5-Nitro-2-thiazolcarboxaldehyd | 536-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Nitro-2-thiazolcarboxaldehyd
• 英文别名: 5-nitro-thiazole-2-carbaldehyde；2-Thiazolecarboxaldehyde, 5-nitro-；5-nitro-1,3-thiazole-2-carbaldehyde
• CAS: 536-48-1
• 化学式: C₄H₂N₂O₃S
• 分子量: 158.137
• InChiKey: PBKXDIXMFQUCHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Nitro-2-thiazolcarboxaldehyd 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以70%的产率得到(5-nitrothiazole-2-yl)methanol
  参考文献：
  名称：

  A Novel Model System for Understanding Anticancer Activity of Hypoxia-Activated Prodrugs

  摘要：

  Reports on the comprehensive factors for design considerations of hypoxia-activated prodrugs (HAPs) are rare. We introduced a new model system composed of a series of highly water-soluble HAPs, providing a platform to comprehensively understand the interaction between HAPs and hypoxic biosystems. Specifically, four kinds of new HAPs were designed and synthesized, containing the same biologically active moiety but masked by different bioreductive groups. Our results demonstrated that the activity of the prodrugs was strongly dependent on not only the molecular structure but also the hypoxic tumor microenvironment. We found the presence of a direct linear relationship between cytotoxicity of the HAPs and the reduction potential of whole molecule/oxygen concentration/reductase expression. Moreover, limited blood vasculature in hypoxic regions was also a critical barrier for effective activation of the HAPs. This study offers a comprehensive insight into understanding the design factors required for HAPs.

  DOI：

  10.1021/acs.molpharmaceut.0c00232