7-O-(Imidazolylcarbonyl)taxol | 146462-54-6

• 英文名称: 7-O-(Imidazolylcarbonyl)taxol
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-9-yl] imidazole-1-carboxylate
• CAS: 146462-54-6
• 化学式: C₅₁H₅₃N₃O₁₅
• 分子量: 947.993
• InChiKey: OXAYTBCHEDFHLA-CEPOORRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  69
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  245
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  7-O-(Imidazolylcarbonyl)taxol 以 二氯甲烷 、 异丙醇 为溶剂， 反应 24.0h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-9-[3-[4-[3-[[(2S,3R)-3-benzamido-2-hydroxy-3-phenylpropanoyl]amino]propylamino]butylamino]propylcarbamoyloxy]-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  紫杉醇和10-去乙酰基紫杉醇的7-和10-精胺结合物的合成作为潜在的前药

  摘要：

  已经开发了在紫杉醇和10-去乙酰基紫杉醇的7和10位带有线性多胺精胺的两种紫杉醇类似物的有效合成方法。这些多胺-紫杉醇-缀合物被分离为水溶性二氟化物盐。本工作的目的是将化学修饰引入紫杉酚骨架中，以增加对肿瘤细胞的药物选择性。在MCF7和MCF7-R细胞系中评估了这些缀合物的细胞毒性活性。观察到的低细胞毒性表明这些缀合物可以充当潜在的前药。

  DOI：

  10.1016/j.tetlet.2006.02.108
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 7-O-(Imidazolylcarbonyl)taxol
  参考文献：
  名称：

  Design and synthesis of a water-soluble taxol analogue : Taxol-sialyl conjugate

  摘要：

  Glycosidation, using the methylthio derivative of N-acetylneuraminic acid 3, of linker alcohol 4 in DME with "long-range participation" produced the alpha-glycosyl linkage with high stereoselectivity. The alpha-linked sialic acid 2 was introduced in taxol without protection of the alcohol functionality in sialic acid. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10189-5

文献信息

• Highly Water Soluble Taxol Derivatives: 7-Polyethylene Glycol Carbamates and Carbonates
  作者：Richard B. Greenwald、Annapurna Pendri、Durgadas Bolikal

  DOI：10.1021/jo00107a010

  日期：1995.1

  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.