3,6-dibromocatechol | 123433-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,6-dibromocatechol
• 英文别名: 3,6-dibromobenzene-1,2-diol；3,6-dibromo-1,2-benzenediol
• CAS: 123433-20-5
• 化学式: C₆H₄Br₂O₂
• 分子量: 267.905
• InChiKey: OFPHOXBUDUVEAS-UHFFFAOYSA-N

物化性质

• 熔点：
  122 °C
• 沸点：
  253.0±35.0 °C(Predicted)
• 密度：
  2.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  3,6-dibromocatechol 在 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 生成 3,6-dibromo-o-benzoquinone
  参考文献：
  名称：

  Paquet, Jacques; Brassard, Paul, Canadian Journal of Chemistry, 1989, vol. 67, p. 1354 - 1358

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6,6-tribromo-2-hydroxycyclohex-2-enone 在 lithium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以65%的产率得到3,6-dibromocatechol
  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

• 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.