3-(2',3',4'-tri-O-acetyl-β-D-arabinopyranosyloxy)benzaldehyde | 403822-06-0

• 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-arabinopyranosyloxy)benzaldehyde
• 英文别名: [(3R,4R,5S,6S)-4,5-diacetyloxy-6-(3-formylphenoxy)oxan-3-yl] acetate
• CAS: 403822-06-0
• 化学式: C₁₈H₂₀O₉
• 分子量: 380.351
• InChiKey: ISLKHQXEOQSJJH-BDXSIMOUSA-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-arabinopyranosyloxy)benzaldehyde 在 三氟化硼乙醚 、 zinc diacetate 、 四氯苯醌 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以60%的产率得到[5,10,15,20-tetrakis[3-(2,3,4-tri-O-acetyl-β-D-arabinopyranosyloxy)phenyl]porphyrinato]zinc(II)
  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：

  间羟基苯甲醛 、 (3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate 以50%的产率得到3-(2',3',4'-tri-O-acetyl-β-D-arabinopyranosyloxy)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：——

  公开号：US20030171305A1

  公开（公告）日：2003-09-11

  Provided is a tetraphenylbacteriochlorin derivative represented by the formula (I): 1 [wherein R 1 , R 2 , R 3 and R 4 , independently from each other, are a residue of a monosaccharide represented by the formulae: 2 (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.

  提供的是由公式(I)表示的四苯基细菌卟啉衍生物： 1 [其中R 1 ，R 2 ，R 3 和R 4 彼此独立，是下列公式的单糖残基： 2 （其中，R是氢或保护基团）]，或其盐。这种四苯基细菌卟啉衍生物或其盐在长波长下具有大的摩尔消光系数，预计具有高的组织穿透性，并且对肿瘤细胞和水溶性表现出高选择性。
• TETRAPHENYLBACTERIOCHLORIN DERIVATIVES AND COMPOSITIONS CONTAINING THE SAME
  申请人：SAN-EI GEN F.F.I., INC.

  公开号：EP1316558A1

  公开（公告）日：2003-06-04

  Provided is a tetraphenylbacteriochlorin derivative represented by the formula (I): [wherein R1, R2, R3 and R4, 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.

  本发明提供了一种由式（I）表示的四苯基细菌氯素衍生物： [其中，R1、R2、R3 和 R4 相互独立地为由式（I）表示的单糖的残基： (其中，R 是氢或保护基团）]或其盐。四苯基细菌氯素衍生物或其盐在长波长下具有较大的摩尔消光系数，预计具有较高的组织穿透性，并且对肿瘤细胞具有较高的选择性和亲水性。
• US6958389B2
  申请人：——

  公开号：US6958389B2

  公开（公告）日：2005-10-25
• US7157432B2
  申请人：——

  公开号：US7157432B2

  公开（公告）日：2007-01-02