3-[2-[2-[2-[2-(甲基二硫烷基)乙氧基]乙氧基]乙氧基]乙氧基]丙酸 | 564476-35-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 中文名称: 3-[2-[2-[2-[2-(甲基二硫烷基)乙氧基]乙氧基]乙氧基]乙氧基]丙酸
• 英文名称: 15-methyldithio-4,7,10,13-tetraoxapentadecanoic acid
• 英文别名: 6,9,12,15-Tetraoxa-2,3-dithiaoctadecan-18-oic acid；3-[2-[2-[2-[2-(methyldisulfanyl)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
• CAS: 564476-35-3
• 化学式: C₁₂H₂₄O₆S₂
• 分子量: 328.451
• InChiKey: HQIUVIXVEAEUFA-UHFFFAOYSA-N

物化性质

• 沸点：
  464.6±45.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  PEG5-羧酸叔丁酯,HO-PEG4叔丁酯,1-羟基-3,6,9,12-四氧杂十五烷-15-酸叔丁酯 在 三乙基硅烷 、 sodium phosphate buffer 、 hydroxylamine buffer 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 14.5h， 生成 3-[2-[2-[2-[2-(甲基二硫烷基)乙氧基]乙氧基]乙氧基]乙氧基]丙酸
  参考文献：
  名称：

  Synthesis of Taxoids with Improved Cytotoxicity and Solubility for Use in Tumor-Specific Delivery

  摘要：

  To develop effective taxane-antibody immunoconjugates, we have prepared a series of modified taxanes that have both improved toxicity and solubility in aqueous systems as compared to paclitaxel (1a). These taxanes have been modified at either the C-10 or C-7 position and were found to be very cytotoxic against both normal and multi-drug-resistant (MDR) cells, as well as up to 30 times more soluble than paclitaxel in various buffer systems.

  DOI：

  10.1021/jm049705s

文献信息

• Conjugated prodrugs of cc-1065 analogs
  申请人：ImmunoGen, Inc.

  公开号：EP2238988A1

  公开（公告）日：2010-10-13

  Prodrugs of analogs of the anti-tumor antibiotic CC-1065 having a cleavable protective group such as a piperazino carbamate, a 4-piperidino-piperidino carbamate or a phosphate, in which the protecting group confers enhanced water solubility and stability upon the prodrug, and in which the prodrug also has a moiety, such as a disulfide, that can conjugate to a cell binding reagent such as an antibody. The therapeutic use of such prodrug conjugates is also described; such prodrugs of cytotoxic agents have therapeutic use because they can deliver cytotoxic prodrugs to a specific cell population for enzymatic conversion to cytoxic drugs in a targeted fashion.

  抗肿瘤抗生素CC-1065类似物的原药具有可裂解的保护基团，如哌嗪氨基甲酸酯、4-哌啶氨基甲酸酯或磷酸酯，其中保护基团赋予原药更高的水溶性和稳定性，原药还具有可与细胞结合试剂（如抗体）共轭的分子，如二硫化物。此外，还介绍了这类原药共轭物的治疗用途；这类细胞毒性药物原药具有治疗用途，因为它们可以将细胞毒性原药以靶向方式输送到特定的细胞群中，使其在酶的作用下转化为细胞毒性药物。
• IMPROVED PRODRUGS OF CC-1065 ANALOGS
  申请人：Immunogen, Inc.

  公开号：EP1492526A2

  公开（公告）日：2005-01-05
• EP1492526A4
  申请人：——

  公开号：EP1492526A4

  公开（公告）日：2007-03-14
• CONJUGATED PRODRUGS OF CC-1065 ANALOGS
  申请人：ImmunoGen, Inc.

  公开号：EP1492526B1

  公开（公告）日：2010-06-16
• Prodrugs of CC-1065 analogs
  申请人：IMMUNOGEN INC.

  公开号：US20030199519A1

  公开（公告）日：2003-10-23

  Prodrugs of analogs of the anti-tumor antibiotic CC-1065 having a cleavable protective group such as a piperazino carbamate, a 4-piperidino-piperidino carbamate or a phosphate, in which the protecting group confers enhanced water solubility and stability upon the prodrug, and in which the prodrug also has a moiety, such as a disulfide, that can conjugate to a cell binding reagent such as an antibody. The therapeutic use of such prodrug conjugates is also described; such prodrugs of cytotoxic agents have therapeutic use because they can deliver cytotoxic prodrugs to a specific cell population for enzymatic conversion to cytoxic drugs in a targeted fashion.