(3'R,3'aS,5'aR,9'aS,9'bS)-3'-(methoxymethyl)-5'a-methylspiro[1,2,4-trioxolane-3,9'-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran]-2'-one | 1058170-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (3'R,3'aS,5'aR,9'aS,9'bS)-3'-(methoxymethyl)-5'a-methylspiro[1,2,4-trioxolane-3,9'-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran]-2'-one
• CAS: 1058170-24-3
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: UFWMHWUUKNSLOE-ZNNJNPNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3'R,3'aS,5'aR,9'aS,9'bS)-3'-(methoxymethyl)-5'a-methylspiro[1,2,4-trioxolane-3,9'-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran]-2'-one 在 tetraphenylporphyrin 作用下， 生成 (3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2,9-dione
  参考文献：
  名称：

  A new sesquiterpene lactone from the roots of Saussurea lappa: Structure–anticancer activity study

  摘要：

  The dried roots of Saussurea lappa, called costus roots, are used in the traditional system of medicine for the treatment of cancer. In our investigation for the anticancer constituents from the hexane extract of this plant, a new sesquiterpene (1) was isolated along with the known compounds costunolide ( 2), beta-cyclocostunolide (3), dihydro costunolide (4) and dehydro costuslactone (5). Their structures were established by the extensive spectroscopic analyses. In addition, costunolide and beta-cyclocostunolide derivatives were synthesized using Michael-type addition reaction of NaOMe to the alpha-methylene-gamma-lactone moiety. All the compounds were tested for their in vitro cytotoxic activity. Compound 1 exhibited potent cytotoxic activity and other compounds displayed moderate activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.008
• 作为产物：
  描述：

  (3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylenedecahydronaphtho[1,2-b]furan-2(3H)-one 在 臭氧 作用下， 以 氯仿 为溶剂， -78.0 ℃ 、2.53 MPa 条件下， 生成 (3'R,3'aS,5'aR,9'aS,9'bS)-3'-(methoxymethyl)-5'a-methylspiro[1,2,4-trioxolane-3,9'-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran]-2'-one
  参考文献：
  名称：

  A new sesquiterpene lactone from the roots of Saussurea lappa: Structure–anticancer activity study

  摘要：

  The dried roots of Saussurea lappa, called costus roots, are used in the traditional system of medicine for the treatment of cancer. In our investigation for the anticancer constituents from the hexane extract of this plant, a new sesquiterpene (1) was isolated along with the known compounds costunolide ( 2), beta-cyclocostunolide (3), dihydro costunolide (4) and dehydro costuslactone (5). Their structures were established by the extensive spectroscopic analyses. In addition, costunolide and beta-cyclocostunolide derivatives were synthesized using Michael-type addition reaction of NaOMe to the alpha-methylene-gamma-lactone moiety. All the compounds were tested for their in vitro cytotoxic activity. Compound 1 exhibited potent cytotoxic activity and other compounds displayed moderate activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.008

文献信息

• A new sesquiterpene lactone from the roots of Saussurea lappa: Structure–anticancer activity study
  作者：A. Robinson、T. Vijay Kumar、E. Sreedhar、V.G.M. Naidu、Sistla Rama Krishna、K. Suresh Babu、P.V. Srinivas、J. Madhusudana Rao

  DOI：10.1016/j.bmcl.2008.06.008

  日期：2008.7

  The dried roots of Saussurea lappa, called costus roots, are used in the traditional system of medicine for the treatment of cancer. In our investigation for the anticancer constituents from the hexane extract of this plant, a new sesquiterpene (1) was isolated along with the known compounds costunolide ( 2), beta-cyclocostunolide (3), dihydro costunolide (4) and dehydro costuslactone (5). Their structures were established by the extensive spectroscopic analyses. In addition, costunolide and beta-cyclocostunolide derivatives were synthesized using Michael-type addition reaction of NaOMe to the alpha-methylene-gamma-lactone moiety. All the compounds were tested for their in vitro cytotoxic activity. Compound 1 exhibited potent cytotoxic activity and other compounds displayed moderate activity. (c) 2008 Elsevier Ltd. All rights reserved.