(3S,3αS,6R,9βS)-6-hydroxy-3,6,9-trimethyl-3α,5,6,6α,7,9β-hexahydroazuleno[4,5-β]furan-2,8(3H,4H)-dione | 1188497-79-1

• 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,3αS,6R,9βS)-6-hydroxy-3,6,9-trimethyl-3α,5,6,6α,7,9β-hexahydroazuleno[4,5-β]furan-2,8(3H,4H)-dione
• 英文别名: 10α-hydroxy-3-oxo-1,7αH,6,11βH-guai-4-en-6,12-olide；(3S,3aS,6R,9bS)-6-hydroxy-3,6,9-trimethyl-3a,4,5,6a,7,9b-hexahydro-3H-azuleno[4,5-b]furan-2,8-dione
• CAS: 1188497-79-1
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: FUKGETHUQZLZRJ-KNVKXQHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,3αS,6R,9βS)-6-hydroxy-3,6,9-trimethyl-3α,5,6,6α,7,9β-hexahydroazuleno[4,5-β]furan-2,8(3H,4H)-dione 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (3S,6R,8S)-6-hydroxy-3,6,9-trimethyl-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-β]furan-8-yl 4-methylbenzoate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages

  摘要：

  A guaiane framework was scaffolded by photochemical rearrangement reactions using α-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) release were evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 6g, 7h, 7i, 7k and 8g, exhibited significant inhibitory effects on NO production, with IC50 values of 14.8, 22.3, 18.3, 17.4 and 7.0 μM, respectively. Their cytotoxicities were also estimated using an MTT assay. The structure-activity relationships of these compounds were also discussed.

  DOI：

  10.1016/j.ejmech.2014.06.043
• 作为产物：
  描述：

  山道年 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 12.0h， 以28%的产率得到(3S,3αS,6R,9βS)-6-hydroxy-3,6,9-trimethyl-3α,5,6,6α,7,9β-hexahydroazuleno[4,5-β]furan-2,8(3H,4H)-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages

  摘要：

  A guaiane framework was scaffolded by photochemical rearrangement reactions using α-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) release were evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 6g, 7h, 7i, 7k and 8g, exhibited significant inhibitory effects on NO production, with IC50 values of 14.8, 22.3, 18.3, 17.4 and 7.0 μM, respectively. Their cytotoxicities were also estimated using an MTT assay. The structure-activity relationships of these compounds were also discussed.

  DOI：

  10.1016/j.ejmech.2014.06.043

文献信息

• Synthesis and cytotoxic activity of α-santonin derivatives
  作者：Francisco F.P. Arantes、Luiz C.A. Barbosa、Elson S. Alvarenga、Antônio J. Demuner、Daniel P. Bezerra、José R.O. Ferreira、Letícia V. Costa-Lotufo、Cláudia Pessoa、Manoel O. Moraes

  DOI：10.1016/j.ejmech.2009.03.036

  日期：2009.9

  Treatment of α-santonin (1) with lithium diisopropyl amide (LDA) followed by capture of the organolithium with phenyl selenium chloride produced the compound 3-oxo-7αH,6βH,11-(phenylselenyl)-eudesma-1,4-dien-6,12-olide (6). Subsequent treatment of compound 6 with hydrogen peroxide gave 3-oxo-7αH,6βH-eudesma-1,4,11-trien-6,12-olide (7). Photochemical reaction of compound 7 led to the formation of 11,1

  以中等至高收率合成了十种α-桑坦宁衍生物。四种衍生物，即10α-乙酰氧基-3-氧代-1,7αH，6,11βH-gua-4--4-en-6,12-内酯（2），异佛丹子酸（3），10α-羟基-3-氧代-1，以α-桑顿素（1）为起始原料，通过不同的光化学反应制备了7αH，6,11βH-gua-4--4-6-6,12-内酯（4）和发光素（5）。使用不同类型的反应器和紫外光源，可以在无水乙酸，乙酸/水（1：1 v / v）或乙腈中进行这些转化。α-降钙素的治疗（1）用二异丙基氨基酰胺锂（LDA）捕获，然后用苯基氯化硒捕获有机锂，生成化合物3-oxo-7αH，6βH，11-（phenylselenyl）-eudesma-1,4-dien-6,12-olide（6）。随后用过氧化氢处理化合物6，得到3-氧代-7αH，6βH-阿德斯马-1,4,11-三烯-6,12-内酰胺（7）。化合物7的光化学反应导致形成11
• Synthesis and structure–activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages
  作者：Hao Chen、Bing-Yang Chen、Chun-Ting Liu、Zeng Zhao、Wen-Hao Shao、Hu Yuan、Kai-Jian Bi、Jiang-Yun Liu、Qing-Yan Sun、Wei-Dong Zhang

  DOI：10.1016/j.ejmech.2014.06.043

  日期：2014.8

  A guaiane framework was scaffolded by photochemical rearrangement reactions using α-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) release were evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 6g, 7h, 7i, 7k and 8g, exhibited significant inhibitory effects on NO production, with IC50 values of 14.8, 22.3, 18.3, 17.4 and 7.0 μM, respectively. Their cytotoxicities were also estimated using an MTT assay. The structure-activity relationships of these compounds were also discussed.