.

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Alkylsulfonyltoluene Derivatives (Diuretics. II.)

Hiroshi Kugita, Mikio Takeda, Toyonari Oine, Ko Higaki

1962 Volume 10 Issue 11 Pages 1008-1012
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1008

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The alkyl groups with a tertiary amino group at the β-carbon atom or an imino group at the α-carbon atom were introduced into the sulfamoyl or N-substituted sulfamoyl group of 4-methylsulfonyl-o-toluenesulfonamides to investigate possible alteration of the biological activity of the parent sulfonamides.

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Studies on Oxytetracycline and Related Compounds. XVII. Synthesis of 1, 3, 11-Trimethoxynaphthacenequinone

Zen-ichi Horii, Takefumi Momose, Masaori Naruse, Yasumitsu Tamura

1962 Volume 10 Issue 11 Pages 1013-1017
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1013

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1, 3, 11-Trimethoxynaphthacenequinone (V) and 1, 3-dimethoxyanthraquinone (XIII) were prepared as shown in Charts 1 and 2. Reduction with sodium hydrogensulfite in alkaline medium converted the quinones, (V), (XIII) and 6-methoxynaphthacenequinone (XV), to 1, 3, 11-trimethoxy-5 (12H)-naphthacenone (VI), 2, 4-dimethoxyanthrone (Xff) and 11-methoxy-5 (12H)-naphthacenone (XVI), respectively.

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Studies on Decomposition and Stabilization of Drugs in Solution. XI. Overall Velocity Constants for Succinylmonocholine Chloride Hydrolysis as a Function of pH.

Tokuji Suzuki

1962 Volume 10 Issue 11 Pages 1017-1023
Published: November 25, 1962
Released on J-STAGE: May 27, 2011

DOIhttps://doi.org/10.1248/cpb.10.1017

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1) The degradative reaction of succinylmonocholine chloride, the first hydrolytic product of succinylcholine chloride, was investigated over the whole pH range of 0.5 to 8.5 from the standpoint of chemical kinetics. The degradation is an apparent monomolecular reaction at a fixed pH value.
2) The decomposition may be accounted for by the six rate constants of bimolecular reaction and the dissociation constant of succinylmonocholine chloride. The rate (hr.^-1) of reaction at 60° can be practically represented by
_??_
The relatively slight variation in k caused by buffer effect as compared with succinylcholine chloride was recognized.
3) The hydrolysis of succinylcholine chloride in aqueous solution at a fixed pH value was fitted to a kinetic expression for a consecutive reaction with two first-order reactions. A good agreement was obtained between calculated and experimental values.

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Syntheses of Bromoazulene Derivatives

Shingo Matsumura

1962 Volume 10 Issue 11 Pages 1024-1028
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1024

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5-Bromo- and 6-bromoazulene derivatives were synthesized by the application of a new synthetic method to azulene derivatives.

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Bromination of Pyrimidines by N-Bromosuccinimide. III. Bromination of Anilino-and Phenoxypyrimidines

Tarozaemon Nishiwake

1962 Volume 10 Issue 11 Pages 1029-1032
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1029

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2-Aminopyrimidines were brominated at their C₅-positions predominantly with NBS in carbon tetrachloride in spite of the presence of an anilino-, haloanilino-, or phenoxygroup at their C₆-positions as substituents.

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Syntheses of Nuclear-substituted Flavonoids and Allied Compounds. IX. Syntheses of Tetramethyl Ether and Dimethyl Ether of Ginkgetin

Koichi Nakazawa

1962 Volume 10 Issue 11 Pages 1032-1038
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1032

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2-Acetyl-3, 5-dimethoxyphenyl 3-iodoanisate (X) and its 6-iodo isomer (XT) were 1 espectively isomerized to diketones (XII, XIII) by means of potassium hydroxide in pyridine, and then cyclized to flavone compounds (XIV, XV), which were finally condensed each other to biflavonyl (XVI) by refluxing in dimethylformamide for 4 hours in the presence of activated natural copper powder. The yield of crude product was 28%. Biflavonyl (XVI) was demethylated to (XVII), when it was treated with aluminum chloride in nitrobenzene at 110°for 1 hour (XVI) and (XVII) were identified respectively with tetramethyl ether and dimethyl ether of ginkgetin in C, H-analyses, mixed melting points and infrared absorption spectra.

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Synthesis of Anomers of 6-O-Tosyl-1, 3, 4-tri-O-acetyl-N-acetyl-D-glucosamine and 1, 6-Anhydro-N-acetyl-β-D-glucosamine

Masuo Akagi, Setsuzo Tejima, Masanobu Haga

1962 Volume 10 Issue 11 Pages 1039-1042
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1039

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Anomeric 6-O-tosyl-1, 3, 4-tri-O-acetyl-N-acetyl-D-glucosamines and 6-deoxy-6-iodocompounds were prepared from N-benzylidene-D-glucosamine. By alkali treatment of the β-anomer of the 6-tosylate, 1, 6-anhydro-N-acetyl-β-D-glucosamine was synthesized, but no anhydride of the α-anomer was obtained.

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On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. II. Reaction of 4-Quinazolinecarbonitrile with Grignard Reagents

Takeo Higashino

1962 Volume 10 Issue 11 Pages 1043-1047
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1043

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Grignard reagents reacted as anionoid with 4-quinazolinecarbonitrile (I).
Reaction of (I) with methylmagnesium iodide, ethylmagnesium bromide, isopropylmagnesium bromide, phenylmagnesium bromide, and benzylmagnesium chloride afforded 4-methyl-(II), 4-ethyl-(III), 4-isopropyl-(IV), 4-phenyl-(V), and 4-benzylquinazoline-(VI), respectively.
The mechanism for these reactions may be suggested as in Chart 2.
Reactions of 4-chloroquinazoline (VII) with Grignard reagents were carried out in order to compare them with those of (I) using the same reagents.
(VII), with isopropylmagnesium bromide, afforded (W) and 4, 4'-biquinazoline (VIII), with phenylmagnesium bromide, (VIII), and with benzylmagnesium chloride, (VI).
The foregoing results showed that the 4-position in (I) was very reactive to anionoid reagents, and some differences in chemical properties existed between (VIII) and (I).

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On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. III. Reaction of 4-Quinazolinecarbonitrile with Ketones

Takeo Higashino

1962 Volume 10 Issue 11 Pages 1048-1052
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1048

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Reactions of 4-quinazolinecarbonitrile (I) with ketones in the presence of 50% sodium hydroxide were carried out in order to elucidate the chemical properties of (I). With acetone afforded 1-(4-quinazolinyl)-2-propanone (II), with 2-butanone, 1-(4-quinazolinyl)-2-butanone (III) and 4-ethylquinazoline (IV), with 3-pentanone (IV), with 3-methyl-2-butanone, 1-(4-quinazolinyl)-3-methyl-2-butanone (V) and 4-isopropylquinazoline (VI), with acetophenone, 2-(4-quinazolinyl) acetophenone (VII), with propiophenone, (IV) and benzoic acid (VIII), w ith cyclohexanone, 4-quinazolinehexanoic acid (IX), and with cyclopentanone, 2-(4-quinazolinyl) cyclopentanone (X). The foregoing experiments showed that the 4-position in (I) was very reactive to anionoid reagents, as already demonstrated in Part I and II of this series.

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On the Reaction of 4-Quinazolinecabonitrile with Nucleophilic Reagents. IV. Reaction of 4-Quinazolinecarbonitrile with Active Methylene Compounds

Takeo Higashino

1962 Volume 10 Issue 11 Pages 1052-1055
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1052

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The reactions of 4-quinazolinecarbonitrile (I) with active methylene compounds were carried out in order to elucidate the chemical properties of (I). In the presence of sodium amide, reactions of (I) with ethyl acetoacetate, diethyl malonate, or ethyl cyanoacetate give ethyl 4-quinazolineacetate (II), and ethyl α-cyano-4-quinazolineacetate (III), respectively. In the presence of potassium carbonate, reactions of (I) with nitromethane, or nitroethane give 4-nitromethylquinazoline (IV), and 4-(1-nitroethyl) quinazoline (V), respectively. The foregoing results showed that the 4-position of (I) was very reactive to anionoid reagents, as was already demonstrated in Parts I, II, and III of this series.

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Studies on Absorption and Excretion of Drugs. II. Kinetics of Penetration of Basic Drug, Aminopyrine, through the Intestinal Barrier in vitro

Hisashi Nogami, Tai Matsuzawa

1962 Volume 10 Issue 11 Pages 1055-1060
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1055

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1) The intestinal absorption of aminopyrine as a representative of the basic drugs was investigated to prove the validity of equation (1) described previously. 2) From the three evidences, that is, a good fit of the data at pH 7.01 to equation (3), the statistical treatment of all the data, and the experiment at equilibrium state, it is concluded that aminopyrine penetrates the intestinal barrier with each specific coefficient, Pu and Pi, according to equation (1). 3) Respective values of the coefficients were statistically determined and the estimated value of Pu was 0.00266 (cc./cm./min.) and that of Pi 0.000242 (cc./cm./min.). From the ratio of Pu/Pi, it may be expected that aminopyrine is absorbed in its undissociated form according to Overton's hypothesis. 4) A fact that aminopyrine slowly penetrates the intestine is consistent with the result reported by Hogben, et al.

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Studies on the Synthetic Analgesics. XVII. Syntheses of 2-(N-tert-Aminoalkylacylamino) thiophene

Norio Sugimoto, Kentaro Okumura, Noboru Shigematsu, Goro Hayashi

1962 Volume 10 Issue 11 Pages 1061-1064
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1061

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Acyl-derivatives of thienylaminoethyl (or propyl) amines have been synthesized. Some of the compounds tested for analgesic activity showed the almost equal as morphine.

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Studies on Central Depressants. VI. Enzymic Studies on Brain Transamidinase and One Possible Metabolic Pathway of 4-Aminoand 3-Hydroxy-4-aminobutyric Acid

Tomitaro Kita, Hiro-o Kamiya

1962 Volume 10 Issue 11 Pages 1065-1070
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1065

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Following Walker's extracting method of kidney transamidinase, brain transamidi-nase the whole brain of the rabbit. Then enzymic reaction was carried out, and reaction mixture was investigated with paper chromatography as a sole experimental technique, and it was found out that the following reaction might be possible. 1. 4-guanidinobutyric acid+glycine→4-aminobutyric acid+guanidinoacetate 2. 3-hydroxy-4-guanidinabutyrie aeid+glycine→3-hydroxy-4-aminobutyric acid+guaninoacetate 3. arginine+glycine→ornithine+guanidinoacetate

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Studies on Pyrone Derivatives. VII. On the Syntheses of Dehydroacetic Acid Analogue having Aroyl Group in its Side Chain

Sadao Iguchi, Atsuko Inoue

1962 Volume 10 Issue 11 Pages 1070-1075
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1070

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1) Dehydroaroyla cetic acids were directly obtained by Friedel-Crafts reaction of triacetic acid lactone (TAL) and aroyl chloride in the presence of an excess of aluminum chloride. They were also derived from the corresponding 4-benzoates of TAL by Fries rearrangement using the excessive aluminum chloride.
2) The monobenzoate of TAL synthesized by the usual method as also reported in the previous reports was definitely shown to be the 4-benzoate rather than the 2-benzoate.
3) None of these new compounds was superior to DHA in the activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli B and Aspergillus niger in vitro.

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Studies on Coenzyme Analogs. XIII. Oxidation of Methylmercaptopurine and its Nucleoside by means of N-Chloro- and N-bromosuccinimide

Morio Ikehara, Akihiro Yamazaki, Toshiko Fujieda

1962 Volume 10 Issue 11 Pages 1075-1080
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1075

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The methylmercapto group situated on the 2- or 6-position of purine and purine nucleoside was readily oxidized to methylsulfonyl group by treatment with N-chlorosuccinimide. In this reaction unprotected nucleoside occasionally caused the cleavage of nucleoside linkage. N-Bromosuccinimide could also be used for replacement of methylmercapto to amino or hydroxy group by successive treatment of the intermediate with water or ammonia.

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Studies on Sulfonylurea Derivatives. III. The Infrared Spectra of 1-p-Tolylthio-3-alkylureas and Corresponding Sulfonyl Compounds

Yoshihiro Nitta, Noriaki Ando

1962 Volume 10 Issue 11 Pages 1081-1084
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1081

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The infrared absorption spectra of eleven 1-p-tolylthio-3-alkylureas and the corresponding sulfonyl compounds were recorded. Comparison of the thio and sulfonyl derivatives is made with respect to the influence exerted by the S or SO₂ group on their respective frequencies due to phenyl and ureido groups. The variations of the absorption positions depend on the electronic nature of each groups. The nature of the alkyl group has relatively little effect on the position of these bands.

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Biogenetic Studies of Natural Products. VIII. Biosynthesis of Anethole byFoeniculum vulgare.(4)

Ko Kaneko

1962 Volume 10 Issue 11 Pages 1085-1087
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1085

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The anethole biosynthesis, using the cell-free enzyme system of Foeniculum plant was established as follows: 4-Hydroxycinnamic acid 4-methoxycinnamic acid 4-methoxycinnamyl alcohol anethole.

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Studies on Acetylenic Compounds. XXV.Ring Closure.(5). New Synthetic Method of Heterocyclic Compounds from α-Amino-and α-N-substitued Aminoacetylenic Compounds

Yasuo Yura

1962 Volume 10 Issue 11 Pages 1087-1093
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1087

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Anew ring closure of α-amino-and α-N-substituted aminoacetylenic compounds has been studied. 2-Methylimidazole and 2-thiazolethiol derivatives were easily synthesized by heating α-aminoacethylenic compound with thioacetamide and carbon disulfide, respectively. By treating 1-(2-propynyl)-urea, 1-(2-propynyl)-thiourea and 1-(2-propynyl)-benzamide with concentrated sulfuric acid, there were obtained 2-imidazolone, 2-imidazolethiole and 2-phenyloxazole derivatives, respectively.

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Studies on Acetylenic Compounds. XXVI. Ring Closure.(6). New Synthetic Method of Heterocyclic Compounds from α-Substituted Acetylenic Compounds

Yasuo Yura

1962 Volume 10 Issue 11 Pages 1094-1098
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1094

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Treatment of α-thiocyanatoacetylenic campaunds with concentrated sulfuric acid gave 2-thiazolol derivatives. 2-Phenyloxazole was also obtained in good yield by cyclization of 2-propynyl benziminoether by a similar procedure.

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Physicochemical Factors Influencing the Absorption of Erythromycin and its Esters

Eino Nelson

1962 Volume 10 Issue 11 Pages 1099-1101
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1099

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It has been reported that within a series of esters of erythromycin prepared with low molecular weight aliphatic acids, the propionyl ester gave considerably higher blood levels after oral administration than others in the series as well as higher levels than erythromycin itself. On the basis of findings from past work dealing with dissolution rates of drugs, it seemed reasonable to believe that their absorption under eqivalent conditions of administration was related to their dissolution rate in both gastric fluid and intestinal fluids, particularly since erythromycin and its esters are rapidly destroyed in solution in acidic mediums. The work to be described now consisted of making dissolution rate determinations on erythromycin and some of its esters in fluids simulating gastric and intestinal fluids with respect to hydrogen ion concentration and on examining the relationship between these rates and the results of the clinical work.

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Studies on the Pyrimidine Derivatives. XX. On the Studies of S-Alkoxycarbonylthiamine.(1)

Akira Takamizawa, Kentaro Hirai

1962 Volume 10 Issue 11 Pages 1102-1106
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1102

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Various kinds of S-alkoxycarbonylthiamine and O, S-bis (ethoxycarbonyl) thiamine were prepared. They showed a thiamine-like activity and were readily absorbed from the intestine. Some of them are excellent in regard to the increase and duration of thiamine blood levels when orally administered.

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Studies on the Pyrimidine Derivatives. XXI. On the Studies of S-Alkoxycarbonylthiamine.(2)

Akira Takamizawa, Kentaro Hirai, Yoshio Hamashima

1962 Volume 10 Issue 11 Pages 1107-1112
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1107

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HCl decomposition of S-ethoxycarbonylthiamine (I) gave 2-methy1-4-amino-5-aminomethylpyrimidine (II), formic acid and 3-ethoxycarbonylthio-5-hydroxy-2-pentanone (III). 3-Ethoxycarbonylthio-5-acetoxy-2-pentanone (VIII) was prepared. A part of it Was decomposed into O-ethoxycarbonylthiamine (IV) and thiamine (V). Also O, S-bis (ethoxycarbonyl) thiamine (IX) decomposed into (II), formic acid and 3-ethoxycarbonylthio-5-ethoxycarbonyl-2-pentanone (X) by heating with HCl. A part was also decomposed into (IV) and (V).(X) was characterized by synthesis. Further, ethylthiocarbonylthiamine (XIV) was prepared, and O-alkoxycarbonylthiamine was obtained by rearrangement of S-alkoxycarbonylthiamine. By the use of this rearrangement, various kinds of O, S-bis (alkoxycarbonyl) thiamine were prepared. All of these thiamine derivatives showed excellent thiamine activity in absorption from intestine and in thiamine blood level.

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Organic Phosphates. XIX. A Novel Phosphorylation of Nucleosides and Related Compounds with Hydrobenzoin Cyclic Phosphate activated by Diphenyl Phosphorochloridate

Tyunosin Ukita, Nobumasa Imura, Kinzo Nagasawa, Norio Aimi

1962 Volume 10 Issue 11 Pages 1113-1118
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1113

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Hydrobenzoin cyclic phosphate, diphenyl phosphorochloridate, and tributylamine were reacted with several hydroxylic compounds (ROH) at 37°for 24-50 hours and the resulting phosphotriesters of type_??_were hydrolyzed to phosphodiesters (esters of 1, 2-diphenyl-2-hydroxyethyl phosphate) which were catalytically hydrogenated to liberate hydrobenzoin moiety and gave the phosphoryl esters of the hydroxylic compounds used.
The reaction was applied to butanol, methyl ribofuranoside to detect the corresponding phosphates. And the method was used for the preparative phosphorylation of methyl 2, 3-O-isopropylideneribofuranoside, 2', 3'-O-isopropylideneuridine and 5'-O-trityluridine.

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Biogenetic Studies on Natural Products. VII. Biosynthesis of Isoflavone in Red Clover

Hiroshi Mitsuhashi, Ko Kaneko, Marekichi Sasaki

1962 Volume 10 Issue 11 Pages 1119-1122
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1119

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It was shown that DL-phenylalanine [2-¹⁴C] was incorporated into C-3 of two kinds of isoflavone, formononetin and genistein, by Trifolium pratense sp., in vivo.
These results indicate that the aryl group undergoes a migration within the C₆-C-C-C fragment, and this observation agrees with Grisebach's experimental data.

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Synthesis of Cinnoline N-Oxides

Masaru Ogata, Hideo Kano, Kazuo Tori

1962 Volume 10 Issue 11 Pages 1123-1125
Published: November 25, 1962
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.10.1123

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The Formation of 6, 19-Epoxy-3, 5-cyclo-steroid

Katsumi Tanabe, Rinji Takasaki, Kiyoshi Sakai, Ryozo Hayashi, Yasuhiro ...

1962 Volume 10 Issue 11 Pages 1126-1127
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1126

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Mutagenic Activity of 4-Hydroxyaminoquinoline 1-Oxide

Tadashi Okabayashi

1962 Volume 10 Issue 11 Pages 1127-1128
Published: November 25, 1962
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.10.1127

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