Regio-and stereoselective phosphonylation of sugars and its application for anti-cancer and anti-HIV agen

糖的区域和立体选择性磷酸化及其在抗癌和抗HIV药物中的应用

• 批准号: 07555588
• 负责人: YAMAMOTO Iwao
• 金额: $ 2.62万
• 依托单位: Shinshu University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (A)
• 财政年份: 1995
• 资助国家: 日本
• 起止时间: 1995 至 1997
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07555588/
• 关键词: phosphenium cation; unsaturated sugar; bioactive; ホスフェニウムイオン; ホスホン化糖; 抗HIV剤; 抗腫瘍剤

Reaction of tri-O-acetylglucal with chloro (diisopropylamino) phosphenium cation gave 1-phosphonylated 2-eno-pyranoside stereo and regioselectivily. After deprotection, endothelin receptor binding accey of the deprotected phosphonylated sugar was investigated, but good results were not obtained.On the other hand, reaction of tri-O-acetylgulucal with diphenylphosphenium cation in dichloromethane, unsaturated sugars having phosphinoyl group on 1-and 3-position was obtained in 51% (1-alpha), 21% (1-beta), and 6% (3-peudaxial), respectively. The stereochemistry of these products were determined by their NOESY spectra. The ozonolysis of 1-phospinoyl-unsaturated sugar in dichloromethane at -78ﾟC gave dialdehyde which cyclyzed in intramolecular aldol-type reaction manner gave franoside in 41% yield. These results will be published elsewhere.

Tri-O-乙酰葡萄糖与氯丙基（二异丙基氨基）磷酸阳离子的反应产生了1-磷酸化的2-雌激素 - 吡喃糖苷立体声和调节性selectivy。脱落后，研究了脱离磷酸化糖的内皮蛋白受体结合递减，但没有获得良好的效果。另一方面，Tri-O-乙酰基乳糖核与二氯二氯磷酸二氯酸磷酸的反应在二氯甲烷中，未饱和糖在1％和3％的51％中，在51％上是1％（1％） （1-beta）和6％（3- peudaxial）。这些产品的立体化学由它们的贵族光谱确定。 1-78 c的二氯甲烷中1磷酸糖的臭氧溶解产生了二醛，在分子内藻体内藻类反应的方式中循环循环，使得franoside的产量为41％的产率。这些结果将在其他地方发布。

项目成果

加坂、藤本、山本、他: "Functionalization of Aminophosphonic Chlorides and Synthesis of Phosphorus Heterocyclic Compounds" Posphorus, Sulfur, and Silicon and related Elements. (印刷中).

Kasaka、Fujimoto、Yamamoto 等人：“氨基膦氯化物的官能化和磷杂环化合物的合成”磷、硫和硅及相关元素（正在出版）。

加坂、藤本、山本、他: "Phosphonylation of Sugar Derivatives using Phosphanylium Cation" Heterocycl. Commun.(印刷中).

Kasaka、Fujimoto、Yamamoto 等人：“使用磷鎓阳离子进行糖衍生物的磷酸化”Heterocycl。