1) α-Dichloroacetamido (or acetamido)-β-hydroxy-p-nitropropiophenone is esterified by acetic anhydride and conc. sulfuric acid to form α-dichloroacetamido (or acetamido)-β-acetoxy-p-nitropropiophenone, but the reaction, if carried out in acetic anhydride and pyridine, results in dehydration to yield α-dichloroacetamido (or acetamido)-α-methylene-p-nitroacetophenone. 2) The Meerwein-Pondorf reduction of α-dichloroacetamido-α-methylene- and α-acetamido-α-methylene-p-nitroacetophenone results in dehydration and migration of the double bond to yield 2-dichloromethyl-4-methyl- and 2, 4-dimethyl-5-p-nitrophenyloxazole, respectively. 3) Seven kinds of compounds tested were found to inhibit the growth of Escherichia coli.
1) Corresponding amnovinyl compounds were obtained by the respective condensation of diphenylformamidines with 2-picoline methiodide, 2, 6-lutidine methiod de and 6-dimethylaminoquinaldine methiodide. 2) Quarternary salts containing styryl or furylvinyl group were synthesized by the application of aromatic aldehydes, furfural and 5-nitrofurfural on 2-picoline methiodide or ethiodide, 2, 6-lutidine methiodide, 6-diethylaminoquinaldine methiodide or allobromide, and 2′-methyl-6-methoxypyrido-2, 3:5′, 4′-thiazole methiodide in boiling ethanol with piperidine as a condensing agent. Some of these compounds were fpund to possess remarkable antibacterial action against staphylococci.
Condensation of 6-dimethylaminoquinaldine methiodide (or ethiodide, butiodide, or allobromide) with aromatic aldehydes, furfural or 5-nitrofurfural, in boiling ethanol in the presence of piperidine yields quarternary salts containing styryl or furylvinyl groups. The compounds were found to have strong antibacterial action against staphylococci.
A mixture of fatty acids (100g.) was obtained from the fruits (1150g.) of Anthriscus sylvestris Hoffm., this mixture being separated into 70g. of solid acids and 18g. of liquid acids. The majority of the solid fatty acids was found to be petroselic acid (I), m. p. 32-33°, the remainder being a small amount of petroselidic acid (II), m. p. 53°. The liquid fatty acids, on oxidation by Hazura's method, yielded a small amount of 6, 7-dihydroxystearic acid, m. p. 122°, and a comparatively large amount of 9, 10, 12, 13-tetrahydroxystearic acid (α-sativlc acid), m. p. 162°, which showed that the majority of the liquid acid is linoleic acid. It is doubtful, however, if petroselidic acid had been contained, per se, in the fruit or whether a portion of petroselic acid had undergone elaidination. This must be confirmed by actual experimentation.
A mixture of fatty acids (140g.) was obtained from the fruits (840g.) of Oenanthe stolonifera DC. This mixture was converted to the methyl ester and fractionally distilled into three distillates from which solid and liquid acids were isolated. Most of the solid acid (75%) is composed of petroselic acid, m. p. 32-33°, C18H34O2 (_??_=1), with a small amount of palmitic acid. By oxidation with Hazura's method liquid acid (25%) yielded a small amount of 9, 10-dihydroxystearic acid, m. p. 127°, and a comparatively large amount of 9, 10, 12, 13-tetrahydroxystearic acid (α-sativic acid), m. p. 162°, which shows that the majority of liquid acid was composed of linoleic acid, containing a small amount of oleic acid.
A mixture of fatty acids (154g.) was obtained from the fruits (1227g.) of Conium maculatum L. These acids were converted to methyl esters and fractionally distilled into Fraction A, b.p.1 130-148°, and Fraction B, b.p.1 149-152°. Each fraction was divided into solid (67%) and liquid (33%) acids. Fraction A yielded, as a solid acid, petroselic acid, m.p. 32-35°. Fraction B yielded, as a solid, an acid of m.p. 30-31°, corresponding to formula C18H34O2 (_??_=1), elaidination of which gave petroselidic acid, m.p. 53°. From the melting point, the primary acid is assumed to be a mixture, chiefly of petroselic acid containing a small amount of petroselidic acid. The liquid acid yielded, by the Hazura oxidation, 9, 10-dihydroxystearic acid in a small amount, and a comparatively large amount of α-sativic acid. These results show that the said fruit oil contains as fatty acids, a large amount of petroselic acid, with a small amount of oleic and linoleic acids, and a very minute amount of petroselidic acid.
Antibacterial action of several derivatives of diphenyl ethers, diphenylene dioxides, phenoxthine, diphenyl sulfides, and diphenyl disulfides were tested against the human strain of Mycobacterium tuberculosis, Staphylococcus aureus and Escherichia coli. Of the compounds tested, 2, 6-di-(α-bromopropionyl)-diphenylene dioxide, 3-hydroxy-4, 6-dibromodiphenyl ether benzoate, 3-hydroxy-4, 6-dibromodiphenyl ether, 1-(4′-phenoxybenzyl)-6, 7-methylenedioxy-1, 2, 3, 4-tetrahydroisoquinoline, and 4, 4′-diaminodiphenyl disulfide, were found to posses a strong antibacterial action against Staph. aureus. Comparatively high antibacterial action against Mycobact. tuberc. was shown by α, β-dinaphthyl and β, β′-dinaphthyl ethers.
By methylation of (2, 3-cis- and -trans-dihydroxycyclohexyl) -acetic acid lactone (V and VI) with methyl iodide in the presence of silver oxide yielded (cis- and trans-2-hydroxy-3-methoxycyclohexyl)-acetic acid lactone (VII and VIII), a liquid substance which failed to give the coloration shown by natural castelamarin, making it doubtful the Bosman's theory that castelamarin is a (2-hydroxy-3-methoxycyclohexyl)-acetic acid lactone. The application of methyl iodide and silver oxide to (2, 3-cis-and-trans-dihydroxycyclohexyl)-malonic acid lactone (XI and XII) results in the methylation of the hydrogen at C7 instead of the hydroxyl at C3. An isomeric racemate of (cis- and -trans-2-hydroxy-3-methoxycyclohexyl)-methylmalonic acid lactone (XVII and XVIII) due to the asymmetric carbon at C11 is present.
2-Benzylamino-4-methyl-6-hydroxypyrimidines were obtained by heating around 200° a mixture of 2-mercapto-4-methyl-6-hydroxypyrimidine and benzylamines. Heating of 2-mercaptopyrimidine and benzylamine results in the formation of a small amount of 2-benzylaminopyrimidine, besides N, N′-dibenzylthiourea. In the same manner, a small amount of 2-benzylamino-4-methylpyrimidines were obtained with N, N′-dibenzylthioureas from 2-mercapto-4-methylpyrimidine and benzylamines. Reaction of 2-methyl-mercapto-4, 6-dihydroxypyrimidine and benzylamine failed to yield 2-benzylamino-4, 6-dihydroxypyrimidine and resulted in the formation of benzylguanidine and malonic dibenzylamide.
3-(β-Diethylaminoethyl)-octahydroquinolizine was prepared by the following method: Condensation of sodium malonate with 2-(β-chloroethyl)- or 2-vinyl-pyridine gives diethyl β-(2-pyridyl)-ethylmalonate, which is reduced to diethyl β-(2-piperidyl)-ethylmalonate, and cyclized with dealcoholation to 3-carbethoxy-4-keto-octahydroquinolizine. Its sodium salt and β-diethylaniinoethyl chloride yield 3-(β-diethylaminoethyl)-3-carbethoxy-4-keto-octahydroquinolizine whose saponification with hydrochloric acid, followed by decarboxylation to the amino acid compound, its esterification, and cyclization with dealcoholation, give 3- (β-diethylaminoethyl)-4-keto-octahydroquinolizine. The Tafel electrolytic reduction of this lactam finally yields the objective compound.
A new compound obtained by the application of carbon disulfide on 2-methyl-4-amino-5-aminomethylpyrimidine (I), (2-methyl-4-aminopyrimidyl-5)-methylammonium (2′-methyl-4′-aminopyrimidyl-5′)-methyldithiocarbamate (VI) and γ-aceto-γ-chloropropyl alcohol (II) or its O-acetate (III), results in the formation of α-aceto-γ-hydroxy (or acetoxy)-propyl (2-methyl-4-aminopyrimidyl-5)-methyldithiocarbamate (IV or V). Treatment of these compounds with dehydrating agents such as NaHSO4, AlCl3 or ZnCl2, results in dehydration-cyclization to 3-(2′-methyl-4′-aminopyrimidyl-5′)-methyl-4-methyl-5-β-hydroxy (or acetoxy)-ethyl-thiothiazolone (2) (VIII or IX).
1-P-(2′, 4′-Dichlorophenoxy)-phenyl-2-acetamido-1, 3-propanediol, m. p. 175-176°, a compound in which 2, 4-dichlorophenoxyl group has been substituted for the nitro group in chloramphenicol, was prepared.
In continuation of the work described in the previous report [This Journal: 72, 69 (1952)], components of four kinds of Sect. Ornus was studied with the following results: Species Location Component Fraxinus borealis Nakai Akita Pref. (northeastern) Aesculin, fraxin, mannitol F. longicuspis S. et Z. Miye Pref. (west central) Aesculin, mannitol Saitama Pref. (eastern) Aesculetin, fraxetin F. sabucina var. pubineavis Nakai Saitama Pref. (eastern) Aesculetin Ishikawa Pref. (northwestern) Aesculetin, fraxin F. sambucina var. velutina Nakai Ishikawa Pref. (northwestern) Aesculetin This result shows that aesculin or aesculetin was obtained without exception from 12 kinds of domestic Sect. Ornus plants, whereas fraxin is present in the majority of these plants growing wild in Europe. The aqueous extract of these barks show strong fluorescence. Fraxin is present in Aesculus turbinata L. growing wild in Japan (loc. cit.). This shows that the domestic plants contain aesculin in Fraxinus species and fraxin in Aesculus species, which is reverse the case in Europe.
In continuation of the previous work [This Journal, 72, 67, 69 (1952)], components of Fraxinus commemoralis Koidz., was studied and syringin and mannitol were. obtained from the plants growing in Yamaguchi Pref., and syringin from those growing in Gumma Pref. This plant belongs to Sect. Fraxinaster, and aqueous extract of the bark fails to show any fluorescence. Whereas the plants of Sect. Ornus invariably yielded aesculin and aesculetin [This Journal: 58, 636 (1938); 60, 508 (1940); et seq.], and the aqueous solution of their bark showed strong fluorescence, those of Sect. Fraxinaster fails to give fluorescence. It may be assumed, from these results, that the presence of fluorescence in the aqueous solution of its bark classifies the plant as belonging to Sect Ornus, and its absence, as belonging to Sect. Fraxinaster.
Twenty-two kinds of 2-styrylbenzothiazoles were prepared by the condensation of aromatic aldehydes with 6-chloro and 4, 6-dichloro-benzothiazoles, using anhydrous zinc chloride or cone-hydrochloric acid as a condensing agent.
A new water-soluble glycoside was isolated in crystallin form from Rhodea jaionica Roth. besides rhodexin A and B described previously [This Journal: 72, 404 (1952)]. This glycoside, designated rhodexin C, corresponds to formula C35H54O14, m.p. 275° (decomp.), [α]D18: -17.7° (70% EtOH). Hydrolysis with 50% alcohol containing 3.3% hydrochloric acid gives dianhydrogitoxigenin. The partition paper chromatography of the sugar thereby obtained showed the presence of rhamnose and glucose. It is assumed, therefore, that rhodexin C is formed by further bonding of 1 mole of glucose to rhodexin B.
The part which comes into the question in automatic combustion in elemental analyses of carbon and hydrogen is the motor action of movable heater. After examining various constructions, a special cam (shown in Fig. 1) was found to give the most simple and steadfast action. An automatic apparatus using such cam was found to give good results.
By the fundamental experiments carried out with electric heating apparatus in micro-Dumas method, following observations were made. (1) The reversible reaction 2CO2⇔2CO+O2 can be made to proceed completely to the left by passing the conbustion air through a fixed burner of oxidized copper layer (over 4cm.) hea ted to 450-600°, at a rate of 10 bubbles per second. (2) Heating the movable electric burner to 850° results, in the presence of oxidized copper, in rapid dissociation of CO2 to CO and O2, and the nitrogen in nitrogenous compounds is quantitatively reduced or oxidized to N2, thereby making it possible to carry out the analysis without the use of reduced copper. However, compounds containing halogen must give definite analytical values only after the use of reduced copper. (3) As long as the temperature of the fixed burner is kept at that point mentioned above, the position of the reduced copper layer may be in the center of the fixed burner or the end of the tube. From experimental results, calculation of corrected value for N2 may be made from the following: Corrected value of N2=(Found value of N2)-(1% of Found value of N2)-0.01cc.
In accordance with the results of fundamental experiments carried out (cf. previous report), an improvement was made on the micro-Dumas method and a method was devised which was very simple of operation. As a fundamental method of analysiss for automatic apparatus, this new method is thought to possess a high adaptability.
Mold preventing action of following 23 compounds against soy sauce were tested: 12 kinds of benzoquinone compounds including p-benzoquinone, p-benzoquinone monoaminoguanylhydrazone nitrate, p-benzoquinone diaminoguanylhydrazone nitrate, p-toluquinone, p-toluquinone monoaminoguanylhydrazone nitrate, p-toluquinone diaminoguanylhydrazone nitrate, α-naphthoquinone, α-naphthoquinone monoaminoguanylhydrazone nitrate, α-naphthoquinone diaminoguanylhydrazone nitrate, thymoquinone, thymoquinone diaminoguan-ylhydrazone nitrate and 2-methyl-5-methoxybenzoquinone; 6 kinds of anthraquinone derivatives including chrysophanol purpurin, anthrachrysone, rufigallic acid, emodicacid and endocrocin; 4 kinds of organic reagents including α-benzildioxime, salicylaldoxime, o-hydroxyquinoline and ammonium nitrosophenylhydroxylamine; and phenan-threnequinone. α-Naphthoquinone and o-hydroxyquinoline showed about the same degree of activity as that of propyl p-hydroxybenzoate used as the control. Especially strong activity was shown by phenanthrenequinone which succeeded in preventing the growth of molds for 42.5 days at 0.001% concentration, for 51.5 days at 0.003%, and for 77 days at 0.005%. Since the control prevented growth of molds for 77 days at 0.01% concentration, the activity of phenanthrenequinone must be classed as very strong. Other compounds were found to be all ineffectual.
Four homologs of p-aminophenyl ω-alcoxyethyl ethers were prepared and their antibacterial activity tested in vitro. These compounds were found to possess considerable activity against Mycobacterium tuberculosis, irrespective of the length of their alkyl chain, and to have far smaller toxicity than that of corresponding p-aminophenyl alkyl ethers.
1) The potentiometric neutralization of diarylarsinic and diarylarsinous acids can effectively be carried out with antimony electrodes. 2) The potentiometric redox titration of diarylarsinous acid was successfully carried out with antimony electrodes. These two methods play an important part in the determination of the arsenic contents of organic arsenical compounds.
The arsenic contents of organic compounds can be determined readily and accurately on semi-micro scale by digesting the compound with hot sulfuric acid and potassium sulfate, in the presence of starch, diluting the solution thus obtained and titrating with standard solution of potassium bromate.
A general method of synthesizing diarylarsinic acid with the use of aryldichloroarsine was made out by enlarging Scheller's method. By this method, many diarylarsinic acids were readily and purely obtained, eight of which are new substances.
By the employment of the present method, an acid for the saccharification of polysaccharides could be chosen without any consideration for the solubility of its salt. Peanut shells, which give a by-product of furfural with the formation of usual monosaccharide, was chosen as the polysaccharide material, and hydrolytic capacity of HCl, HClO4, H2SO4, HNO3 and H2C2O4 was compared, as well as electrolytic deacidification of their saccharifying solutions was attempted. As a result, it was found that acids such as HCl, HClO4, and HNO3, for which no neutralization agents could be found in industrial application, could be used both for saccharification and electrolytic neutralization. However, HNO3 and H2C2O4 undergo electrolytic reduction during electrolytic neutralization that disappearance of specific acid residue becomes rapid. This was the first instance of HClO4 being used for saccharification but it was found to have no oxidative or reductive action, saccharifying power being as excellent as HCl, and can be completely deacidified by electrolysis, similar to H2SO4, and quantitatively recovered. In this way, HClO4 has been discovered as an acid for saccharification by this method, although unusable by the existing method.
Experiments were carried out to confirm the theory that some heavy metal ions promote saccharification. Saccharification of peanut shells with 0.8 N HClO4 solution was carried out with the addition of one of Fe+++, Al+++, Cu++, Pb++ and Hg++, and the formation of monosaccharide and furfural was observed. Elimination of heavy metal ions from saccharifying solutions by electrolysis was also examined. It was found, from these experimental results, that the presence of heavy metal ions during saccharification had neither favorable nor adverse effect, although it was also found that these metallic ions were all quantitatively removed by electrolytic deacidification of acid saccharifying solutions.
o-Aminophenol alkyl ethers, possessing odd-numbered straight carbon chain as the alkyl group, were synthesized and their antibacterial action against human type Mycobacterium tuberculosis was examined with their hydrochlorides on Kirchner medium. The compounds synthesized were propyl, amyl, heptyl, nonyl, undecyl and tridecyl ethers. The effect of these alkyls against bacteriostasis was found to be the same as that obtained with even-numbered alkyl chains and no difference in bacteriostatic specificity was found to exist between odd-and even-numberedchains.
Mono- and dialkyl ethers of pyrocatechol were synthesized. Antibacterial action of the monoethers against avian type tubercle bacilli were examined, in vitro, in Kirchner medium and by the S. C. C. method. The compounds synthesized were mono- and dimethyl, ethyl, butyl, hexyl, octyl, decyl, dodecyl, tetradecyl, and hexadecyl ethers. Antitubercular action of monoethers were found to be very small, the effect of the size of the alkyl group against tuberculostasis being very indistinct.
The reaction mechanism whereby thiochrome (II) is formed by the application of cyanobromide to 3-(2′-methyl-4′-aminopyrimidyl-5′)-methyl-4-methyl-5-β-hydroxyethyl-thiazol-2-thione (I) has been confirmed as follows: the cyclization to (II) occurs under liberation of hydrogen thiocyanide between the amino and the thiocyano groups in the initially formed thiocyano compound (VI), and not by the secondary cyclization of a thiazolone compound (III) formed from the initially formed thiocyano compound (VI). It was also found that thiochrome (II) is formed by the cyclization under liberation of mercaptane, under the same mechanism as above, upon the application of dimethyl sulfate, ethyl iodide, benzyl chloride or monochloroacetic acid to (I).
By the bromination of an oily mixture (III) of arctigenin (I) and its isomer, l-α-3, 4-dimethoxybenzyl-β-3′-methoxy-4′-hydroxybenzylbutyrolactone (II), bromoarctigenin (V), C21H21O6Br3, was obtained as crystals of m. p. 194-195°. Debromination of (V) with copper-coated zinc yielded arctigenin, m. p. 100-102°, C21H24O6, thus completing synthesis of arctigenin. Oxidation of the methyl ether (VI) of (V) with potassium permanganate yields 6-bromoveratric acid, m. p. 182-183°, and 5, 6-dibromoveratric acid, while the same oxidation of (V) yields 6-bromoveratric acid. This has confirmed that, of the three bromine atoms, one has entered the 6-position in the β-benzene nucleus of butyrolactone, while the other two has entered the 5- and 6-position in the α-benzene nucleus.
Several kinds of hydroxy-4-methylcoumarins were prepared and their antioxidative action against vitamin A in liver oil was examined. It was found that dihydroxydi-hydro derivatives possessed the most effective action, followed by the dihydroxy derivatives, monohydroxy derivatives being the most ineffective. An alcoholic extract of germs, insoluble in ether, possessed acertain a mount of cooperative action in increasing this antioxidative action. This is assumed to be the same kind of relationship that is shown by the ether extract and the ether-insoluble alcoholic extract of the germs towards antioxidative action against vitamin A oil.
A flavone glycoside was obtained from the fruits of Rosa multiflora Thunb. (=R. polyantha Sieb. et Zucc.) from which amorphous kaempherol-rhamnoglucoside, multiflorin, had been isolated by Kondo, et al. Hydrolysis of the glycoside with 1% H2SO4 gave quercetin, glucose and rhamnose. Kaempferol was not found in any fraction. The presence of multiflorin, therefore, is doubted.
Antibacterial action of clove oil and its principle, eugenol, was examined for 15 kinds of microörganisms, including Staphlococcus aureus. These were found to be effective in preventing the growth of Brucella and Mycobacterium at 1:16, 000 to 1:64, 000 concentration and at 1:8000 concentration, respectively. The antibacterial action of clove was found to be represented by its essential oil, or rather, by eugenol itself.
Antimicrobial action of chenopodium oil and its various fractions was examined. In tests with bacteria, it was found to be slightly effective against Mycobacterium, but possessed no perceptible action at 1:1000 dilutions. It was, however, found fairly effective against dermatopathogenic fungi, especially the ascaridol fraction which prevented growth of the mold at 1:6, 400 dilution, the action being unchanged upon the addition of serum or by continuous cultivation, without too irritating an action against human skin. This has, in a way, confirmed the general use of chenopodium oil as a home remedy for athlete's foot.
Inhibitory action of clove oil and eugenol against six kinds of microörganisms including Trichophyton, Achorion, and Epidermophyton was examined on Sabouraud glucose-agar medium. They were found to be effective at 1:8, 000 to 1:16, 000 dilutions, the effect remaining constant by the addition of serum, and the microbes failed to become resistant to the oil. Since the oil and its principle possessed no irritating action, they seemed possible to be applied clinically.
The capon's comb test as a suitable means of biological assay was reëxamined and the five values, (L), (L+H), (L×H), “B-area” and the “total area”, of capon's comb were criticized from the viewpoints of statistics. Analysis were carried out as follows: 1) Experimental design of 4×4 Latin-square and its analysis of variance (Tables I, II and III). 2) Test of the significances of the linear, quadratic and cubic relationship between log doses and the responses (Table IV). 3) Tests of the significances of correlation coefficients (Table V). 4) Factorial analysis of test assay for testosterone with two doses of standard (D2, D4) and two doses of unknown (D1, D3), based on the experimental results. Comparison of the potency ratio to the dose ratio (√2) (Table VI). After these analyses were carried out for each value (Table VII), “B-area” (Fig. 1 and (1), (2)) was certified by the present experiment to be the most suitable value for this androgen assay.
Detection of poisonous shellfish, asari and oysters, was carried out by the phenolphthalein reaction, in place of mice test, for two years from January 1950 to December 1951. It was thereby concluded that poisonous shellfish give positive phenolphthalein reaction.
Quercetin was obtained, and confirmed as its methyl and acetyl derivatives, from the flowers of Astilbe Thunbergii Miquel, collected during its flowering time on Mount Hiei, near Kyoto. A substance of m.p. 170-180°, giving positive Mg-HCl reaction, was also obtained but in a very minute amount. Astilbin and bergenin were obtained from the rhizome. Hydrolysis of astilbin gave rhamnose and distylin (3, 5, 6, 3′, 4′-pentahy-droxyflavanone). Methyl and acetyl derivatives of distylin were also obtained, as well as quercetin by its oxidation with 10% H2SO4. Bergenin was also confirmed as its acetyl and methyl derivatives. The fact that quercetin from the flowers and astilbin from rhizome were obtained from Astilbe Thunbergii is very interesting from phytophysiology and from phytotaxonomy together with the fact that whereas distylin has been individually found in Distylium racemosum S. et Z., and bergenin from Corylopsis spicata S. et Z., in Hamamelidaceae family, both have been found together in Astilbe genus of Saxifragaceae family.
1) Conditions were found for obtaining santonin 2, 4-dinitrophenylhydrazone quantitatively. 2) Comparison was made of the results of assay on santonin in J. P. sample or crude drug, obtained by the baryta and the 2, 4-dinitrophenylhydrazone methods. 3) Correct results cannot be expected with 2, 4-dinitrophenylhydrazone gravimetric method if crude drug was used as the material. 4) A red purple color, with absorption maximum at 500mμ, appears when 1% sodium hydroxide is added to the acetone solution of santonin-2, 4-dinitrophenylhydrazone. 5) Extinction coefficients were measured by the Beckman spectrophotometer (500mμ) in different concentrations. This experimental equation was calculated by the method of least squares from these data as follows: γ=1214ε-4.339 6) The standard deviation, δ, is 0.015, and the concentration limit which corresponds to 2δ limit is ±47.5γ.
1) Transmission maximum of four kinds of filters was determined by the Beckman spectrophotometer for use in the colorimetric determination of the reddish purple color that appears upon the addition of 1% NaOH to the acetone solution of santonin-2, 4-dinitrophenylhydrazone. They have a transmission maximum at 500 mμ, but some of the filter were transparent above 650 mμ. The inclination and linearity of concentration-absorption curves decrease when, these filters are used. Two kinds of filters were prepared for the present experiments which gave more pronounced inclination and linearity to the curves but which were opaque above 650 mμ. 2) Filters must be kept in a dark place to avoid discoloration, and their properties must be checked from time to time. 3) By selenium-cell filter photometer, light absorptions (ε) were measured with the prepared filter in different concentrations (γ). The experimental equation was calculated from these data as follows: γ=1445ε+14.12 4) The standard deviation, δ, is 0.021, and the concentration limit, which corresponds to 2δ limit, is ±42.4γ.
l-2-p-Nitrobenzenesulfoaminomethylthiazolidine-4-carboxylic acid, l-2-p-nitrobenzoylaminomethylthiazolidine-4-carboxylic acid and l-2-benzoylaminocarbethoxymethylthiazolidine-4-carboxylic acid were prepared by the reaction of the hydrolyzates of p-nitrobenzenesulfoaminoacetal or p-nitrobenzoylaminoacetal, and ethyl formylhippurate and cysteine.
The alcoholic extracts of 53 kinds of shelf-fungi were tested for their antibacterial action against Staphylococcus aureus (Friedlender) and E. coli by the dilution method. Digests of Grifola sp. and Fomes sp. were found to have the most strong action against Staphylococus aureus.
N1-p-Aminosalicylsulfanilamide (V), m.p. 119° (decomp.), was prepared by the following two routes: i) Fusion of phenyl p-nitrosalicylate (I), sulfanilamide (II) and anhydrous potassium carbonate to yield N1-p-nitrosalicylsulfanilamide (III), m.p. 212° (decomp.), giving positive FeCl3 and diazo reactions, which easily was reduced to (V). ii) Reaction of N4-acetyl compound (VI) of (II) and (I), under the same conditions as for (i) yields N1-p-nitrosalicyl-N4-acetylsulfanylamide (VII), m.p. 243° (decomp.), giving positive FeCl3 reaction and negative diazo reaction. Reduction of (VII) gives N1-p-aminosalicyl-N4-acetylsulfanilamide (VIII), m.p. 218-219° (decomp.), which is saponified to (V). Saponification of (VII) yielded (III), whose acetylation provided (VII). From all these experimental results, it can be seen that the salicyl group in (III), (VII), (VIII), and (V) is attached to the N1 of (II). In a similar manner, reaction of p-phenolsulfonamide (IX) with (I), in the presence of potassium carbonate, yieldedr N-(p-nitrosalicyl)-p-phenolsulfonamide (X), m.p. 205° (decomp.), whose reduction gave N-(p-aminosalicyl) compound (XI), m.p. 132-133° (decomp.).