Synthesis of 4-Hydroperoxy-1,3,2-diazaphosphorinane-2-oxides related to the Activated Cyclophosphamide
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概要
- 論文の詳細を見る
Activated cyclophosphamide analogues having a 4-hydroperoxy-1,3,2-diazaphos-phorinane-2-oxide ring were synthesized by ozonolytic cyclization reaction of N-3-butenyl-phosphorodiamidates. Stereochemistries of the 1,3,2-diazaphosphorinane derivatives were investigated by proton magnetic resonance (PMR) spectroscopy. Both the chemical and PMR properties of these derivatives were similar to those of the corresponding 1,3,2-oxazaphosphorinane derivatives. The 1,3,2-diazaphosphorinane derivatives practically had no antileukemic activity against L1210-BDF_1 mice, providing a further evidence that the 1,3,2-oxazaphosphorinane ring of cyclophosphamide-related compounds is not replaceable by other ring systems for promoting antitumor activity.
- 公益社団法人日本薬学会の論文
- 1978-03-25
著者
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高見沢 映
新潟薬科大学
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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
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- 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
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- 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
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- 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
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