6-(2-aminoethyl)amino-5-chlorouracil | 399550-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-(2-aminoethyl)amino-5-chlorouracil
• 英文别名: 6-(2-aminoethylamino)-5-chloro-1H-pyrimidine-2,4-dione
• CAS: 399550-08-4
• 化学式: C₆H₉ClN₄O₂
• 分子量: 204.616
• InChiKey: UBIZYYDQUSJYIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  96.2
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 乙二胺 、 2,4-dihydroxy-5,6-dichlorpyrimidin 生成 6-(2-aminoethyl)amino-5-chlorouracil
  参考文献：
  名称：

  Novel 6-substituted uracil analogs as inhibitors of the angiogenic actions of thymidine phosphorylase11Abbreviations: AEAC, 6-(2-aminoethyl)amino-5-chlorouracil; CIMU, 5-chloro-6-(1-imidazolyl-methyl) uracil; FGF, fibroblast growth factor; HUVEC, human umbilical vein endothelial cell(s); PD-ECGF, platelet-derived endothelial cell growth factor; PNP, purine nucleoside phosphorylase; TGF, transforming growth factor; TNF-α, tumor necrosis factor-α; TP, thymidine phosphorylase; UP, uridine phosphorylase; and VEGF, vascular endothelial growth factor.

  摘要：

  Thymidine phosphorylase (TP) catalyzes the reversible phosphorolysis of thymidine and other pyrimidine 2'-deoxyribonucleosides. In addition, TP has been shown to possess angiogenic activity in a number of in vitro and in vivo assays, and its angiogenic activity has been linked to its catalytic activity. A series of 5- and 6-substituted uracil derivatives were synthesized and evaluated for their abilities to inhibit TP activity. Among the most active compounds was a 6-amino-substituted uracil analog, 6-(2-aminoethyl)amino-5-chlorouracil (AEAC), which was a competitive inhibitor with a K-i of 165 nM. The inhibitory activity of AEAC was selective for TP, as it did not inhibit purine nucleoside phosphorylase or uridine phosphorylase at concentrations up to 1 mM. Human recombinant TP induced human umbilical vein endothelial cell (HUVEC) migration in a modified Boyden chamber assay in vitro, and this action could be abrogated by the TP inhibitors. The actions of the inhibitors were specific for TP, as they had no effect on the chemotactic actions of vascular endothelial growth factor (VEGF). HUVEC migration was also induced when TP-transfected human colon and breast carcinoma cells were co-cultured in the Boyden chamber assay in place of the purified angiogenic factors, and a TP inhibitor blocked the tumor cell-mediated migration almost completely. These studies suggest that inhibitors of TP may be useful in pathological conditions that are dependent upon TP-driven angiogenesis. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0006-2952(01)00783-3

文献信息

• Methods and compositions for the treatment of anti-angiogenic resistant cancer
  申请人：Institut d'Investigació Biomèdica de Bellvitge (IDIBELL)

  公开号：EP3067369A1

  公开（公告）日：2016-09-14

  The present invention corresponds to the field of cancer treatment and is related to compounds and compositions for their use in the treatment of cancer, in particular to inhibitors of platelet derived-endothelial cell growth factor (PD-ECGF) for their use in the treatment of cancer resistant to anti-angiogenic therapy.

  本发明属于癌症治疗领域，涉及用于治疗癌症的化合物和组合物，特别是血小板衍生内皮细胞生长因子（PD-ECGF）抑制剂，用于治疗对抗血管生成疗法有抗药性的癌症。
• BIOSYNTHETIC LABELING AND SEPARATION OF RNA
  申请人：THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY

  公开号：EP1625234A1

  公开（公告）日：2006-02-15
• EP1625234A4
  申请人：——

  公开号：EP1625234A4

  公开（公告）日：2007-08-22
• Biosynthetic labeling and separation of RNA
  申请人：——

  公开号：US20040259135A1

  公开（公告）日：2004-12-23

  A purine or pyrimidine analog having a reactive moiety not normally present in RNA is incorporated into RNA during a defined time period in a cell of interest, where the cell of interest comprises a phosphoribosyltransferase or nucleoside kinase that can specifically incorporate the analogs into the corresponding nucleotide. The nucleotide is then retained by the cell until it is synthesized in RNA. The labeled RNA can be specifically purified away from all other molecules and finds use in hybridization to microarrays; hybridization to blots; real time PCR; reverse transcriptase PCR, in vitro translation; cross-linking to interacting molecules, and the like.
• [EN] BIOSYNTHETIC LABELING AND SEPARATION OF RNA<br/>[FR] ETIQUETAGE BIOSYNTHETIQUE ET SEPARATION DE L'ARN
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2004101825A1

  公开（公告）日：2004-11-25

  A purine or pyrimidine analog having a reactive moiety not normally present in RNA is incorporated into RNA during a defined time period in a cell of interest, where the cell of interest comprises a phosphoribosyltransferase or nucleoside kinase that can specifically incorporate the analogs into the corresponding nucleotide. The nucleotide is then retained by the cell until it is synthesized in RNA. The labeled RNA can be specifically purified away from all other molecules and finds use in hybridization to microarrays; hybridization to blots; real time PCR; reverse transcriptase PCR, in vitro translation; cross-linking to interacting molecules, and the like.