3-trimethylsiloxyfriedel-3-ene | 161739-60-2

• 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-trimethylsiloxyfriedel-3-ene
• 英文别名: [(4aS,6aS,6aS,6bR,8aR,12aR,14aR,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-1,2,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydropicen-3-yl]oxy-trimethylsilane
• CAS: 161739-60-2
• 化学式: C₃₃H₅₈OSi
• 分子量: 498.908
• InChiKey: GCXSFKKLRKCUNM-JIJLTMQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.38
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-trimethylsiloxyfriedel-3-ene 在 碳酸氢钠 、 过碘酸 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3,4-Secofriedelan-4-on-3-oic-acid
  参考文献：
  名称：

  Hemisynthetic Secofriedelane Triterpenes with Inhibitory Activity against the Growth of Human Tumor Cell Lines in Vitro

  摘要：

  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.

  DOI：

  10.1021/np0498915
• 作为产物：
  描述：

  三甲基氯硅烷 、 无羁萜 在 六甲基二硅氮烷 作用下， 以 正戊烷 为溶剂， 反应 48.0h， 以84%的产率得到3-trimethylsiloxyfriedel-3-ene
  参考文献：
  名称：

  Hemisynthetic Secofriedelane Triterpenes with Inhibitory Activity against the Growth of Human Tumor Cell Lines in Vitro

  摘要：

  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.

  DOI：

  10.1021/np0498915

文献信息

• Synthetic Secofriedelane and Friedelane Derivatives as Inhibitors of Human Lymphocyte Proliferation and Growth of Human Cancer Cell Lines in Vitro
  作者：Cristina Moiteiro、Fátima Justino、Regina Tavares、M. J. Marcelo-Curto、M. Helena Florêncio、Maria São José Nascimento、Madalena Pedro、Fátima Cerqueira、Madalena M. M. Pinto

  DOI：10.1021/np010217m

  日期：2001.10.1

  Controlled silylation of friedelin (1) from cork smoker wash solids, a byproduct generated during processing of corkboard by steam baking, gave 3-trimethylsiloxyfriedel-2-ene (3) in high yields. Oxidation of 3 with OsO(4)/NMMO produced 2alpha-hydroxyfriedelan-3-one (cerin) (5), from which the new 2,3-secofriedelan-2-al-3-oic acid (6) was obtained quantitatively by periodic acid oxidation. Oxidation

  来自软木吸烟者洗涤固体的弗瑞德林（1）的受控甲硅烷基化（软木在蒸汽烘烤过程中产生的副产物）以高收率得到3-三甲基甲硅烷氧基弗瑞德-2-烯（3）。用OsO（4）/ NMMO氧化3产生2alpha-hydroxyfriedelan-3-one（cerin）（5），从中通过定量获得新的2,3-secofriedelan-2-al-3-oic acid（6）。高碘酸氧化。用DDQ氧化3得到Friedel-1-en-3-one（8）。3的还原性臭氧分解得到2alpha，3beta-dihydroxyfriedelane，厚皮二醇A（7）。化合物6被证明是有效的人类淋巴细胞增殖抑制剂（IC（50）= 10.7 microM）和人类癌细胞系生长（GI（50）= 5.4-17.2 microM）。首次描述了化合物（3、4、5、6a，7和8）的（13）C NMR数据。
• 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.