3-(10'-oxodecanoyl)chroman-2,4-dione | 808761-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(10'-oxodecanoyl)chroman-2,4-dione
• 英文别名: 10-(2,4-Dioxochromen-3-yl)-10-oxodecanal
• CAS: 808761-96-8
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: FDVPQTISUQNJIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-甲基烯丙基胺 、 3-(10'-oxodecanoyl)chroman-2,4-dione 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 生成 3-[10-[Methyl(prop-2-enyl)amino]decanoyl]chromene-2,4-dione
  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：

  10-十一碳烯基氯酸 在 哌啶 、 吡啶 、 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 11.0h， 生成 3-(10'-oxodecanoyl)chroman-2,4-dione
  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.