3-Acryloylamino-propionic acid pentafluorophenyl ester | 219797-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-Acryloylamino-propionic acid pentafluorophenyl ester
• CAS: 219797-98-5
• 化学式: C₁₂H₈F₅NO₃
• 分子量: 309.192
• InChiKey: VZNLXCDWSMAFDL-UHFFFAOYSA-N

物化性质

• 沸点：
  414.459±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.437±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-Acryloylamino-propionic acid pentafluorophenyl ester 在 偶氮二异丁腈 、 TEA 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N-[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-3-(3-octylsulfanylpropanoylamino)propanamide
  参考文献：
  名称：

  Synthesis of cotelomers derived from tris(hydroxymethyl)acrylamidomethane (THAM) bearing cytosine arabinoside moieties. Preliminary investigation of their biological activity

  摘要：

  The telomerization of tris(hydroxymethyl)acrylamidomethane (THAM) and cytosine arabinoside (Ara-C) polymerizable derivatives in the presence of transfer reagent such as alkane or perfluoroalkane thiol is described. The cytotoxic activities of these different compounds are determined on B16, a mouse melanoma cell line. Noteworthy is that all telomers exhibit a biological activity. These preliminary results show that macromolecular carriers such as cotelomers penetrate into the cell and release the drug after an enzymatic hydrolysis. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02122-3
• 作为产物：
  描述：

  N-丙烯酰-β-丙氨酸 、 五氟苯酚 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-Acryloylamino-propionic acid pentafluorophenyl ester
  参考文献：
  名称：

  Synthesis of cotelomers derived from tris(hydroxymethyl)acrylamidomethane (THAM) bearing cytosine arabinoside moieties. Preliminary investigation of their biological activity

  摘要：

  The telomerization of tris(hydroxymethyl)acrylamidomethane (THAM) and cytosine arabinoside (Ara-C) polymerizable derivatives in the presence of transfer reagent such as alkane or perfluoroalkane thiol is described. The cytotoxic activities of these different compounds are determined on B16, a mouse melanoma cell line. Noteworthy is that all telomers exhibit a biological activity. These preliminary results show that macromolecular carriers such as cotelomers penetrate into the cell and release the drug after an enzymatic hydrolysis. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02122-3

文献信息

• Synthesis of new cotelomers derived from tris(hydroxymethyl) aminomethane bearing arabinofuranosylcytosine moieties. Preliminary results on their in vitro and in vivo antitumoral activities
  作者：Christiane Contino、Jean-Claude Maurizis、Monique Ollier、Maryse Rapp、Jean-Michel Lacombe、Bernard Pucci

  DOI：10.1016/s0223-5234(99)80032-4

  日期：1998.10

  As an approach to the development of drug delivery systems, a new class of low macromolecular carriers called telomers bearing both antitumor agent such as arabinofuranosylcytosine (Ara-C) and galactose moieties were synthesized. These compounds were prepared by telomerization of tris(hydroxymethyl) acrylamidomethane (THAM) or monogalactosylated THAM and Ara-C polymerizable derivatives in the presence of transfer reagent such as alkanethiol or perfluoroalkanethiol. Their antitumor activities were assessed both in vitro and in vivo against a mouse cell Line, murine B16 melanoma. The biological results show that the cytotoxic effect of Ara-C is preserved in vitro and in vivo when the drug is grafted to the telomeric structure. (C) Elsevier, Paris.