Photocyclization of γ-chlorotiglyl-L-tryptophan Methyl Ester Yields Azocinoindole and Azepinoindole Derivatives
スポンサーリンク
概要
- 論文の詳細を見る
We aimed to synthesize ten-membered lactams ring-closed at C-4 of the indole by photocyclization reaction of γ-chlorotiglyl L-tryptophan methyl ester 5a for structure-activity study of medium-ring lactams related to indolactams having tumor-promoting activity. However, the ^<13>C-NMR spectra of the products showed that two eight-membered lactams ring-closed at C-4 of the indole, (4S, 7S)-1,3,4,5,6,7-hexahydro-4-methoxycarbonyl-7-methyl-6-oxo-7-vinylazocino[4,5,6-cd]indole (6a) and its (4S, 7R)-epimer 7a, and a seven-membered lactam ring-closed at C-2 of the indole, (2S, 5S)-1,2,3,4,5,6-hexahydro-2-methoxycarbonyl-5-methyl-4-oxo-5-vinylazepino[4,5-b]indole (8a), were produced rather than the expected ten-membered lactams 3a and 4a. That is, this photocyclization linked the carbon atom adjacent to the amide-carbonyl groups to the indole ring.
- 社団法人日本薬学会の論文
- 1993-02-15
著者
-
首藤 紘一
Faculty of Pharmaceutical Sciences, University of Tokyo
-
遠藤 泰之
東北薬科大学薬学部
-
首藤 紘一
東京大学薬学部
-
首藤 紘一
東京大学・薬・薬化学
-
永田 龍二
東京大学薬学部
-
遠藤 泰之
Faculty of Pharmaceutical Sciences, The University of Tokyo
-
Shudo K
Res. Foundation Itsuu Lab. Tokyo Jpn
-
永田 龍二
Faculty of Pharmaceutical Sciences, University of Tokyo
関連論文
- Reactions of K-Region Oxides of Carcinogenic and Noncarcinogenic Aromatic Hydrocarbons. Comparative Studies on Reactions with Nucleophiles and Acid-catalyzed Reactions
- 1-IV-1 新規non-seco-ステロイド型ビタミンD誘導体の創製(ビタミン学の原点・栄養学への21世紀的回帰, 日本ビタミン学会第59回大会)
- A204 脱皮ホルモン活性物質に応答するレポータージーンアッセイの開発と新規殺虫剤クロマフェノジドの評価
- サイトカイニン特異的結合蛋白の分子同定
- レチノイド アンタゴニスト
- SYNERGISTS FOR RETINOID IN CELLULAR DIFFERENTIATION OF HUMAN PROMYELOCYTIC LEUKEMIA CELLS HL-60
- レチノイドの作用の分離とレチノイドアンタゴニスト レセプター選択的化合物の試薬・医薬への開発
- 植物ホルモン「サイトカイニン」の構造展開と分子標的
- 植物耐病因子ベンツオキサジノンの化学
- SPECIFIC OXIDATION OF RETINOIC ACID TO 4-OXO-RETINOIC ACID IN DILUTED ACID SOLUTIONS
- Retinoidal Dienamides and Related Aromatic Amides. Replacement of the 9-Ene Structure of Retinoic Acid with a trans- or cis-Amide Group
- Synthesis and Biological Activity of Carboxyphenylquinolines and Related Compounds as New Potent Retinoids. Retinobenzoic Acids. VII
- Enhancement of Human Papillomavirus Type 18 Gene Expression in HeLa Cells by 12-O-Tetradecanoylphorbol-13-acetate, 3β, 5α-Dihydroxycholestan-6-one, and Cholesterol
- 4-Pyridylureas are surprisingly Potent Cytokinins. The Structure-Activity Relationship
- Synthesis of a Mutagenic Principle isolated from Tryptophan Pyrolysate
- ISOLATION AND STRUCTURAL DETERMINATION OF MUTAGENIC SUBSTANCES IN COAL TAR
- ADVANCED COMPUTATIONAL DOCKING OF TWO TELEOCIDIN CONGENERS TO CYS2 DOMAIN OF PROTEIN KINASE Cδ
- ベンズアニリド及びN-メチルベンズアニリドの立体化学
- A Potent Mutagen isolated from a Pyrolysate of L-Ornithine
- A Potent Mutagen isolated from a Pyrolysate of L-Ornithine
- Ultramicro Analysis of Benzo [α] pyrene in Food
- Synthesis and Mutagenicity of 10-Azabenzo [α] pyrene-4,5-oxide and Other Pentacyclic Aza-arene Oxides
- 228 実験的アレルギー性脳脊髄炎(EAE)におよぼすレチノイド化合物Am-80の影響
- TELEOCIDINS AND BENZOLACTAMS INHIBIT CELL KILLING BY HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 (HIV-1)
- 4.カルボラン含有ビタミンD誘導体の創製とVDR結合様式(第320回会議研究発表要旨,脂溶性ビタミン総合研究委員会)
- カルボランの特性をいかしたアンドロゲン受容体リガンドの創製
- Structural and Biological Links between Urea- and Purine-cytokinins
- Cytokinin Activity of Pyrimidine Derivatives
- Photocyclization of γ-chlorotiglyl-L-tryptophan Methyl Ester Yields Azocinoindole and Azepinoindole Derivatives
- Docking Study of Bryostatins to Protein Kinase Cδ Cys2 Domain
- Studies on the Constituents of Isodon trichocarpus KUDO. II. The Structures of Enmenin, Enmelol, and Ememodin
- Studies on the Constituents of Isodon trichocarpus KUDO. I. Isolation of the Constituents and the Structures of Isodonol, Enmedol, and Enmenol
- DIFFERENTIATION INDUCERS OF HUMAN PROMYELOCYTIC LEUKEMIA CELLS HL-60. AZOBENZENECARBOXYLIC ACIDS AND STILBENECARBOXYLIC ACIDS
- Chalcone Carboxylic Acids. Potent Differentiation Inducers of Human Promyelocytic Cells HL-60
- NEW TYPE INDUCERS OF DIFFERENTIATION OF HUMAN HL-60 PROMYELOCYTIC LEUKEMIA CELLS. TEREPHTHALIC ANILIDES
- ホウ素クラスター : カルボランの有機化学 : 合成, 構造, 立体分子構築への応用
- 創薬化学における新規3次元的疎水性構造単位の開発と応用(最前線,ポストゲノム時代の有機化学)
- ヘクソカズラの果実の成分研究 : 新規イリドイドPaederia lactoneの構造
- ホウ素クラスターの医薬化学への応用
- 70(P-55) γ-置換ブテノリドを活用する天然物のエナンチオ制御合成(ポスター発表の部)
- ビニルおよびアリル置換キラルブテノリド類のエナンチオ制御合成
- Enhancing Effect of Tumor Promoters, Phorbol Esters and Teleocidins on Nuclear Receptor-Mediated Transcription
- Identification of Protein Disulfide Isomerase as a Phorbol Ester-Binding Protein
- New Estrogenic Antagonists Bearing Dicarba-closo-dodecaborane as a Hydrophobic Pharmacophore
- Functionalization of Polymethylcarboranes. Preparation and Reactivity of 2,3,4,5,6,7,8,9,10,11-Decamethyl-1,12-dicarba-closo-dodecaborane(12)-1-carboxylic Acid
- Dicarba-closo-dodecaboranes as a Pharmacophore. Novel Potent Retinoidal Agonists
- Dicarba-closo-dodecaboranes as a Pharmacophore. Retinoidal Antagonists and Potential Agonists
- 生理活性化合物としてのホウ素クラスター--医薬品への応用をめざして
- 3β, 5α-DIHYDROXYCHOLESTAN-6-ONE EXISTS IN HUMAN BLOOD
- ROLE OF THE HYDROPHOBIC MOIETY OF TUMOR PROMOTERS. SYNTHESIS AND ACTIVITY OF BENZOLACTAMS WITH ALKYL SUBSTITUENTS AT VARIOUS POSITIONS
- Photoaffinity Labeling of Tumor Promoter-Binding Protein (CN-TPBP) and Preparation of Affinity Sorbent Gels
- ROLE OF THE HYDROPHOBIC MOIETY OF TUMOR PROMOTERS. SYNTHESIS AND ACTIVITY OF 9-ALKYLATED BENZOLACTAMS
- 発がんプロモーターの活性立体構造の解析
- Deletion Mutants of Human Deoxycytidine Kinase mRNA in Cells Resistant to Antitumor Cytosine Nucleosides
- Isolation of Deoxycytidine Kinase from Ehrlich Carcinoma Cells by Affinity Chromatography Based on a Substrate Analog, 2'-C-Cyano-2'-deoxy-1-β-D-arabinofuranosyl-N^4-palmitoylcytosine
- α-Glucosidase Inhibitors with a 4, 5, 6, 7-Tetrachlorophthalimide Skeleton Pendanted with a Cycloalkyl or Dicarba-closo-dodecaborane Group
- Modulators of Tumor Necrosis Factor α Production Bearing Dicarba-closo-dodecaborane as a Hydrophobic Pharmacophore
- Rearrangement of 4-Acetoxy-2H-1,4-benzoxazin-3 (4H)-one
- ELUCIDATION OF THE STRUCTURES OF OLIVORETIN B AND C
- SYNTHESIS OF OPTICALLY ACTIVE TELEOCIDIN DERIVATIVES. ABSOLUTE CONFIGURATION OF TELEOCIDIN B AND OLIVORETIN A
- ELUCIDATION OF THE STRUCTURE OF OLIVORETIN A AND D (TELEOCIDIN B)
- 8 テレオシジン類の活性立体構造の決定 : 立体配座固定化合物の合成と生物活性(口頭発表の部)
- Reaction of Phenanthrene-9,10-oxide with Tetracyanoethylene
- Synthesis of Non-K-region Dihydrodiols and Epoxides of Carcinogenic Dibenz [c, h] acridine
- Identification of an Ultimate Mutagen of 10-Azabenzo [α] pyrene : Microsomal Oxidation of 10-Azabenzo [α] pyrene to 10-Azabenzo [α] pyrene-4,5-oxide
- 1.カルボランの脂溶性ファーマコフォアとしての特性 : 核内ビタミンD_3受容体リガンドへの応用(脂溶性ビタミン総合研究委員会 第303回会議研究発表要旨)
- 3.カルホラン含有レチノイト(第300回脂溶性ビタミン総合研究委員会研究発表要旨)
- ORBITAL DISTORTION IN DIBENZOBICYCLO[2.2.2]OCTATRIENES. BIASED EPOXIDATION AND DIHYDROXYLATION OF THE OLEFIN MOIETY
- The Hammett Acidity Function H_0 of Trifluoromethanesulfonic Acid-Trifluoroacetic Acid and Related Acid Systems. A Versatile Nonaqueous Acid System
- ORBITAL DISTORTION ARISING FROM REMOTE SUBSTITUENTS NITRATION AND REDUCTION OF SPIRO[CYCLOPENTA-1,9'-FLUORENE]-2-ONES
- Synthesis of Mutagens isolated from Tryptophan Pyrolysate and of Some Analogs, 3-Amino-5H-pyrido [4,3-b] indoles
- Synthesis of Mutagenic Principles Isolated from L-Glutamic Acid Pyrolysate
- Cellular localization and functional characterization of the equilibrative nucleoside transporters of antitumor nucleosides
- Synthesis of Oxygenated Cholesterols as Structural Mimics of Phorbol Ester-Type Tumor Promoters
- Expression of the Ligand-Binding Domain-Containing Region of Retinoic Acid Receptors α, β and γ in Escherichia coli and Evaluation of Ligand-Binding Selectivity
- フェノキセニウムイオンの生成と反応
- テレオシジンの活性立体配座 : 新規活性分子のデザインと合成
- ANIONIC HETERO[3,3]REARRANGEMENTS. N, O-DIACYLHYDROXYLAMINES TO SUCCINIC ACID DERIVATIVES
- Alkylation of Phenols by Phenanthrene 9,10-Oxide
- ISOLATION AND STRUCTURE ELUCIDATION OF TELEOCIDIN B-1,B-2,B-3,AND B-4
- Preparation of Pure Isomers of Dinitropyrenes
- Modification of Deoxyribonucleic Acid with Reductively Activated Mitomycin C. Structures of Modified Nucleotides
- MOLECULAR REQUIREMENTS FOR EPIGENETIC MODULATORS. SYNTHESIS OF ACTIVE FRAGMENTS OF TELEOCIDINS LYNGBYATOXIN
- NEW DIMERIC ANALOGS OF 2-AMINODIPYRIDO [1,2-a : 3', 2'-d] IMIDAZOLE : SYNTHESIS AND INTERACTION WITH DNA
- ALKYLATION OF DNA WITH A MITOMYCIN DERIVATIVE, 7-N-(p-HYDROXYPHENYL)-MITOMYCIN C. REDUCTIVE ALKYLATION AND PREFERENTIAL BINDING TO ADENINE
- Synthesis of Mutagenic Heteroaromatics : 2-Aminoimidazo [4,5-f] quinolines
- Reaction of Benzene with Diphenyl Sulfoxides
- Reaction of 1-Naphthylhydroxylamine with Calf Thymus Deoxyribonucleic Acid. Isolation and Synthesis of N-(Guanin-C^8-yl)-1-naphthylamine
- Identification of a Reactive Metabolite of the Mutagen, 2-Amino-3-methylimidazolo [4,5-f] quinoline
- Alkylation of 5'-Guanylic Acid by Reductively Activated Mitomycin C
- Structure of a Base in DNA modified by Glu-P-1
- Structural Identification of a Modified Base in DNA covalently Bound with Mutagenic 3-Amino-1-methyl-5H-pyrido [4,3-b] indole
- Synthesis of Phenanthrene-9,10-imine Tosylate. A Stable Arene Imine
- Photoisomerisation of N-Carboethoxy-2,3-homoazepine
- Wave Length Dependent Photolysis of Phenanthrene Oxide
- Synthesis of Gibbane Derivatives from Enmein
- Conversion of Enmein to (-)-Kaurane. The Absolute Stereochemistry of Enmein
- Twist Form of Teleocidin Derivatives is Active in in Vivo Tumor Promotion by (-)-Benzolactam-V8-310
- A new chiral synthesis of a bicyclic enedione containing a seven-membered ring mediated by a combination of chiral amine and bronsted acid
- Enantioselective Intramolecular Aldol Reaction Mediated by a Combination of L-Amino Acid and Bronsted Acid to Construct a Bicyclic Enedione Containing a 7-Membered Ring