p-nitrophenyl 3,6-dideoxy-3-chloro-β-L-guloside | 183878-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-nitrophenyl 3,6-dideoxy-3-chloro-β-L-guloside
• 英文别名: (2S,3R,4S,5R,6R)-4-chloro-2-methyl-6-(4-nitrophenoxy)oxane-3,5-diol
• CAS: 183878-43-5
• 化学式: C₁₂H₁₄ClNO₆
• 分子量: 303.699
• InChiKey: HMFDYMLVTYNIDQ-JYKCKQTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 3,6-dideoxy-3-chloro-β-L-guloside 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 以65%的产率得到p-Aminophenyl 3-deoxy-β-L-fucoside
  参考文献：
  名称：

  Lectin-Mediated Drug Targeting: Discrimination of Carbohydrate-Mediated Cellular Uptake between Tumor and Liver Cells with Neoglycoconjugates Carrying Fucose Epitopes Regioselectively Modified in the 3-Position

  摘要：

  The circumvention of efficient "carbohydrate traps" in the liver is required for targeting glycoconjugates on tumor cells. As shown in the model system of bovine serum albumin (BSA) conjugates, the nature of R(1)-R(3) of the fucose epitope plays an important role in the discrimination of cellular uptake between tumor and liver cells as well as in the cytotoxic activity.

  DOI：

  10.1002/(sici)1521-3773(19991216)38:24<3680::aid-anie3680>3.0.co;2-9
• 作为产物：
  描述：

  2-硝基苯--Β-吡喃半乳糖苷 在 盐酸 、 甲醇 、 sodium methylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 p-nitrophenyl 3,6-dideoxy-3-chloro-β-L-guloside
  参考文献：
  名称：

  Lectin-Mediated Drug Targeting: Discrimination of Carbohydrate-Mediated Cellular Uptake between Tumor and Liver Cells with Neoglycoconjugates Carrying Fucose Epitopes Regioselectively Modified in the 3-Position

  摘要：

  The circumvention of efficient "carbohydrate traps" in the liver is required for targeting glycoconjugates on tumor cells. As shown in the model system of bovine serum albumin (BSA) conjugates, the nature of R(1)-R(3) of the fucose epitope plays an important role in the discrimination of cellular uptake between tumor and liver cells as well as in the cytotoxic activity.

  DOI：

  10.1002/(sici)1521-3773(19991216)38:24<3680::aid-anie3680>3.0.co;2-9

文献信息

• Sugar-modified cytostatics
  申请人：Bayer Aktiengesellschaft

  公开号：US06271342B1

  公开（公告）日：2001-08-07

  The invention relates to cytostatics which, by modification with sugar, are tumor-specific. Suitable spacers ensure serum stability and at the same time an intracellular action.

  这项发明涉及通过与糖类改性的细胞毒药物，这些药物具有肿瘤特异性。合适的间隔物确保血清稳定性，同时也保证细胞内作用。
• KOHLENHYDRATMODIFIZIERTE CYTOSTATIKA
  申请人：BAYER AG

  公开号：EP0819135B1

  公开（公告）日：1999-11-17
• US6271342B1
  申请人：——

  公开号：US6271342B1

  公开（公告）日：2001-08-07
• Lectin-Mediated Drug Targeting: Discrimination of Carbohydrate-Mediated Cellular Uptake between Tumor and Liver Cells with Neoglycoconjugates Carrying Fucose Epitopes Regioselectively Modified in the 3-Position
  作者：Hans-Georg Lerchen、Joerg Baumgarten、Norbert Piel、Victoria Kolb-Bachofen

  DOI：10.1002/(sici)1521-3773(19991216)38:24<3680::aid-anie3680>3.0.co;2-9

  日期：1999.12.16

  The circumvention of efficient "carbohydrate traps" in the liver is required for targeting glycoconjugates on tumor cells. As shown in the model system of bovine serum albumin (BSA) conjugates, the nature of R(1)-R(3) of the fucose epitope plays an important role in the discrimination of cellular uptake between tumor and liver cells as well as in the cytotoxic activity.