Purines. LXXI. Preparation and Alkylation of 7-Alkyladenine 1-Oxides : A General Synthesis of 1-Alkoxy-7-alkyladenines
スポンサーリンク
概要
- 論文の詳細を見る
7-Methyladenine (6a) and 7-ethyladenine (6b) afforded the N(1)-oxides 7a, b in 78% yield each on treatment with m-chloroperoxybenzoic acid at room temperature; this is analogous to the previously reported N-oxidation of 7-benzyladenine (6c) to give the N(1)-oxide 7c. When treated with an excess of methyl iodide, ethyl iodide, or benzyl bromide in N, N-dimethylacetamide at room temperature, each of the 1-oxides 7a-c underwent alkylation almost exculsively at the oxygen atom of the N-oxide group. The products, isolated in good yields, were the salts 8d-l・HX of the nine 1-alkoxy-7-alkyladenines, in which either the O-alkyl or the N(7)-alkyl group is any one of methyl, ethyl, and benzyl. The UV and ^1H-NMR spectral data for 8・HX and some of their free bases 8 are presented.
- 公益社団法人日本薬学会の論文
- 1996-03-15
著者
-
伊藤 信彰
奈良県立医科大学法医学教室
-
藤井 澄三
金沢大学薬学部
-
Itaya T
Faculty Of Pharmaceutical Sciences Kanazawa University
-
Ito N
Fukuoka Univ. Fukuoka Jpn
-
ITAYA Taisuke
Faculty of Pharmaceutical Sciences, Kanazawa University
-
Itaya Taisuke
Faculty Of Pharmaceutical Sciences Kanazawa University
-
FUJII Tozo
Faculty of Pharmaceutical Sciences, Kanazawa University
-
ITO Nobuaki
Faculty of Pharmaceutical Sciences, Kanazawa University
-
Fujii Tozo
Faculty Of Pharmaceutical Sciences Kanazawa University
-
藤井 澄三
Shinshu Univ. Nagano Jpn
関連論文
- 紙巻タバコを嚥下後,左手くびと腹部を自傷し,自絞死した1例
- 近親者間の父権肯定確率計算 : 父と擬せられる男が大叔父にあたり, しかもすでに死亡している場合の親子鑑定
- 近親者が擬父の場合の父権肯定確率
- 酵素金コロイド電顕法を用いたヒト唾液腺におけるフコース局在の観察
- ヒト舌下腺ならびに顎下腺腺房細胞におけるアルデヒドパラロ-ザニリン染色について〔英文〕
- 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
- B-11 Histochemical Analysis of poly-N-acetyl-Iactosamine Structures in Human Thyroid Neoplasms by using Lectins and Endo-β-galactosidase(E-β-G) Digestion
- Variable glyceryl dinitrate formation as a function of glutathione S-transferase.
- Variable Glyceryl Dinitrate Formation as a Function of Glutathione S-Transferase
- 甲状腺腫瘍に発現される血液型関連糖鎖抗原の検討
- 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
- IC-O31 ヒト各組織細胞における血液型B抗原密度のGSAI-B4レクチン染色とα-galactosidase処理による推定
- 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
- 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
- Existence of Blood Group Related Antigens in Nuclear Heterochromatin in Mucous Cells of Human Cervical Glands.
- Relationship between Lectin Binding Properties and the Expression of Blood Group ABH Antigens in Vascular Endothelia and Red Blood Cells from 18 Primate Species
- Histochemical Demonstration of Mucin Type Glycoproteins in Human Tissues Using Lectin Staining Method in Combination with Exo-and Endo-Glycosidase Digestion Procedures
- 肺臓炭粉沈着--20年前との比較〔英文〕
- Effects of Exoglycosidase Digestion upon Lectin Stainings in Human Pancreas
- LOCALIZATION OF BLOOD GROUP ANTIGENS IN HUMAN PANCREAS WITH LECTIN-HORSERADISH PEROXIDASE CONJUGATES
- 膵臓脂肪腫症の1例とその血液型抗原〔英文〕
- ヒト組織のアルデヒドフクシン染色に対する塩基性フクシン色素成分の影響〔英文〕
- Localization of blood group antigens in formalin-fixed, paraffin-embedded human salivary glands and pancreas with lectin-HRP conjugate
- 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.
- Quinolizidines. XXX. A ready access to the dibenzo[a,f]quinolizidine ring system from 1,2,3,4-tetrahydroquinoline
- 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)
- Aldehyde Fuchsin(AF) Positive Granules of the Human Submandibular Glands
- 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
- Effects of hydroxylamine and molybdate on the formation of nitrate reductase in the yeast Rhodotorula
- 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