| 1569294-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• CAS: 1569294-05-8
• 化学式: C₁₅H₂₁N₅O
• 分子量: 287.365
• InChiKey: XFSPFQPBNYAZNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.14
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 N-(2-(N,N-diethylamino)ethyl)-6-(3-(2-((2-iodobenzyl)oxy)ethyl)ureido)quinoxaline-2-carboxamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Quinoxaline Derivatives of ICF01012 as Melanoma-Targeting Probes

  摘要：

  The aim of this study was the synthesis and pharmacokinetic selection of a best melanin-targeting ligand for addressing anticancer agents to pigmented melanoma. Seven quinoxaline carboxamide derivatives were synthesized and radiolabeled with iodine-125. Biodistribution studies of compounds [I-125]1a-g performed in melanoma-bearing mice tumor showed significant tumor uptake (range 2.43-5.68%ID/g) within 1 h after i.v. injection. Fast clearance of the radioactivity from the nontarget organs mainly via the urinary system gave high tumor-to-blood and tumor-to-muscle ratios. Given its favorable clearance and high tumor-melanoma uptake at 72 h, amide 1d was the most promising melanoma-targeting ligand in this series. Compound Id will be used as building block for the design of new melanoma-selective drug delivery systems.

  DOI：

  10.1021/ml400468x

文献信息

• Melanoma-targeted delivery system (part 1): Design, synthesis and evaluation of releasable disulfide drug by glutathione
  作者：Radhia El Aissi、Jean-Michel Chezal、Sébastien Tarrit、Olivier Chavignon、Emmanuel Moreau

  DOI：10.1016/j.ejmech.2015.06.055

  日期：2015.8

  Here we describe the design and synthesis of a prodrug developed for pigmented melanoma therapy, consisting of a Melanin-Targeting Probe (MTP) conjugated to 5-iodo-2'-deoxyuridine (IUdR) with a reduction-sensitive pre-determined breaking point. Compared with the non-cleavable conjugate (17b), prodrug (17a) bearing a self-immolative disulfide linker achieved complete release of lUdR within 20 min in the presence of reducing agents such as DTT or glutathione. Analytical results also showed that prodrug (17a) was more sensitive than parent non-cleavable conjugate (17b) for a concentration range of glutathione similar to that found in the intracellular compartment of tumours. (C) 2015 Elsevier Masson SAS. All rights reserved.