((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate | 1234514-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: ((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate
• CAS: 1234514-01-2
• 化学式: C₂₅H₂₈O₇S
• 分子量: 472.559
• InChiKey: FUBJJEUXKFJMPI-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate 在 2,6-二甲基吡啶 、 N,N-二甲基丙烯基脲 、 sodium periodate 、 copper(l) iodide 、 四氧化锇 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)acetaldehyde
  参考文献：
  名称：

  Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions

  摘要：

  We have synthesised a focused library of derivatives of natural products containing the pyranonaphthoquinone moiety including the first report of such a scaffold with an appended tetrazole functionality. Examples include kalafungin derivatives as well as analogues of nanaomycin and eleutherin. These compounds were assessed for cytotoxic activation by breast cancer cell lines engineered to express the prototypic human one-and two-electron quinone bioreductive enzymes, NADPH: cytochrome P450 oxidoreductase (POR) and NAD(P)H: quinoneoxidoreductase 1 (NQO1; DT-diaphorase), respectively. Several compounds were observed to be cytotoxic at sub-micromolar level and a pattern of increased aerobic potency was observed in cells over expressing POR. A subset of analogues was assessed under anoxic conditions, where cytotoxicity was reduced, implicating redox cycling as a major mechanism of toxicity. The substrate specificity for reductive enzymes is relevant to the future design of bioreductive prodrugs to treat cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.052
• 作为产物：
  描述：

  、 对甲苯磺酰氯 在 三乙胺 作用下， 反应 6.0h， 以82 mg的产率得到((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  使用“点击化学”合成纳那霉素抗生素的三唑类似物

  摘要：

  使用萘叠氮化物的“咔哒”偶极环加成法与各种炔烃，然后氧化成所需的吡喃萘甲醌，制备了纳那霉素家族的一系列三唑类似物。

  DOI：

  10.1016/j.tet.2010.04.048