Synthetic Studies of Indoles and Related Compounds. XXVII. A New Synthesis of Crenatine from Ethyl Indole-2-carboxylate

スポンサーリンク

概要

• 論文の詳細を見る

• Crenatine (1a), which is a member of a new class of β-carboline alkaloids having an oxygen functionality at the 4-position, was synthesized starting from ethyl 1-benzylindole-2-carboxylate (12a) via cyclization of an elaborated C_2-subsitituent to the 3-position of the indole nucleus and aluminum chloride-catalyzed debenzylation of the protected indolic nitrogen. 1-Ethyl-4-hydroxy-9-methyl-β-carboline (26b), a positional isomer of crenatine with regard to the methyl group, was also synthesized through the same methodology.

• 社団法人日本薬学会の論文
• 1991-09-25

著者

• 渡辺 敏子

  School Of Pharmaceutical Sciences Toho University

• 桜井 克己

  Shcool Of Pharmaceutical Sciences Toho University

• Murakami Yukihisa

  富山大学和漢医薬学総合研究所 複合薬物薬理学

• Mukarami Yukihisa

  Institute Of Natural Medicine Toyama Medical And Pharmaceutical University

• Murakami Yukihisa

  Division Of Medicinal Pharmacology Institute Of Natural Medicine Toyama Medical And Pharmaceutical U

• Murakami Yukihisa

  Research Institute For Wakan-yaku (traditional Sino-japanese Medicines)

• 大本 太一

  Shcool Of Pharmaceutical Sciences Toho University

• 木村 泰久

  Shcool Of Pharmaceutical Sciences Toho University

• Watanabe Toshifumi

  Pharmaceutical Research Laboratories Ii Pharmaceutical Research Division Takeda Chemical Industries

• 村上 泰興

  Shcool of Pharmaceutical Sciences, Toho University

• 横山 祐作

  Shcool of Pharmaceutical Sciences, Toho University

• 青木( 旧姓石山)

  Shcool of Pharmaceutical Sciences, Toho University

• 鈴木 英治

  Shcool of Pharmaceutical Sciences, Toho University

• 篠原 恒康

  Shcool of Pharmaceutical Sciences, Toho University

• 宮城 智恵美

  Shcool of Pharmaceutical Sciences, Toho University

• 高橋 威文

  Shcool of Pharmaceutical Sciences, Toho University

• 渡辺 敏子

  Shcool of Pharmaceutical Sciences, Toho University

• 宮城 智恵美

  School of Pharmaceutical Sciences, Toho University

• Watanabe T

  Chiba Univ. Chiba Jpn

• 篠原 恒康

  Shcool Of Pharmaceutical Sciences Toho University

• Watanabe Toshiko

  Faculty Of Pharmaceutical Sciences Chiba University

• Watanabe Toshiko

  Graduate School Of Pharmaceutical Sciences Chiba University

• Watanabe Toshihiro

  Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.

• 高橋 威文

  Shcool Of Pharmaceutical Sciences Toho University

• Murakami Y

  Department Of Bioactive Molecules National Institute Of Infectious Diseases

• Suzuki H

  Tokyo Metropolitan Univ. Tokyo Jpn

• 横山 祐作

  東邦大学薬学部

• 宮城 智恵美

  School Of Pharmaceutical Sciences Toho University

• 青木( 旧姓石山)

  Shcool Of Pharmaceutical Sciences Toho University

関連論文

• Enhanced expression of BCL2/adenovirus EIB 19-kDa-interacting protein 3 mRNA, a candidate for intrinsic depression-related factor, and effects of imipramine in the frontal cortex of stressed mice
• Effects of Manganese Complexes of Curcumin and Diacetylcurcumin on Kainic Acid-Induced Neurotoxic Responses in the Rat Hippocampus(Pharmacology)
• Hypouricemic Effects of Acacetin and 4,5-O-Dicaffeoylquinic Acid Methyl Ester on Serum Uric Acid Levels in Potassium Oxonate-Pretreated Rats(Pharmacology)
• Fischer Indolization and Its Related Compounds. XIX. Syntheses of Ethyl 4-Methoxy- and Ethyl 5-Methoxy-1-phenyl-3H-benz [e] indole-2-carboxylates
• Enhanced Expression of BCL2/Adenovirus EIB 19-kDa-Interacting Protein 3 mRNA, a Candidate for Intrinsic Depression-Related Factor, and Effects of Imipramine in the Frontal Cortex of Stressed Mice
• Effects of Choto-san and Its Related Constituents on Endogenous Antioxidant Systems(Pharmacology)
• Antioxidant and Free Radical-Scavenging Activity of Choto-san and Its Related Constituents(Pharmacology)
• Fischer Indolization of Variously ortho-Substituted Phenylhydrazones (Fischer Indolization and Its Related Compounds. XXV)
• Fischer Indolization of Ethyl Pyruvate 2-[2-(Trifluoromethyl)phenyl]-phenylhydrazone and New Insight into the Mechanism of the Goldberg Reaction. (Fischer Indolization and Its Related Compounds. XXVI)
• A NEW SYNTHESIS OF EUPOLAURAMINE FROM A BENZ [f] INDOLE DERIVATIVE
• Formal Total Synthesis of Aglaiastatin:Pd(0)-mediated Construction of Benzofurocyclopentane System
• Relations between the Averaged ^C Nuclear Magnetic Resonance Chemical Shift and the Carcinogenic Activity of Polycyclic Aromatic Hydrocarbons
• 89(P02) 光学活性4-ブロモトリプトファンを利用した麦角アルカロイドChanoclavine-Iの全合成(ポスター発表の部)
• Effects of Mitragynine on cAMP Formation Mediated by δ-Opiate Receptors in NG108-15 Cells
• Anticonvulsant Activity of Paeonimetabolin-I Adducts Obtained by Incubation of Paeoniflorin and Thiol Compounds with Lactobacillus brevis
• Effects of Paeoniflorin Derivatives on Scopolamine-Induced Amnesia Using a Passive Avoidance Task in Mice; Structure-Activity Relationship
• Synthesis of Non-peptidic Tryptamine Derivative (THS-12) which stimulates TPO Responsive Cell Growth (Synthetic Studies on Indoles and Related Compounds 51)
• Synthetic Studies on Indoles and Related Compounds 50. Improved Synthesis of 7,9-Didecarboxymethoxathine
• Synthetic Studies of Indoles and Related Compounds. XXVIII. Intramolecular Vinylation of Pyrrole Derivatives Using Palladium : a New Synthetic Method for Substituted Indoles
• Synthetic Studies of Indoles and Related Compounds. XXVII. A New Synthesis of Crenatine from Ethyl Indole-2-carboxylate
• A NEW GENERAL SYNTHETIC ROUTE FOR 1-SUBSITUTED 4-OXYGENATED β-CARBOLINES
• Fischer Indolization and Its Related Compounds. XVIII. Formation of Four Unexpected Angular Benz [e] indoles on Fischer Indolization of Ethyl Phenylpyruvate 2-[(1,4-Dimethoxy-2-naphthyl) hydrazone]
• Synthesis and Biological Activity of Novel 2-(α-Alkoxyimino)benzylpyridine Derivatives as K^+ Channel Openers
• Synthesis and Biological Activity of Novel 1,3-Benzoxazine Derivatives as K^+ Channel Openers
• Synthetic Studies on Indoles and Related Compounds. XXVI. The Debenzylation of Protected Indole Nitrogen with Aluminum Chloride. (2)
• Permanent Occlusion of Bilateral Internal Carotid Arteries Produces Cognitive Deficits in Two Learning Behavior Tasks
• Possible Involvement of Signal Transducers and Activators of Transcription 3 System on Depression in the Model Mice Brain
• Chotosan Enhances Macrophage Colony-Stimulating Factor mRNA Expression in the Ischemic Rat Brain and C6Bu-1 Glioma Cells(Biochemistry)
• Chotosan, a Kampo Formula, Ameliorates Chronic Cerebral Hypoperfusion-Induced Deficits in Object Recognition Behaviors and Central Cholinergic Systems in Mice
• Preventive Effect of Chotosan, a Kampo Medicine, on Transient Ischemia-Induced Learning Deficit Is Mediated by Stimulation of Muscarinic M_1 But Not Nicotinic Receptor(Pharmacology)
• Social Isolation Stress-Induced Oxidative Damage in Mouse Brain and Its Modulation by Majonoside-R2, a Vietnamese Ginseng Saponin(Pharmacology)
• The Effects of Choto-san on the mRNA Expression of Alzheimer's Disease Related Factors in the Permanent Ischemic Rat Brain(Pharmacology)
• Evaluation of the Nitric Oxide Radical Scavenging Activity of Manganese Complexes of Curcumin and Its Derivative(Pharmacology)
• Berberine Exerts Neuroprotective Actions against in Vitro Ischemia-Induced Neuronal Cell Damage in Organotypic Hippocampal Slice Cultures : Involvement of B-Cell Lymphoma 2 Phosphorylation Suppression(Pharmacology)
• Cytoprotective and Cytotoxic Effects of Curcumin : Dual Action on H_2O_2-Induced Oxidative Cell Damage in NG108-15 Cells
• Protective effect of Choto-san and its related constituents on hydrogen peroxide-induced cell damage in NG108-15 cells
• Ameliorative Effects of Paeoniflorin, a Major Constituent of Peony Root, on Adenosine A_1 Receptor-Mediated Impairment of Passive Avoidance Performance and Long-Term Potentiation in the Hippocampus
• GTS-21, a Nicotinic Agonist, Attenuates Multiple Infarctions and Cognitive Deficit Caused by Permanent Occlusion of Bilateral Common Carotid Arteries in Rats
• Chronic Cerebral Hypoperfusion-Induced Neuropathological Changes in Rats
• Tacrine Improves Working Memory Deficit Caused by Permanent Occlusion of Bilateral Common Carotid Arteries in Rats
• Effect of Pilocarpine on Striatal Acetylcholine Release in Dopamine-Depleted Rats
• A Wild-type Japanese Measles Virus Strain Inducing Predominant Early Down-regulation of CD46
• Molecular Cloning of a Complementary DNA for a Membrane Cofactor Protein (MCP, CD46)/Measles Virus Receptor on Vero Cells and Its Functional Characterization
• Fischer Indolization of Ethyl Pyruvate 2-Bis(2-methoxyphenyl)hydrazone and New Insight into the Mechanism of Fischer Indolization.(Fischer Indolization and Its Related Compounds. XXVII)
• Fischer Indolization and Its Related Compounds. XXIV. Fischer Indolization of Ethyl Pyruvate 2-(2-Methoxyphenyl)phenylhydrazone
• Fischer Indolization and Its Related Compounds. XXIII. Fischer Indolization of Ethyl Pyruvate 2-(2,6-Dimethoxyphenyl)phenylhydrazone
• Control of Spermidine and Spermine Levels in Rat Tissues by trans-4-Methylcyclohexylamine, a Spermidine-Synthase Inhibitor(Analytical Biochemistry)
• Mammalian Spermidine Synthase : Identification of Cysteine Residues and Investigation of the Putrescine Binding Site(Analytical Biochemistry)
• Synthesis of Decalin Type Chiral Synthons Base on Enzymatic Function
• A New 5-HT_3 Receptor Ligand. II. Structure-Activity Analysis of 5-HT_3 Receptor Agonist Action in the Gut
• New Synthetic Method for Dehydrotryptophan Derivatives. Synthetic Studies on Indoles and Related Compounds. XXXIV
• New Steroid and Matairesinol Glycosides from Safflower (Carthamus tinctorius L.) Oil Cake
• Antioxidative Compounds Isolated from Safflower (Carthamus tinctorius L.) Oil Cake
• Constituents of Pollen. XV. : Constituents of Biota orientalis (L.) ENDL. (1)
• Constituents of Hibiscus moscheutos L. I
• Constituents of Pollen. XIV. Constituents of Cedrus deodar a LOUD. (3)(Pharmacognosy,Chemical)
• Studies on the Sesquiterpenes from Ambrosia elatior LINNE(Organic,Chemical)
• Constituent of Pollen. XIII. Constituents of Cedrus deodara LOUD. (2)(Pharmacognosy,Chemical)
• Studies on the Constituents of Pollen. X. On the Constituents of Pollen Grains of Ambrosia elatior LINNE (2)
• Studies on the Chemical Constituents of Stem Bark of Millettia leucantha : Isolation of New Chalcones with Cytotoxic, Anti-herpes Simplex Virus and Anti-inflammatory Activities
• Identification of Inhibitory Component in Cinnamon : O-Methoxycinnamaldehyde Inhibits CYP1A2 and CYP2E1
• Studies on the Constituents of Seeds of Pachyrrhizus erosus and Their Anti : Herpes Simplex Virus (HSV) Activities
• Estimation of Chemical Structure of Notopterol Metabolites
• Facilitatory and Inhibitory Effects of Harmaline on the Tryptophan- Induced 5-Hydroxytryptamine Syndrome and Body Temperature Changes in Pargyline-Pretreated Rats
• ライフサイエンス分野における産学連携 : 大学における知的財産と今後の展開について
• ピッツバーグの熱い日々
• Studies on Nonpeptide Angiotensin II Receptor Antagonists. IV. Synthesis and Biological Evaluation of 4-Acrylamide-1H-imidazole Derivatives
• Studies on Nonpeptide Angiotensin II Receptor Antagonists. III. Synthesis and Biological Evaluation of 5-Alkylidene-3,5-dihydro-4H-imidazol-4-one-Derivatives
• Studies on Nonpeptide Angiotensin II Receptor Antagonists. II. Synthesis and Biological Evaluation of 5H-Pyrazolo[1,5-b][1,2,4]triazole Derivatives with a C-Linked Oxygen Functional Group at the 6-Position
• Studies no Nonpeptide Angiotensin II Receptor Antagonists. I. Synthesis and Biological Evaluation of Pyrazolo[1,5-b][1,2,4]triazole Derivatives with Alkyl Substituents
• γ-Herpesviruses and cellular signaling in AIDS-associated malignancies
• Effect of Herbimycin A on Tyrosine Kinase Receptors and Platelet Derived Growth Factor (PDGF)-Induced Signal Transduction
• 0895 EFFECT OF ENDOTHELIN RECEPTOR ANTAGONIST, TAK-044 ON SURVIVAL RATE AND MYOCARDIAL DAMAGE IN A MURINE MODEL OF VIRAL MYOCARDITIS
• Thieno[2,3-d]pyrimidine-3-acetic Acids A New Class of Nonpeptide Endothelin Receptor Antagonists
• Hepatoprotective effect of the endothelin receptor antagonist TAK-044 against ischemia-reperfusion injury in the cirrhotic rat liver
• 薬学におけるこれからの有機化学教育
• Halogenated Bis(methylthio)tetrathiafulvalenes as a Unique Donor System
• Synthesis of Novel Succinamide Derivatives Having the 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one Skeleton as Potent and Selective M_2 Muscarinic Receptor Antagonists. I
• Paeoniflorin ameliorates acquisition impairment of a simple operant discrimination performance caused by unilateral nucleus basalis magnocellularis lesion in rats
• Reaction of Ethyl Acylindole-2-carboxylates with Thallium Trinitrate (Synthetic Studies on Indoles and Related Compounds. XXXIII)
• A Study for Palladium-catalyzed Chemoselective Vinylation at C-3 Position of 4-Bromo-1-tosylindole
• Substituent Effects in the Fischer Indolization of (2-Sulfonyloxyphenyl)-hydrazones (Fischer Indolization and Related Compounds . XXX)
• Constituents of Pollen. VIII. Constituents of Podocarpus macrophylla D. DON
• Neuropharmacological Actions of Pluchea indica LESS Root Extract in Socially Isolated Mice
• Synthesis and Pharmacological Evaluation of 2-(3-Piperidyl)-1,2,3,4-tetrahydroisoquinoline Derivatives as Specific Bradycardic Agents
• Synthesis and Biological Evaluation of 1,2,3,4-Tetrahydroisoquinoline Derivatives as Potent and Selective M_2 Muscarinic Receptor Antagonists
• Synthesis and Biological Evaluation of Phenylacetyl Derivatives Having Low Central Nervous System Permeability as Potent and Selective M_2 Muscarinic Receptor Antagonists
• New Findings on the Hemetsberger-Knittel Reaction (Synthetic Studies on Indoles and Related Compounds. XLIII)
• Synthesis of Novel Succinamide Derivatives Having a 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one Skeleton as Potent and Selective M_2 Muscarinic Receptor Antagonists. II
• β-Acylation of Ethyl Pyrrole-2-carboxylate by Friedel-Crafts Acylation : Scope and Limitations (Synthetic Studies on Indoles and Related Compounds. XXXVIII)
• インドールアミン酸素添加酵素(IDO)の病態生理学的意義と阻害剤の開発
• An Improved Synthesis of Optically Pure (R)-4-Bromo-N-methyl-1-tosyltrytophan Derivative, a Key Intermediate in the Synthesis of Ergot Alkaloids
• 保護基を用いない有機合成
• 91(P-48) 保護基なしの全合成 : 無保護アミノ酸の反応を利用した光学活性Clavicipitic Acidの全合成(ポスター発表の部)
• An Efficient Method of Synthesizing Optically Pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan Methyl Ester, a Key Intermediate in the Synthesis of Optically Active Ergot Alkaloids
• Edited by P. A. Grieco Organic Synthesis in Water
• 第17回メディシナルケミストリーシンポジウム/第6回医薬化学部会年会に参加して
• New Strategy for Indole Synthesis from Ethyl Pyrrole-2-carboxylate (Synthetic Studies on Indoles and Related Compounds. XXXIX)
• 2-Chloro-N, N-dibenzoylaniline : a Selective N-Benzoylating Reagent
• Berberine Exerts Neuroprotective Actions against in Vitro Ischemia-Induced Neuronal Cell Damage in Organotypic Hippocampal Slice Cultures : Involvement of B-Cell Lymphoma 2 Phosphorylation Suppression

もっと見る 閉じる

スポンサーリンク