3-hydroxyfriedel-3-en-2-one | 17947-03-4

• 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: 3-hydroxyfriedel-3-en-2-one
• 英文别名: (4aS,6aS,6aS,6bR,8aR,12aR,14aR,14bS)-3-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-5,6,6a,7,8,9,10,12,12a,13,14,14b-dodecahydro-1H-picen-2-one
• CAS: 17947-03-4
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: QEACUYQTRMGOSD-MZRSIZMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxyfriedel-3-en-2-one 在 lead(IV) acetate 、 氢氧化钾 作用下， 生成 3ξH-A-nor-friedelanone-(2)
  参考文献：
  名称：

  Friedelin的基本自动氧化

  摘要：

  在叔丁醇钾的存在下碱催化三萜酮弗里德林自氧化得到四种产物，并研究了它们的结构和形成机制。这些化合物的常见中间体被认为是 4-hydroperoxyfriedelan-3-one，而不是 Friedelane-2,3-dione。3-Oxafriedel-1-ene-2-羧酸是主要产物2-羟基-3-oxafriedelane-2-羧酸的脱水产物。

  DOI：

  10.1246/bcsj.60.2117
• 作为产物：
  描述：

  2α-bromofriedel-3-one 在 silver(I) acetate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以66%的产率得到3-hydroxyfriedel-3-en-2-one
  参考文献：
  名称：

  Talapatra, Bani; Lahiri, Biswanath; Basak, Amit, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 8, p. 741 - 745

  摘要：

  DOI：

文献信息

• Assignment of carbon-13 nuclear magnetic resonance spectra of some friedelanes
  作者：Amarendra Patra、Swapan Kumar Chaudhuri

  DOI：10.1002/mrc.1260250202

  日期：1987.2

  diacetate and friedelane‐2β‐3β‐diyl diacetate have been made. The carbon signals of 3‐oxofriedelan‐29‐ol and its acetate, methyl 3‐oxofriedelan‐29‐oate, 3‐oxofriedelan‐30‐ol, maytenfoliol, maytensifolin‐A, maytensifolin‐B, pachysonol and pristimerin reported in the literature have also been considered for their specific resonance assignments. A few signal assignments of some friedelanes, viz. friedelan‐28‐ol

  醋酸色林、2α-吡啶-N-oxyfriedelan-3-one、表色素及其醋酸盐、3α-羟基friedelan-2-one及其醋酸盐、3-羟基friedel-3-en-2-one的碳13共振分配及其醋酸酯、弗里德兰-3,7-二酮、3β-羟基弗里德兰-7-one、菜叶酚、弗里德内酯和弗里德内酯-2α-乙酸酯、弗里德兰-2α,3β-二醇及其二乙酸酯、弗里德兰-2β,3α-二乙酸酯, pachysandiyl-A diacetate 和 Friedelane-2β-3β-diyl diacetate 已经被制备出来。文献报道的 3-oxofriedelan-29-ol 及其乙酸盐、3-oxofriedelan-29-oate、3-oxofriedelan-30-ol、maytenfoliol、maytensifolin-A、maytensifolin-B、pachysonol 和 pristimerin
• Potential Anti-Tumor-Promoting Activity of 3α-Hydroxy-D:A-friedooleanan-2-one from the Stem Bark of <i>Mallotus philippensis</i>
  作者：Reiko Tanaka、Tomoko Nakata、Chiharu Yamaguchi、Shun-ichi Wada、Takeshi Yamada、Harukuni Tokuda

  DOI：10.1055/s-2008-1034347

  日期：2008.3

  Four known friedelane-type triterpenoids, friedelin (1), 3-hydroxy-D:A-friedoolean-3-en-2-one (2), 2β-hydroxy-D:A-friedooleanan-3-one (3), and 3α-hydroxy-D:A-friedooleanan-2-one (4), and two known lupane-type triterpenoids, lupeol (5) and betulin (6), were isolated from the stem bark of Mallotus philippensis. Isolates 1 - 4 and their synthetic analogues, 3-acetoxy-D:A-friedoolean-3-en-2-one (2a) and 3α-acetoxy-D:A-friedooleanan-2-one (4a), were tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol 13-acetate (TPA). The inhibitory effect of compounds 2 (IC50 = 292 mol ratio/32 pmol/TPA) and 4 (IC50 = 288) was stronger than those of the other compounds tested and the positive control, curcumin (IC50 = 343). Compound 4 strongly inhibited mouse skin tumor promotion in an in vivo two-stage carcinogenesis model. Studies have been conducted to identify the biologically active compounds extracted from the leaves, bark, and cones of trees that currently have no specific commercial use and are therefore treated as waste in the forestry industry.

  从菲利蒲桃（Mallotus philippensis）的茎皮中分离出了四种已知的油炸榄香烯类三萜，即油炸榄香烯（1）、3-羟基-D:A-油炸榄香烯-3-烯-2-酮（2）、2δ-羟基-D:A-油炸榄香烯-3-酮（3）和3±-羟基-D:A-油炸榄香烯-2-酮（4），以及两种已知的羽扇豆类三萜，即羽扇豆醇（5）和白桦脂素（6）。测试了分离物 1 - 4 及其合成类似物 3-acetoxy-D:A-friedoolean-3-en-2-one (2a) 和 3α-acetoxy-D:A-friedoolean-2-one (4a)对 12-O-tetradecanoylphorbol 13-acetate (TPA) 诱导的 Epstein-Barr 病毒早期抗原 (EBV-EA) 激活的抑制作用。化合物 2（IC50 = 292 mol ratio/32 pmol/TPA）和化合物 4（IC50 = 288）的抑制作用强于其他测试化合物和阳性对照姜黄素（IC50 = 343）。在体内两阶段致癌模型中，化合物 4 能强烈抑制小鼠皮肤肿瘤的生长。目前，从树叶、树皮和球果中提取的生物活性化合物没有具体的商业用途，因此在林业中被作为废物处理。
• Hemisynthetic Secofriedelane Triterpenes with Inhibitory Activity against the Growth of Human Tumor Cell Lines in Vitro
  作者：Cristina Moiteiro、César Manta、Fátima Justino、Regina Tavares、Maria João M. Curto、Madalena Pedro、Maria São José Nascimento、Madalena Pinto

  DOI：10.1021/np0498915

  日期：2004.7.1

  Seco acids 7 and 9 and hydroxylated analogues 5 and 6 derived from friedelane triterpenes were synthesized stereoselectively in high yields. Compounds 5-9 were evaluated for their ability to inhibit in vitro the growth of three human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer). Only compounds 7 and 9 were found to possess significant growth inhibitory effects, exhibiting GI(50) values that range from 24.6 to 32.8 muM and 10.9 to 17.6 muM, respectively.
• Pradhan, Bhim Prasad; Chakraborty, Satyajit; Sinha, Rajendra P, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 4, p. 395 - 398
  作者：Pradhan, Bhim Prasad、Chakraborty, Satyajit、Sinha, Rajendra P、Subba, Gyan Chandra、Weyerstahl, Peter

  DOI：——

  日期：——
• Pradhan; Dutta; Ghosh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 1, p. 7 - 12
  作者：Pradhan、Dutta、Ghosh、Ghosh

  DOI：——

  日期：——