1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)-1,6-heptadiene-1,5-dione | 904912-40-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)-1,6-heptadiene-1,5-dione
• 英文别名: (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)hepta-1,4,6-trien-3-one
• CAS: 904912-40-9
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: NLMMJZSGEQGKCK-PDHRXESYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)-1,6-heptadiene-1,5-dione 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以65%的产率得到1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)heptane-3,5-dione
  参考文献：
  名称：

  A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

  摘要：

  Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 degrees C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.085
• 作为产物：
  描述：

  在 盐酸 作用下， 生成 1,7-bis(4-hydroxy-3,5-dimethoxyphenyl)-1,6-heptadiene-1,5-dione
  参考文献：
  名称：

  A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

  摘要：

  Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 degrees C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.085

文献信息

• Nurfina, A. N.; Reksohadiprodjo, M. S.; Timmerman, H., European Journal of Medicinal Chemistry, 1997, vol. 32, # 4, p. 320 - 328
  作者：Nurfina, A. N.、Reksohadiprodjo, M. S.、Timmerman, H.、Jenie, U. A.、Sugiyanto, D.、Goot, H. van der

  DOI：——

  日期：——
• Antitumor Agents. 250. Design and Synthesis of New Curcumin Analogues as Potential Anti-Prostate Cancer Agents
  作者：Li Lin、Qian Shi、Alexander K. Nyarko、Kenneth F. Bastow、Chin-Chung Wu、Ching-Yuan Su、Charles C.-Y Shih、Kuo-Hsiung Lee

  DOI：10.1021/jm051043z

  日期：2006.6.1

  In a continuing study of curcumin analogues as potential drug candidates to treat prostate cancer at both androgen-dependent and androgen-refractory stages, we designed and synthesized over 40 new analogues classified into four series: monophenyl analogues ( series A), heterocycle-containing analogues ( series B), analogues bearing various substituents on the phenyl rings ( series C), and analogues with various linkers ( series D). These new compounds were tested for cytotoxicity against two human prostate cancer cell lines, androgen-dependent LNCaP and androgen-independent PC-3. Antiandrogenic activity was also evaluated in LNCaP cells and PC-3 cells transfected with wild-type androgen receptor. Ten compounds possessed potent cytotoxicity against both LNCaP and PC-3 cells, seven only against LNCaP, and one solely against PC-3. This study established an advanced structure-activity relationship ( SAR), and these correlations will guide the further design of new curcumin analogues with better anti-prostate cancer activity.