Purines. IXXVII. An Alternative Synthesis of N^6-Demethylcaissarone from 9-Methyl-8-oxoadenine by Regioselective N(3)-Methylation : Utilization of the N(7)-Benzyl and N(1)-Benzyloxy Groups as Control Synthons

スポンサーリンク

概要

• 論文の詳細を見る

• An alternative synthesis of 3,9-dimethyl-8-oxoadenine (N^6-demethylcaissarone) hydrochloride (5a・HCl) starting from 9-methyl-8-oxoadenine (17) is described. The synthesis proceeded through N(7)-benzylation, N(1)-oxidation, and O-benzylation to afford the 1-benzyloxy derivative 25,which afforded the ring-opened formamide derivative 26 on treatment with dilute aqueous NaOH. Methylation of the monocycle 26 with MeI in the presence of K_2CO_3,followed by acid-catalyzed cyclization and subsequent catalytic hydrogenolysis afforded 5a・HCl. The key intermediate 25 was alternatively prepared from 17 by N-oxidation and subsequent O, N(7)-dibenzylation with PhCH_2Br in the presence of K_2CO_3.

• 公益社団法人日本薬学会の論文
• 1997-10-15

著者

• 藤井 澄三

  金沢大学薬学部

• Itaya T

  Faculty Of Pharmaceutical Sciences Kanazawa University

• ITAYA Taisuke

  Faculty of Pharmaceutical Sciences, Kanazawa University

• KANAI Tae

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Kanai T

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Kanai Tae

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Itaya Taisuke

  Faculty Of Pharmaceutical Sciences Kanazawa University

• HOZUMI Yoshitaka

  Faculty of Pharmaceutical Sciences, Kanazawa University

• TAKADA Yasutaka

  Faculty of Pharmaceutical Sciences, Kanazawa University

• FUJII Tozo

  Faculty of Pharmaceutical Sciences, Kanazawa University

• SHIMADA Mayumi

  Faculty of Pharmaceutical Sciences, Kanazawa University

• NISHIKAWA Toshiko

  Faculty of Pharmaceutical Sciences, Kanazawa University

• MORI Shigeji

  Faculty of Pharmaceutical Sciences, Kanazawa University

• SAITO Tohru

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Fujii Tozo

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Mori S

  Fukushima Medical Coll. Fukushima Jpn

• Shimada Mayumi

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Takada Y

  Rikkyo Univ. Tokyo Jpn

• Takada Yasutaka

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

• Mori Shigeji

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Hozumi Y

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Hozumi Yoshitaka

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Nishikawa Toshiko

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Saito Tohru

  Faculty Of Pharmaceutical Sciences Kanazawa University

関連論文

• 天然含窒素複素環の化学(その2)プリン塩基・ヌクレオシドの合成と反応
• 天然含窒素複素環の化学(その1)数種の植物に出現するBenzo[α]quinolizidine環系及びIndolo[2,3-α]quinolizidine環系アルカロイドの合成と構造決定
• 含窒素複素環の化学 : 私の40年
• 日本薬学会教育賞受賞笹本光雄氏の業績
• 日本薬学会学術賞紹介 日野亨氏の業績
• 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
• Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines
• Variable glyceryl dinitrate formation as a function of glutathione S-transferase.
• Variable Glyceryl Dinitrate Formation as a Function of Glutathione S-Transferase
• Quinolizidines. XXVI. : A Synthesis of (±)-Deplancheine
• 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
• Preparation of New Nitrogen-Bridged Heterocycles. 58. : Syntheses and Intramolecular Arene-π Interactions of 3-(Allylthio)- and 3-(Propargylthio)thieno[3,4-b]indolizine Derivatives
• Preparation of New Nitrogen-Bridged Heterocycles. 54. Increased Arene-Arene Interactions of 3-(Bicyclic and Tricyclic Arylmethylthio)thieno[3,4-b]indolizine Derivatives
• Preparation of New Nitrogen-Bridged Heterocycles. 53. Syntheses of 3-(Benzylthio)thieno[3,4-b]indolizine Derivatives and Their Intramolecular Arene-Arene Interactions
• 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)
• Purines. LXII. Both Enantiomers of N^6-(1,3-Dimetyl-2-butenyl)adenine and Their 9-β-D-Ribofuranosides : Synthesis and Cytokinin Activity
• Purines. LV. Syntheses and cytokinin activities of some adenine and adenosine derivatives related to 1'-methylzeatin
• Pourines. XLV. : Syntheses and Cytokinin Activities of the Cis Isomers of (1'R)-1'-Methylzeatin and Its 9-β-D-Ribofuranoside
• Purines. XXXV. : Synthesis and Cytokinin Activity of Racemic 1'-Methylzeatin
• Purines. XXXIII. Syntheses and Cytokinin Activities of Both Enantiomers of 1'-Methylzeatin and Their 9-β-D-Ribofuranosides
• Effects of Trimethylsilylation of Copper (II)-Phthalocyanine Sulfonyl-Aminopropyl Silica Gels on the Separation of π-Electron-Rich Compounds by High-Performance Liquid Chromatography
• Separation of π-Electron-Rich Compounds by Using Anion-Exchange Resin Modified with Cu^-Phthalocyanine Derivative as Stationary Phase for Chromatography
• Aminopropyl-Silica Gel Modified with Nickel(II)-Phthalocyanine for Separation of π-Electron Rich Compounds by High Performance Liquid Chromatography
• 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
• Quinolizidines. XX. Racetnic and Chiral Syntheses of the Alangium Alkaloids 9-Demethylprotoemetinol and 10-Demethylprotoemetinol(Organic,Chemical)
• Quinolizidines. XXV. : An Extension of the "Lactim Ether Route" to the Racemic Syntheses of Several Indolo[2,3-α]quinolizidine Alkaloids
• Quinolizidines. XVIII. Synthesis of (-)- and (+)-ankorines through a lactim ether route
• 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. XXIX. Syntheses of 9-Alkyl-2-deuterio-N^6-methoxyadenines and 2-Deuterio-N^6,9-dimethyladenine : Tautomerism in 9-Substituted N^6-Alkoxyadenines(Organic,Chemical)
• Structure of Wyosine, the Condensed Tricyclic Nucleoside of Torula Yeast Phenylalanine Transfer Ribonucleic Acid
• Benzoquinolizidine環系ウリノキ科アルカロイドの構造と合成
• Quinolizidines. XXXIII. A chiral synthesis of (-)-ophiorrhizine, a pentacyclic quaternary indole alkaloid from ophiorrhiza major RIDL
• Syntheses of several cyclopentano-monoterpene lactones using 1,3-dioxin vinylogous ester
• Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines
• 植物塩基の解体と組換え : Alangiumアルカロイドの合成と構造研究の戦略
• Synthesis and Structure of the Hypermodified Nucleoside of Rat Liver Phenylalanine Transfer Ribonucleic Acid
• Efficient synthesis and hydrolysis of cyclic oxalate esters of glycols
• Synthesis and Structure of the Marine Ascidian 8-Oxoadenine Aplidiamine
• Purines. LXXIX. Synthesis and Hydrolysis of 3-Methoxyadenine and Its N^6-Benzyl Derivative Leading to the Corresponding 2-Hydroxyadenines
• Purines. LXXVIII. An Alternative Synthesis of the Sea Anemone Purine Alkaloid Caissarone
• Purines. IXXVII. An Alternative Synthesis of N^6-Demethylcaissarone from 9-Methyl-8-oxoadenine by Regioselective N(3)-Methylation : Utilization of the N(7)-Benzyl and N(1)-Benzyloxy Groups as Control Synthons
• Purines. LXXVI. Alkylation of 8-Oxoadenine Derivatives : Syntheses of 3,7-Dialkyl-, 3,9-Dialkyl-, and 3,7,9-Trialkyl-8-oxoadenines
• Purines. LXXV. Dimroth Rearrangement, Hydrolytic Deamination, and Pyrimidine-Ring Breakdown of 7-Alkylated 1-Alkoxyadenines : N(1)-C(2) versus N(1)-C(6) Bond Fission
• Purines. LXXIV. Syntheses and Rearrangements of 8-Oxoadenines Monomethylated at the N^6-, 1-, and 3-Positions
• Purines. LXXII. Oxidation of N^6-Alkyladenines with m-Chloroperoxybenzoic Acid Leading to N^6-Alkyladenine 1-Oxides
• Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines
• The alkaline phosphatase in human plexus chorioideus.
• Purines. XLVII. Dimroth Rearrangement versus Hydrolytic Deamination of 1-Ethyladenine
• Quinolizidines. XXX. A ready access to the dibenzo[a,f]quinolizidine ring system from 1,2,3,4-tetrahydroquinoline
• Syntheses of cis-Zeatin and Its 9-(2-Deoxy-β-D-ribofuranosyl) Derivative : A Novel Synthetic Route to the Side Chain at C(6), and Cytokinin Activity
• Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana
• Quinolizidines. XXVII. Racemic and chiral syntheses of the Neisosperma and Ochrosia alkaloid ochropposinine
• Quinolizidines. XXIV. : Syntheses of Ankorine Congeners in Different Oxidation States
• Quinolizidines. XIX. Synthesis of (-)-9-demethyltubulosine
• 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
• 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
• A straightforward preparation of chiral 5-(aminomethyl)oxazole derivatives from α-amino esters and α-lithiated isocyanides
• Quinolizidines. XXI. : Syntheses of (±)- and (-)-Alancines(Organic,Chemical)
• 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
• Reactions of oxalyl chloride with 1,2-cycloalkanediols in the presence of triethylamine
• Isomerization through Cleavage and Recombination of Imidazolide Linkage in the Condensed Tricyclic System Related to Hypermodified Bases of Phenylalanine Transfer Ribonucleic Acids
• Bamberger Fission and Reclosure of 1-Alkyl-5-(alkylamino)imidazole-4-carbonitriles Leading to Their 2-Oxo Derivatives
• Purines. LXXIII. Syntheses of 8-Alkoxy- and 8-Hydroxy-3-alkyladenines from 3-Alkyladenine 7-Oxides through 7-Alkoxy-3-alkyladenines
• Reaction of Phosgene with the Tricycle Related to the Minor Base of Phenylalanine Transfer Ribonucleic Acids
• Practical Synthesis of Wybutosine, the Hypermodified Nucleoside of Yeast Phenylalanine Transfer Ribonucleic Acid
• Studies towards the Synthesis of the Hypermodified Nucleoside of Rat Liver Phenylalanine Transfer Ribonucleic Acid : Improved Synthesis of the Base β-Hydroxywybutine
• Synthesis of Optically Active (2-Arylvinyl)glycine Derivatives by Palladium-Catalyzed Arylation of (S)-N-(Benzyloxycarbonyl)vinylglycine
• ラクタム類の研究(第16報)X線結晶解析による1-Benzyl-5-ethyl-1,2,5,6-tetrahydro-2-oxo-4-pyridineacetic Acidの分子構造
• アデニン環の開裂と再閉環
• Synthetic studies on the starfish alkaloid imbricatine. Construction of an ent-imbricatine framework
• Synthesis of (±)-(4aα,6α,7α,7aα)-hexahydro-6-hydroxy-7- methylcyclopenta[c]pyran-3(1H)-one, a structure common to abelialactone, Aglykon A1, and isoboonein

もっと見る 閉じる

スポンサーリンク