Studies on Antibiotics and Related Substances. X. Syntheses of Some Unsaturated Ketocarboxylic Acids, Anti-tumor Substances
スポンサーリンク
概要
- 論文の詳細を見る
1) 2-(Dimethylaminomethyl)-3-ketobutane-1-carboxylic acid hydrochloride (VI) as well as 5-dimethylamino-3-ketopentane-1-carboxylic acid hydrochloride (I) has been obtained from levulinic acid, paraformaldehyde and dimethylamine hydrochloride by means of the Mannich reaction. Thermal degradation of I and VI afforded δ-methylenelevulinic acid (IV) and β-methylenelevulinic acid (VII), respectively.<BR>2) 3-(Dimethylaminomethyl)-4-ketopentane-1-carboxylic acid hydrochloride (XII) as well as 6-dimethylamino-4-ketohexane-1-carboxylie acid hydrochloride (VIII) has been obtained from 5-ketocaproic acid, paraformaldehyde and dimethylamine hydrochloride by means of the Mannich reaction. Thermal degradation of XII and VIII afforded 4-keto-5-hexene-1-carboxylic acid (XI) and 4-keto-3-methylene-pentane-1-carboxylie acid (XIII), respectively.<BR>3) The structures of IV, VII, XI and XIII have been proven.<BR>4) Some derivatives of above-mentioned carboxylic acids have been described.<BR>5) It has been found that IV, VII, XI and XIII possess significant antitumor and antibacterial activites; especially calcium salt of 4-keto-5-hexene-1-carboxylic acid (XI) gave an excellent result in animal experiments.
- 社団法人 日本化学会の論文
著者
-
Umezawa Sumio
Department of Applied Chemistry Faculty of Engineering Keio University
-
Kinoshita M.
Department of Chemistry Faculty of Science The University of Tokyo
-
Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
-
Umezawa Sumio
Department of Applied Chemistry Engineering Faculty of Keio University
-
Umezawa Sumio
Department of Applied Chemistry Engineering Faculty Keio University
関連論文
- Studies on Antibiotics and Related Substances. XV. Syntheses of Acetobromo Derivatives of 3-Amino-3-deoxyglucose and 6-Amino-6-deoxyglucose
- The Absorption Spectra of the Molecular Complexes of Aromatic Compounds with p-Bromanil
- Studies on Antibiotics and Related Substances. XVIII. The Synthesis of 5-Methyl-2-methylenecyclopentanone-3-carboxylic Acid, an Antitumor Substance, and Related Mannich Bases
- Studies on Antibiotics and Related Substances. X. Syntheses of Some Unsaturated Ketocarboxylic Acids, Anti-tumor Substances
- Studies on Antibiotics and Related Substances. XIII. Syntheses of 10-Methylene-11-oxododecanoic Acid and 9-Methylene-10-oxoundecanoic Acid, Antitumor Substances
- Studies on Antibiotics and Related Substances. XVII. Syntheses of trans-2-Aminocyclohexyl-D-glucosaminides
- Studies on Antibiotics and Related Substances. XI. Methylated Amino-sugar Moieties from Methylated Kanamycin
- Studies on Antibiotics and Related Substances. XIV. Synthesis of trans-2-Aminocyclohexyl-D-glucosaminide
- Synthesis of Di-N-acetyl-di-N-benzyloxycarbonyl-O-cyclohexylidenestreptidine
- Synthetic studies of amphotericin B. III. An enantiospecific synthesis of the C-1-C-19 segment of the amphotericin B aglycon.
- Total synthesis of aminoglycoside antibiotics, apramycin and saccharocin (KA-5685).
- Synthetic approach to 2,3,5-triamino-2,3,5-trideoxy-D-arabonic acid derivatives from 3,4,6-triazido-3,4,6-trideoxy-1,2-O-isopropylidene-.ALPHA.-D-glucopyranose.
- Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins.
- Syntheses of (3S, 4R, 15S)-4,15-Dimethyl-1,5-dioxa-3-(3′-formamidosalicylamido)-cyclopentadecane-2,6-dione and Its (15R)-Epimer, New Antimycin Analogs
- Total synthesis of a macrocyclic lactone antibiotic A26771B and its isomers using carbohydrates.
- Studies on Aminosugars. XXXVI. Syntheses of 3′,4′-Dideoxy-and 3′,4′,5″-Trideoxyribostamycin
- A novel synthesis of a branched-chain amino sugar, methyl 2-amino-2,3-dideoxy-3-C-formyl-.ALPHA.-D-xylofuranoside-3'R,5-hemiacetal.
- Synthetic studies of rifamycins. III. The partial synthesis of rifamycin ansa-chain compounds from their degradation products.
- Synthetic studies of rifamycins. IV. The synthesis of rifamycin ansa-chain compound using carbohydrate.
- Synthesis of 6′-Amino-1-N-[(S)-4-Amino-2-Hydroxybutyryl]-6′-Deoxylividomycin A
- Studies on Aminosugars. XXXV. Syntheses of 3′,4′-Dideoxyneamine and 3′- and 4′-O-Methylneamines
- Studies on Aminosugars. XXIX. Syntheses of Nucleosides of 3-Amino-3-deoxy-3-C-hydroxymethyl-β-D-ribofuranose
- Synthesis of Butirosin B and Its 3′,4′-Dideoxy Derivative
- Synthesis of "Reversed" Nucleosides of Some Purine and Pyrimidine Bases
- Studies on Aminosugars. XXX. The Synthesis of 3′-Deoxykanamycin
- Synthesis of 6-(2-Amino-2-deoxy-β-D-glucopyranosylamino)- and 6-(β-D-Glucopyranosylamino)purine
- Synthesis of Some Nucleoside Analogs of Substituted 1,2,3-Triazole
- Total synthesis of elaiophylin (azalomycin B).
- Synthetic studies of rifamycins. II. Syntheses of methyl 2,4,6,7-tetradeoxy-4-C-methyl-3-O-METHYL-.ALPHA.-L-arabino-heptopyranosid-6-ulose and its derivatives utilizable in the construction of the rifamycin ansa chain portion.
- Studies on Aminosugars. XXXI. Synthesis of 3,4-Dideoxy-3-enosides and the Corresponding 3,4-Dideoxysugars
- Synthetic studies of rifamycins. VIII. An improved practical synthesis of the ansa-chain compounds for the rifamycin W synthesis.
- Synthesis of Cyclic α-Amino Acids. IV. Syntheses of Adenine Nucleosides of 3-Amino-3-C-carboxy-3-deoxy-D-ribofuranose and 3-Amino-3-C-carboxy-3-deoxy-D-ribopyranose
- Studies on Aminosugars. XXIV. The Facile Elimination of the Derivatives of a Pyranosid-4-ulose
- An enantiospecific synthesis of the C-21-C-37 segment of the aglycon of amphotericin B.
- Synthesis of (3S, 4S)- and (3S, 4R)-4-Amino-3-hydroxy-6-methylheptanoic Acid, and Their N-(Acetyl-L-valyl-L-valyl) Derivatives
- Stereospecific Synthesis of Natural (+)Blastmycinone and Its Three (2R)-Diastereomers
- Synthetic studies of erythromycins. IV. Total synthesis of erythronolide A.
- Total Syntheses of Antimycin A3 and Its Diastereomer