As an exploratory experiment on syntheses of sorigenins (I), 1-methoxy-3-hydroxymethyl-2-naphthoic acid γ-lactone (VIII) and 3-hydroxymethyl-4-methoxy-2-naphthoic acid γ-lactone (XV) were synthesized. Compound (VIII) was prepared from 3-hydroxymethyl-3, 4-dihydro-1 (2H)-naphthalenone (IV) as shown in Chart 1. Compound (XV) was prepared through reduction of 3-ethoxycarbonyl-4-hydroxy-2-naphthoic acid (XVIII) and its methyl ether (XX) with lithium aluminium hydride. Reductions of 1-methoxy-2, 3-naphthalenedicarboxylic anhydride (XIV) and of the halfester prepared by alcoholysis of (XIV) with lithium aluminium hydride were found to give a mixture of (VIII) and (XV).

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Synthesis of β-sorigen. in dimethyl ether (XIV) and 3-hydroxymethyl-4-hydroxy-5-methoxy-2-naphthoic acid γ-lactone (XIX) were described. The structure of β-sorigenin was synthetically established as 3-hydroxymethyl-1, 8-dihydroxy-2-naphthoic acid γ-lactone (II: R, R'=H).

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Condensation of ethyl 4-hydroxy-2-naphthoate (IV) and chloral hydrate with sulfuric acid followed by methylation, alkaline hydrolysis and decarboxylation gave 4-methoxynaphtho [2, 3-c] furan-1 (3H)-one (II). On the other hand, the methyl ether (V) of (IV) was transformed to 5-methoxynaphtho [1, 2-c] furan-3 (1H)-one (VIII) by a similar sequence of reactions. Synthesis of (VIII) by another route starting from ethyl 1-methyl-4-hydroxy-2-naphthoate gave a synthetic confirmation to the structure of (VIII).

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Reaction of difluoroboron compound of β-hujaplicin and bromine afforded 8-bromo compound, which gave β-dolabrin and 8-alkoxyhinokitiol by a treatment of base in alcohol.

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1, 6-Anhydro-β-D-glucopyranose was synthesized from 6-O-p-toluenesulfonyl-1, 2, 3, 4-tetra-O-acetyl-β-D-glucopyranose by a treatment with sodium methoxide. Since 1, 6-anhydro-β-D-glucose is not obtainable from 6-deoxy-6-iodo-1, 2, 3, 4-tetra-O-acetyl-α-Dglucopyranose, this procedure is applicable to distinguish α, β-anomers chemically.
Some conformational discussions are made.

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Studies on the metabolic fate of alizarin dimethyl ether in rat has been elucidated. It was mainly demethylated to alizarin 1-methyl ether and alizarin, and a trace of unchanged alizarin dimethyl ether was obtained. The mechanism of biological demethylation at carbon 1 and 2-positions of alizarin dimethyl ether is found to be different from that of chemical reaction. Metabolic products derived from alizarin and its 1-methyl ether were also detected by paper chromatography.

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1) The degradative reaction of succinylcholine chloride was investigated over the pH range of 0.9 to 8.5 by ion exchange chromatographic method from the standpoint of chemical kinetics. The decomposition was recognized as a first-order reaction at any given pH value with respect to succinylcholine chloride. From the data obtained at the lower pH regions, there action constants (L.·mol.-1·hr.-1) catalyzed by hydrogen ion were determined as follows:
_??_

2) From the data obtained at higher pH regions, the presence of catalysis of general base besides hydroxyl ion was shown. It was recognized that the velocity constant was affected by a buffer concentration even in the same pH and the same ionic strength.
3) From the observed rate constants against varying acetate ion concentrations in the acetate buffers (μ=0.2) for two different pH values (4.69, 3.98) at 60°, the secondorder rate constant, k_CH3COO^-, was determined as 5.01×10^-2 (L.·mol.^-1·hr.^-1).
4) The catalytic constant (L.·mol.^-1·hr.^-1) of hydroxyl ion, k_OH^-, for succinylcholine chloride was obtained, maintaining at the initial pH value without buffering agent. The reaction constants catalyzed by hydroxyl ion were determined as follows:
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5) The rate constant (hr.^-1) in an acetate buffer (μ=0.2) at an optional concentration was expressed as follows:
k=6.47×10^-1 (H⁺) +5.01×10^-6 (H₂O) +2.04×10⁵ (OH^-) +5.01×10^-2 (CH₃COO^-)
It was concluded that the use of buffering agent is not always recommended for the storage of succinylcholine chloride solution, because it accelerates hydrolysis of succinylcholine chloride.

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It was found that the crystalline derivatives were readily obtainable when various hydrazine compounds were reacted with retinal. Many hydrazone-type derivatives of retinal were prepared and their physical properties, stability, toxicity and biopotency were examined.
All such derivatives are more stable than vitamin A palmitate, their toxicity being low, and some of them showed considerably higher vitamin A activity.
Retinal azine is obtained as crystals of m. p.189° in a good yield when retinal is reacted with hydrazine-hydrate in the presence of an organic acid as a promotor. This compound is expected to have higher biological activity. p-Aminobenzoylhydrazone of retinal showed the biopotency equivalent to that of vitamin A.

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It has been reported that 2-naphthyl allylic ethers undergo the Claisen rearrangement to give naphthol derivatives. 2-naphthyl propargyl ether derivatives, _??_^{-O·CH₂C≡C-R} (R=H, CH₃, Ph.), replacing the double bond of allylic ethers by a triple bond, do not undergo the Claisen rearrangement but a new ring-closure to give 3H-naphtho [2, 1-b] pyran derivatives. Moreover, 1-naphthyl derivatives, _??_^{O·CH₂C≡C-Ph}also undergo the same ring-closure to give 4-phenyl-2H-naphtho [1, 2-b] pyran. The structures of new pyran derivatives obtained by the new ring-closure were confirmed by the melting point, infrared and ultraviolet spectra of the authentic samples which were synthesized by another routes.

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When 3-methoxy- and 3-hydroxy-6-chloropyridazine 1-oxides (Ia, b) were nitrated with nitric acid and concentrated sulfuric acid, mono-nitro compounds (IIa.b) were produced.(IIa) was shown as 4-nitro compound, (IIa) was converted to 3-methoxy-4, 6-dichloropyridazine 1-oxide (IV) with acetyl chloride. The reaction of (IIa) and (IV) with sodium methoxide occurred at their 4-positions respeetively.

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On N-oxidation of 3-aminopyridazine and its three derivatives, it was found that their main products were 2-oxides, and 3-acetamidopyridazine gave a small amount of 1-oxide, besides. Further, diazotization of 3-amino-6-chloropyridazine 2-oxide, and thermal cyclization of ethyl-3-pyridazinecarbamate 2-oxide were investigated for additional confirmation of the position of N-oxide.

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Condensation of 5-phthalimido-2-tetralone (Ic) and methyl 2-methyl-3-methylaminopropionate (XIV) by the method of Nelson, et al. yielded (IIIc) as a major product and (IVc) as a minor product. The structures of both products were established mainly by comparison of their infrared and ultraviolet spectra with those of several compounds having similar structures. Consequently, it was found that nine vinylogous lactams newly prepared could be classified into two groups, normal vinylogous lactams (IVb, c), (VIIIa, b, c) and crass-canjugated ones (IIIa-d), (VI), from their spectral data and their behaviors towards lithium aluminum hydride reduction.

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The Stobbe condensation of methyl 4-oxo-1, 2, 3, 4-tetrahydro-2-naphthoate (III) with2, 4-dimethoxybenzaldehyde gave the chalconecarboxylic acid (IV), which was derived to 3-(5-bromo-2, 4-dimethoxybenzyl)-4-methoxy-2-naphthoic acid (XIV) by 6 steps. The compound (XIV) was also prepared from 1-methoxy-2, 3-naphthalenedicarboxylic anhydride (XV) by 4 steps. Cyclizatian reactian of (XIV) emplaying stannic chlaride as a candensing agent resulted in a replacement of bromine atom substituted in the nucleus with hydrogen to form 1, 3, 11-trimethoxy-5(12H)-naphthacenone (I). The whole reaction schema was illustrated in Chart 1.

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Some factors affecting on the metabolism of cyclobarbital (EHB) by the rat liverpreparation were examined.
Sex difference was especially shown in the formation of 3-OH-EHB, but no difference in that of 3-keto-EHB was shown.
The pretreatment of female rats with EHB enhanced both the formation of 3-OHEHB and that of 3-keto-EHB in approximately same proportion as controls. However, the pretreatment with 3-OH-EHB increased the formation of 3-OH-EHB and decreased that of 3-keto-EHB from EHB. The conversion of 3-OH-EHB to 3-keto-EHB was depressed by the pretreatment with testosterone or 3-OH-EHB. On the other hand, the conversion of 3-keto-EHB to 3-OH-EHB was stimulated by such a treatment. Another metabolite of EHB, 3-keto-EHB, has not stimulatory effect on the EHB-metabolism.
The removal of the adrenal glands did not prevent the stimulatory effect of EHB.

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Reactivity of 3, 6-dichloropyridazine 1-oxide (II) to nucleophilic substitution was examined. 3-Chlorine atom was always more reactive than 6-chlorine atom. Chlorine of 3-substituted-6-chloropyridazine 1-oxide was more reactive than that of 3-substituted-6-chloropyridazine.

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Reactions of N-dimethylaminophenylnitrones, having either pyridine or quinoline ring, as α-substituent, with six sorts of reagent such as SO₂, P (OPh) ₃, PO (OPh) ₃, were examined. The observation that the deoxygenation and the rearrangement reaction of these nitrones were competitive each other confirmed the conclusion that-I effect of the heteroaromatic ring was responsible for deoxygenation and that +M effect of Noxide group might cause rearrangement.

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Nitroue group B and tertiary amine oxides were found to be deoxygenated by carbon disulfide and some of the nitrones were rearranged by the carbonyl sulfide secon dary formed.

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Examination of various compounds effective aginst lung worm parasitic to swine and a great problem in dairy industry showed that copper DL-methionine is an effective agent, both from fundamental experiments and clinical test, and has little toxicity. In the present series of experiment, in vitro culture of the lung worms was attempted and anthelmintic effect of various compounds was tested by this in vitro culture, Copper (II) ion was found to be specifically effective. Copper (II) i on is absorbed through the digestive tract of the worm to become toxic and is not absorbed through the body surface. Effect of copper (II) i on is lowering of respiration and one of its reasons was thought to be the marked inhibition of succinic dehydrogenase action of the worms.
The lung worm lives in the swine lung rich with oxygen and its oxygen consumption is great so that its inhibition proves lethal to the worm.

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Derivetives of 1, 1-bis (2-chloroethyl) hydrazine, especially of amino acid hydrazine type, were prepared for the purpose of testing their latent antitumor activity.

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Compound G, a metabolite of Oospora saslphurea-ochracea v. Beyma, was shown to be desmethylsulochrin (I, R¹:R²:R⁴:H, R³:CH₃).

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When 3, 6-dichloropyridazine and 3-alkoxy-6-chloropyridazines were oxidized with monoperphthalic acid or hydrogen peroxide-glacial acetic acid, the corresponding Noxides were produced. With the latter reagent, however, 6-substituted-3(2H)-pyridazinones gave rise to byproducts. The N-oxidation of 3-alkoxy-6-chloropyridazines was shown to take place at the 1-position of the molecules. By catalytic dehalogenation, several 3-alkoxypyridazine 1-oxides were also prepared.

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