2H-1-Benzopyran-2-one, 7-[[4-(1-pyrrolidinyl)-2-butynyl]oxy]- | 808761-84-4

• 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: 2H-1-Benzopyran-2-one, 7-[[4-(1-pyrrolidinyl)-2-butynyl]oxy]-
• 英文别名: 7-(4-pyrrolidin-1-ylbut-2-ynoxy)chromen-2-one
• CAS: 808761-84-4
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: STZQYMXOEXDVIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-羟基香豆素 在 copper diacetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 22.0h， 生成 2H-1-Benzopyran-2-one, 7-[[4-(1-pyrrolidinyl)-2-butynyl]oxy]-
  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.