HIGHLY WATER-SOLUBLE TAXOL DERIVATIVES - 7-POLYETHYLENE GLYCOL CARBAMATES AND CARBONATES
HIGHLY WATER-SOLUBLE TAXOL DERIVATIVES - 7-POLYETHYLENE GLYCOL CARBAMATES AND CARBONATES
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DOI：
10.1021/jo00107a010
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发表时间：
1995-01-27
影响因子：
3.6
通讯作者：
BOLIKAL, D
中科院分区：
文献类型：
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作者：
GREENWALD, RB;PENDRI, A;BOLIKAL, D
高度水溶性的紫杉醇衍生物（0.1mmol/mL）的第一个实施例是通过在紫杉醇的7-位上经由甲烷或碳酸酯键连接聚乙二醇（分子量2-5 kD）来制备的。当使用较低分子量的聚乙二醇（350和750）时，溶解度明显较低（1.87 × 10（-3）mmol/mL），但仍明显高于紫杉醇本身。另外的7-取代的紫杉醇衍生物也通过利用由糖和离子和多官能化合物组成的小分子来制备。然而，大多数这些衍生物的溶解度，从HPLC保留时间计算，没有显着不同的紫杉醇本身。使用甲氧基乙酸酯作为保护基团在这些合成进行了讨论。
The first examples of highly water soluble taxol derivatives (0.1 mmol/mL) were prepared by the attachment of polyethylene glycol (molecular weight 2-5 kD) at the 7-position of taxol via a methane or carbonate linkage. When lower molecular weight polyethylene glycols (350 and 750) were used, the solubilities were considerably lower (1.87 x 10(-3) mmol/mL) but still substantially greater than taxol itself. Additional 7-substituted taxol derivatives were also prepared by utilizing small molecules consisting of sugars and ionic and multifunctional compounds. However, most of these derivatives had solubilities, calculated from HPLC retention times, that did not differ significantly from taxol itself. The use of methoxyacetate as a protecting group during these syntheses is discussed.