Nine compounds of N, N-dimethyl-2-(p-alkylbenzhydrylthio) ethylamine hydrochloride series and twelve compounds of N, N-dimethyl-2-(p-alkylthiobenzhydrylthio) ethylamine hydrochloride series were synthesized. Several compounds of the latter series were found to possess fairly good in vivo effect on the Nakayama strain of Japanese B encephalitis virus, while none of the compounds synthesized showed in vitro effect against the virus.

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In order to find antiviral compounds, alkyl group was introduced into the neurotropic structure of 1-phenyl-3-dimethylamino-1-propanol and activity of the resulting alkyl derivatives were examined against the Nakayama strain of Japanese B encephalitis virus and the PR-8 strain of influenza A virus. 1-(p-Decylphenyl)-3-dimethylamino-1-propanol and 1-(p-dodecylphenyl)-3-dimethylamino-1-propanol showed in vivo effect on the Nakayama strain, and 1-(p-ethylphenyl)-3-dimethylamino-1-propanol exerted in ovo activity on the PR-8 strain.

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Eight compounds of 1-(p-alkylphenyl)-1-phenyl-2-methylamino-1-propanol were synthesized and their antiviral activities were examined. Several compounds in this series were found to be slightly effective on the PR-8 strain of influenza A virus in chorioallantoic membrane and fairly effective on the Nakayama strain of Japanese B encephalitis virus in vivo.

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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.

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New position isomers of cycloheximide named ψ-cycloheximides were prepared from dihydrocycloheximides by mild oxidation and (IV) was assigned to their structures.

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The seven compounds of N-alkanoyl-8-ethoxy-5-quinolinesulfonamide were synthesized and their in vitro and in vivo effects were tested on the Nakayama strain of Japanese B encephalitis virus. Among them, N-decanoyl-8-ethoxy-5-quinolinesufonamide was selected as the most effective. The optimum effective dose, effective time, acute toxicity, and minimum hemolytic action of this compound were examined and it was found to be more promising than PANS-610 in view of in vitro activity, in vivo effect, and effective time.

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There is a remarkable contradiction between the report of Katagiri, et al., that the liver of the cattle contains an enzyme which converts 6, 7-dimethylribolumazine into riboflavin, and that of Suzuoki, et al. that the former was nearly ineffective in their curative tests on the riboflavin-deficient rats. The present authors duplicated the method of Katagiri, et al., and confirmed that a phosphate buffer extract of the liver of the cattle transformed 6, 7-dimethylribolumazine into riboflavin in vitro. The same technique was applied to the liver of rats, but no increase of riboflavin was observed. Addition of diacetyl or sodium acetate as a carbon donor also gave the same result. These data are in good agreement with the result of Suzuoki, et al. in their tests on the whole body of the animal. Further the same experiments were attempted with the liver of rabbits and the result was the same as in the case of the liver of rats. On the other hand, a rabbit was fasted for a definite time and administered with 6, 7-dimethylribolumazine. The urine excreted before and after the administration was collected separately and subjected to paper partition chromatography. As a result, a distinct spot of riboflavin was observed in the "foreurine"but it became faint in the "after-urine, "and a conspicuous spot of 6, 7-dimethylribolumazine appeared in its stead. Although this result is merely qualitative, it is consistent with the result of the experiment on the liver homogenate of animals.

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5-Amino-6-hydroxyethylaminouracil was heated in neutral water, and a sparingly soluble, green fluorescent substance and a more soluble, blue fluorescent substance were obtained. The latter was identified with 9-hydroxyethylbisalloxazine. A similar result was obtained with 5-amino-6-butylaminouracil, yielding a green and a blue fluorescent substances. The latter was found to be 9-butylbisalloxazine and the former was concluded to have been produced by the condensation of two moles of the diaminouracil derivative under elimination of one mole of ammonia. A similar phenomenon was assumed to take place with 5-amino-6-ribitylaminouracil, an intermediate in the synthesis of 6, 7-dimethylribolumazine.

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1-Dialkylamino-2, 3-dichloropropanes, 2-dialkylamino-1, 3-dichloropropanes, and several new derivatives of nitrogen mustard having 2-chloropropyl group were synthesized and tested on Yoshida sarcoma. Mode of alkylation and hydrolysis in vitro of the former two types of compound were also discussed.

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3β, 17β-Diacetoxyandrost-5-en-16-one and 3β-methoxy-17β-acetoxyandrost-5-en-16-one were ethynylated with lithium acetylide. The resulting 16α-ethynyl-16β, 17β-diol afforded 16, 17-acetonide on treating with acetone, one of which was converted into 16α-ethynyl-16β, 17β-dihydroxyandrost-4-en-3-one by Oppenauer oxidation of the corresponding 3-ol and hydrolysis of 16, 17-acetonide.

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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.

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The main dye produced in the color reaction of fructose with diphenylamine was isolated in crystalline form as chloride and sulfate. Its probable structure was presented and the reaction mechanism was assumed.

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P¹-5'-Adenosine P²-(2-mercaptoethyl) pyrophosphate was prepared by the reaction of adenosine 5'-phosphoramidate dicyclohexylguanidinium salt and 2-mercaptoethyl phosphate. This compound has no activity for acetylation reaction in the pigeon liver enzyme systems.

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2-Oxo-3-β-D-ribofuranosyl-2, 3-dihydropyrimidine 5'-diphosphate and 5'-triphosphate were synthesized by the reaction of 2-oxo-3-β-D-ribofuranosylpyrimidine 5'-phosphate with orthophosphoric acid in the presence of DCC. The structure of both compounds was chemically elucidated.

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Cyclization of N, N'-Dimethylfumaranilide (VII) with aluminium chloride gave N, 1-dimethyl-2-oxo-3-indolineacetanilide (VIII) and not a carbostyril derivative (VIII'). The structure of (VIII) was confirmed by the alkylation of 1-methyloxindole.

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