7-(8'-oxooctyloxy)chromen-2-one | 808761-81-1

• 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: 7-(8'-oxooctyloxy)chromen-2-one
• 英文别名: 8-(2-Oxochromen-7-yl)oxyoctanal
• CAS: 808761-81-1
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: GKLNLZFSCPCVDX-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  474.4±45.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 7-(8'-oxooctyloxy)chromen-2-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 7-(8-Morpholin-4-yl-octyloxy)-chromen-2-one
  参考文献：
  名称：

  Umbelliferone aminoalkyl derivatives, a new class of squalene-hopene cyclase inhibitors

  摘要：

  The synthesis is described of several aminoalkyl derivatives of coumarin, obtained in good yields under microwave or high-intensity ultrasound irradiation. These compounds proved uniformly active as inhibitors of squalene-hopene cyclase (SHC) from Alicyclobacilhis acidocaldarius. Their design stemmed from our recent finding that the umbelliferone nucleus acquires inhibitory properties towards SHC when functionalized with a suitable chain such as the omega-epoxyfarnesyl group. Under our experimental conditions the most active ones, such as 7-(4'-allyimethylamino-but-2-ynyloxy)chromen-2-one (IC50 0.75 mM), approached the potency of anticholesteremic drug Ro 48-8071 (IC50 0.35 mM), an effective inhibitor of both squalene- and oxidosqualene-cyclases (OSC). Tests are in progress to determine their efficacy on different eukaryotic OSCs. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.06.010
• 作为产物：
  描述：

  8-溴-1-辛醇 在 Celite 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 7-(8'-oxooctyloxy)chromen-2-one
  参考文献：
  名称：

  Umbelliferone aminoalkyl derivatives, a new class of squalene-hopene cyclase inhibitors

  摘要：

  The synthesis is described of several aminoalkyl derivatives of coumarin, obtained in good yields under microwave or high-intensity ultrasound irradiation. These compounds proved uniformly active as inhibitors of squalene-hopene cyclase (SHC) from Alicyclobacilhis acidocaldarius. Their design stemmed from our recent finding that the umbelliferone nucleus acquires inhibitory properties towards SHC when functionalized with a suitable chain such as the omega-epoxyfarnesyl group. Under our experimental conditions the most active ones, such as 7-(4'-allyimethylamino-but-2-ynyloxy)chromen-2-one (IC50 0.75 mM), approached the potency of anticholesteremic drug Ro 48-8071 (IC50 0.35 mM), an effective inhibitor of both squalene- and oxidosqualene-cyclases (OSC). Tests are in progress to determine their efficacy on different eukaryotic OSCs. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.06.010

文献信息

• Umbelliferone aminoalkyl derivatives, a new class of squalene-hopene cyclase inhibitors
  作者：Giancarlo Cravotto、Gianni Balliano、Silvia Tagliapietra、Giovanni Palmisano、Andrea Penoni

  DOI：10.1016/j.ejmech.2004.06.010

  日期：2004.11

  The synthesis is described of several aminoalkyl derivatives of coumarin, obtained in good yields under microwave or high-intensity ultrasound irradiation. These compounds proved uniformly active as inhibitors of squalene-hopene cyclase (SHC) from Alicyclobacilhis acidocaldarius. Their design stemmed from our recent finding that the umbelliferone nucleus acquires inhibitory properties towards SHC when functionalized with a suitable chain such as the omega-epoxyfarnesyl group. Under our experimental conditions the most active ones, such as 7-(4'-allyimethylamino-but-2-ynyloxy)chromen-2-one (IC50 0.75 mM), approached the potency of anticholesteremic drug Ro 48-8071 (IC50 0.35 mM), an effective inhibitor of both squalene- and oxidosqualene-cyclases (OSC). Tests are in progress to determine their efficacy on different eukaryotic OSCs. (C) 2004 Elsevier SAS. All rights reserved.