During the course of syntheses of furan derivatives of antibacterial properties, the authors designated those substances having one or more “antibacterial group”, i.e. nitro and halogen radicals, in one molecule as an “antibacterial body” and those atomic groups assumed to affect changes in the activities or selectivities of the bacteria, the “auxo-antibacterial group”. It was found that the antibacterial activity diminished greatly when the nitro-radical in 2-(5-nitro)-furaldehyde semicarbazone was substituted by Clatom. The new compound, 2-(5-nitro)-furylacrolein semicarbazone, possesses uniform antibacterial activity comparable to 2-(5-nitro)-furaldehyde semicarbazone.
In accordance with the ideas expressed in the previous report (cf. Report III), the authors chose 2-(5-nitro)-furoic acid and 2-(5-nitro)-furylacrylic acid for condensation with 12 kinds of amines. As a result of bacterial tests with the new compounds obtained, 2-(5-nitro)-furylacrylylamide showed in vitro effect of about the same degree as that of 2-(5-nitro)-furaldehyde semicabrazone reported earlier by Gilman.
Several new compounds were synthesized in order to test the antibacterial activities of furyl and furfuryl type sulfides and sulfones by the presence or absence of nitro-radical at 5-position in furan nucleus.
1) Corresponding betaine hydrochloride was prepared from N-chloroacetylvaline and pyridine. Treatment of the former with excess of pyridine and acetic anhydride or of β-hydroxyvaline with acetic anhydride gives 2-methyl-4-isopropylidene-5-oxazolone. 2) By the hydrolysis of methyl α-acetylamino-β-benzylmercapto-β, β-dimethylpropionate to the corresponding acid, debenzylation of this with liquid ammonia and metallic sodium, and finally isolation of N-acetyl radical, penicillamine was obtained in good yield. 3) Addition of HS to 2-phenyl-4-isopropylidene-5-oxazolone gave N-benzoyl-penicillamine. This compound is easily benzylated to give S-benzyl-N-benzoyl-penicillamine.
1) S-Benzyl-N-benzoyl-penicillamine showed resistance to hydrolysis by caustic alkalis. 2) S-Benzylpenicillamine-hydantoin and penicillamine-hydantoin were prepared from S-benzyl-penicillamine. Valine-hydantoin was obtained by the treatment of the former with Raney Ni, and 5-isopropylidene-hydantoin by the treatment of the two by alkali. 3) Treatment of S-benzyl-penicillamine and its N-acyl compound with an excess of acetic anhydride gave corresponding α, β-unsaturated azulactone. This reaction is suitable for indirect racemization of l-series compounds. 4) Treatment of S-benzyl-l-penicillamine with alkali and a slight excess of acetic anhydride resulted in its racemization. 5) Observations were made of the relationship between desulfurization and racemization of penicillamine derivatives by acetic anhydride.
Three compounds, zinc dithiocarbamate (I), zinc dimethyl-dithiocarbamate (II) and zinc diethyl-dithiocarbamate (III), were prepared and their therapeutic effect against dermatic mycosis was tested in various drug forms. (III) was the most effective, followed by (II), (I) being the weakest. The most effective preparation was an ointment made of (III), talc powder, diethyl phthalate and vegetable oil, which gave relief to most of the patients tested by the application for 7-10 days. (III) was synthesized from NaOH, CS2 and diethylamine, reacted in an aqueous solution and Zn-sulfate solution added to the solution of diethyl-dithio-carbamate formed. (III) was obtained in a good yield. Treadwell, Hall: “Analytical Chemistry” Nth English Edition, Vol. II, p. 671.
In order to utilize them as vascular contraction agent to be used in the nose, 2-aminoheptane was synthesized by various methods. (1) Using alcoholic ammonia on 2-bromoheptane: Usual yield, 43%; use of copper powder as catalyst increased the yield to 43.6%. (2) Reduction of methyl-n-amylketoxime: Yield from reduction by Na and EtOH, 34.5%; by 2.5% Na⋅Hg, yield 22.4%; by 3% Na⋅Hg, yield 23.7%; No yield by reduction with Zn⋅AcOH; Electrolytic reduction using Pb plates for both electrodes, 50% H2SO4 for both baths, electric density 200amp/cm2, temperature ca. 20°, time 4hrs., yield 53.9%.
1) Neutralization curves of 3-amino-4-hydroxyphenylarsonous acid and 3-amino-4-hydroxyphenylarsinedichloride hydrochloride were examined by the glass-membrane electrode method. A new knowledge was obtained as to the equilibrium of acid-base in both substances. 2) From the two neutralization curves, several knowledges were obtained as to the preparation and titration of mapharsol and dichlorophenarsine hydrochloride.
Reaction of o- or p-arsanilic acid hydrochloride with dicyanodiamide and cyanamide in aqueous solution resulted in the syntheses of 4-biguanido-, 2, 4-guanylcarbamido- and 2, 4-guanido-phenylarsonic acid. The reaction with dicyanodiamide results in biguanido compound when p-compound is used but guanylcarbamido compound, in which the hydrolysis had proceeded still further, is obtained when o-compound is used. In vitro test of p-compound against dysenteric amoeba showed 4-guanylcarbamidophenylarsonic acid to be the only compound to possess greater efficacy compared to carbarsone.
Various kinds of formalizing agent is used in the preparation of the powdered Scopolia extract. These agents have great effects on the result of quantitative determination so that the method given in the Pharmacopoeae cannot be applied directly. Following method is proposed by the author for the quantitative determination of alkaloids in powdered Scopolia extract. 12g of the sample is taken to which are added 100cc ether and 10cc 15% aqueous ammonia and shaken well. 1-5cc Water is added to this and shaken for 1hr., filtered through cotton wool, 1g talc added to the filtrate, shaken, 5cc water added, shaken, 1.5g finely powered tragacanth added and shaken well. A definite amount of this ether solution is taken, filtered through a dry filter paper, evaporated over a water bath of about 60° and the residue dissolved in 1cc alcohol. To this are added 5cc n/10 HCl and about 1cc CCl4, shaken slightly to allow colored portion to transit to CCl4 layer and 5cc water added. This finally is titrated with n/10 KOH solution with 2 drops of methyl red as an indicator.
Total alkaloid of Macleya cordata was extracted as a crude sulfate and was tested for local anesthetic properties using rabbits. Its 1% solution was found to be stronger in action than 1% solution of procaine hydrochloride, its 2.5% solution slightly stronger than the 0.5% solution of cocaine hydrochloride but slightly weaker than 0.8% solution of the latter. Its toxicity seemed to be comparatively weaker when applied orally. Simplified method of the extraction of this alkaloid was studied aud it was found that the alkaloid was adsorbed by acid clay. Investigation is under way to utilize this method in extraction.
Mibulactone, C15H22O4, m.p. 228-229°, [α]D10: +156.36°, gives 1-methyl-7-ethylnaphthalene (picrate, m.p. 95°) by heating with selenium. The former is a lactone having 2 active hydrogen and its acetylation gives a mono-acetylated compound, acetylmibulactone, m.p. 218°, and its catalytic reduction with Pt gives dihydromibulactone, m.p. 227°. Acetylation of the latter gives dihydro-acetylmibulactone, m.p. 239°. Oxidation of mibulactone with Na2Cr2O7 gives ketomibulactone, m.p. 261°, and its catalytic reduction, dihydro-ketomibulactone, m.p. 249°, which can also be obtained by the Na2Cr2O7-oxidation of dihydromibulactone. From the results of these experiments it is known that mibulactone possesses identical structure as that of santonin, a lactone compound possessing one each of secondary and tertiary hydroxyl radicals and one double bond.
As a result of the microchemical examinations of the distribution of triterpenoid in plants, 287 positive cases were obtained from 617 samples tested. They were: 22 in Compositae, 5 in Campanulaceae, 12 in Caprifoliaceae, 13 in Oleaceae, 6 in Myrsinaceae, 26 in Ericaceae, 6 in Cornaceae, 7 in Araliaceae, 6 in Elaeagnaceae, 9 in Theaceae, 14 in Aquifoliace, 7 in Leguminosae, 30 in Rosaceae, 5 in Ranunclaceae, 12 in Fagaceae, 6 in Liliaceae and 101 in others. It follows, therefore, that the distribution of triterpenoid in plants is unexpectedly wide-spread and could be classed as an ordinary component present. The amount of triterpenoid content is generally greater in evergreen plants having thick leaves with well developed cuticula.
The following samples were chosen from the 233 samples showing strong positive reaction in detection of triterpenoid and experiments were made to isolate triterpenoid crystals by the extraction, chiefly of leaves, with AcOEt: (1) Osmanthus fragrans Lour. var. latifolius Makino. (2) Osmanthus fragrans Lour. var. aurantiacus Makino. (3) Ligustrum japonicum Thumb. (above 3 from Oleaceae). (4) Aucuba japonica Thumb. Goldorange (Cornaceae). (5) Vaccinium fracteatum Thumb. (6) Rhododendron linearifolium Sieb. et Zucc. var. macrosephalum Makino. (7) Pieris japonica D. Don. (above 3 from Ericaceae). (8) Ternstroemia japonica Thumb. (Theaceae). (9) Ilex latifolia R. Br. (Apuifoliaceae). (10) Elaeagnus glabra Thumb. (Elaeagnaceae). (11) Gilibertia trifida Makino (Araliaceae). (12) Pittosporum Tobira Ait. (Pittosporaceae). Ursolic acid was proved from (1), (6) and (9). pure crystals were not obtained from the others due to scarcity of sample but it is certain that these also contain triterpenoid.
1) Triacontane, C30H62, and a kind of sesquiterpenolactone were isolated from the seeds of Carpesium abrotanoides (Compositae) and the latter was named carpesia-lactone. 2) Carpesialactone is a viscuous liquid, b.p.5 200-202°, possesses powerful irritating properties and bitter taste. It easily polymerizes and corresponds to C15H20O3. 3) This lactone absorbs 2mol. hydrogen and forms tetrahydro-carpesialactone, C15H24O3, b.p.5 218-220°, loses polymerizability and becomes stable. 4) Both carpesialactone and tetrahydrocarpesialactone give positive Liebermann's reaction and form azulene by dry distillation with selenium or charcoal dust. 5) Tetrahydrocarpesialactone seems to be reduced by selenium or hydriodic acid and gives oily substance of specific odor, b.p. 215°, being assumed as alkylated decaline in both casses. The latter compound has similar specific gravity and refraction as those of decaline derivatives.
Dehydrogenation of hydrodeoxynupharidine by Pd or Se gives two kinds of substances, one, C15H23-25N and the other C15H21-23ON. By separate oxidation of these compounds by alkaline KMnO4 gave the same white crystailline powder, decompn. 254°; its methyl ester, white needles, m.p. 161-2°. Both these compounds showed no depression in the melting point when fused respectively with pyridine-2, 5-dicarboxylic acid and its dimethyl ester.
The dried flowers of Lonicera japonica Thumb. are used as a diuretic. The author previously reported isolation of waxy substance as one of its components and named it lonicera wax. As other componets, the author recently obtained yellow needles, m.p. 325°, and colorless prisms, m.p. 225°. The former corresponds to C15H10O6. 1 1/2H2O, gives acetylated compound of white needles, m.p. 214-5°, and methylated compound of yellow needles, m.p. 161-3°, by diazomethane. These compounds showed no depression in m.p.s when fused respectively with luteolin, tetraacetyl-luteolin and trimethylluteolin. Colorless prisms corresponds to C6H12O6. 2H2O and is identical with i-inositol.
Yellowish-green, needle crystals of m.p. 177° were isolated from the leaves of Nerium odorum Soland. It corresponds to C27H30O16⋅2H2O and gives one molecule each of quercetin, glucose and rhamnose by hydrolysis. This corresponds to rutin as found in literature.
1) The authors accepted the proposal of Schechter that obakulactone, evodine, dictamnolactone and limonin should hereafter be designated as limonin on the basis of its identity and priority. 2) The bitter principle, C26H30O9, m.p. 300°, isolated from Evodia rutaecarpa Benth. et Hook. was established as a new compound and was named “rutaevin”, 3) The authors obtained evidences that limonin molecule possessed a furan ring.
Studies on the Japanese cassia bark have been limited to those on root bark and much have been left as to the nature of branch or tree bark. However, both tree and branch barks are being used at the present time and, moreover, foreign products are chiefly barks off cinnamon trees and branches. Under the present experiment, it has become clear that anatomical difference exists between barks from trees above and below the ground. These findings as the basis, the authors expect to discuss on foreign cinnamon bark which are chiefly from branches or trunks.
A colorless, prismatic crystal, decompn. 188-190°, was isolated from the precipitate obtained by the addition of basic lead acetate to aqueous extract of bovine liver. Recrystallization from dil. acetone gave crystals of m.p. 100-101°, containing water of crystallization, and possessing no optical rotation. Many properties are similar to those of taurine but no definite proof could be obtained.
In the metamorphosis of tadpoles front legs appear first, followed by shortening of the tail in ordinary growth but when thyroid preparations are given, shortening of the tail occurs first followed by the appearance of front legs. Curves obtained by plotting the thyroid preparation used and shortening of the tail showed efficacy of the drug. Comparison of the relationship between iodine content and physiological action of iodo-casein showed the activity to be in the order of following iodine content: 7.55%, 7.73%, 6.85% and 9.22%. In this case, content of free iodine over 0.5% results in inhibitory action. Comparison of iodo-casein and thyroid gland powder showed the former to be slow-working and the latter fast-working. The hydrolysis product of iodo-casein showed powerful physiological action with about 1/10 the amount of thyroid gland powder.
Cholic acid, taurine and cholesterol were identified from the bile of Seriola quinqueradiata belonging to Toleostei. Another sterol series crystals of m.p. 164.5° were obtained which corresponded approximately to formula C24H42O5, [α]D20=+77.01° and were not precipitated by digitonin. Crude cholic acid separated from the bile of Eumetopia tubata belonging to marine mammals, was purified as a Ba-salt and a free acid, m.p. 193°, was isolated from the soluble Ba-salt. This acid corresponds to formula C27H46O6, has [α]D20=+41.89° and gives positive reactions to Milius, Hammasten and Libermann tests. Acetylation gives tetraacetate and oxidation by CrO3 in glacial acetic acid gives triketo-monocarboxylic acid which corresponds to 3, 7, 12-triketocholanic acid, an oxidation product of cholic acid. It is assumed that the side chain was cleaved at C24-position so that the authors assumed following structure for the substance with m.p. 193°.
Oil from Ommastrephes sloani pacificus (from the Hokkaido) has of late been watched with interest as a source of cholesterol. From 10kg of oil, 150g of unsaponifiable substance were obtained which did not contain any sterol substance other than cholesterol although it did contain batyl alcohol. The oil itself was esterified and from the distillation residue of fatty acid ester were obtained two substances of m.p. 78° and 144°, respectively. The former was identified as cholesterol-palmitate and the latter, a free cholesterol. Body oil of Chollarinus alascanus (caught in Choshi in 1944) was examined with absorption spectrum and it was found to contain 180 units of vitamin A in its unsaponifiable substances but no vitamin D. General properties of this oil are as follows: m.p. 17-19°; specific gravity at 30°, 0.9085; refractive index, nD401.4700; saponification value, 182.6; unsaponifiable matter; 0.82% (containing 25.8% sterol); iodine value (Wijs). 137.3; acid value, 1.64; Reichert Meissel value, 0.49; Polenske value, 1.36; acetyl value, 13.18. Fatty acid, m.p. 20°; solidifying point 14°; neutralization value, 185.9; iodine value, 99.9; refractive index, nD401.4622. The unsaponifiable substance from the body oil of Phoca vitulina L. (caught in Kurilles Is. in 1942) also contained vitamin A and was positive to SbCl3. The values of the oil were: sp. gr. at 30° 0.9101; saponification value, 194.6; unsaponifiable matter, 0.18%; iodine value, 155.7. Fatty acid; neutralization value, 200.5; iodine value, 118.6.
The author made a study of equine pituitary oil and compared it with equine cerebrol. Pituitary oil is a viscuous liquid with saponification value of 136.2 and iodine value of 93.4, while cerebrol is a solid having saponification value of 50.5 and iodine value of 56.6. Cholesterol content of the two are 1.84% and 18.4%, respectively, showing that that in pituitary oil is only 1/10 of cerebrol. Palmitic acid was isolated as a saturated fatty acid from pituitary oil, which seems to constitute majority of the component. Oleic acid was obtained as an unsaturated fatty acid and a number of oxidized acids of unknown origin were also obtained.
It was learned that when alkali is added to aluminum sulfate solution containing a large amount of Fe... and Fe.., Fe... reacts quantitatively with OH′ prior to Al.... This mechanism was utilized in removing all Fe... present in Al-sulfute solution by the addition of the necessary amount of alkali. The small amount of Fe... still remaining could be formed into Fe.. by a suitable reduction agent. One recrystallization would then give pure alum virtually containing no iron which can be obtained in a highest yield at that concentration.
Bovine blood is hydrolyzed and histidine is adsorbed by acid clay at weak acidity or neutrality. This acid clay is subjected to washing by acid and alkali so that all other amino acids are removed, content of histidine can then be increased. This is then subjected to electrolytic dialysis by which inorganic ions are removed as well as lysine, arginine and other mono-amino acids. Histidine is then precipitated by the use of 3, 4-dichlorobenzenesulfonic acid and led to histidine monohydrochloride. If care is taken in the procedure, yield of over 60% can be obtained. Compared to the well-known method of using a sublimate, this method seems inferior due to the complicated procedure but if the isolation and utilization of amino acids in bovine blood other than histidine are taken into consideration, this adsorption method seems to warrant further study in the future.
Electrolytic reduction of p-toluenesulfonyl chloride in alcohlic sulfuric acid solution with lead electrode resulted in obtaining p-thiocresol as the final product and p, p′-ditolyldisulfide, p, p′-ditolyldisulfoxide and p-toluenesulfinic acid as intermediate compounds. As a result of the electrolytic reduction of these intermediates and p-toluenesulfinyl chloride, p-toluenesulfonic acid and p, p′-ditolyldisulfone, it was learned that -disulfide and -sulfinyl chloride possessed good current efficiencies and were easily reduced while -disulfoxide and -sulfinic acid possessed poor efficiencies and -sulfonic acid and -disulfone could not be reduced. Electrolytic reduction of a mixture of p-thiocresol and p-toluenesulfinic acid revealed the formation of -disulfide, this reaction being assumed as mol.: mol. Electrolysis of p-toluenesulfonyl chloride results in speedy formation of -disulfoxide which is reduced and forms thiocresol and -sulfinic acid. A mixture of these two compounds, while being reduced, reacts chemically to form -disulfide which is assumed to give a final product of thiocresol.
It has already been reported by Naito and Suzuki (J. Pharm. Soc., Japan, 56, 807 (1936)) that phenylthiosemicarbazide gives sharp color reactions by the application of Cu, Ni, Co and Pt ions. The authors experimented with the quantitative determination of Pt by the use of this reagent. As a result, it was found that this method had advantages over the heretofore used KCl method. The method experimented was as follows: Pt is led to its chloride in the usual manner, the solution corrected to pH 6-7, saturated 50% alcoholic solution of this reagent is added and warmed on a water bath. The deep blue precipitate formed is filtered on a filter paper, washed, dried and fused in a porcelain crucible. Pt is weighed as metal Pt.
A fixed amount of the mixed solution of V... and VO.. is titrated by normal KMnO4 solution by which total V is obtained. Another amount of the sample is titrated by KMnO4 with diphenyl-amine as an indicator by which the amount (in cc) of KMnO4 solution used would correspond to the amount of V... and difference in the amount of KMnO4 used in there two titrations would correspond to the amount of VO... The mixed solution of V.. and V... is titrated by n-KMnO4 solution by which total V is obtained. Another amount of sample is then taken, silver solution added by which Ag is reduced to Ag and, at the same time, V.. is oxidized to V.... After filtering off the precipitated Ag, the solution is titrated by KMnO4 and the two ions can be quantitatively determined separately from the amount of KMnO4 used.
The authors previously isolated 12 kinds of soil bacteria which could metabolize benzoic acid or its derivatives and examined their metabolic activities. In the present experiment, the authors isolated further kinds of soil bacteria possessing metabolic activities different from the former 12. Comparative studies on the metabolism of these bacteria were made with benzoic, p-hydroxybenzoic, salicylic, m-hydroxybenzoic, anisic, piperonylic. p-nitrobenzoic, phenylacetic, cinnamic, o-coumaric and dl-mandelic acids. Some bacteria metabolized p-methoxycinnamic acid.
Comparison of growth inhibitory action against E. coli, B. typhi and S. aureus were tested with quinolinic, cinchomeronic and lutidinic acids in 500 volume dilutions. Quinolinic acid was ineffective in inhibiting the growth of any of the bacteria tested but the others were effective. These three kinds of pyridine-dicarboxylic acids were ineffective, especially, to those bacteria at the logarithmic stage of growth.
A Streptomyces sp., No. 406, isolated by the authors, is similar to Streptomyces lavendulae but the antibiotic produced by this strain has high toxicity. From its antibacterial spectrum and chemical behavior, it is presumed to be similar to streptothricin.
A Streptomyces sp., No. 8049, isolated by the authors, is assumed to be Streptomyces griseus. The antibiotic produced by this strain has low toxicity and is assumed to be similar to streptomycin from its antibacterial spectrum and chemical behavior.
A crystalline substance possessing antibacterial activity was obtained from a strain of Aspergillus terreus from soil. This substance was found to contain chlorine and was named ‘terrecin’. Antibacterial activities of this substance against a number of bacteria showed it to be effective against gram-positive bacteria and to possess powerful inhibitory action against anthrax bacilli and anaerobic Cl. Welchii. Toxicity tests carried out with mice showed the substance to have only a very slight toxicity.
B. Natto was cultivated in a medium (pH 7.0) made of glucose, Na-glutamate and aqueous extract of soy beans. A substance was obtained from the filtrate of this media which inhibits the growth, in vitro, of Staph. aureus. Bacteriological, physical and chemical properties of this substance are explained.
In order to observe the relationship between chemical structure and antibacterial properties of branched-chain fatty acids in α- and β-positions, fatty acids with terpenyl radicals at α- and β-positions were synthesized. Chief of these compounds correspond to a general formula of R-CH-R′-COOH and those synthesized included compounds with R=ethyl, propyl, butyl, amyl, phenyl and geranyl, with R′=dihydrocitronellyl and geranyl radicals, all compounds being synthesized according to malonic ester method. Moreover, isofarnesic acid, an isomer of farnesic acid which is a sesquiterpenic acid found in nature, was synthesized from citronellal. Antibacterial activities of this compound were compared with that of l-rhodinic acid to which iso-farnesic acid is structurally similar.
Antibacterial properties of fatty acids possessing terpenyl (A Group) and phenyl (B Group) radicals at α- and β-positions were tested, in vitro, against staphylococcus (Terashima strain), avian type Mycobacterium tuberculosis and E. coli. In A Group, α-butyldihydrocitronellylacetic acid (at 64, 000 dilution) was effective in inhibiting growth of staphylococci and isofarnesic acid (at 64, 000 dilution), against tuberculous bacilli. The maximum of antibacterial power in A Group is attained in compounds with C14-C16. In B Group, no difference could be observed in compounds having phenyl radical at α- or β-positions. The maximum of antibacterial power was shown in compounds with C20 to C22, the highest inhibitory action against tuberculous bacilli being shown by α-phenylmyristic acid (at 600, 000 dilution). Inhibition of growth of E. coli was shown by A Group compounds at 1, 000 dilution or under, and by B Group compounds at 40, 000 to 80, 000 dilution. Efficacies of both A and B Group compounds were decreased by the addition of equine serum to the amount of 0.5%, the efficacy of α-phenylmyristic acid decreasing to 130.
Nine kinds of acids were chosen to test their effects on the growth, respiration, dehydrogenation and deoxidation of Staphyllococcus aureus, avian type Mycobacterium tuberculosis and Escherichia Coli. Those tested were: (1) α-phenylmyristic acid; (2) β, β-Diheptylpropionic acid; (3) Dihydrocitronellylbutyl-acetic acid; (4) Oleic acid; (5) Linoleic acid; (6) Dihydrorhodinic acid; (7) α-Phenyl-butyric acid; (8) α-ethyleicosanoic acid and (9) desoxycholic acid. It was found that growth, respiration, dehydrogenation and deoxidation of Staph. aureus were obstructed by the compounds (1), (2), (3), (4), (5) and (9), in that order of strength, but other acids did not seem to bear much effect in this case. In the case of Mycob. tuberculosis, compounds (1), (2), (3), (4) and (5) obstructed its growth, respiration or dehydrogenase system but the compound (9) did not give any adverse effect. In the case of E. coli, compounds (1) to (9) had almost no effect on inhibition of growth and only a weak action in obstructing respiration and dehydrogenase system. It follows, therefore, that there exists a certain parallel relationship between the antibacterial power of branched-chain fatty acids and its obstruction effect on respiration or dehydrogenase system. Some observations from the point of surface chemistry are also reported.
The authors investigated the extent of changes received by branched-chain fatty acids when introduced into an animal body. As such samples, following were synthesized: (1) 3-methylpelargonic acid, (2) 2-methylcaprylic acid, (3) 3-ethylenanthic acid, and (4) 2-ethylhexanol. These were given to rabbits, either orally or by subcutaneous injections. In all cases, the methyl radical at the end changed into carboxyl radical in the body and dicarboxylic acids were obtained. In the cases of (1) and (4), these were identified by the syntheses of 3-methyl-azelaic and 2-ethyladipic acids, respectively.
In vitro tests of antibacterial actions of sulfanilamides, behavior of bacteria against antagonists of sulfanilamides, and the adsorbability on charcoal powder were experimented. As a result, it seems probable to assume that the antibacterial power was increased by the strengthening of adsorbability resulting from bonding of heterocyclic radical to sulfanilamide.
Amino-compounds, such as p-Aminobenzoic acid, sulfanilamide, p-anisidine, p-nitraniline, aniline, p-aminophenol-β-glucoside and p-aminobenzyl ether of partially hydrolysed product of Arabic gum, were coupled to diphtheric toxin and diphtheric azo-toxins were obtained. Lf Value of diphtheric azo-toxin decreased to 1/2-1/3, and the toxicity to 1/3⋅6-1⋅6. Immunity was slightly visible in antitoxin tests but there seemed to be no practical value. Sedimentation tests, cross reaction and inhibition tests showed that various amino compounds gave specific properties to diphtheric toxin as haptane. These results and Lf values and toxicity gave definite indication of the specific properties of diphtheric azo-toxin.
As a result of systematic research, in cooperation with Dr. Ishii, for compounds effective against Katayama nosophora, a host for Shistosoma japonica, o-tolylurethane, carbethoxy-p-nitrophenol, ethyl diphenylcarbamate and dimethyl chloro-phthalate were found to be effective as snailcide in laboratory tests.