(E)-4-[(2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]but-2-en-1-ol | 1456515-45-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-4-[(2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]but-2-en-1-ol
• CAS: 1456515-45-9
• 化学式: C₂₂H₃₆O₂
• 分子量: 332.527
• InChiKey: CEXQXWUJGBLQRC-WPYBIJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-[(2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]but-2-en-1-ol 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 异辛烷 为溶剂， 反应 12.33h， 以71%的产率得到((2S,3S)-3-(((1'R,4a'S,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)methyl)oxiran-2-yl)methanol
  参考文献：
  名称：

  Derivatives of grindelic acid: From a non-active natural diterpene to synthetic antitumor derivatives

  摘要：

  Using several reactions that include homologations and asymmetric epoxidations as well as Ugi and Huisgen couplings, we generated a small focused library of new derivatives from the labdane-type diterpene grindelic acid. These compounds were evaluated as cytotoxic agents against a panel of five human solid tumor cell lines (HBL-100, HeLa, SW1573, T-47D, and WiDr). The presence of the diamide functionalizations enhanced the cytotoxic effect. N-Benzyl-N-(1-(benzylamino)-2-methyl-1-oxopropan-2-yl)grindelicamide, proved to be the most active product in all cell lines tested, with values of 0.95 (+/- 0.38) mu M against HBL-100 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.013
• 作为产物：
  描述：

  (2R,5S)-4,4'aalpha,5,5',6',7',8',8'a-八氢-2',5,5',5',8'abeta-五甲基螺[呋喃-2(3H),1'(4'H)-萘]-5-乙酸 在 lithium aluminium tetrahydride 、 三氧化硫吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 、 水 、 二甲基亚砜 为溶剂， 反应 2.25h， 生成 (E)-4-[(2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]but-2-en-1-ol
  参考文献：
  名称：

  Derivatives of grindelic acid: From a non-active natural diterpene to synthetic antitumor derivatives

  摘要：

  Using several reactions that include homologations and asymmetric epoxidations as well as Ugi and Huisgen couplings, we generated a small focused library of new derivatives from the labdane-type diterpene grindelic acid. These compounds were evaluated as cytotoxic agents against a panel of five human solid tumor cell lines (HBL-100, HeLa, SW1573, T-47D, and WiDr). The presence of the diamide functionalizations enhanced the cytotoxic effect. N-Benzyl-N-(1-(benzylamino)-2-methyl-1-oxopropan-2-yl)grindelicamide, proved to be the most active product in all cell lines tested, with values of 0.95 (+/- 0.38) mu M against HBL-100 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.013

文献信息

• Derivatives of grindelic acid: From a non-active natural diterpene to synthetic antitumor derivatives
  作者：Guillermo F. Reta、Alejandra I. Chiaramello、Celina García、Leticia G. León、Víctor S. Martín、José M. Padrón、Carlos E. Tonn、Osvaldo J. Donadel

  DOI：10.1016/j.ejmech.2013.06.013

  日期：2013.9

  Using several reactions that include homologations and asymmetric epoxidations as well as Ugi and Huisgen couplings, we generated a small focused library of new derivatives from the labdane-type diterpene grindelic acid. These compounds were evaluated as cytotoxic agents against a panel of five human solid tumor cell lines (HBL-100, HeLa, SW1573, T-47D, and WiDr). The presence of the diamide functionalizations enhanced the cytotoxic effect. N-Benzyl-N-(1-(benzylamino)-2-methyl-1-oxopropan-2-yl)grindelicamide, proved to be the most active product in all cell lines tested, with values of 0.95 (+/- 0.38) mu M against HBL-100 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.