A New Class of Nitrosoureas. VII. Synthesis and Antitumor Activity of 3-Substituted 1-(2-Chloroethyl)-3-(methyl α-D-glucopyranosid-3-yl)-1-nitrosoureas
スポンサーリンク
概要
- 論文の詳細を見る
A series of five 3,3-disubstituted nitrosoureas having the nitrosoureido group at the C-3 position of methyl glucoside were prepared and tested for antitumor activities. Heating of methyl 2,3-anhydro-α-D-allopyranoside (I) with various alkylamines followed by reaction with 2-chloroethyl isocyanate gave two regioisomers (II and III). The major product (II) and the minor product (III) were determined to be the ureido derivatives of methyl glucoside and methyl altroside, respectively. Nitrosation of II with dinitrogen tetroxide gave 3-substituted 1-(2-chloroethyl)-3-(methyl α-D-glucopyranosid-3-yl)-1-nitrosoureas (VI) in good yields. All the nitrosoureas obtained were remarkably active against leukemia L-1210 and Ehrlich ascites carcinoma. The structure-activity relationships of positional isomers with respect to the nitrosoureido group are discussed.
- 公益社団法人日本薬学会の論文
- 1982-12-25
著者
-
武田 幹男
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,
-
森川 民雄
Organic Chemistry Research Laboratory
-
辻原 健二
Research Laboratories, Tanabe Seiyaku Co., Ltd.
-
森川 民雄
Research Laboratories, Tanabe Seiyaku Co., Ltd.
-
新井 淑久
Research Laboratories, Tanabe Seiyaku Co., Ltd.
-
武田 幹男
Research Laboratories, Tanabe Seiyaku, Co., Ltd.
-
武田 幹男
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
-
新井 淑久
Research Laboratories Tanabe Seiyaku Co. Ltd.
-
辻原 健二
Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.
-
辻原 健二
Research Laboratories Tanabe Seiyaku Co. Ltd.
関連論文
- Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides : Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams
- Synthesis of C-Nor Emetine Pyman
- Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. IV. Modification of the Phenylpiperazino Moiety of 2-(Phenylpiperazino-alkoxyphenyl)thiazolidine-3-carbothloamides and the Corresponding Carboxamides(Medicinal Chemistry,Chemical)
- Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. II. 2-(Phenylpiperazinoalkoxyphenyl)thiazolidine-3-thioearboxamides and the Corresponding Carboxamides(Medicinal Chemistry,Chemical)
- A New Synthetic Route to 1,5-Benzothiazepines. Synthesis of Derivatives of Diltiazem
- Asymmetric Reduction of Aromatic Ketones. I. Enantioselective Synthesis of Denopamine
- Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents; III Optically Active Isomers of Ar-Methyl-2-(2-(2-(4-phenylpiperazino)-ethoxy)phenyl)thiazolidine-3-carboxamides(Medicinal Chemistry,Chemical)
- Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. I. 2-Phenylthiazolidine-3-thiocarboxamides(Medicinal Chemistry,Chemical)
- Synthesis of Novel Pyridotriazepinones as Antisecretory Agents(Organic,Chemical)
- Antiulcer Activity of Dehydroabietic Acid Derivatives
- A New Class of Nitrosoureas. II. Synthesis and Antitumor Activity of 1-(2-Chloroethyl)-3,3-disubstituted-1-nitrosoureas having a Glucopyranosyl, Mannopyranosyl or Galactopyranosyl Moiety
- Studies on 1,2,3,4-Tetrahydroisoquinolines. IV. β-Adrenoceptor Activity and Absolute Stereochemistry of (-)-5,7-Dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
- Studies on 1,2,3,4-Tetrahydroisoquinolines. III. Syntheses and β-Adrenoceptor Activities of Methyl Derivatives of Trimetoquinol
- Studies on Antiallergic Agents. I. Phenyl-substituted Heterocycles with a 5-Tetrazolyl or N-(5-Tetrazolyl) carbamoyl Group
- Studies on 1,2,3,4-Tetrahydroisoquinolines. VI. Reutilization of the Unwanted (R)-Isomer of (S)-(-)-5,7-Dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (TA-073)
- Studies on 1,2,3,4-Tetrahydroisoquinolines. V. A Convenient Synthesis of (±)-5,7-Dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (Racemic TA-073)
- Synthesis of the Metabolites of Clentiazem
- Asymmetric Reduction of Aromatic Ketones. II. An Enantioselective Synthesis of Methyl (2R, 3S)-3-(4-Methoxyphenyl)glycidate
- Synthesis of the Optically Active trans-Isomers of Diltiazem and Their Cardiovascular Effects and Ca-Antagonistic Activity
- Synthesis of N-Substituted C-Normorphinans and Their Pharmacological Properties
- Reactions of 3-Phenylglycidic Esters. V. Reaction of Methyl 3-(4-Methoxyphenyl) glycidate with 2-Nitroaniline and Synthesis of 1,5-Benzodiazepine Derivatives
- Reaction of 3-Phenylglycidic Esters. III. Reaction of cis-3-Arylglycidic Esters with Various Thiophenols
- Reaction of 3-Phenylglycidic Esters. IV. Reaction of Methyl 3-(4-Methoxyphenyl) glycidate with 2-Nitrophenol and Synthesis of 1,5-Benzoxazepine Derivatives
- A New Class of Nitrosoureas. IX. Synthesis and Antitumor Activity of 3-Substituted 1-(2-Chloroethyl)-3-(methyl α-D-glucopyranosid-6-yl or methyl 2-acetamido-2-deoxy-α-D-glucopyranosid-6-yl)-1-nitrosoureas
- A New Class of Nitrosoureas. VIII. Synthesis and Antitumor Activity of 3-Substituted 1-(2-Chloroethyl)-3-(trans-2-hydroxy-cyclohexyl)-1-nitrosoureas
- Azabicycloalkanes as Analgetics. I. Synthesis of 1-Phenyl-6-azabicyclo [3,2,1] octane Derivatives
- A New Class of Nitrosoureas. III. Synthesis and Antitumor Activity of 3,3-Disubstituted-1-(2-chloroethyl)-1-nitrosoureas having an Arabinopyranosyl, Xylopyranosyl or Ribopyranosyl Moiety
- Azabicycloalkanes as Analgetics. VII. 1-Phenyl-3-azabicyclo [3. 3. 1] nonanes
- Azabicycloalkanes as Analgetics. VI. 5-Phenyl-2-azabicyclo [3,2,1] octanes
- Azabicycloalkanes as Analgetics. V. 4-Phenyl-2-azabicyclo [2,2,2] octanes
- Azabicycloalkanes as Analgetics. IV. 4-Phenyl-2-azabicyclo [2,2,1] heptanes
- Augmentation of Tumor Immunity by 6-Mercaptopurine (6-MP) and Its Analogs in the Double Grafted Tumor System in Mice
- Water-Soluble Antitumor Agents. I. Synthesis and Biological Activity of 6-S-Aminoacyloxymethyl Mercaptopurine Derivatives
- Azabicycloalkanes as Analgetics. II. An Improved Synthesis of 1-Phenyl-6-azabicyclo [3,2,1] octane Derivatives
- Stereoselective Reactions. V. Design of the Asymmetric Synthesis of Lignan Lactones. Synthesis of optically Active Podorhizon and Deoxypodorhizon by 1,3-Asymmetric Induction
- A New Class of Nitrosoureas. VII. Synthesis and Antitumor Activity of 3-Substituted 1-(2-Chloroethyl)-3-(methyl α-D-glucopyranosid-3-yl)-1-nitrosoureas
- 環状イミン類の新しい不斉還元剤 : 不斉水素化トリアシルオキシホウ素ナトリウム
- A New Class of Nitrosoureas. VI. Synthesis and Antitumor Activity of 3-Substituted-1-(2-chloroethyl)-3-(methyl-α-D-glucopyranosid-2-yl)-1-nitrosoureas
- A New Class of Nitrosoureas. V. Structure of Isomeric L-Arabinosylureas and Isomerization Thereof
- A New Class of Nitrosoureas. I. Synthesis and Antitumor Activity of 1-(2-Chloroethyl)-3,3-disubstituted-1-nitrosoureas having a Hydroxyl Group at the β-Position of the Substituents
- Synthesis of Bridged 2-Phenylcyclohexylamines as Potential Analgetics
- Synthesis of B/C trans-Fused Morphine Structures. VI. Mass Spectrum, Optical Rotatory Dispersion and Circular Dichroism of B/C trans-Morphine Derivatives
- Synthesis of B/C trans-Fused Morphine Structures. IV. Synthesis of B/C trans-Isomorphine
- 抗うつ剤としてのDidenzo[b, e][1,4]diazepine誘導体の合成
- Synthesis of a B/C trans-fused Morphine Structure
- 14.B/Cトランス・モルフィン環化合物の合成
- Syntheses of Morphine-like Structures. IV. Further Studies on Addition of Borane to 9-Methylenebenzomorphan
- Syntheses of Morphin-like Structures. III. Stereochemical Control of Addition of Borane to 9-Methylenebenzomorphan
- Syntheses of Morphine-like Structures. II. 2'-Methoxy-9-hydroxymethyl-2,5-dimethyl-6,7-benzomorphan
- Syntheses of Morphine-like Structures. I. 9-Hydroxymethyl-2,5-dimethyl-6,7-benzomorphan.
- Studies on Benzoisogranatanine Derivatives. II. Synthesis of 1-Phenethyl-2,4-propano-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines.
- Alkylsulfonyltoluene Derivatives (Diuretics. II.).
- Alkylsulfonyltoluene Derivatives (Diuretics. I.).
- N-置換スルホニルジアミドの塩基性加水分解