4'-bromomethyl-6,8,8-triethyldesmosdumotin B | 1242265-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-bromomethyl-6,8,8-triethyldesmosdumotin B
• 英文别名: 2-[4-(Bromomethyl)phenyl]-6,8,8-triethyl-5-hydroxychromene-4,7-dione
• CAS: 1242265-99-1
• 化学式: C₂₂H₂₃BrO₄
• 分子量: 431.326
• InChiKey: YVZSEROOSGRGTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6,8,8-Triethyl-7-methoxy-2-[4-(methoxymethyl)phenyl]chromene-4,5-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 4'-bromomethyl-6,8,8-triethyldesmosdumotin B 、 4'-propyl-6,8,8-triethyldesmosdumotin B
  参考文献：
  名称：

  Antitumor Agents. 280. Multidrug Resistance-Selective Desmosdumotin B Analogues

  摘要：

  6,6,8-Triethyldesmosdumotin B (2) was discovered as a MDR-selective flavonoid with significant in vitro anticancer activity against a multidrug resistant (MDR) cell line (KB-VIN) but without activity against the parent cells (KB). Additional 2 analogues were synthesized and evaluated to determine the effect of B-ring modifications on MDR-selectivity. Analogues with a B-ring Me (3) or Et (4) group had substantially increased MDR selectivity. Three new disubstituted analogues, 35, 37, and 49, also had high collateral sensitivity (CS) indices of 273, 250, and 100, respectively. Furthermore, 2-4 also displayed MDR selectivity in an MDR hepatoma-cell system. While 2-4 showed either no or very weak inhibition of cellular P-glycoprotein (P-gp) activity, they either activated or inhibited the actions of the first generation P-gp inhibitors verapamil or cyclosporin, respectively.

  DOI：

  10.1021/jm100846r