5-(furan-2-yl)-2,2,10-trimethyl-2H,8H-pyrano[2,3-f]chromen-8-one | 1604839-02-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-(furan-2-yl)-2,2,10-trimethyl-2H,8H-pyrano[2,3-f]chromen-8-one
• CAS: 1604839-02-2
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: QNXYTJHFQKVUHO-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  483.8±45.0 °C(predicted)
• 密度：
  1.219±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  5-(furan-2-yl)-2,2,10-trimethyl-2H,8H-pyrano[2,3-f]chromen-8-one 在 硝酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 2.0h， 以31%的产率得到2,2,10-Trimethyl-5-(5-nitro-2-furyl)pyrano[2,3-h]chromen-8-one
  参考文献：
  名称：

  Synthetic Calanolides with Bactericidal Activity against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  It is urgent to introduce new drugs for tuberculosis to shorten the prolonged course of treatment and control drug-resistant Mycobacterium tuberculosis (Mtb). One strategy toward this goal is to develop antibiotics that eradicate both replicating (R) and nonreplicating (NR) Mtb. Naturally occurring (+)-calanolide A was active against R-Mtb. The present report details the design, synthesis, antimycobacterial activities, and structure-activity relationships of synthetic calanolides. We identified potent dual-active nitro-containing calanolides with minimal in vitro toxicity that were cidal to axenic Mtb and Mtb in human macrophages, while sparing Gram-positive and -negative bacteria and yeast. Two of the nitrobenzofuran-containing lead compounds were found to be genotoxic to mammalian cells. Although genotoxicity precluded clinical progression, the profound, selective mycobactericidal activity of these calanolides will be useful in identifying pathways for killing both R- and NR-Mtb, as well as in further structure-based design of more effective and drug-like antimycobacterial agents.

  DOI：

  10.1021/jm4019228
• 作为产物：
  描述：

  2-呋喃硼酸 、 2,2,10-trimethyl-8-oxo-2H,8H-pyrano[2,3-f]chromen-5-yl trifluoromethanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 乙二醇二甲醚 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以73%的产率得到5-(furan-2-yl)-2,2,10-trimethyl-2H,8H-pyrano[2,3-f]chromen-8-one
  参考文献：
  名称：

  Synthetic Calanolides with Bactericidal Activity against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  It is urgent to introduce new drugs for tuberculosis to shorten the prolonged course of treatment and control drug-resistant Mycobacterium tuberculosis (Mtb). One strategy toward this goal is to develop antibiotics that eradicate both replicating (R) and nonreplicating (NR) Mtb. Naturally occurring (+)-calanolide A was active against R-Mtb. The present report details the design, synthesis, antimycobacterial activities, and structure-activity relationships of synthetic calanolides. We identified potent dual-active nitro-containing calanolides with minimal in vitro toxicity that were cidal to axenic Mtb and Mtb in human macrophages, while sparing Gram-positive and -negative bacteria and yeast. Two of the nitrobenzofuran-containing lead compounds were found to be genotoxic to mammalian cells. Although genotoxicity precluded clinical progression, the profound, selective mycobactericidal activity of these calanolides will be useful in identifying pathways for killing both R- and NR-Mtb, as well as in further structure-based design of more effective and drug-like antimycobacterial agents.

  DOI：

  10.1021/jm4019228