Synthesis, Stereochemistry and Antitumor Activity of 4-Hydroperoxyiso-phosphamide (NSC-227114) and Related Compounds
スポンサーリンク
概要
- 論文の詳細を見る
4-Hydroperoxyisophosphamide and its analogues were simply synthesized by ozonolysis reactions of O-(3-butenyl)-N, N'-bis (2-chloroethyl) phosphorodiamidate and related O-(3-butenyl) phosphoramidates. An acid-catalyzed isomerization of 4-hydroperoxyisophosphamide proceeded with inversion of its phosphorus configuration giving 2-epi-4-hydroperoxyisophosphamide. Both isomers readily afforded C_4-substituted isophosphamide derivatives by reactions with nucleophilic agents and acid. L1210 antileukemic activities were tested for the isomers and some analogues revealing that the C_4-hydroperoxylation of isophosphamide resulted in a marked enhancement of its activity and that the inverted stereochemistry of an alkylating functionality at the phosphorus atom is also effective in promoting the antitumor action as an alternative activated species of isophosphamide.
- 公益社団法人日本薬学会の論文
- 1977-08-25
著者
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高見沢 映
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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岩田 豪
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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高見沢 映
新潟薬科大学
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牧野 逸男
塩野義製薬株式会社研究所
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牧野 逸男
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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岩田 豪
Shionogi Research Laboratory Shionogi And Co. Ltd.
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牧野 逸男
塩野義製薬研究所
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高見沢 映
Shionogi Research Laboratory Shionogi & Co. Ltd.
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松本 佐市
Shionogi Research Laboratory, Shionogi and Co., Ltd.
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松本 佐市
Shionogi Research Laboratory Shionogi And Co. Ltd.
関連論文
- Studies on Pyrimidine Derivatives and Related Compounds. LXXV. Reactions of Thiazolium Salts with Diethyl Acylphosphonates and Hydroxylation of Some 3-Oxo-2,3-dihydro-4H-1,4-thiazine Derivatives
- Studies on Pyrimidine Derivatives and Related Compounds. XLVII. Reaction of Thiamine with Dialkyl Acylphos-phonates or Methyl Phenylacyl-phosphinates : Takamizawa Reaction 6
- Studies on Pyrimidine Derivatives and Related Compounds. XLVI. The Reactions of Diethyl Acetylphosphonate with Thiamine : Takamizawa Reaction (5).
- Studies on the Pyrimidine Derivatives and Related Compounds. XL. Reaction of 3-Benzyl-4-methyl-5-(2-hydroxyethyl)thiazolium Salts with Diethyl Benzoylphosphonate
- Studies on the Pyrimidine Derivatives and Related Compounds. XXXIX. On the Oxidation Products of 2-Pheny1-4-(2-methyl-4-amino-5-pyrimidyl)methyl-5-methyl-6-(2-benzoyloxy or hydroxy)-ethyl-4H-1,4-thiazin-3(2H)-one
- 14.ビタミンB_1関連チアゾール誘導体とDiethylbenzoylphosphonateとの反応(第155回会議研究発表要旨)
- Studies on the Pyrimidine Derivatives. XXVII. A New Method for Synthesis of Diethyl Ethoxycarbonylphosphite from Tris (ethoxythiocarbonyl) Phosphorotrithioite, and on the Reactions of these Organo-phosphorus Compounds with Thiamine Sodium Salt.
- Studies on Pyrimidine Derivatives and Related Compounds. LIII. The Reaction of Thiamine with Diethyl Acetylphosphonate (Supplement) and the Synthesis of Pseudothiamine
- Studies on Pyrimidine Derivatives and Related Compounds. LII. Reaction of Thiamine with Phosphites. (1)
- Studies on the Pyrimidine Derivatives and Related Compounds. XXXV. On the Reaction Product of Thiamine with Diethyl Benzoylphosphonate
- ピリミジン誘導体および関連化合物の研究 : (LV)ビタミンB_1-モノグルタミン酸塩の合成と安定性
- 5.ビタミンB_1グルタミン酸塩の合成とその安定性(第181回会議研究発表要旨)
- Studies on Cyclophosphamide Metabolites and Their Related Compounds. I
- チアミン遊離塩基と臭化シアンあるいは過酸化水素との反応
- 6.Thiamine Free BaseとBrCNとの反応(ビタミンB研究委員会 : 第244回会議研究発表要旨)
- Studies on Pyrimidine Derivatives and Related Compounds. XCIV. On the Oxidation Products of 2-Substituted-2,3-dihydro-4H-1,4-thiazin-3-one Derivatives. (2)
- On the Reaction of Dialkyl Acylphosphonate with 2-Methyl-1,3,4-thiadiazolium Salts
- On the Reaction of Dialkyl Acylphosphonate with 2-Methylthiazolium Salts
- On the Reactions of 1,3,4-Oxadiazolium Salts with Dialkyl Acylphosphonates. A Novel Synthesis of 1,3,4-Oxadiazin-5-one Derivatives
- Pyrimidine誘導体及び関連化合物の研究(第89報) : ビタミンB_1とジエチルアシルホスホネートとの反応
- Studies on Pyrimidine Derivatives and Related Compounds. LXXXVII. Reaction of Thiamine Analogues with Diethyl Benzoylphosphonate
- On the Reactions of Oxazolium Salts with Dialkyl Acylphosphonates. A Novel Synthesis of 1,4-Oxazin-3-one and Azetidin-2-one Derivatives
- Studies on Pyrimidine Derivatives and Related Compounds. LXXVII. Reaction of Thiamine Analogues with Diethyl Benzoylphosphonate
- Studies on Pyrimidine Derivatives and Related Compounds. LXXIII. Syntheses and Reactions of Thiamine Sulfur Analogues and Related Derivatives. (2)
- Studies on Pyrimidine Derivatives and Related Compounds. LXXII. Syntheses and Reactions of Thiamine Sulfur Analogues and Related Derivatives. (1)
- Studies on Pyrimidine Derivatives and Related Compounds. LXXI. Reaction of Thiamine Anhydride with Thiols
- Studies on Pyrimidine Derivatives and Related Compounds. LXX. A Novel Reaction of Thiamine Anhydride
- Studies on Pyrimidine Derivatives and Related Compounds. LXIX. Sythesis of Thiamine Free Base
- Studies on Pyrimidine Derivatives and Related Compounds. LXVIII. Reactions of Dialkyl Acylphosphonates with 1,3-Disubstituted Benzimidazolium Halides
- Studies on Pyrimidine Derivatives and Related Compounds. LXVII. Reaction of Thiadiazolium Derivatives with Dialkyl Acylphosphonates
- Studies on Pyrimidine Derivatives and Related Compounds. LXVI. Reactions of Dialkyl Acylphosphonates with 1,3,4-Thiadiazolium Derivatives
- Investigation on the Reaction of Benzazolium Salts with Base
- Studies on Pyrimidine Derivatives and Related Compounds. LIX. Syntheses of 2,3-Dihydro-1H-pyrazolo [5,1-b] purin-2-ones
- 7.Triethylammonium 2[4-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-methyl-6-phenyl-5-oxo-5,6-dihydro-4H-1,4-thiazin-2-yl]ethyl pyrophosphateの合成(ビタミンB研究委員会 : 第224回会議研究発表要旨)
- 6.ThiamineとDiethyl acylphosphonateの反応補遺(ビタミンB研究委員会 : 第224回会議研究発表要旨)
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- Syntheses of New Cyclophosphamide Derivatives Having 1,3,4,2-Oxadiazaphosphorinane and Related heterocyclic Systems
- Addition Reaction of 3-Substituted-4-methyl-5- (2-hydroxy) ethyl-thiazolium Salt with Diaryl Carbodiimide
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- Studies on Pyrimidine Derivatives and Related Compounds. LXII. Cycloadditions of Alkyl Isothiocyanates with Thiamine and Related Thiazolium Ylids and Facile Conversions of the Adducts to Dihydroimidazo [4,5-d] thiazole Derivatives
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- 2-2.Thiamine Free Baseの酸化について(ビタミンB研究委員会 : 第235回会議研究発表要旨)
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- Studies on Pyrimidine Derivatives and Related Compounds. LXXX. Unusual Reactions of Thiamine Free Base with Electrophilic Reagents. (2)
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- 1.α-ケトアルデヒドのThiamineおよびHydride acceptorによる酸化 : (α-ケトアルデヒド代謝におけるThiamineの新しい役割に対する化学的モデル)(THE JOURNAL OF VITAMINOLOGY : 掲載論文要旨)
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- Studies on Pyrimidine Derivatives and Related Compounds. LXV. On the Reactions of Thiamine with Carbon Disulfide
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