3-(10'-undecenoyl)chroman-2,4-dione | 808761-95-7

• 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'-undecenoyl)chroman-2,4-dione
• 英文别名: 3-Undec-10-enoylchromene-2,4-dione
• CAS: 808761-95-7
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: SRZJOICOPOXSEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(10'-undecenoyl)chroman-2,4-dione 在 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 3.0h， 以30%的产率得到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
• 作为产物：
  描述：

  4-羟基香豆素 、 10-十一碳烯基氯酸 在 哌啶 、 吡啶 作用下， 反应 8.0h， 以70%的产率得到3-(10'-undecenoyl)chroman-2,4-dione
  参考文献：
  名称：

  Novel Squalene-Hopene Cyclase Inhibitors Derived from Hydroxycoumarins and Hydroxyacetophenones

  摘要：

  角鲨烯-蒎烯环化酶（SHC）是预测与氧化角鲨烯环化酶（OSC）分子相互作用的有用模型酶。我们研究了多种香豆素衍生的 SHC 抑制剂的结构-活性关系，并提出了结构简化建议。伞形酮和 2,4-二羟基苯乙酮为设计 SHC 抑制剂提供了方便的起始核。含有ω-环氧法呢酰基或只有普通烷基链的衍生物对在大肠杆菌中表达的重组 SHC 有抑制作用。

  DOI：

  10.1248/cpb.52.1171

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.
• Novel Squalene-Hopene Cyclase Inhibitors Derived from Hydroxycoumarins and Hydroxyacetophenones
  作者：Giancarlo Cravotto、Gianni Balliano、Silvia Tagliapietra、Simonetta Oliaro-Bosso、Gian Mario Nano

  DOI：10.1248/cpb.52.1171

  日期：——

  Squalene-hopene cyclase (SHC) is a useful model enzyme for predicting molecular interactions with oxidosqualene cyclase (OSC). Structure–activity relationships were investigated for numerous coumarin-derived inhibitors of SHC, and structural simplifications are suggested. Both umbelliferone and 2,4-dihydroxyacetophenone provide convenient starting nuclei for the design of SHC inhibitors. Derivatives bearing an ω-epoxyfarnesyl moiety or just a plain alkyl chain showed an inhibitory effect on a recombinant SHC from Alicyclobacillus acidocaldarius expressed in Escherichia coli.

  角鲨烯-蒎烯环化酶（SHC）是预测与氧化角鲨烯环化酶（OSC）分子相互作用的有用模型酶。我们研究了多种香豆素衍生的 SHC 抑制剂的结构-活性关系，并提出了结构简化建议。伞形酮和 2,4-二羟基苯乙酮为设计 SHC 抑制剂提供了方便的起始核。含有ω-环氧法呢酰基或只有普通烷基链的衍生物对在大肠杆菌中表达的重组 SHC 有抑制作用。