Purines. XLII. : Synthesis and Glycosidic Hydrolysis of 7-Alkyladenosines Leading to an Alternative Synthesis of 7-Alkyladenines
スポンサーリンク
概要
- 論文の詳細を見る
A full account is given of the synthesis and glycosidic hydrolysis of 7-alkyladenosines (4), which established an alternative synthesis of 7-alkyladenines (11). Methylation of N^6-methoxyadenosine(5)with MeI in AcNMe_2 at 30℃ for 8h gave N^6-methoxy-7-methyladenosine, which was isolated in the form of the sulfate [7a (X=1/2SO_4)] in 55% yield. N^6-Methoxy-N^6-methyladenosine (9a) was a by-product in this methylation. Demethoxylation of 7a (X=1/2SO_4)by catalytic hydrogenolysis using hydrogen and Raney Ni catalyst produced, after replacement of the anion with perchlorate ion, 7-methyladenosine perchlorate [4a (X=ClO_4)] in a pure and crystalline form. 7-Ethyladenosine perchlorate [4b (X=ClO_4)] was also synthesized from N^6-benzyloxyadenosine (6) through a parallel route via N^6-benzyloxy-7-ethyladenosine sulfate [8b (X=1/2SO_4)]. On treatment with H_2O at 98-100℃ for 40 min, 4a (X=ClO_4) and 4b (X=ClO_4) furnished 7-methyladenine (11a) and 7-ethyladenine (11b) in 84% and 55% yields, respectively. Similar hydrolyses of 7a (X=ClO_4) and 8b (X=1/2SO_4) gave N^6-methoxy-7-methyladenine (12a) and N^6-benzyloxy-7-ethyladenine (12b), respectively. Catalytic hydrogenolysis of 12b using hydrogen and Raney Ni catalyst afforded 11b in 82% yield. In 0.1 N aqueous HCl at 25℃, 4a (X=ClO_4) and 4b (X=ClO_4) were found to undergo glycosidic hydrolysis at rates of 2.22×10^<-3> min^<-1> (half-life 5.2h) and 1.69×10^<-3> min^<-1> (half-life 6.8h), respectively. Comparison of these rate constants with those of the other three N^X-methyladenosines (1-3) has revealed that the ease with which depurinylation occurs decreased in going through the series 3-(2)>7-(4a)≫N^6-(3)≥1-methyladenosine (1). On treatment with 1 N aqueous NaOH at 60℃ for 3h, 4a (X=ClO_4) was hydrolyzed to give 11a in 44% yield.
- 公益社団法人日本薬学会の論文
- 1990-07-25
著者
-
斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
-
藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
-
藤井 澄三
Shinshu Univ. Nagano Jpn
関連論文
- Lactams. XIII. Alkylation of Lactim Ethers : A Novel Synthetic Route to N-(2-Arylethyl) lactams from N-Unsubstituted Lactams
- Purines. LXX. An Extension of the "Phenacylamine Route" to the Syntheses of the 7-N-Oxides of 6-Mercaptopurine and 6-Methylthiopurine, and Antileukemic Activity of Some Purine N-Oxides
- Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
- Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
- Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
- Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
- Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
- Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
- Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
- 2-(3-Pyridyl)thiazolidine-4-carboxamide Derivatives. II. Structure-Activity Relationships and Active Configuration of 2-(3-Pyridyl)thiazolidine-4-carboxamides as Platelet-Activating Factor Receptor Antagonists
- 2-(3-Pyridyl)thiazolidine-4-carboxamides. 1. Novel Orally Active Antagonists of Platelet-Activating Factor (PAF)
- Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines
- Involvement of a Cytochrome P4502D Subfamily in Human Liver Microsomal Bunitrolol 4-Hydroxylation
- Lactams. VII. Stereochemical Characterization and Cis-Trans Isomerization of 5-Ethyl-2-oxo-4-piperidineacetic Acid and Related Compounds
- Synthesis and Biological Activity of the Metabolites of N-[2-(1-Azabicyclo[3.3.0]octan-5-yl)ethyl]-2-nitroaniline Fumarate (SK-946)
- Synthesis of (1-Azabicyclo[3.3.0]octanyl)methyl-Substituted Aromatic Heterocycles and Their Muscarinic Activity
- Lactams. XVII. Synthesis and Stereochemical Characterization of Diethyl cis-and trans-5-Ethyl-2-oxo-4-piperidinemalonate
- Synthesis and Thromboxane A_2 Antagonistic Activity of [[1-Aryl(or Benzyl)-1-(benzenesulfonamide)methyl]phenyl]alkanoic Acid Derivatives
- Quinolizidines. XXVI. : A Synthesis of (±)-Deplancheine
- Laxative and Anti-diarrheal Activity of Polycarbophil in Mice and Rats
- An Improved Synthesis of Butyl 4-[(4-Amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224)
- Synthesis and Gastrointestinal Prokinetic Activity of Novel Benzamide Derivatives with Amphoteric Side Chains
- Calcium Polycarbophil, a Water Absorbing Polymer, Increases Bowel Movement and Prevents Sennoside-Induced Diarrhea in Dogs
- Purines. XLI. : An Alternative Synthesis and the Chemical Behavior of 7,9-Dialkyladeninium Salts
- Purines. XXXVIII. A General Synthesis of 7,9-Dialkyladeninium Salts from 9-Alkyladenines by Regioselective Alkylation : Utilization of an N^6-Alkoxy Group as a Control Synthon
- Purines. XXX. : Ring Fission of 3,7-Dialkyladenines by Alkaline Hydrolysis
- Purines. XXVIII. Preparation of Some 3,7-Dialkyladenines from 3-Alkyladenines by Alkylation : A Subordinate Formation of 3,9-Dialkyladenines
- Purines. XXI. Synthesis of Adenine 1-Oxides Carrying an Allylic Side Chain at the 9-Position
- Lactams. XX. Decarboxylation of Unsaturated Acids incorporated into Six-Membered Lactam Systems
- Decalcification of Calcium Polycarbophil in Rats
- Structure-Activity Relationship(SAR)Studies on Oxazolidinone Antibacterial Agents.1. Conversion of 5-Substituent on Oxazolidinone
- Lactams. VIII. The Alkaline Ferricyanide Oxidation of 3-Substituted 1-(3,4-Dimethoxyphenethyl) pyridinium Salts : Effects of Hydrocarbon Substituents on Orientation of the Oxidation
- Lactams. VI. Synthesis and Nuclear Magnetic Resonance Study of 1-Aralkyl-3-methyl- and -5-methyl-2(1H)-pyridones
- Cytotoxicity of Organochlorine Pesticides and Lipid Peroxidation in Isolated Rat Hepatocytes
- Cytotoxicity of Organochlorine Pesticides and Lipid Peroxidation in Rat Hepatocytes (Proceedings of the 22nd Symposium on Toxicology and Environmental Health)
- Cytotoxicity of Paraquat and Phospholipid Peroxidation in Rat Hepatocytes (Proceedings of the 21st Symposium on Toxicology and Environmental Health)
- Cytotoxicity of Halogenated Hydrocarbons and Cellular Phospholipid Peroxidation in Isolated Rat Hepatocytes (Proceedings of the 20th Symposium on Toxicology and Environmental Health)
- ゼアチンおよび N^6- イソペンテニルアデニンの 1'- メチル誘導体とそれらのリボヌクレオシド体のレタス種子発芽におけるサイトカイニン活性について(A. 理学)
- Characterization of the Neurochemical Effects of N-[2-(1-azabicyclo[3,3,0]octan-5-yl)ethyl]2-nitroaniline fumarate (SK-946) as a Cognition Activator
- P-3 海綿由来アデニン環含有ジテルペノイドの合成研究 : (±)-Agelasimine-Aおよび(±)-Agelasimine-Bの合成(ポスター発表の部)
- Purines. LXV. Preparatory study for the syntheses of the marine sponge purines agelasimines-A and -B: Synthesis and acetylation of their N(7)-benzyl analogues
- Purines. LXIV. Syntheses of 9-Methyl-2-azaadenine 1-Oxide, Its O-Methyl Derivative, and 1-Substituted 5-Azidoimidazole-4-carboxamides
- Purines. LXIII. Syntheses of Azepinomycin, an Antitumor Antibiotic from Streptomyces Species, and Its 3-β-D-Ribofuranodise and Their 8-Imino Analogues
- Purines. LXI. An Attempted Synthesis of 2'-Deoxy-7-methyladenosine : Glycosidic Hydrolyses of the N^6-Methoxy Derivative and 2'-Deoxy N^x-methyladenosines
- Purines. LIX. An Alternative Synthesis of 7-Alkyl-1-methyladenines by Regioselective Alkylation, Fission, and Reclosure of the Adenine Ring
- Purines. LVIII. A Synthesis of 7-Alkyl-1-methyladenines from Adenosine by Regioselective Alkylation : Uilization of a 1-Methoxy Group as a Control Synthon
- Purines. LVII. Regioselective Alkylation of N^6,9-Disubstituted 8-Oxoadenines : Syntheses of the Sea Anemone Purine Caissarone and Some Positional Isomers and Analogues
- Purines. LIV. Intramolecular Cyclization of 9-Ethyl-1-(2-hydroxyethyl)adenine Caused by Nucleophiles : Formation of N^6,1-Ethanoadenine Derivatives
- Purines. LIII. Deamination of 1-(ω-Hydroxyalkyl)adenine Derivatives by Nucleophiles
- Purines. XLIX. Synthesis and Proton Nuclear Magnetic Resonance Study of 3,7-Dialkylxanthines and 1,3,7-Trialkylxanthines
- Purines. XLVIII. Syntheses and Proton Nuclear Magnetic Resonance Study of 2-Deuterioadenines Substituted or Unsubstituted at the 9-Position and of Their N-Oxygenated Derivatives
- Purines. XLVI. Preparation of 1-Ethyladenine from Adenosine
- Immunoliposome-Mediated Gene Transfer into Cultured Myotubes
- Examination of Local Anti-inflammatory Activities of New Steroids, Hemisuccinyl Methyl Glycolates
- Application of Sweet Potato Fiber to Skin Wound in Rat
- Gastroprokinetic Effect of a New Benzamide Derivative Itopride and Its Action Mechanisms in Conscious Dogs
- Synthesis of 5-(Alkylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamides : Key Intermediates for the Synthesis of 3-Alkyl-9-β-D-ribofuranosylpurine Derivatives
- Purines. XXXII. : Synthesis and Ring Fission of 3,9-Dialkyladenines
- Purines. XXV. Fission and Reclosure of the Adenine Ring by the Use of Modified Benzyloxy Groups at the 1-Position
- Purines. XXII. Methylation of 1-, 3-, 7-, 9-, and N^6-Methyladenines Bearing a Methoxyl Group at the N^6-Position : A Synthesis of 7,9-Dimethyladenine
- Purines. XX. Synthesis of 1-Substituted 5-Aminoimidazole-4-carboxamidines and Related Compounds
- Modification by Fluoride, Bromide, Iodide, Thiocyanate and Nitrite Anions of Reaction of a Myeloperoxidase-H_2O_2-Cl^- System with Nucleosides
- Effects of Fluvastatin and Its Major Metabolites on Low-Density Lipoprotein Oxidation and Cholesterol Esterification in Macrophages
- Fluvastatin, an HMG-CoA Reductase Inhibitor, Protects LDL from Oxidative Modification in Hypercholesterolemic Rabbits
- In Vitro Inhibitory Effects of the Optical Isomers and Metabolites of Fluvastatin on Copper Ion-Induced LDL Oxidation
- An in Vitro Study of the Hydroxyl Radical Scavengin Property of Fluvastatin, and HMG-CoA Reductase Inhibitor
- 2-(3-Pyridyl)thiazolidine-4-carboxamide Derivatives. III. Synthesis of Metabolites and Metabolism of 2-(3-Pyridyl)thiazolidine-4-carboxamides YM461 and YM264 as Platelet-Activating Factor (PAF) Receptor Antagonists
- Purines. XLVII. Dimroth Rearrangement versus Hydrolytic Deamination of 1-Ethyladenine
- Synthesis of [[(Benzenesulfonamido)alkyl]phenyl]alkanoic Acid Derivatives Containing Pyridyl or Imidazolyl Groups and Their Thromboxane A_2 Receptor Antagonistic and Thromboxane A_2 Synthase Inhibitory Activities
- Synthesis of the Selective 5-Hydroxytryptamine 4 (5-HT_4) Receptor Agonist (+)-(S)-2-Chloro-5-methoxy-4-[5-(2-piperidylmethyl)-1,2,4-oxadiazol-3-yl]aniline
- Intramolecular Oxymercuration with Mercuric Triflate
- Mercuric Triflate-TMU Catalyzed Hydration of Terminal Alkyne to give Methyl Ketone under Mild Conditions
- Effects of N-[2-(1-Azabicyclo[3,3,0]octan-5-yl)ethyl]2-nitroaniline Fumarate (SK-946), a Novel Cognition Activator, on Learning and Memory in Rodent Models
- Novel 5-Hydroxytryptamine 4 (5-HT_4) Receptor Agonists. Synthesis and Gastroprokinetic Activity of 4-Amino-N-[2-(1-aminocycloalkan-1-yl)ethyl]-5-chloro-2-methoxybenzamides
- Purines. XXXVII. : Synthesis and Reduction of 3,9-Diallkyladenine Salts Deuterated at the 2-Position : Their Use in the Proton Nuclear Magnetic Resonance Study of Isotopically Unmodified Species
- Purines.XXXIX. : The Crystal Structure of 9-Benzyl-N^6-methoxyadenine
- Purines. XXXI. : An X-Ray Crystallographic Structure Analysis of 3-Methyladenosine p-Toluenesulfonate
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. Synthesis and Structure-Activity Relationships of 9-Methyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-4-one Derivatives
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. IV. Synthesis and Pharmacological Evaluation of the Oxidation Products of (-)-(R)-5-[(1-Methyl-1H-indol-3-yl)carbonyl]-4,5,6,7-tetrahydro-1H-benzimidazole Hydrochloride (YM060 : Ramosetron)
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. III. Pharmacological Evaluations and Molecular Modeling Studies of Optically Active 4,5,6,7-Tetrahydro-1H-benzimidazole Derivatives
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. II. Synthesis and Structure-Activity Relationships of 4,5,6,7-Tetrahydro-1H-benzimidazole Derivatives
- Novel 5-Hydroxytryptamine (5-HT_3) Receptor Antagonists. I. Synthesis and Structure-Activity Relationships of Conformationally Restricted Fused Imidazole Derivatives
- Purines. XLIV. : A Kinetic Study of the Dimroth Rearrangement of the Marine Sponge Purine 1,9-Dimethyl-8-oxoadenine and Related Compounds
- Purines. XLIII. : A Total Synthesis of the Marine Sponge Base 6-Imino-1,9-dimethyl-8-oxopurine
- 53 桿菌tRNA構成成分,7-Methyladenosineの合成と加水分解(口頭発表の部)
- Purines. XLII. : Synthesis and Glycosidic Hydrolysis of 7-Alkyladenosines Leading to an Alternative Synthesis of 7-Alkyladenines
- Purines. XL. : Preparation of 9-(ω-Carboxyalkyl)-3-methyladenines
- Purines. XXXVI. : Fission and Reclosure of the Adenine Ring in 3,9-Disubstituted Adenines : Effects of Substituents
- Purines. XXXIV. : 3-Methyladenosine and 3-Methyl-2'-deoxyadenosine : Their Synthesis, Glycosidic Hydrolysis, and Ring Fission
- A General and Convenient Synthesis of 7-Alkyladenines from Adenine by Regioselective Alkylation Utilizing Blocking/Deblocking at the 3-Position
- Purines. XXVII. : Hydrolytic Deamination versus Dimroth Rearrangement in the 9-Substituted Adenine Ring : Effect of an ω-Hydroxyalkyl Group at the 1-Position
- Purines. XXVI. The Dimroth Rearrangement of 9-Substituted 1-Methyladenines : Accelerating Effect of a β-D-Ribofuranosyl Group at the 9-Position
- Purines. XXIV. Methylation of N^6-Alkoxyadenines and N^6-Methyladenine
- Purines. XXIII. Synthesis of N^6-Alkoxy-1,3-dialkyladeninium Salts and an Attempt to Synthesize 1,3-Dimethyladenine
- Purines. XIII. Ring Opening of 3-Alkyladenines with Carbobenzoxy Chloride : Transformation into 8-Hydroxylated Adenines
- Purines. X. A Convenient Method for Synthesis of 2', 3'-O-Isopropylidene-adenosine 1-Oxide
- Purines. XVIII. Kinetic Studies of the Dimroth Rearrangement of 1-Alkoxy-9-methyladenines and 1-Benzyloxyadenosine : Effect of 1-Benzyloxy and 9-β-D-Ribofuranosyl Groups on the Rates of the Ring-opening and the Reclosure
- Effect of a Novel Non-steroidal Anti-inflammatory Drug (M-5011) on Cytokine Levels in Rats With Monosodium Urate Crystal-Induced Pleurisy
- Purines. XI. The Synthesis of N-Alkoxyadenosines and Their 2', 3'-O-Isopropylidene Derivatives
- Cytotoxicity of Chlorinated Hydrocarbons and Lipid Peroxidation in Isolated Rat Hepatocytes (Proceedings of the 19th Symposium on Toxicology and Environmental Health)