diethyl 4,4'-dihydroxy-5,5'-dimethoxy-8,3'-neolign-7,7'-dien-9,9'-dionate | 864668-60-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: diethyl 4,4'-dihydroxy-5,5'-dimethoxy-8,3'-neolign-7,7'-dien-9,9'-dionate
• 英文别名: ethyl 2-[5-(3-ethoxy-3-oxoprop-1-enyl)-2-hydroxy-3-methoxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 864668-60-0
• 化学式: C₂₄H₂₆O₈
• 分子量: 442.466
• InChiKey: ZXDNUJOKAWUSMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl 4,4'-dihydroxy-5,5'-dimethoxy-8,3'-neolign-7,7'-dien-9,9'-dionate 在 ammonium hydroxide 作用下， 反应 1.0h， 以58%的产率得到4,4'-dihydroxy-5,5'-dimethoxy-8,3'-neolign-7,7'-dien-9,9'-diamide
  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
• 作为产物：
  描述：

  阿魏酸 在 氯化亚砜 、 potassium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 2.67h， 生成 diethyl 4,4'-dihydroxy-5,5'-dimethoxy-8,3'-neolign-7,7'-dien-9,9'-dionate
  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

• 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.