3-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyloxy)benzaldehyde | 403822-09-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyloxy)benzaldehyde
• 英文别名: [(3R,4S,5R,6S)-4,5-diacetyloxy-6-(3-formylphenoxy)oxan-3-yl] acetate
• CAS: 403822-09-3
• 化学式: C₁₈H₂₀O₉
• 分子量: 380.351
• InChiKey: ISLKHQXEOQSJJH-XDNAFOTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  吡咯 、 3-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyloxy)benzaldehyde 在 三氟化硼乙醚 、 zinc diacetate 、 四氯苯醌 、 盐酸 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以86%的产率得到5,10,15,20-tetrakis[3-(2,3,4-tri-O-acetyl-β-D-xylopyranosyloxy)phenyl]porphyrin
  参考文献：
  名称：

  Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in HeLa Cells¶

  摘要：

  Thirty-two glycoconjugated porphyrins were synthesized by a modification of Lindsey method in the presence of Zn(OAc)(2).2H(2)O as a template. The Zn2+ ion template strategy improved the yield about three-fold in the case of meta-substituted tetraphenylporphyrins. In addition, free-base porphyrins were obtained almost quantitatively by demetalation with 4 M HCl. Sixteen deacetylated glycoconjugated porphyrins were tested as candidate photodynamic therapy (PDT) drugs using HeLa cells. Most of the deacetylated glycoconjugated porphyrins showed higher cellular uptake than tetraphenylporphyrin tetrasulfonic acid (TPPS), and 5,10,15, 20-tetrakis[4-(beta-D-arabinopyranosyloxy)phenyl]porphyrin (p-5d) in particular showed 18.5-fold higher uptake than TPPS. The photocytotoxicity of 5,10,15,20-tetrakis[4-(beta-D-glucopyranosyloxy)phenyl]porphyrin (p-5a), p-5d and TPPS was examined with HeLa cells, using a light dose of 16 J/cm(2). These photosensitizers had no cytotoxicity in the dark, but their photocytotoxicity increased in the order of TPPS < p-5a < p-5d. These results suggest p-5d is a good candidate for a PDT drug.

  DOI：

  10.1562/2004-03-07-ra-103.1
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-D-xylopyranosyl bromide 、 间羟基苯甲醛 以50%的产率得到3-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyloxy)benzaldehyde
  参考文献：
  名称：

  Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in HeLa Cells¶

  摘要：

  Thirty-two glycoconjugated porphyrins were synthesized by a modification of Lindsey method in the presence of Zn(OAc)(2).2H(2)O as a template. The Zn2+ ion template strategy improved the yield about three-fold in the case of meta-substituted tetraphenylporphyrins. In addition, free-base porphyrins were obtained almost quantitatively by demetalation with 4 M HCl. Sixteen deacetylated glycoconjugated porphyrins were tested as candidate photodynamic therapy (PDT) drugs using HeLa cells. Most of the deacetylated glycoconjugated porphyrins showed higher cellular uptake than tetraphenylporphyrin tetrasulfonic acid (TPPS), and 5,10,15, 20-tetrakis[4-(beta-D-arabinopyranosyloxy)phenyl]porphyrin (p-5d) in particular showed 18.5-fold higher uptake than TPPS. The photocytotoxicity of 5,10,15,20-tetrakis[4-(beta-D-glucopyranosyloxy)phenyl]porphyrin (p-5a), p-5d and TPPS was examined with HeLa cells, using a light dose of 16 J/cm(2). These photosensitizers had no cytotoxicity in the dark, but their photocytotoxicity increased in the order of TPPS < p-5a < p-5d. These results suggest p-5d is a good candidate for a PDT drug.

  DOI：

  10.1562/2004-03-07-ra-103.1

文献信息

• Tetraphenylbacteriochlorin derivatives and compositions containing the same
  申请人：Yano Shigenobu

  公开号：US20060003946A1

  公开（公告）日：2006-01-05

  Provided is a tetraphenylbacteriochlorin derivative represented by the formula (I): [wherein R 1 , R 2 , R 3 and R 4 , independently from each other, are a residue of a monosaccharide represented by the formulae: (wherein, R is a hydrogen or a protecting group)], or its salt. The tetraphenylbacteriochlorin derivative or its salt has a large molar extinction coefficient at long wavelengths which are expected to have a high tissue-penetrating property, and exhibits high selectivity to tumor cells and hydrophilicity.

  提供的是一种四苯基叶绿素衍生物，其化学式表示为(I): [其中R1、R2、R3和R4分别独立地表示单糖的残基，该单糖的化学式表示为：（其中，R是氢或保护基）]，或其盐。该四苯基叶绿素衍生物或其盐在长波长处具有较大的摩尔消光系数，预计具有高组织穿透性，并且对肿瘤细胞具有高选择性和亲水性。
• US7157432B2
  申请人：——

  公开号：US7157432B2

  公开（公告）日：2007-01-02