2,2-二溴-2-氟-1-(3-硝基-4-甲氧基-苯基)乙醇 | 824976-11-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,2-二溴-2-氟-1-(3-硝基-4-甲氧基-苯基)乙醇
• 英文名称: 2,2-dibromo-2-fluoro-1-(3-nitro-4-methoxy-phenyl)ethanol
• 英文别名: 2,2-dibromo-2-fluoro-1-(4-methoxy-3-nitrophenyl)ethanol
• CAS: 824976-11-6
• 化学式: C₉H₈Br₂FNO₄
• 分子量: 372.973
• InChiKey: MYWANHLJSZABEC-UHFFFAOYSA-N

物化性质

• 沸点：
  409.5±45.0 °C(Predicted)
• 密度：
  1.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-二溴-2-氟-1-(3-硝基-4-甲氧基-苯基)乙醇 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到1,1-dibromo-1,2-difluoro-2-(3-nitro-4-methoxy-phenyl)ethane
  参考文献：
  名称：

  [EN] FLUOROCOMBRETASTATIN AND DERIVATIVES THEREOF
  [FR] FLUOROCOMBRETASTATINE ET SES DERIVES

  摘要：

  公开号：

  WO2005007603A3
• 作为产物：
  描述：

  氟三溴甲烷 、 3-硝基-4-甲氧基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 以57.4%的产率得到2,2-二溴-2-氟-1-(3-硝基-4-甲氧基-苯基)乙醇
  参考文献：
  名称：

  Synthesis and Biological Activity of Fluorinated Combretastatin Analogues

  摘要：

  With the aim of understanding the influence of fluorine on the double bond of the cis-stilbene moiety of combretastatin derivatives and encouraged by a preliminary molecular modeling study showing a different biological environment on the interaction site with tubulin, we prepared, through various synthetic approaches, a small library of compounds in which one or both of the olefinic hydrogens were replaced with fluorine. X-ray analysis on the difluoro-CA-4 analogue demonstrated that the spatial arrangement of the molecule was not modified, compared to its nonfluorinated counterpart. SAR analysis confirmed the importance of the cis-stereochemistry of the stilbene scaffold. Nevertheless, some unpredicted results were observed on a few trans-fluorinated derivatives. The position of a fluorine atom on the double bond may affect the inhibition of tubulin polymerization and cytotoxic activity of these compounds.

  DOI：

  10.1021/jm701362m

文献信息

• Fluorocombretastatin and derivatives thereof
  申请人：Giannini Giuseppe

  公开号：US20060160778A1

  公开（公告）日：2006-07-20

  The present invention is related to new derivatives of Combretastatin, of Formula obtained by total synthesis. The strategy developed for each of the compounds is to i) replace a halogen (i.e. fluorine atom) to hydrogen on olefinic bound; ii) replace an aromatic ring in a natural product with an amino-aromatic ring. Said compounds recognize and bind the tubulin site: are useful for treating pathological states which arise from or are exacerbated by cell proliferation—as anticancer and/or antiangiogenic activity, in a mammal—to pharmaceutical compositions comprising these compounds.

  本发明涉及通过全合成获得的Combretastatin新衍生物，其化学式为。每种化合物的策略是：i）在烯丙基键上用氢替换卤素（即氟原子）；ii）用氨基芳香环替换天然产物中的芳香环。所述化合物识别并结合微管蛋白位点：适用于治疗由细胞增殖引起或加剧的病理状态，作为哺乳动物中的抗癌和/或抗血管生成活性，以及包含这些化合物的制药组合物。
• [EN] FLUOROCOMBRETASTATIN AND DERIVATIVES THEREOF<br/>[FR] FLUOROCOMBRETASTATINE ET SES DERIVES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2005007603A3

  公开（公告）日：2005-07-07
• FLUOROCOMBRETASTATIN AND DERIVATIVES THEREOF
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP2112990A2

  公开（公告）日：2009-11-04
• US7572778B2
  申请人：——

  公开号：US7572778B2

  公开（公告）日：2009-08-11
• Synthesis and Biological Activity of Fluorinated Combretastatin Analogues
  作者：Domenico Alloatti、Giuseppe Giannini、Walter Cabri、Isabella Lustrati、Mauro Marzi、Andrea Ciacci、Grazia Gallo、M. Ornella Tinti、Marcella Marcellini、Teresa Riccioni、Mario B. Guglielmi、Paolo Carminati、Claudio Pisano

  DOI：10.1021/jm701362m

  日期：2008.5.1

  With the aim of understanding the influence of fluorine on the double bond of the cis-stilbene moiety of combretastatin derivatives and encouraged by a preliminary molecular modeling study showing a different biological environment on the interaction site with tubulin, we prepared, through various synthetic approaches, a small library of compounds in which one or both of the olefinic hydrogens were replaced with fluorine. X-ray analysis on the difluoro-CA-4 analogue demonstrated that the spatial arrangement of the molecule was not modified, compared to its nonfluorinated counterpart. SAR analysis confirmed the importance of the cis-stereochemistry of the stilbene scaffold. Nevertheless, some unpredicted results were observed on a few trans-fluorinated derivatives. The position of a fluorine atom on the double bond may affect the inhibition of tubulin polymerization and cytotoxic activity of these compounds.