(3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one | 90807-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• 英文别名: (3S,3aS,9aS,9bS)-3,6-dimethyl-9-methylidene-3,3a,4,5,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• CAS: 90807-54-8
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: BEOCXRAFSKTCDN-PYJNHQTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one 在 六甲基磷酰三胺 、 双氧水 、 溶剂黄146 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 8.0h， 生成 1β,10β-epoxyguaia-4(14),11(12)-dieno-13,6α-lactone
  参考文献：
  名称：

  Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives

  摘要：

  The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from I-a-santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an alpha-methylene gamma-lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.

  DOI：

  10.1021/np980092u
• 作为产物：
  描述：

  1β-Mesyloxyeudesm-4(14)-eno-13,6α-lactone 在 potassium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 22.0h， 生成 mokkolactone 、 (11S)-guaia-3,9-dieno-12,6α-lactone 、 (3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one 、 (3S,3aS,6aR,9aR,9bS)-3,6-Dimethyl-9-methylene-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
  参考文献：
  名称：

  Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives

  摘要：

  The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from I-a-santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an alpha-methylene gamma-lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.

  DOI：

  10.1021/np980092u

文献信息

• Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives
  作者：Saori Yuuya、Hisahiro Hagiwara、Toshio Suzuki、Masayoshi Ando、Atsushi Yamada、Kouji Suda、Takao Kataoka、Kazuo Nagai

  DOI：10.1021/np980092u

  日期：1999.1.1

  The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from I-a-santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an alpha-methylene gamma-lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.