2-[2-[2-[3-(Pyridin-3-ylmethylcarbamoyl)pyridin-2-yl]oxyethoxy]ethoxy]ethyl prop-2-enoate | 521293-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[2-[2-[3-(Pyridin-3-ylmethylcarbamoyl)pyridin-2-yl]oxyethoxy]ethoxy]ethyl prop-2-enoate
• 英文别名: 2-[2-[2-[3-(pyridin-3-ylmethylcarbamoyl)pyridin-2-yl]oxyethoxy]ethoxy]ethyl prop-2-enoate
• CAS: 521293-53-8
• 化学式: C₂₁H₂₅N₃O₆
• 分子量: 415.446
• InChiKey: MGRLDHADOILJSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氯乙氧基-2-乙氧基二乙醇 在 4-二甲氨基吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 48.0h， 生成 2-[2-[2-[3-(Pyridin-3-ylmethylcarbamoyl)pyridin-2-yl]oxyethoxy]ethoxy]ethyl prop-2-enoate
  参考文献：
  名称：

  Hydrotropic Polymers:  Synthesis and Characterization of Polymers Containing Picolylnicotinamide Moieties

  摘要：

  Our previous studies on low molecular weight hydrotropes showed that nicotinamide derivatives increased the aqueous solubility of paclitaxel by several orders of magnitude. We were interested in knowing whether the polymeric forms of those low molecular weight hydrotropes could maintain hydrotropic properties. N-Picolylnicotinamide (PNA) was one of the best hydrotropes identified for paclitaxel, and polymers based on PNA were synthesized and tested for their hydrotropic properties. The pendent hydrotropic PNA moieties were attached to the polymer backbone through either an oligo(ethylene glycol) or a phenyl group as a spacer. The PNA moiety was bound to the polymer backbone either at the 2-position or at the 6-position of the pyridine ring of nicotinamide to result in poly(2-(4-vinylbenzyloxy)-N-picolylnicotinamide) (P(2-VBOPNA)) or poly(6-(4-vinylbenzyloxy)-N-picolylnicotinamide) (P(6-VBOPNA)), respectively. The ability of PNA-containing polymers to increase the aqueous solubility of paclitaxel was examined by measuring the concentration of dissolved paclitaxel in various polymer concentrations. The PNA-containing polymers increased the water solubility of paclitaxel by more than 3 orders of magnitude, and the hydrotropic property of the polymers was pronounced even at low polymer concentrations. P(2-VBOPNA) showed a higher hydrotropic property than P(6-VBOPNA). At the polymer concentration of 40 mg/mL, the water solubility of paclitaxel was enhanced up to 700-fold, depending on the type of polymer used. On the other hand, PNA displayed an efficient solubilizing ability at above 100 mg/mL. Fluorescence study indicated that the hydrotropic polymers formed noncovalent molecular assemblies through the self-association of pendent hydrotropic PNA moieties at much lower concentration range ((2.1-4.6) x 10(-2) mg/mL) than PNA (22 mg/mL). This observation supports the high solubilization abilities of hydrotropic polymers for paclitaxel. These results suggest a hydrotropic property of the PNA-based polymers operates under the same mechanism as PNA itself. The cross-linked networks of PNA-based hydrotropic polymers (i.e., hydrotropic hydrogels) were as effective as water-soluble polymers in solubilizing paclitaxel. This study shows that hydrotropic polymers and hydrogels that are prepared based on low molecular weight hydrotropic agent are as effective as the low molecular weight counterpart.

  DOI：

  10.1021/ma021629k

文献信息

• Hydrotropic Polymers:  Synthesis and Characterization of Polymers Containing Picolylnicotinamide Moieties
  作者：Sang Cheon Lee、Ghanashyam Acharya、Jaehwi Lee、Kinam Park

  DOI：10.1021/ma021629k

  日期：2003.4.1

  Our previous studies on low molecular weight hydrotropes showed that nicotinamide derivatives increased the aqueous solubility of paclitaxel by several orders of magnitude. We were interested in knowing whether the polymeric forms of those low molecular weight hydrotropes could maintain hydrotropic properties. N-Picolylnicotinamide (PNA) was one of the best hydrotropes identified for paclitaxel, and polymers based on PNA were synthesized and tested for their hydrotropic properties. The pendent hydrotropic PNA moieties were attached to the polymer backbone through either an oligo(ethylene glycol) or a phenyl group as a spacer. The PNA moiety was bound to the polymer backbone either at the 2-position or at the 6-position of the pyridine ring of nicotinamide to result in poly(2-(4-vinylbenzyloxy)-N-picolylnicotinamide) (P(2-VBOPNA)) or poly(6-(4-vinylbenzyloxy)-N-picolylnicotinamide) (P(6-VBOPNA)), respectively. The ability of PNA-containing polymers to increase the aqueous solubility of paclitaxel was examined by measuring the concentration of dissolved paclitaxel in various polymer concentrations. The PNA-containing polymers increased the water solubility of paclitaxel by more than 3 orders of magnitude, and the hydrotropic property of the polymers was pronounced even at low polymer concentrations. P(2-VBOPNA) showed a higher hydrotropic property than P(6-VBOPNA). At the polymer concentration of 40 mg/mL, the water solubility of paclitaxel was enhanced up to 700-fold, depending on the type of polymer used. On the other hand, PNA displayed an efficient solubilizing ability at above 100 mg/mL. Fluorescence study indicated that the hydrotropic polymers formed noncovalent molecular assemblies through the self-association of pendent hydrotropic PNA moieties at much lower concentration range ((2.1-4.6) x 10(-2) mg/mL) than PNA (22 mg/mL). This observation supports the high solubilization abilities of hydrotropic polymers for paclitaxel. These results suggest a hydrotropic property of the PNA-based polymers operates under the same mechanism as PNA itself. The cross-linked networks of PNA-based hydrotropic polymers (i.e., hydrotropic hydrogels) were as effective as water-soluble polymers in solubilizing paclitaxel. This study shows that hydrotropic polymers and hydrogels that are prepared based on low molecular weight hydrotropic agent are as effective as the low molecular weight counterpart.