Synthesis of 14,15-Epoxyisobufadienolides
スポンサーリンク
概要
- 論文の詳細を見る
In order to clarify the structure-activity relationship of the cardiotonic steroids the synthesis of the 14,15-epoxyisobufadienolides, in which C-17 is linked to 6-position of the α-pyrone ring, has been undertaken. When refluxed with triphenyltin hydride in xylene, pregna-14,16-dien-20-ones underwent selective hydrogenation to yield the corresponding ⊿^<14>-unsaturated compounds. Condensation with ethyl orthoformate followed by cyclization with malonic acid gave the ⊿^<14>-isobufadienolides. Subsequent treatment with N-bromoacetamide and then with alumina resulted in formation of the desired 14β, 15β-epoxyisobufadienolides (VIIIa, b). The epimeric 14α, 15α-epoxides (VIa, b) were also prepared with the object of comparing the biological activity.
- 公益社団法人日本薬学会の論文
- 1970-03-25
著者
-
南原 利夫
Pharmaceutical Institute, Tohoku University
-
合屋 周次郎
Pharmaceutical Institute, Medical Faculty, University of Kyushu
-
島田 和武
東北大学薬学部
-
島田 和武
Pharmaceutical Institute, Tohoku University
-
合屋 周次郎
Pharmaceutical Institute Tohoku University
-
合屋 周次郎
Pharmaceutical Institute Medical Faculty University Of Kyushu
-
南原 利夫
Pharmaceutical Institute Tohoku University
-
島田 和武
Faculty Of Pharmaceutical Sciences Kanazawa University
関連論文
- Studies on Steroid Conjugates. VIII. Synthesis of 16β-Hydroxyestrone 16-Glucuronide Acetate-Methyl Ester
- Occurrence of Bufogenin Conjugates in the Skin of Korean Toad(Organic,Chemical)
- Occurrence of Marinobufotoxin and Telocinobufotoxin Homologs in the Skin of Bufo bankorensis BORBOUR(Organic,Chemical)
- Occurrence of Bufadienolides in the Skin of Bufo viridis LAUR.
- Syntheses of 4-Hydroxyesteriol Monoglucuronides and Monosulfates
- Isolation and Characterization of Cinobufagin 3-Glutaroyl-L-arginine Ester from Bufo bufo gargarizans CANTOR
- Studies on High-Performance Liquid Chromatography with Electrochemical Detection. The pH-Dependency of Enzymic Sulfation of Catechol Estrogens
- Preparation of Specific Antisera to Digoxin Using Hapten-[C-17]-and [C-12]-Bovine Serum Albumin Conjugates
- Syntheses of 4-Hydroxyestrogen Monoglucuronides and Monosulfates
- Isolation and Characterization of Cardiac Steroids from Seeds of Elaeopendron glaucum PERS. Structures of Elaeodendrosides A, D, E, H, I, J and Elaeodendrogenin
- Isolation and Characterization of a New Type of Bufotoxin from the Skin of Bufo americanus
- Isolation and Characterization of Cardiotonic Steroids from the Bulb of Urginea altissima BAKER
- New Derivatization of Amines for Electrochemical Detection in Liquid Chromatography
- Isolation and Characterization of Cardiotonic Steroid Conjugates from the Skin of Bufo marinus (L.) SCHNEIDER
- New Derivatization for Liquid Chromatographic Resolution of Amino Acid Enantiomers
- Studies on Cardiotonic Steroids from the Skin of Japanese Toad
- Mechanism for Interference of Carbamazepine in Porter-Silber Reaction for Determination of Urinary 17-Hydroxycorticosteroids
- Separation and Determination of Cardiac Steroids by High-Pressure Liquid Chromatography
- Isolation and Characterization of Human Urinary Metabolites of Meclomen
- Synthesis of N-(Steroid-17-yl)-maleimide
- The Mechanism of Lithium Aluminum Hydride Reduction of 13α-Steroidal 16,17-Bromohydrins
- An Enzyme Immunoassay System with a Monoclonal Antibody for the Determination of 11-Deoxycortisol(Analytical,Chemical)
- Production and Specificity of a Monoclonal Anti-11-deoxycortisol Antibody
- Bridging Phenomena in Steroid Immunoassays. The Effect of Bridge Length on Sensitivity in Enzyme Immunoassay
- THE BRIDGE LENGTH EFFECT ON SENSITIVITY IN STEROID ENZYME IMMUNOASSAY
- AN ENZYME IMMUNOASSAY METHOD WITH A MONOCLONAL ANTIBODY FOR THE DETERMINATION OF 11-DEOXYCORTISOL
- Enzyme Immunoassay for Plasma 11-Deoxycortisol. Application to Metyrapone Test
- PRODUCTION OF A MONOCLONAL ANTI-11-DEOXYCORTISOL ANTIBODY
- The Specificity of Enzyme Immunoassays for Plasma 11-Deoxycortisol
- Radioimmunoassay of 11-Deoxycortisol. Specificity of Antisera raised against 11-Deoxycortisol-[C-4]-Bovine Serum Albumin Conjugates
- The Specificity in Enzyme Immunoassay for Plasma and Urine Cortisol
- Specificity of Antisera raised against Cortisol-4-Bovine Serum Albumin Conjugates in Radioimmunoassay
- Immunoaffinity Extraction of 4-Hydroxy-2-(4-methylphenyl) benzothiazole and Its Metabolites for Determination by Gas Chromatography-Mass Spectrometry
- Preparation of New Haptens for Use in Immunoassay of Glycine-Conjugated Bile Acids
- Sensitivity and Specificity in Enzyme Immunoassay of Testosterone
- Synthesis of Corticosteroid Haptens Possessing the Bridge at the C-4 Position
- The Preparation of Steroid N-Hydroxysuccinimide Esters and Their Reactivities with Bovine Serum Albumin
- New Synthesis of 16β-Hydroxydehydroepiandrosterone and Related Ketols, with Special Reference to Preparation of Haptens
- Chemical Synthesis of 11-Deoxycortisol Metabolites
- Glucuronidation of Testosterone by Rat Liver Microsomes
- Production of optically Specific Antiserum to l-Pentazocine
- Specificity of Antiserum raised against Estetrol using 6-O-Carboxymethyloxime-Bovine Serum Albumin Conjugate
- Specificity of Antisera raised against Estradiol using New Hapten-Carrier Conjugates
- Syntheses of New Haptens for Radioimmunoassay of Estradiol
- Occurrence of Cysteine Conjugate of 2-Hydroxyestrone in Rat Bile, with Special Reference to Its Formation Mechanism
- Studies on Metabolism of 3-Deoxysteroids. X. Increased Activity of 3-Deoxyestrone Hydroxylases in Liver Microsomes of Rats pretreated with Phenobarbital and 3-Methylcholanthrene
- Studies on Metabolism of 3-Deoxysteroids. VIII. Isolation and Characterization of Conjugated Metabolites of 3-Deoxyestrone
- Estrogen-Glutathione Conjugate : Metabolite of 3-Deoxyestrone in Rat
- Studies on Metabolism of 3-Deoxysteroids. VII. Migration of Deuterium during Aryl Hydroxylation of 3-Deoxyestrone
- Occurrence of "NIH Shift"during Hydroxylation of Aromatic Steroid
- Studies on Metabolism of 3-Desoxyestrone. II. Isolation and Characterization of Urinary Metabolites of 3-Desoxyestrone in Rabbit
- Further Studies on Metabolites of 3-Desoxyestrone in Rabbit Urine
- Studies on Metabolism of 3-Desoxyestrone. I. Synthesis of 16,17-Oxygenated Estra-1,3,5 (10)-trienes
- Metabolites of 3-Desoxyestrone in Rabbit Urine
- Syntheses of C_ 13α-Steroidal Progestagens
- Syntheses of 13α-Progestagens
- Epimerization of C-17 Substituent during Formation of Isobufadienolide
- Studies on the Comparative Ability of β-Glucuronidase Preparations to Hydrolyze Bile Acid Glucuronides
- Synthesis and Biochemical Aromatization of 14β-and 13α-Androst-4-en-3-ones
- REDUCTIVE BIOTRANSFORMATION OF 3-OXO BILE ACIDS IN HUMAN BLOOD
- Studies on Estetrol. I. Synthesis of 15α, 16α, 17β-Trihydroxy-androst-4-en-3-one
- Synthesis of Epimeric 2-Deuterioestr-4-ene-3,17-diones
- Use of New Silylating Agents for Identification of Hydroxylated Steroids by Gas Chromatography-Electron Impact-Mass Spectrometry
- Analytical Chemical Studies on Steroids. XX. Zimmermann Reaction and Deuterium Exchange Reactivity of Oxosteroids and Related Compounds
- The Bromination of 13α-Androstan-15-one
- Studies on Steroid Conjugates. XII. Occurrence of 16-Epiestriol 16-Glucuronide in Human Pregnancy Urine
- Studies on Steroid Conjugates. XI. Biosynthesis of 16-Epiestriol Glucosiduronate
- Studies on Steroid Conjugates. V. Synthesis of 16-Epiestriol 3-Glucuronide
- Acyl Transfer during Borohydride Reduction of Steroidal 16,17-Ketol Acetates
- Studies on Steroid Conjugates. II. Synthesis of 16-Epiestriol Monoglucuronides
- Chemistry of 3-Phenylcholestan-3-ols
- Enzyme Labeling of Steroids by the Activated Ester Method
- Syntheses of Estriol Monoglucuronides.
- A Direct Enzyme Immunoassay of 6β-Hydroxycortisol in Human Urine
- Studies on Steroid Conjugates. XIV. Participation of Glucuronidation in Selective O-Methylation of Catechol Estrogen in the Rat
- Evidence for O-Methylation of Catechol Estrogen 2-Glucuronoside with Retention of Conjugate in the Rat
- Isolation and Characterization of Biliary Metabolites of Estrone in the Rat
- Isomeric 2,16α-Dihydroxyestrone Methyl Ethers : New Metabolites in Rat Bile
- Studies on Steroid Conjugates. X. Significance of Conjugation involved in Biosynthesis of 2-Methoxyestrogen
- 2-Methoxyestrone 3-Glucuronide : A New Biliary Metabolite in the Rat
- C-2 Hydroxylation of 2-Deuterioestrogen in the Rat. Lack of "NIH Shift"
- Studies on Steroid Conjugates. IV. Synthesis of Catechol Estrogen Monoglucuronides
- Studies on Steroid Conjugates. III. New Syntheses of 2-Methoxyestrogens
- The Synthesis and Zimmermann Reaction of Some Androsten-16-ones
- Studies on Metabolism of 3-Desoxyestrone. III. Synthesis of 6-Oxygenated Estra-1,3,5 (10)-trienes and Related Compounds
- 7-Oxodihydrokarounidiol [7-Oxo-D : C-friedo-olean-8-ene-3α, 29-diol], a Novel Triterpene from Trichosanthes kirilowii
- Triterpenoid Ketones from Lingnania chungii MOCLURE : Arborinone, Friedelin and Glutinone
- Chemical Conversion of Corticosteriods to 3α, 5α-Tetrahydro Derivatives. Synthesis of 5α-Cortol 3-Glucuronides and 5α-Cortolone 3-Glucuronides
- Chemical Conversion of Corticosteroids to 3α, 5α-Tetrahydro Derivatives. Synthesis of Allotetra-hydrocortisol Glucuronides and Allotetrahydrocortisone Glucuronides
- Sensitivity of Steroid Enzyme Immunoassays. Comparison of Four Label Enzymes in an Assay System Using a Monoclonal Anti-steroid Antibody
- UNEXPECTED LOSS OF IMMUNOREACTIVITY OF A GLUCOSE OXIDASE-LABELED ANTIGEN IN A STEROID ENZYME IMMUNOASSAY SYSTEM
- Bound/Free Separation Methods in Steroid Enzyme Immunoassay with Monoclonal Antibody
- Sensitivity of Steroid Enzyme Immunoassays. : Use of 3,3', 5,5'-Tetramethylbenzidine as a Chromogen in the Assay System with Glucose Oxidase Label
- Enzyme Labeling of Steroids by the N-Succinimidyl Ester Method. Preparation of Glucose Oxidase-Labeled Antigen for Use in Enzyme Immunoassay(Analytical,Chemical)
- A Comparison of Chromogenic Substrates for Horseradish Peroxidase as a Label in Steroid Enzyme Immunoassay
- Enzyme Labeling of Steroids by the N-Succinimidyl Ester Method. Preparation of Alkaline Phosphatase-Labeled Antigen for Use in Enzyme Immunoassay
- Chemical Conversion of Corticosteroids to 3α, 5α-Tetrahydro Derivatives. Synthesis of Allotetrahydro-11-deoxycortisol Glucuronides
- Syntheses of 16,17-Dihydroxy-17-methyl-5α-androstano [3,2-c] isoxazoles
- Analytical Chemical Studies on Steroids. LXIII. Steroid Numbers of Androstanones and Their Oxime Derivatives on Gas Chromatography
- Reactions of 5α, 14β-Pregn-16-en-20-one with Nucleophiles