bis-N,N′-benzyloxycarbonylrhodamine 110 | 1346661-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: bis-N,N′-benzyloxycarbonylrhodamine 110
• 英文别名: benzyl N-[3-oxo-6'-(phenylmethoxycarbonylamino)spiro[2-benzofuran-1,9'-xanthene]-3'-yl]carbamate
• CAS: 1346661-15-1
• 化学式: C₃₆H₂₆N₂O₇
• 分子量: 598.612
• InChiKey: ABVSSMDUHGDXFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  氯甲酸苄酯 、 rhodamine 110 chloride 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以13%的产率得到bis-N,N′-benzyloxycarbonylrhodamine 110
  参考文献：
  名称：

  Development and Bioorthogonal Activation of Palladium-Labile Prodrugs of Gemcitabine

  摘要：

  Bioorthogonal chemistry has become one of the main driving forces in current chemical biology, inspiring the search for novel biocompatible chemospecific reactions for the past decade. Alongside the well-established labeling strategies that originated the bioorthogonal paradigm, we have recently proposed the use of heterogeneous palladium chemistry and bioorthogonal Pd(0)-labile prodrugs to develop spatially targeted therapies. Herein, we report the generation of biologically inert precursors of cytotoxic gemcitabine by introducing Pd(0)-cleavable groups in positions that are mechanistically relevant for gemcitabine's pharmacological activity. Cell viability studies in pancreatic cancer cells showed that carbamate functionalization of the 4-amino group of gemcitabine significantly reduced (>23-fold) the prodrugs' cytotoxicity. The N-propargyloxycarbonyl (N-Poc) promoiety displayed the highest sensitivity to heterogeneous palladium catalysis under biocompatible conditions, with a reaction half-life of less than 6 h. Zebrafish studies with allyl, propargyl, and benzyl carbamate-protected rhodamines confirmed N-Poc as the most suitable masking group for implementing in vivo bioorthogonal organometallic chemistry.

  DOI：

  10.1021/jm500531z