1-(2-((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)ethyl)-4-(((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)-1H-1,2,3-triazole | 1456515-67-5

• 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: 1-(2-((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)ethyl)-4-(((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)-1H-1,2,3-triazole
• 英文别名: 1-[2-[(2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]ethyl]-4-[[(2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]methyl]triazole
• CAS: 1456515-67-5
• 化学式: C₄₁H₆₅N₃O₂
• 分子量: 631.986
• InChiKey: DATNAQNYRKMIFV-ZXEXYEBMSA-N

物化性质

• 沸点：
  679.9±65.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 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 、 正丁基锂 、 copper(ll) sulfate pentahydrate 、 草酰氯 、 三苯基甲烷 、 sodium ascorbate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正庚烷 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 34.25h， 生成 1-(2-((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)ethyl)-4-(((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)-1H-1,2,3-triazole
  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.