[1,1'-biphenyl]-4'-monol-4-bromo-2,3-dimethoxy | 1314936-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1,1'-biphenyl]-4'-monol-4-bromo-2,3-dimethoxy
• 英文别名: 4-(4-Bromo-2,3-dimethoxyphenyl)phenol；4-(4-bromo-2,3-dimethoxyphenyl)phenol
• CAS: 1314936-94-1
• 化学式: C₁₄H₁₃BrO₃
• 分子量: 309.159
• InChiKey: RQHOWTCHGMOSFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1,1'-biphenyl]-4'-monol-4-bromo-2,3-dimethoxy 在 potassium fluoride dihydrate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.17h， 生成 4,4"-dihydroxy-2',3'-dimethoxy [1,1':4',1"-terphenyl]-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, biological evaluation and modeling studies of terphenyl topoisomerase IIα inhibitors as anticancer agents

  摘要：

  We report the synthesis and evaluation of a series of novel terphenyls. Compound 17 had the most potent anticancer activity, indicating that the phenolic hydroxyl was a key group. A DNA relaxation test showed that compound 17 had a strong inhibitory effect on TOP2 alpha, but not on TOP1, which was consistent with the docking analysis results. We performed a 3D-QSAR study using CoMFA and CoMSIA to determine, for the first time, the chemical-biological relationship in the inhibition of TOP by terphenyls. The CoMFA and CoMSIA model had good modeling statistics: leave-one-out q(2) of 0.605 and 0.622, r(2) of 0.998 and 0.994, and r(2), pred (test set) of 0.742 and 0.660. These results suggest that the ortho-phenolic hydroxyl on ring A is important for producing terphenyls with more efficacious activity. (C) 2015 Elsevier Masson SAS. All rights. reserved.

  DOI：

  10.1016/j.ejmech.2015.03.010
• 作为产物：
  描述：

  3,6-dibromocatechol 在 potassium fluoride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 0.17h， 生成 [1,1'-biphenyl]-4'-monol-4-bromo-2,3-dimethoxy
  参考文献：
  名称：

  A novel p-terphenyl derivative inducing cell-cycle arrest and apoptosis in MDA-MB-435 cells through topoisomerase inhibition

  摘要：

  A novel series of p-terphenyl derivatives (1-4, 1a-4a) was successfully synthesized and their in vitro anticancer activities were evaluated. Compound 1, showing the best antiproliferative activity with IC50 < 1 mu M against MDA-MB-435 cells, was further investigated. Compound 1 brought about a remarkable accumulation of MDA-MB-435 cells in G2/M phase prior to the induction of apoptosis. Further antitumor mechanism study indicated that compound 1, which inhibited the enzyme activity of Topo I and Topo II alpha by interfering predominantly with the enzyme, could be topoisomerase suppressors instead of poisons. We conclude that compound 1 represents a novel class of Topo catalytic suppressors for developing new chemotherapeutic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.020

文献信息

• A novel p-terphenyl derivative inducing cell-cycle arrest and apoptosis in MDA-MB-435 cells through topoisomerase inhibition
  作者：Jin Qiu、Baobing Zhao、Yan Shen、Wang Chen、Yudao Ma、Yuemao Shen

  DOI：10.1016/j.ejmech.2013.07.020

  日期：2013.10

  A novel series of p-terphenyl derivatives (1-4, 1a-4a) was successfully synthesized and their in vitro anticancer activities were evaluated. Compound 1, showing the best antiproliferative activity with IC50 < 1 mu M against MDA-MB-435 cells, was further investigated. Compound 1 brought about a remarkable accumulation of MDA-MB-435 cells in G2/M phase prior to the induction of apoptosis. Further antitumor mechanism study indicated that compound 1, which inhibited the enzyme activity of Topo I and Topo II alpha by interfering predominantly with the enzyme, could be topoisomerase suppressors instead of poisons. We conclude that compound 1 represents a novel class of Topo catalytic suppressors for developing new chemotherapeutic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis, biological evaluation and modeling studies of terphenyl topoisomerase IIα inhibitors as anticancer agents
  作者：Jin Qiu、Baobing Zhao、Wanxia Zhong、Yuemao Shen、Houwen Lin

  DOI：10.1016/j.ejmech.2015.03.010

  日期：2015.4

  We report the synthesis and evaluation of a series of novel terphenyls. Compound 17 had the most potent anticancer activity, indicating that the phenolic hydroxyl was a key group. A DNA relaxation test showed that compound 17 had a strong inhibitory effect on TOP2 alpha, but not on TOP1, which was consistent with the docking analysis results. We performed a 3D-QSAR study using CoMFA and CoMSIA to determine, for the first time, the chemical-biological relationship in the inhibition of TOP by terphenyls. The CoMFA and CoMSIA model had good modeling statistics: leave-one-out q(2) of 0.605 and 0.622, r(2) of 0.998 and 0.994, and r(2), pred (test set) of 0.742 and 0.660. These results suggest that the ortho-phenolic hydroxyl on ring A is important for producing terphenyls with more efficacious activity. (C) 2015 Elsevier Masson SAS. All rights. reserved.