(E)-3-hydroxy-4-((5-chloro-3-ethylbenzothiazol-2(3H)-ylidene)methyl)cyclobut-3-ene-1,2-dione | 1420042-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (E)-3-hydroxy-4-((5-chloro-3-ethylbenzothiazol-2(3H)-ylidene)methyl)cyclobut-3-ene-1,2-dione
• CAS: 1420042-21-2
• 化学式: C₁₄H₁₀ClNO₃S
• 分子量: 307.757
• InChiKey: XLMRLGOELJAKLM-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(biphenylsulfonio hexafluorophosphate(V))-3-ethyl-2-methylbenzothiazol-3-ium 、 (E)-3-hydroxy-4-((5-chloro-3-ethylbenzothiazol-2(3H)-ylidene)methyl)cyclobut-3-ene-1,2-dione 以 甲苯 、 正丁醇 为溶剂， 反应 5.0h， 以0.18 g的产率得到(E)-2-((E)-(5-chloro-3-ethylbenzothiazol-2(3H)-ylidene)methyl)-4-((5-(diphenylsulfonio)-3-ethylbenzothiazol-3-ium-2-yl)methylene)-3-oxocyclobut-1enolate hexafluorophosphate
  参考文献：
  名称：

  Selective Cell Death by Photochemically Induced pH Imbalance in Cancer Cells

  摘要：

  Singlet oxygen sensitized photodynamic therapy (PDT) relies on the concentration of oxygen in the tissue to be treated. Most cancer lesions, however, have poor vasculature and, as a result, are hypoxic, significantly hindering PDT efficacies. An oxygen-independent PDT method may circumvent this limitation. To address this, we prepared sulfonium salts that produced a pH drop within HCT 116 cells via the generation of a photoacid within the cytosol. This process was driven by one- or two-photon absorption (1PA or 2PA) of the endocytosed photoacid generators (PAGs). One of these PAGs, which had a significantly lower dark cytotoxicity and was more efficient in generating a photoacid, effectively induced necrotic cell death in the HCT 116 cells. The data suggest that PAGs may be an attractive alternative PDT modality to selectively induce cell death in oxygen-deprived tissue such as tumors.

  DOI：

  10.1021/ja3122312
• 作为产物：
  描述：

  (E)-3-butoxy-4-((5-chloro-3-ethylbenzothiazol-2(3H)-ylidene)methyl)cyclobut-3-ene-1,2-dione 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 生成 (E)-3-hydroxy-4-((5-chloro-3-ethylbenzothiazol-2(3H)-ylidene)methyl)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Selective Cell Death by Photochemically Induced pH Imbalance in Cancer Cells

  摘要：

  Singlet oxygen sensitized photodynamic therapy (PDT) relies on the concentration of oxygen in the tissue to be treated. Most cancer lesions, however, have poor vasculature and, as a result, are hypoxic, significantly hindering PDT efficacies. An oxygen-independent PDT method may circumvent this limitation. To address this, we prepared sulfonium salts that produced a pH drop within HCT 116 cells via the generation of a photoacid within the cytosol. This process was driven by one- or two-photon absorption (1PA or 2PA) of the endocytosed photoacid generators (PAGs). One of these PAGs, which had a significantly lower dark cytotoxicity and was more efficient in generating a photoacid, effectively induced necrotic cell death in the HCT 116 cells. The data suggest that PAGs may be an attractive alternative PDT modality to selectively induce cell death in oxygen-deprived tissue such as tumors.

  DOI：

  10.1021/ja3122312