[2-[2-Azido-3-[1,3-bis(phenylmethoxy)propan-2-yloxy]propoxy]-3-phenylmethoxypropoxy]methylbenzene | 156536-13-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: [2-[2-Azido-3-[1,3-bis(phenylmethoxy)propan-2-yloxy]propoxy]-3-phenylmethoxypropoxy]methylbenzene
• CAS: 156536-13-9
• 化学式: C₃₇H₄₃N₃O₆
• 分子量: 625.765
• InChiKey: MWEBDOBIFVQCNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  46
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [2-[2-Azido-3-[1,3-bis(phenylmethoxy)propan-2-yloxy]propoxy]-3-phenylmethoxypropoxy]methylbenzene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 2-amino-1,3-bis(1,3-dibenzyl-2-glyceroxy)-2-propane
  参考文献：
  名称：

  Synthesis and Biological Properties of Water-Soluble p-Boronophenylalanine Derivatives. Relationship between Water Solubility, Cytotoxicity, and Cellular Uptake

  摘要：

  Water-soluble p-boronophenylalanine (BPA) derivatives having cascade polyols, the monohydroxy derivative BPA(OH) (4), the dihydroxy analogue BPA(OH)(2) (5), and the tetrahydroxy analogue BPA(OH)(4) (6), were synthesized in order to elucidate a relationship between the molecular structures and the cellular uptake. Biological properties of these compounds in addition to BPA (1) itself were investigated. Water solubility increased in the order of BPA < BPA(OH) less than or equal to BPA(OH)(2) < BPA(OH)(4). Cytotoxicity to B-16 melanoma and TIG hybrobrast cells decreased in the order of BPA >> BPA(OH) greater than or equal to BPA(OH)(2) > BPA(OH)(4). The cellular uptake by both B-16 and TIG cells decreased in the order of BPA >> BPA(OH) greater than or equal to BPA(OH)2 > BPA(OH)4, whereas the uptake ratio of B-16/TIG increased in the order of BPA < BPA(OH) less than or equal to BPA(OH)(2) < BPA(OH)(4). The latter ratio indicates the selectivity on the uptake by a cancer to normal cell.

  DOI：

  10.1021/jm00010a012
• 作为产物：
  描述：

  Trifluoromethane sulfonic acid-[1,3-bis-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-prop-2-yl]-ester 在 sodium azide 作用下， 以 异丁酰胺 、 水 为溶剂， 反应 12.0h， 生成 [2-[2-Azido-3-[1,3-bis(phenylmethoxy)propan-2-yloxy]propoxy]-3-phenylmethoxypropoxy]methylbenzene
  参考文献：
  名称：

  WO2006/69678

  摘要：

  公开号：

文献信息

• WO2006/69676
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2006/69678
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Biological Properties of Water-Soluble p-Boronophenylalanine Derivatives. Relationship between Water Solubility, Cytotoxicity, and Cellular Uptake
  作者：Hisao Nemoto、Jianping Cai、Satoshi Iwamoto、Yoshinori Yamamoto

  DOI：10.1021/jm00010a012

  日期：1995.5

  Water-soluble p-boronophenylalanine (BPA) derivatives having cascade polyols, the monohydroxy derivative BPA(OH) (4), the dihydroxy analogue BPA(OH)(2) (5), and the tetrahydroxy analogue BPA(OH)(4) (6), were synthesized in order to elucidate a relationship between the molecular structures and the cellular uptake. Biological properties of these compounds in addition to BPA (1) itself were investigated. Water solubility increased in the order of BPA < BPA(OH) less than or equal to BPA(OH)(2) < BPA(OH)(4). Cytotoxicity to B-16 melanoma and TIG hybrobrast cells decreased in the order of BPA >> BPA(OH) greater than or equal to BPA(OH)(2) > BPA(OH)(4). The cellular uptake by both B-16 and TIG cells decreased in the order of BPA >> BPA(OH) greater than or equal to BPA(OH)2 > BPA(OH)4, whereas the uptake ratio of B-16/TIG increased in the order of BPA < BPA(OH) less than or equal to BPA(OH)(2) < BPA(OH)(4). The latter ratio indicates the selectivity on the uptake by a cancer to normal cell.