Antiviral Effect and Syntheses of 4-Amino-6-alkylamino-s-triazine-2-carboxylic Acid Derivatives. Researches on Chemotherapeutic Drugs against Viruses. XXXVI.

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概要

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• New compounds of 4-amino-6-alkylamino-s-triazine-2-carboxylic acid and N-amidino-4-amino-6-alkylamino-s-triazine-2-carboxamide were synthesized from 1-alkyl-3-(4,5-dioxo-2-imidazolidinylidene) guanidine prepared by condensation of 1-alkylbiguanide with diethyl oxalate and examined as to their antiviral effect. Among these compounds, N-amidino-4,6-diamino-s-triazine-2-carboxamide was found to possess an inhibitory effect on polio virus.

• 公益社団法人日本薬学会の論文
• 1963-10-25

著者

• 古川 潮

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 上田 武雄

  Pharmaceutical Institute, Keio-Gijuku University

• 豊島 滋

  Pharmaceutical Institute, Keio-Gijuku University

• 豊島 滋

  慶大・医学部・薬化学研究所・化学療法部門

• 豊島 滋

  Pharmaceutical Institute Keio-gijuku University

• 古川 潮

  Pharmaceutical Instiute, Keio-Gijuku University

関連論文

• Syntheses and Antiviral Effect of p-Alkylbenzenesulfonamide Derivatives
• Reaction of 1,1-(2,2'-Oxydiethyl) biguanide with Dicyanodiamide.
• Reaction of 1,1-(2,2'-Oxydiethyl) biguanide with Dicyanodiamide.
• Syntheses and Antiviral Activity of 3-Thioxo-6-aryl-3,4-dihydro-as-triazin-5 (2H)-one and 6-Aryl-as-triazine-3,5 (2H, 4H)-dione.
• Synthesis and Antiviral Effect of Hexahydro-s-triazines.
• Studies on Antitumor Substances. XIV. Syntheses of Bisquarternary Ammonium Salts and the Reaction with Nucleophiles
• Studies on Antitumor Substances. VII. Reaction of N-Amidino-O-alkylisourea with Some Carboxylic Esters
• The Mechanism for the Reaction of Biguanides with Diethyl Oxalate
• Syntheses of New Pyrazoline Derivatives
• Studies on Antitumor Substances. VI. Chemical Behaviors of Thiosulfonates, Disulfonyl Sulfides, and Related Compounds.
• Studies on Antitumor Substances. V. Reaction of Thiosulfonates with Active Methylene Compounds.
• Facile Reduction of Intermediates from Carboxylic Acids and 6-Nitro-1-(2-nitrophenylsulfonyloxy)benzotriazole with Sodium Borohydride to Alcohols
• The Reaction of 1,3-Disubstituted Thioureas with α, ω-Dibromoacyl Chlorides and the Formation of Spiro Compounds
• Reactions of p-Toluenesulfinic Acid with Dialkoxy or Diamino Sulfides and Disulfides
• Inhibitory Effect of Guanidine on Several Viruses Including Polio and Measles.
• 核置換アルキルエフェドリン及びp-アルキルノルエフェドリンの合成研究
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• Facile Preparations of 1,4-(Diphenylmethyleneamino) piperazine-2,5-diones and N-Phenylmethyleneamino-β, γ, and δ-lactams from Benzylidene Hydrazines and α, β, γ, and δ-Haloacyl Halides
• Reaction of Biguanides and Related Compounds. XV. Cyclizations of Arylbiguanides and 2-Guanidinobenzimidazole with Bifunctional Unsaturated Dicarboxylates to s-Triazines and Imidazolines
• Behavior of Sulfinic Acid toward N-Chloramines and Related Compounds
• Facile Formation of 1,3-Disubstituted 2,3,5,6-Tetrahydro-2-thioxopyrimidin-4 (1H)-ones and 2-N, 3-Disubstituted 2,3,5,6-Tetrahyro-2-imino-1,3-thiazin-4-ones from Thioureas and β-Haloacyl Halides
• Convenient One-pot Syntheses of Sulfinates, Sulfinamides, and Thiosulfinates by Sulfinylation with p-Toluenesulfinic Acid and Activating Reagents
• A One-Pot Synthesis of β-Lactams by the Reaction of β-Haloacyl Chlorides with α-Amino Acids
• Convenient Syntheses of Cyclic Carboxamides from α, β, γ, δ and ε-Halocarboxamides under Phase Transfer Conditions
• Direct Conversion of Sulfinic Acid to Sulfonic Acid Derivatives
• Thermal Dimerization of Sulfinyl Compounds
• Novel One-step Preparation of Sulfinic Acid Derivatives from Sulfinic Acid
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• Asymmetric Syntheses of β-Amino Acids by the Reduction of Enamines
• Reaction of Epoxides. VI. Reaction of 2,3-Epoxypropyl Aryl Ether with Ethyl-N-phenylformimidate and N, N'-Diphenylformamidine
• Reaction of Biguanides and Related Compounds. XIV. Cyclization of Amidinothioureas with Some Carbonyl Compounds
• Asymmetric Syntheses of β-Amino Acid and Aspartic Acid by Reformatsky Reaction
• Asymmetric Syntheses of β-Amino Acids by the Addition of Chiral Amines to C=C Double Bonds
• Behaviors of N-(Substituted thio) phthalimides, N-(Substituted thio)-succinimides, and N-(Substituted thio) isatins toward Some Nucleophiles
• Reaction of Biguanides and Related Compounds. XIII. Benzilic Acid Rearrangement. The Reactions of 1,2-Cyclohexanedione and 9,10-Phenanthrenequinone with Arylbiguanides and N-Amidino-0-alkylisoureas
• Conversion of Bis (β-carbamoylethyl) Disulfides into Bis (β-carbamoylethyl) Trisulfides
• Reaction of Biguanides and Related Compounds. XII. Condensations of Arylbiguanides and Amidinoisoureas with Isatins
• Pyrazolines and Oxazolines. Reaction of Arylcarbonylethylthiosulfates with Hydrazines and Hydroxylamines
• Reaction of Epoxides. V. 1,3-Dipolar Cycloaddition Reaction of Epoxides with Carbon-Nitrogen Double Bond Compounds
• Reaction of Biguanides and Related Compounds. X. Formation of s-Triazinethiones by the Condensation of Arylbiguanides with 2,3-Trithiocarbonates
• Thiation of Enamine of Cyclohexanone with Arensulfenamides
• Reaction of Biguanides and Related Compounds. IX. Condensation of N-Amidino-O-alkylisourea and 1-Substituted 3-Amidino-2-thiourea with Benzil
• Reaction of Biguanides and Related Compounds. VIII. The Condensation of Arylbiguanides and N-Amidino-O-alkylisoureas with Diketene and Ethyl Acetoacetate
• The Reaction of Benzyl Phenylmethanethiosulfinate with Amines
• Reaction of Epoxides. IV. Addition of 2,3-Epoxypropyl Phenyl Ether to Oximes and Hydrazones
• Criss-cross Cycloaddition of Epoxides to Aromatic Aldazines
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• Reactions of β-Carbonylethylthiosulfates and β-Carbamoylethyl Disulfides with Amines
• Reaction of Biguanides and Related Compounds. VI. Condensation of N-Amidino-O-alkylisourea with β-Diketone
• Sulfenylation of Morpholine Enamine of Cyclohexanone with Sulfenamides and Thiosulfonates
• Mechanism for the Reaction of Sodium Benzylthiosulfate with Morpholine
• Researches on Chemotherapeutic Drugs against Viruses. XII. : Syntheses and Antiviral Effects of 3-Alkylphenylazo-4-hydroxynaphthalenesulfonic Acid and Its Sulfonamide Derivatives.
• Researches on Chemotherapeutic Drugs against Viruses. XI. : Syntheses and Antiviral Effects of 3-Alkylphenylazo-4-aminonaphthalenesulfonic Acid and Its Sulfonamide Derivatives.
• Studies on Pyridazine Derivatives. IV. N-Oxidation of 3-Aminopyridazine and Its Ring Substitutes.
• Studies on Pyridazine Derivatives. III. Improved Synthetic Method of 3-Sulfanilyl-6-alkoxypyridazine.
• Studies on Pyridazine Derivatives. II. Synthesis of 6-Substituted 3-(p-Nitrophenyl)-, 3-(p-Tolyl)- and 3-(p-Aminomethylphenyl) sulfonamidopyridazines.
• Studies on Pyridazine Derivatives. I. Synthesis and Antimicrobial Activity of 6-Substituted 3-Aminopyridazine and its Sulfonamido Derivatives.
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• Syntheses of Compounds related to Guanidine and their Inhibitory Action on Growth of HeLa Cells.
• Researches on Chemotherapeutic Drugs against Viruses. XXV. Studies on the Syntheses and Antiviral Effect of 2-Dimethylaminoethyl Alkylphenyl Ethers
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• Researches on Chemotherapeutic Drugs against Viruses. XVI. : Chemotherapeutic Effect of N^1-Dodecanoyl-N^4-acetylaminonaphthalenesulfonamide-(1) on Neurotropic Viruses.
• Researches on Chemotherapeutic Drugs against Viruses. XIV. : Syntheses of several Quinolinium and Pyridinium Anionides.
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• Studies on Antitumor Substances. XII. Synthesis of Bis (2,3-epoxypropyl) amine Derivatives and the Reaction with Some Nucleophiles
• Reactions of Epoxides. I. Synthesis of Trithiocarbonate by the Reaction of Epoxide with Alkali Xanthate
• Studies on Antitumor Substances. XI. Reactions of Bunte Salts with Nucleophiles
• Formation of Trisulfide from Thiosulfonate with Amine Catalyst
• Synthesis of N-Alkyl-4-morpholinecarboxamidine.
• Reaction of Disulfide and Trisulfide with N-Chlorocarboxamide
• Reaction of Biguanides and Related Compounds. III. Reaction of Biguanide and Amidinoisourea with Oxamate
• Reaction of Biguanides and Related Compounds. II. Reaction of Biguanides with Benzil
• Reaction of Biguanides and Related Compounds. I. Reaction of Biguanides with β-Diketone
• Studies on Antitumor Substances. XIII. Reaction of Sodium Ethoxycarbonylmethylthiosulfate and Sodium Phenacylthiosulfate with Amine
• Reaction of N-Amidinoamidine with Diethyl Oxalate and Ethyl Oxamate
• Studies on Application of Amino Acid as Medicinal Agent. II. Reaction of Amino Acid Ester with Difunctional Grignard Reagent
• Studies on Antitumor Substances. X. Reactions of Thiosulfonates with Some Nucleophilic Compounds
• Studies on Antitumor Substances. IX. Chemical Behaviors of Thiosulfonate toward Active Methylene Compound
• Studies on Antitumor Substances. VIII. Syntheses of 4-Amino-6-substituted Amino-2-substituted sym-Triazine Derivatives
• Studies on Application of Amino Acid as Medicinal Agent. I. Syntheses of Amino-tert-alcohol Derivatives
• Reaction of Epoxides. III. The Synthesis of 2-Amino-5-substituted 4,5-Dihydrothiophene from Substituted Propylene Sulfides and Ethyl Cyanoacetate
• Reaction of Biguanides and Related Compounds. V. The Base-catalyzed Condensation of Benzil with 1,1-Dialkylguanidine
• Reaction of Cyclic Trithiocarbonate with Amine and Phenylhydrazine
• Reaction of Biguanides and Related Compounds. IV. Reaction of Arylbiguanide with Benzoylacetone in the Presence of a Small Amount of the Arylbiguanide Hydrochloride
• A Stereoselective Synthesis of α-Chloro-α-phenylacetamide by the Reaction of optically Active Schiff Base with Dichlorocarbene
• The Conversion of α-Carbonylmethylthiosulfates into Thiocarboxamides
• Antitumor Effects of Pentamethylene Bismethanethiosulfonate Hydrolysates and Difunctional Bunte Salt
• Syntheses and Antiviral Effects of 3-Amino-6-alkyl-as-triazin-5-ol Derivatives.
• Syntheses of 4,6-Diamino-s-triazine-2-carboxamide Derivatives.
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• Reaction of 1-Arylbiguanide with Some Carboxylic Esters.
• Studies on Syntheses of Dimethylated Ephedrine Derivatives.

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