Studies on Vitamin B_1 and Related Compounds. CIX. A Novel Cleavage of Thiamin and Its Homologues by the Reaction with Aromatic Aldehydes
スポンサーリンク
概要
- 論文の詳細を見る
A novel cleavage reaction of thiamin to give 4-amino-2,5-dimethylpyrimidine (III) and 2-benzoyl-5-(2-hydroxyethyl)-4-methylthiazole (IV) has been discovered. The reaction involves the treatment of thiamin chloride hydrochloride (I) with two mole equivalents of triethylamine and an excess of benzaldehyde in methanol. The finding was further extended to the reactions of thiamin and its homologs with a variety of aromatic aldehydes to give several new 2-acylthiazoles. The pyrimidine moiety of thiamin was indispensable for these reactions. On the other hand, the reaction of thiamin with cinnamaldehyde gave 2,9a-dimethyl-9-(2-hydroxyethyl)-7-(3-methoxy-3-phenylpropionyl)-5,9,9a, -10-tetrahydro-7H-pyrimido [4,5-d] thiazolo [3,4-a] pyrimidine (XV).
- 社団法人日本薬学会の論文
- 1970-03-25
著者
-
岸本 彰二
Pharmaceutical Research Laboratories Iii Takeda Chemical Industries Ltd.
-
岸本 彰二
Chemistry Research Laboratories, Takeda Chemical Industries, Ltd.
-
岡 良和
Chemical Research Laboratories, Research and Development Division, Takeda Chemical Industries, Ltd.
-
平野 弘
Chemical Research Laboratories, Research and Development Division, Takeda Chemical Industries, Ltd.
-
岸本 彰二
Pharmaceutical Research Laboratories Iii Pharmaceutical Research Division Takeda Chemical Industries
-
岡 良和
Chemical Research Laboratories Research And Development Division Takeda Chemical Industries Ltd.
-
平野 弘
Chemical Research Laboratories Central Research Division Takeda Chemical Industries Ltd.
-
平野 弘
Chemical Research Laboratories Research And Development Division Takeda Chemical Industries Ltd.
関連論文
- Chemical Modification of Fumagillin. III. Modification of the Spiro-epoxide
- Chemical Modification of Fumagillin. II. 6-Amino-6-deoxyfumagillol and Its Derivatives
- Chemical Modification of Fumagillin. I. 6-O-Acyl, 6-O-Sulfonyl, 6-O-Alkyl, and 6-O-(N-Substituted-carbamoyl)fumagillols
- Synthesis of Carumonam (AMA-1080) and a Related Compound Starting from (2R, 3R)-Epoxysuccinic Acid
- Chemical Modification of Sulfazecin. Synthesis of 4-Methoxycarbonyl-2-azetidinone-1-sulfonic Acid Derivatives
- 1-Indancarboxylic Acids. V. Syntheses of Phenoxy- and (2-Thienylcarbonyl)-1-indancarboxylic Acids, New Antiinflammatory Agents
- 1-Indancarboxylic Acids. IV. A Convenient Synthesis of Antiinflammatory 4-Aroyl-1-indancarboxylic Acids and Their Absolute Configurations
- 1-Indancarboxylic Acids. I. Electrophilic Substitution Reactions of 1-Indancarboxylic Acid and Synthesis of 6-Substituted 1-Indancarboxylic Acids as Potential Antiinflammatory Agents
- Synthesis and Reaction of 1-(N, N-Disubstituted amino) pyrazoles
- Potential Antiinflammatory Agents. V. Synthesis of Metabolites of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) using Microbiological Hydroxylation
- Potential Antiinflammatory Agents. IV. Stereoselective Synthesis of 6-Chloro-5-(3'- and 4'-hydroxycyclohexyl) indan-1-carboxylic Acids related to Metabolites of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284)
- Potential Antiinflammatory Agents. III. Syntheses of 1-Substituted 6-Chloro-5-cyclohexylindans as Related Compounds of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284)
- Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids
- 6-Chloro-5-cyclohexylindan-l-carboxylic Acid (TAI-284), a New Antiinflammatory Agent
- Studies on Vitamin B_1 and Related Compounds. CX. Rearrangements of α-Hydroxybenzylthiamin and Its Homologues
- Studies on Vitamin B_1 and Related Compounds. CIX. A Novel Cleavage of Thiamin and Its Homologues by the Reaction with Aromatic Aldehydes
- Decomposition of Thiamine in Alcohol Solution. I
- 14.アルコール類によるThiamineの分解反応(1)(ビタミンB研究委員会 : 第212回会議研究発表要旨)
- Studies on Vitamin B_1 and Related Compounds.CVII.Synthesis of Hydroxyethylthiamine Homologs
- Studies on Vitamin B_1 and Related Compounds. CVI. A Novel Synthesis of Hydroxyethylthiamine
- 1.Thiamine anhydrideの幾何異性体(ビタミンB研究委員会 第187回会議研究発表要旨)
- Synthesis and Human Immunodeficiency Virus (HIV)-1 Protease Inhibitory Activity of Tripeptide Analogues Containing a Dioxoethylene Moiety
- Synthesis and Biological Activity of (S)-2-Amino-3-(2,5-dihydro-5-oxo-4-isoxazolyl)propanoic Acid (TAN-950 A) Derivatives
- 含窒素複素環式化合物の合成研究-29-Furo〔2,3-d〕pyridazine誘導体の合成
- Decomposition of Thiamine in Alcohol Solution. II
- 7.チアゾール核2位置換ビタミンB_1誘導体(III)(第159回会議研究発表要旨)
- 11.チアゾール核2位置換ビタミンB_1誘導体(V) : ビタミンB_1の芳香族アルデヒドによる分解反応(第166回会議研究発表要旨)
- 1.Thiamine disulfideと亜硫酸との反応(第165回会議研究発表要旨)
- 20.チアゾール核2位置換ビタミンB_1誘導体(第160回会議研究発表要旨)
- 13.チアゾール核2位置換ビタミンB_1誘導体(II)Dihydrothiamine誘導体(第155回会議研究発表要旨)
- Design and Synthesis of N-[N-[(S)-1-Ethoxycarbonyl-3-phenylprolyl]-L-alanyl]-N-(indan-2-yl)glycine (CV-3317), a New, Potent Angiotensin Converting Enzyme Inhibitor
- Synthesis of 3-Aryl-6-aminocyclohex-2-enol Derivatives
- 3. HydroxyethylthiamineからThiochromeの生成する反応(ビタミンB研究委員会第200回会議研究発表要旨)
- 1.Thiamine tert-alkyldisulfideのS-Oxide誘導体の合成(ビタミンB研究委員会 第192回会議研究発表要旨)
- 89.S-AcylthiamineとImidazolideの反応(一般研究発表要旨)
- 12.チアゾール核2位置換ビタミンB_1誘導体(I) : Hydroxyethylthiamine関連化合物(第155回会議研究発表要旨)
- Thiol型Thiamine新誘導体の合成と反応(第2報)
- Thiol型Thiamine新誘導体の合成と反応(第1報)
- 1.アルコールによるThiamineの分解反応(続報)(ビタミンB研究委員会 : 第213回会議研究発表要旨)
- チアミンとα-ハロカルボニル化合物との反応(ビタミンB研究委員会 : 第205回会議研究発表要旨)