Synthesis of Pyrazolone Derivatives. XIV. Synthesis of 3-Mercaptomethyl-2-methyl-1-phenyl-3-pyrazolin-5-one Derivatives
スポンサーリンク
概要
- 論文の詳細を見る
For pharmacological evaluation of new improved antipyretic and analgesic agents, several kinds of 3-mercaptomethyl-2-methyl-1-phenyl-3-pyrazolin-5-one derivatives were synthesized. The reaction between 2,4-dimethyl-3-mercaptomethyl-1-phenyl-3-pyrazolin-5-one (I) and 2-nitrochlorobenzene (XVIII) in the presence of sodium ethoxide under colling with ice gave bis (2,4-dimethyl-5-oxo-1-phenyl-3-pyrazolin-3-yl)-trans-ethylene (XXIV) and 2-nitrobenzenethiol (XXVII) in addition to the objective compound (XXI). The same reaction under reflux afforded 2,4-dimethyl-5-oxo-1-phenyl-3-pyrazolin-3-carboxylic acid (XXX) and bis (2-nitrophenyl) sulfide (XXXII) as by-products. These by-products were proved to be formed by the splitting of XXI in the presence of sodium ethoxide. The improved synthesis was effected by using dimethylformamide as an aprotic solvent without the formation of undesirable substances.
- 公益社団法人日本薬学会の論文
- 1969-07-25
著者
-
伊藤 磯雄
名古屋市立大学薬学部
-
伊藤 磯雄
Faculty Of Pharmaceutical Sciences Nagoya City University
-
植田 泰誠
Faculty Of Pharmaceutical Sciences Nagoya City University
関連論文
- Synthesis of Pyrazolone Derivatives. XXIX. Synthesis of 1,3-Dioxolane-indazole Derivatives
- Synthesis of Compounds related to Antitumor Agents. V. On the Reaction of Aliphatic Carboxylates with 2,4-Diamino-5-hydroxy-6-methylpyrimidine
- Synthesis of Compounds related to Antitumor Agents. VI. The Conversion of 2,4-Dialkoxypyrimidines into N-Dialkyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidines in the Presence of p-Toluenesulfonic Acid Derivatives
- Synthesis of Compounds related to Antitumor Agents. IV. On the Reaction of Aromatic Carboxylates with 2,4-Diamino-5-hydroxy-6-methylpyrimidine
- Synthesis of Compounds Related to Antitumor Agents. III. On the Additions of Acyl Halide, Dialkyl Acetylenedicarboxylate and N-Substituted Maleimides to 2,4-Diamino-5-hydroxy-6-methylpyrimidine
- 抗腫瘍剤関連化合物の合成研究-7-Imidazolo〔1,2-c〕pyrimidine類の合成研究
- Synthesis of Compounds Related to Antitumor Agents. II. Studies on the Synthesis of Oxazolo [4,5-d] pyrimidine Nucleoside Derivatives
- Novel Annelations of Xanthines by the Reaction of 8-Aminoxanthines with Dimethyl Acetylene-dicarboxylate
- Synthesis of Isoselenazolo- or Isothiazolo[4,3-e][1,4]diazepines
- ピラツォロン誘導体の合成研究(第18報) : 1,2,4,5,6,7-Hexahydro-3H-pyrazolo[4,3-c]pyridine類の合成
- Studies on Chemical Modification of Monensin. V. Synthesis, Sodium Ion Permeability, Antibacterial Activity, and Crystal Structure of 7-O-(4-Substituted benzyl)monensins
- Studies on Cardiac Ingredients of Plants. XI. Synthesis of New Bufotoxin Homologues Utilizing Scillarenin (the Genuine Aglycone of Proscillaridin), and Their Biological Activities
- Ring Transformation Medeated by Lewis Acids and Oxidizing Agents.Synthesis of 2-Methoxy-1H-imidazole from 5-Aminopyrimidin-4(3H)-one
- Studies on the Chemical Modification of Monensin. IV. Synthesis, Sodium Ion Permeability, and Biological Activity of 7-O-Acyl-and 7-O-Alkylmonensins
- Studies on Cardiac Ingredients of Plants. IX. Chemical Transformation of Proscillaridin by Utilizing Its 1,4-Cycloadducts as Key Compounds and Biological Activities of Their Derivatives
- The Oxidized Products of 8-Methoxypsoralen (8-MOP) with H_2O_2-NaOCl
- Studies on Glycolipids. III. Glyceroglycolipids from an Axenically Cultured Cyanobacterium, Phormidium tenue
- 強心性植物成分の研究(第8報)強心配糖体Proscillaridinの硝酸エステル体の合成とその薬理作用
- Utilization of Organoselenium Compounds. II. Reaction of Fused Isoselenazoles with Alkylamines(Organic,Chemical)
- Studies on the chemical Modification of Monensin. III. Synthesis and Sodium Ion transport Activity of macrocylic Monenslamino Acid-1,29-lactones
- Studies on the Chemical Modification of Monensin. II. : Measurement of Sodium Ion Permeability of Monensylamino Acids Using Sodium-23 Nuclear Magnetic Resonance Spectroscopy
- Studies on the Chemical Modification of Monensin. I. : Synthesis and Crystal Stuructures of NaBr Complexes of Monensylamino Acids
- ピラゾロン誘導体の合成研究(第42報)2-Methyl-1-phenyl-6,7-dihydro-1H, 5H-pyrazolo[5,1-b][1,3]oxazin-8-ium Bromideの合成と鎮痛作用について
- ピラゾロン誘導体の合成研究(第40報)4-Alkoxyimino(or alkylamino-methylene)-3-methylcarbamoyl-1-methyl(or phenyl)-2-pyrazolin-5-one-の合成と鎮痛作用について
- Synthesis of Pyrazolone Derivatives. XXXIX. Synthesis and Analgesic Activity of Pyrano [2,3-c] pyrazoles
- 抗腫瘍性抗生物質の骨格変換に関する研究(第2報)Naphtho[2,3-g]-quinolineおよびNaphtho[2,3-g]quinoxaline誘導体の合成
- Studies on Synthetic Methods for 5-Amino-4 (3H)-pyrimidones. I. A Novel Ring Expansion Reaction of 4-Aminoantipyrines to 5-Amino-4 (3H)-pyrimidones
- Synthesis of Organometallic Complexes. II. Reaction of (Ferrocenylmethyl) trimethylammonium Iodide with Thiol-Type Nucleophiles
- Synthesis of Polycyclines. II. Synthesis of 12-Hydroxy-5a, 6,-7,8,9,10,11,11a-octahydro-5 (12H)-naphthacenones
- Synthesis of Pyrazolone Derivatives. XXXVI. Synthetic and Pharmacological Studies on (4S, 7R)-4,7-Methano-1H (or 2H)-indazoles and indazolium Compounds
- Synthesis of Pyrazolone Derivatives. XXXV. Synthetic and Pharmacological Studies on Some (4S, 7R)-4,7-Methano-1H-indazoles
- ピラツォロン誘導体の合成研究(第38報)(1R, 4S)-3-Diazobornane-2-oneと活性アセチレンとのCycloadditionにおける[1,5]Sigmatropic転位について
- ピラツォロン誘導体の合成研究(第37報)(4S, 7R)-2-Amino-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole関連化合物の合成と薬理
- Synthesis of Polycyclines. I. Diels-Alder Reaction of 5-Nitronaphthoquinone with Unsymmetrical Butadienes
- Synthesis of Pyrazolone Derivatives. XXXI. Asynmetric Synthesis of 3a-Alkyl-3,3a, 4,5,6,7-hexahydro-2H-indazol-3-ones
- Synthesis of Organometallic Complexes. I. Synthesis of Ferrocenylpyrazolone Derivatives
- Synthesis of Pyrazolone Derivatives. XXX. Synthesis of Pyrazolo [3,4-b] [1,4] oxazepines
- Synthetic Studies on Pyridoxine Derivatives. II. Synthesis of 3-(3-Hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl) methyl-4-methyl-5-substitutedthiazoline-2-thiones
- Synthesis of Pyrazolone Derivatives. XXIII. Benzo[5,6]cyclohepta[1,2-c]pyrazole-3,10-dione and Related Compounds
- Synthesis of Pyrazolone Derivatives. XXII. Synthesis of Benzo-[4,5] cyclohepta [1,2-c] pyrazole-diones
- Synthesis of Pyrazolone Derivatives. XIII. Synthesis of N, N-Dialkyl-N'-substituted-N'-[3 (4-substituted-2-methyl-5-oxo-1-phenyl-3-pyrazolin-3-yl) methyl] ethylenediamine
- Synthesis of Antibiotics. I. Synthesis of N-Substituted Compounds of Monochloroacylamide and Their Antitrichophyton Effect
- Studies on Cardiac Ingredients of Plants. VII : Chemical Transformation of Proscillaridin by Means of the Diels-Alder Reaction and Biological Activities of Its Derivatives
- PHOTOCHEMICAL TRANSFORMATION OF BUFADIENOLIDE
- Syntheses of Dihydrodioxepinopyridines, Dihydrodioxocinopyridines, and a Dihydrooxazepinopyridine
- Studies on the Chemical Transformations of Rotenoids. IV. : Synthesis of Novel Benzofuro[2,3-d]pyridazines Fused with Tetrazole, 1,2,4-Triazole and 1,2,4-Triazine
- Transformation of Pyrazolo [3,4-c] [1,5] benzothiazepines into Quinolines
- Synthesis of Coumarins by Nucleophilic Denitrocyclization Reaction(Organic,Chemical)
- Synthesis of Imidazo[4,5-c][1,2,6]thiadiazine 2-Oxides from Hydrolytes of Xanthines and Determination of Their Vasodilating Activity
- Synthesis of Imidazo[4,5-e][1,4]diazepine and Imidazo[4,5-e][1,4]-oxazepine Derivatives Using Caffeidine, a Hydrolysis Product of Caffeine
- Studies on Xanthine Derivatives. II. : Synthesis of 1,2,3,7-Tetrahydro-6H-purin-6-ones from Xanthine Hydrolyzates
- Synthesis of Pyrazolone Derivatives. XXVI. Reaction of 1-Methyl-2-phenyl-1,2,3,10-tetrahydro-4H-benzo [6,7] thiepino [3,4-c] pyrazole-3,4-dione with Dimethyl Acetylenedicarboxylate
- Syntheses, Antitumor Activity and Vascular Relaxing Effect of Purino[7,8-g]-6-azapteridines and [1,2,4]Triazino-[3,2-f]purines(Organic,Chemical)
- 強心性植物成分の研究 : キサンチン誘導体の構造変換と生理活性について
- Synthesis of 5-Amino-4 (3H)-pyrimidinones. II. Synthesis of 5-Acyl- and 5-Alkylamino-3-phenyl-6-methyl-4 (3H)-pyrimidinones and Determination of Their Analgesic and Antiinflammatory Activities
- Diphenylmethane誘導体の研究(第4報)Diphenylglycine誘導体の合成
- ピラツォロン誘導体の合成研究(第25報)Thiopyrano[3,4-c]pyrazole誘導体の合成
- Phenethylamineの含イオウ化合物の閉環反応について(第3報)Bischler-Napieralski反応によるN-(Phenylthiomethyl)benzamide類の転位閉環反応
- Pyridoxine誘導体の合成研究(第1報)5-Substituted-3-(2-methyl-3-hydroxy-5-hydroxymethyl-4-pyridyl)methyl-4-methylthiazoline-2-thione類の合成
- NOVEL UTILIZATION OF ORGANOSELENIUM COMPOUNDS. I. A FACILE TRANSFORMATION OF FUSED ISOSELENAZOLES TO FUSED PYRIDINES
- NOVEL RING TRANSFORMATION OF 5-AMINO-4 (3H)-PYRIMIDINONES INTO IMIDAZOLES AND IMIDAZOLES INTO A 1,2,4-TRIAZINE
- AN UNUSUAL TRANSFORMATION OF 5-AMINO-6-METHYL-3-PHENYL-4 (3H)-PYRIMIDONE WITH SELENIUM DIOXIDE : X-RAY CRYSTAL STRUCTURE OF 3-PHENYLCARBAMOYL-4-METHYL-1,2,5-SELENADIAZOLE
- Synthesis of N-Methyl-2-[8-(3,4-dimethoxyphenyl)-1,4-dioxaspiro-[4,5] decan-8-yl] ethylamine
- 悪性腫瘍診断薬の研究-1-Ethyl β-Oxo-γ-amino-γ-(3-oxocyclohexane)acetomalonateの合成
- β-ケト酸誘導体の合成研究(第1報) : 2-Bromo-3-oxoglutaric Esterの求核試薬に対する反応性
- Diphenylmethane 誘導体の研究 (第5報) N-Alkylaminopropyl-1,1-diphenyl-methylamine 類およびN-Alkylaminopropyl-1,2-diphenylethylamine 類の合成および薬理作用について
- 1,1-Diphenylmethylamine誘導体の薬理学的研究(第1報)N-Alkyl-1,1-diphenylmethylamine誘導体の局所麻酔作用について
- Diphenylmethane誘導体の研究(第3報)N-Substituted-1-(2,3-dimethoxyphenyl)-1-(2-, 3- or 4-substituted phenyl) methylamine誘導体の合成
- Diphenylmethane誘導体の研究(第2報)N-Substituted-1-(3,4-dimethoxyphenyl)-1-(2-, 3- or 4-substituted phenyl) methylamine誘導体の合成
- Synthesis of 1-(2,3-and 3,4-Dimethoxyphenyl)-1-phenyldimethylamine
- ピラツォロン誘導体の合成研究(第27報) 4-(N-Phenyl)aminopyrazoloneおよび3-(N-Phenyl)aminomethylpyrazolone誘導体の合成
- ピラツォロン誘導体の合成研究-28-ピラツォリン環の3位および4位の反応性について
- Synthesis of Pyrazolone Derivatives. XXIV. Reaction of Pyrazolo [3,4-c]-[1,5] benzothiazepines with Wohl-Ziegler's Reagents
- 抗腫瘍剤関連化合物の合成研究(第1報)Oxazolo[4,5-d]pyrimidine類ならびにPyrimido[5,4-b][1,4]oxazine類の合成研究
- ピラツォロン誘導体の合成研究(第20報)4-Bromo-3-(2-formamidophenyl)-thiomethyl-2-methyl-1-phenyl-3-pyrazolin-5-oneの閉環反応について
- Synthesis of Pyrazolone Derivatives. XVII. Synthesis of a Pyrazolo [3,4-c]-[1] benzoxepin and Pyrazolo [3,4-c] [1,5] benzoxazepines
- Synthesis of Pyrazolone Derivatives. XVI. Synthesis of Pyrazolo [3,4-c] [1,5] -benzothiazepines and 3- (2-Benzothiazolyl) -3-pyrazolin-5-ones
- Synthesis of Pyrazolone Derivatives. XV. Synthesis of 1-Methyl-2-phenyl-1,2,3,10-tetrahydro-4H-pyrazolo [3,4-c] [1] benzothiepin-3,4-dione and Its Derivatives
- Synthesis of Pyrazolone Derivatives. XIV. Synthesis of 3-Mercaptomethyl-2-methyl-1-phenyl-3-pyrazolin-5-one Derivatives
- Synthesis of Pyrazolone Derivatives. XII. Synthesis of 3-Mercaptomethyl-2-methyl-4-substituted-1-phenyl-3-pyrazolin-5-one
- Synthesis of Pyrazolone Derivatives. XI. Synthesis of 6-Substituted 1,2,6,7-Tetrahydro-3H-pyrazolo[4,3-c]pyridine
- Synthesis of Pyrazolone Derivatives. X. Synthesis of 2,4,6-Trioxohexahydro-5-pyrimidinyl Derivatives