α,α'-Diveratrylidenbernsteinsaeure | 24289-99-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: α,α'-Diveratrylidenbernsteinsaeure
• 英文别名: 2.3-Bis-(3.4-dimethoxy-benzyliden)-bernsteinsaeure；diveratrylidene-succinic acid；Diveratralbernsteinsaeure；α.δ-Bis-(3.4-dimethoxy-phenyl)-fulgensaeure；Diveratryliden-bernsteinsaeure；2,3-Bis[(3,4-dimethoxyphenyl)methylidene]butanedioic acid
• CAS: 24289-99-4
• 化学式: C₂₂H₂₂O₈
• 分子量: 414.412
• InChiKey: RDNZVLBCRYBJGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  α,α'-Diveratrylidenbernsteinsaeure 在 乙酰氯 作用下， 生成 (Z,Z)-bis-(3,4-dimethoxybenzylidene)succinic anhydride
  参考文献：
  名称：

  Stobbe, Justus Liebigs Annalen der Chemie, 1911, vol. 380, p. 77

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 丁二酸二乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 α,α'-Diveratrylidenbernsteinsaeure
  参考文献：
  名称：

  Synthesis of neolignans as microtubule stabilisers

  摘要：

  Tubulin is a well established target for anticancer drug development. Lignans and neolignans were synthesized as tubulin interacting agents. Neolignans 10 and 19 exhibited significant anticancer activity against MCF-7 and MDAMB-231 human breast cancer cell lines. Both the compounds effectively induced stabilization of microtubule at 4 and 20 mu M concentrations respectively. Neolignan 10 induced G2/M phase arrest in MCF-7 cells. Docking experiments raveled that 10 and 19 occupied the same binding pocket of paclitaxel with some difference in active site amino acids and good bioavailability of both the compounds. In in vivo acute oral toxicity 10 was well tolerated up to 300 mg/kg dose in Swiss-albino mice. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.067

文献信息

• Stobbe; Leuner, Justus Liebigs Annalen der Chemie, 1911, vol. 380, p. 76
  作者：Stobbe、Leuner

  DOI：——

  日期：——
• Synthesis of neolignans as microtubule stabilisers
  作者：B. Sathish Kumar、Aastha Singh、Amit Kumar、Jyotsna Singh、Mohammad Hasanain、Arjun Singh、Nusrat Masood、Dharmendra K. Yadav、Rituraj Konwar、Kalyan Mitra、Jayanta Sarkar、Suaib Luqman、Anirban Pal、Feroz Khan、Debabrata Chanda、Arvind S. Negi

  DOI：10.1016/j.bmc.2013.12.067

  日期：2014.2

  Tubulin is a well established target for anticancer drug development. Lignans and neolignans were synthesized as tubulin interacting agents. Neolignans 10 and 19 exhibited significant anticancer activity against MCF-7 and MDAMB-231 human breast cancer cell lines. Both the compounds effectively induced stabilization of microtubule at 4 and 20 mu M concentrations respectively. Neolignan 10 induced G2/M phase arrest in MCF-7 cells. Docking experiments raveled that 10 and 19 occupied the same binding pocket of paclitaxel with some difference in active site amino acids and good bioavailability of both the compounds. In in vivo acute oral toxicity 10 was well tolerated up to 300 mg/kg dose in Swiss-albino mice. (C) 2014 Elsevier Ltd. All rights reserved.
• Stobbe, Justus Liebigs Annalen der Chemie, 1911, vol. 380, p. 77
  作者：Stobbe

  DOI：——

  日期：——