2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]isochromen-6-one | 1027802-09-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]isochromen-6-one
• 英文别名: 2,2-dimethyl-3,4-dihydropyran[3,4-c]isocromen-6[2H]-one；ARQ 501 metabolite M6；2,2-dimethyl-3,4-dihydropyrano[3,2-c]isochromen-6-one
• CAS: 1027802-09-0
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: NHUYGTCSYVBPOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-(3-methylbut-2-enyl)isochroman-1,4-dione 在 硫酸 作用下， 反应 0.5h， 以30%的产率得到2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]isochromen-6-one
  参考文献：
  名称：

  Synthetic methods for the preparation of ARQ 501 (β-Lapachone) human blood metabolites

  摘要：

  ARQ 501 (3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione), a synthetic version of beta-Lapachone, is a promising anti-cancer agent currently in multiple Phase II clinical trials. Promising anti-cancer activity was observed in Phase I and Phase II trials. Metabolism by red blood cells of drugs is an understudied area of research and the metabolites arising from oxidative ring opening (M2 and M3), decarbonylation/ ring contraction (M5), and decarbonylation/ oxidation (M4 and M6) of ARQ 501 offer a unique opportunity to provide insight into these metabolic processes. Since these metabolites were not detected in in vitro incubations of ARQ 501 with liver microsomes and were structurally diverse, confirmation by chemical synthesis was considered essential. In this report, we disclose the synthetic routes employed and the characterization of the reference standards for these blood metabolites as well as additional postulated structures, which were not confirmed as metabolites. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.073