CSIC-E1131B | 1220476-21-0

• 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: CSIC-E1131B
• 英文别名: Ethyl 4,4-dimethyl-8-propan-2-yl-2,3-dihydrochromene-6-carboxylate；ethyl 4,4-dimethyl-8-propan-2-yl-2,3-dihydrochromene-6-carboxylate
• CAS: 1220476-21-0
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: CZDHBFRQTKJHDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  CSIC-E179 、 氯甲酸乙酯 在 叔丁基锂 作用下， 生成 CSIC-E1131B
  参考文献：
  名称：

  Development of Chromanes as Novel Inhibitors of the Uncoupling Proteins

  摘要：

  The uncoupling proteins (UCPs) are mitochondrial carriers that modulate the energetic efficiency and, as a result, can lower superoxide levels. Here, we describe the discovery of a small-molecule inhibitor of the UCPs. Screening of potential UCP1 regulators led to the identification of chromane derivatives that inhibit its proton conductance. Members of the UCP family can act as a defense against oxidative stress and, thus, UCP2 plays a protective role in tumor cells. High UCP2 levels have been associated with chemoresistance. We demonstrate that chromanes also inhibit UCP2 and, in HT-29 human carcinoma cells, cause oxidative stress. The chromane derivatives can act synergistically with chemotherapeutic agents; for instance, they increase the toxicity of arsenic trioxide in HT-29 cells. These findings open a promising line in the development of novel anticancer agents.

  DOI：

  10.1016/j.chembiol.2010.12.012

文献信息

• Development of Chromanes as Novel Inhibitors of the Uncoupling Proteins
  作者：Eduardo Rial、Leonor Rodríguez-Sánchez、Patricio Aller、Arancha Guisado、M. Mar González-Barroso、Eunate Gallardo-Vara、Mariano Redondo-Horcajo、Esther Castellanos、Roberto Fernández de la Pradilla、Alma Viso

  DOI：10.1016/j.chembiol.2010.12.012

  日期：2011.2

  The uncoupling proteins (UCPs) are mitochondrial carriers that modulate the energetic efficiency and, as a result, can lower superoxide levels. Here, we describe the discovery of a small-molecule inhibitor of the UCPs. Screening of potential UCP1 regulators led to the identification of chromane derivatives that inhibit its proton conductance. Members of the UCP family can act as a defense against oxidative stress and, thus, UCP2 plays a protective role in tumor cells. High UCP2 levels have been associated with chemoresistance. We demonstrate that chromanes also inhibit UCP2 and, in HT-29 human carcinoma cells, cause oxidative stress. The chromane derivatives can act synergistically with chemotherapeutic agents; for instance, they increase the toxicity of arsenic trioxide in HT-29 cells. These findings open a promising line in the development of novel anticancer agents.