Toluene-4-sulfonic acid 2-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-1-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)-ethyl ester | 164075-50-7

• 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: Toluene-4-sulfonic acid 2-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-1-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)-ethyl ester
• 英文别名: 1,3-Bis[1,3-bis(phenylmethoxy)propan-2-yloxy]propan-2-yl 4-methylbenzenesulfonate
• CAS: 164075-50-7
• 化学式: C₄₄H₅₀O₉S
• 分子量: 754.942
• InChiKey: IWHMQJJHMCWIPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  54
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 2-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-1-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)-ethyl ester 在 lithium aluminium tetrahydride 、 sodium azide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 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：

  1,9-di-O-benzyl-2,8-bis(benzyloxymethyl)-3,7-dioxanonane 、 对甲苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 17.0h， 生成 Toluene-4-sulfonic acid 2-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-1-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)-ethyl ester
  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

文献信息

• 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.