N-{2-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-ethyl}-acrylamide | 186594-89-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-{2-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-ethyl}-acrylamide
• 英文别名: N-[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-3-(prop-2-enoylamino)propanamide
• CAS: 186594-89-8
• 化学式: C₁₅H₂₀N₄O₇
• 分子量: 368.346
• InChiKey: MIZMKZSLSPUIBR-ULTHFGNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  161
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-辛硫醇 、 N-{2-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-ethyl}-acrylamide 在 偶氮二异丁腈 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以66%的产率得到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 new cotelomers derived from tris(hydroxymethyl) aminomethane bearing arabinofuranosylcytosine moieties. Preliminary results on their in vitro and in vivo antitumoral activities

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(99)80032-4
• 作为产物：
  描述：

  N-丙烯酰-β-丙氨酸 在 三乙烯二胺 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 反应 15.0h， 生成 N-{2-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-ethyl}-acrylamide
  参考文献：
  名称：

  Synthesis of new cotelomers derived from tris(hydroxymethyl) aminomethane bearing arabinofuranosylcytosine moieties. Preliminary results on their in vitro and in vivo antitumoral activities

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(99)80032-4

文献信息

• Synthesis of cotelomers derived from tris(hydroxymethyl)acrylamidomethane (THAM) bearing cytosine arabinoside moieties. Preliminary investigation of their biological activity
  作者：Christiane Contino、Monique Ollier、Jean Claude Maurizis、Jean Michel Lacombe、Bernard Pucci

  DOI：10.1016/s0040-4039(96)02122-3

  日期：1996.12

  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