ethyl (5-azidomehtyluracil-1-yl)acetate | 1392300-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (5-azidomehtyluracil-1-yl)acetate
• 英文别名: Ethyl 2-[5-(azidomethyl)-2,4-dioxopyrimidin-1-yl]acetate；ethyl 2-[5-(azidomethyl)-2,4-dioxopyrimidin-1-yl]acetate
• CAS: 1392300-21-8
• 化学式: C₉H₁₁N₅O₄
• 分子量: 253.217
• InChiKey: WHOKCZNOHKFIAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (5-azidomehtyluracil-1-yl)acetate 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl [5-(N-(2-naphthylcarboxyl)aminomethyl)uracil-1-yl]acetate
  参考文献：
  名称：

  C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells

  摘要：

  The K562 cell line has been proposed as a useful experimental system to identify anti-tumor compounds acting by inducing terminal erythroid differentiation. K562 cells exhibit a low proportion of hemoglobin-synthesizing cells under standard cell growth conditions, but are able to undergo terminal erythroid differentiation when treated with a variety of anti-tumor compounds. In this paper we report a screening study on a set of different modified C(5) uracil derivatives for the evaluation of their antiproliferative effect in connection with erythroid differentiation pathways, and for defining a new class of drug candidates for the treatment of chronic myelogenous leukemia. Activity of the derivatives tested can be classified in two effect: an antiproliferative effect linked to a high level of erythroid differentiation activity and an antiproliferative effect without activation of gamma globin genes The highest antiproliferative effect and erythroid induction was shown by compound 9, a thymine derivative bearing a n-octyl chain on nitrogen N(1), whereas thymine did not show any effect, suggesting the importance of the linear alkyl chain in position N(1). To our knowledge this compound should be considered among the most efficient inducers of erythroid differentiation of K562 cells. This work is the starting point for the quest of more effective and specific drugs for the induction of terminal erythroid differentiation, for leading new insights in the treatment of neoplastic diseases with molecules acting by inducing differentiation rather than by simply exerting cytotoxic effects. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2011.09.024
• 作为产物：
  描述：

  5-(氯甲基)尿嘧啶 在 sodium azide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl (5-azidomehtyluracil-1-yl)acetate
  参考文献：
  名称：

  C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells

  摘要：

  The K562 cell line has been proposed as a useful experimental system to identify anti-tumor compounds acting by inducing terminal erythroid differentiation. K562 cells exhibit a low proportion of hemoglobin-synthesizing cells under standard cell growth conditions, but are able to undergo terminal erythroid differentiation when treated with a variety of anti-tumor compounds. In this paper we report a screening study on a set of different modified C(5) uracil derivatives for the evaluation of their antiproliferative effect in connection with erythroid differentiation pathways, and for defining a new class of drug candidates for the treatment of chronic myelogenous leukemia. Activity of the derivatives tested can be classified in two effect: an antiproliferative effect linked to a high level of erythroid differentiation activity and an antiproliferative effect without activation of gamma globin genes The highest antiproliferative effect and erythroid induction was shown by compound 9, a thymine derivative bearing a n-octyl chain on nitrogen N(1), whereas thymine did not show any effect, suggesting the importance of the linear alkyl chain in position N(1). To our knowledge this compound should be considered among the most efficient inducers of erythroid differentiation of K562 cells. This work is the starting point for the quest of more effective and specific drugs for the induction of terminal erythroid differentiation, for leading new insights in the treatment of neoplastic diseases with molecules acting by inducing differentiation rather than by simply exerting cytotoxic effects. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2011.09.024

文献信息

• Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA₂DNA triplexes
  作者：Alex Manicardi、Lucia Guidi、Alice Ghidini、Roberto Corradini

  DOI：10.3762/bjoc.10.154

  日期：——

  Pyrene derivatives can be incorporated into nucleic acid analogs in order to obtain switchable probes or supramolecular architectures. In this paper, peptide nucleic acids (PNAs) containing 1 to 3 1-pyreneacetic acid units (PNA1–6) with a sequence with prevalence of pyrimidine bases, complementary to cystic fibrosis W1282X point mutation were synthesized. These compounds showed sequence-selective switch-on of pyrene excimer emission in the presence of target DNA, due to PNA₂DNA triplex formation, with stability depending on the number and positioning of the pyrene units along the chain. An increase in triplex stability and a very high mismatch-selectivity, derived from combined stacking and base-pairing interactions, were found for PNA2, bearing two distant pyrene units.

  吡啶衍生物可以被合并到核酸类似物中，以获得可切换的探针或超分子结构。本文中，含有1至3个1-吡啶乙酸单元（PNA1-6）的肽核酸（PNAs）被合成，其序列以嘧啶碱基为主，与囊性纤维化W1282X点突变相互补。这些化合物在存在目标DNA时显示出吡啶激聚体发射的序列选择性开关，这是由于PNA2-DNA三联体形成，其稳定性取决于吡啶单元沿链的数量和位置。对于携带两个相距较远的吡啶单元的PNA2，发现了三联体稳定性的增加以及非常高的错配选择性，这是由于堆叠和碱基配对相互作用的结合所导致的。
• C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells
  作者：Eleonora Brognara、Ilaria Lampronti、Giulia Breveglieri、Alessandro Accetta、Roberto Corradini、Alex Manicardi、Monica Borgatti、Alessandro Canella、Chiara Multineddu、Rosangela Marchelli、Roberto Gambari

  DOI：10.1016/j.ejphar.2011.09.024

  日期：2011.12

  The K562 cell line has been proposed as a useful experimental system to identify anti-tumor compounds acting by inducing terminal erythroid differentiation. K562 cells exhibit a low proportion of hemoglobin-synthesizing cells under standard cell growth conditions, but are able to undergo terminal erythroid differentiation when treated with a variety of anti-tumor compounds. In this paper we report a screening study on a set of different modified C(5) uracil derivatives for the evaluation of their antiproliferative effect in connection with erythroid differentiation pathways, and for defining a new class of drug candidates for the treatment of chronic myelogenous leukemia. Activity of the derivatives tested can be classified in two effect: an antiproliferative effect linked to a high level of erythroid differentiation activity and an antiproliferative effect without activation of gamma globin genes The highest antiproliferative effect and erythroid induction was shown by compound 9, a thymine derivative bearing a n-octyl chain on nitrogen N(1), whereas thymine did not show any effect, suggesting the importance of the linear alkyl chain in position N(1). To our knowledge this compound should be considered among the most efficient inducers of erythroid differentiation of K562 cells. This work is the starting point for the quest of more effective and specific drugs for the induction of terminal erythroid differentiation, for leading new insights in the treatment of neoplastic diseases with molecules acting by inducing differentiation rather than by simply exerting cytotoxic effects. (C) 2011 Elsevier B.V. All rights reserved.