3-allyloxypropanal diisopropyl acetal | 191666-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-allyloxypropanal diisopropyl acetal
• 英文别名: 1,1-Di(propan-2-yloxy)-3-prop-2-enoxypropane
• CAS: 191666-39-4
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: BYWJDFATZNJTGL-UHFFFAOYSA-N

物化性质

• 沸点：
  254.9±35.0 °C(Predicted)
• 密度：
  0.894±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氟脲嘧啶 、 3-allyloxypropanal diisopropyl acetal 在 三甲基氯硅烷 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以72%的产率得到(RS)-1-(3-allyloxy-1-isopropoxypropyl)-5-fluorouracil
  参考文献：
  名称：

  Chemical modifications on the acyclic moiety of 3-(2-hydroxyethoxy)-1-alkoxypropyl nucleobases. 2. Differentiation and growth inhibition in rhabdomyosarcoma cells after exposure to a novel 5-fluorouracil acyclonucleoside

  摘要：

  A series of new 5FU acyclonucleoside analogues has been synthesized and tested for their in vitro cytotoxicity versus HT-29 colon carcinoma. The only active compound is 1-{[3-(3-cloro-2-hydroxypropoxy)-1-methoxy]propoxy}-5-fluorouracil 14, which is 8-fold less active than 5-fluorouracil. The rest of the newly prepared compounds showed no significant activity We selected 14 as the drug in the treatment of an human embryonal cell line RD derived from rhabdomyosarcoma. Such treatment caused time-dependent growth inhibition. Interestingly, RD cells treated with 14 at a concentration of 90 mu M for 6 days showed phenotypic differentiation, with increased expression of desmin, alpha-actinin and tropomyosin. We conclude that exposure of this human embryonal rhabdomyosarcoma cell line to a 90 mu M concentration released the neoplastic cells from their blockade, allowing them to recover normal myogenic development. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00415-8
• 作为产物：
  描述：

  3-allyloxypropionaldehyde 、 异丙醇 在 硫酸 作用下， 反应 16.0h， 以50%的产率得到3-allyloxypropanal diisopropyl acetal
  参考文献：
  名称：

  Chemical modifications on the acyclic moiety of 3-(2-hydroxyethoxy)-1-alkoxypropyl nucleobases. 2. Differentiation and growth inhibition in rhabdomyosarcoma cells after exposure to a novel 5-fluorouracil acyclonucleoside

  摘要：

  A series of new 5FU acyclonucleoside analogues has been synthesized and tested for their in vitro cytotoxicity versus HT-29 colon carcinoma. The only active compound is 1-{[3-(3-cloro-2-hydroxypropoxy)-1-methoxy]propoxy}-5-fluorouracil 14, which is 8-fold less active than 5-fluorouracil. The rest of the newly prepared compounds showed no significant activity We selected 14 as the drug in the treatment of an human embryonal cell line RD derived from rhabdomyosarcoma. Such treatment caused time-dependent growth inhibition. Interestingly, RD cells treated with 14 at a concentration of 90 mu M for 6 days showed phenotypic differentiation, with increased expression of desmin, alpha-actinin and tropomyosin. We conclude that exposure of this human embryonal rhabdomyosarcoma cell line to a 90 mu M concentration released the neoplastic cells from their blockade, allowing them to recover normal myogenic development. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00415-8

文献信息

• Chemical modifications on the acyclic moiety of 3-(2-hydroxyethoxy)-1-alkoxypropyl nucleobases. 2. Differentiation and growth inhibition in rhabdomyosarcoma cells after exposure to a novel 5-fluorouracil acyclonucleoside
  作者：Jose A. Gómez、Joaquín Campos、Juan A. Marchal、María A. Trujillo、Consolación Melguizo、José Prados、Miguel A. Gallo、Antonia Aránega、Antonio Espinosa

  DOI：10.1016/s0040-4020(97)00415-8

  日期：1997.5

  A series of new 5FU acyclonucleoside analogues has been synthesized and tested for their in vitro cytotoxicity versus HT-29 colon carcinoma. The only active compound is 1-[3-(3-cloro-2-hydroxypropoxy)-1-methoxy]propoxy}-5-fluorouracil 14, which is 8-fold less active than 5-fluorouracil. The rest of the newly prepared compounds showed no significant activity We selected 14 as the drug in the treatment of an human embryonal cell line RD derived from rhabdomyosarcoma. Such treatment caused time-dependent growth inhibition. Interestingly, RD cells treated with 14 at a concentration of 90 mu M for 6 days showed phenotypic differentiation, with increased expression of desmin, alpha-actinin and tropomyosin. We conclude that exposure of this human embryonal rhabdomyosarcoma cell line to a 90 mu M concentration released the neoplastic cells from their blockade, allowing them to recover normal myogenic development. (C) 1997 Elsevier Science Ltd.