2-bromo-N-(3,4-dimethoxybenzyl)benzamide | 895680-72-5

• 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: 2-bromo-N-(3,4-dimethoxybenzyl)benzamide
• 英文别名: 2-bromo-N-[(3,4-dimethoxyphenyl)methyl]benzamide
• CAS: 895680-72-5
• 化学式: C₁₆H₁₆BrNO₃
• 分子量: 350.212
• InChiKey: AMOCYMPCRNJSJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(3,4-dimethoxybenzyl)benzamide 、 4-氟苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以83.48%的产率得到N-(3,4-dimethoxybenzyl)-4'-fluoro[1,1'-biphenyl]-2-carboxamide
  参考文献：
  名称：

  Discovery of Potent Cytotoxic Ortho-Aryl Chalcones as New Scaffold Targeting Tubulin and Mitosis with Affinity-Based Fluorescence

  摘要：

  A series of new ortho-aryl chalcones have been designed and synthesized. Many of these compounds were found to exhibit significant antiproliferation activity toward a panel of cancer cell lines. Selected compounds show potent cytotoxicity against several drug resistant cell lines including paclitaxel (Taxol) resistant human ovarian carcinoma cells, vincristine resistant human ileocecum carcinoma cells, and doxorubicin resistant human breast carcinoma cells. Further investigation revealed that active analogues could inhibit the microtubule polymerization by binding to colchicine site and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. Furthermore, affinity-based fluorescence enhancement was observed during the binding of active compounds with tubulin, which greatly facilitated the determination of tubulin binding site of the compounds. Finally, selected compound 26 was found to exhibit obvious in vivo antitumor activity in A549 tumor xenografts model. Our systematic studies implied a new scaffold targeting tubulin and mitosis for novel antitumor drug discovery.

  DOI：

  10.1021/jm500024v
• 作为产物：
  描述：

  2-溴苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 2-bromo-N-(3,4-dimethoxybenzyl)benzamide
  参考文献：
  名称：

  Discovery of Potent Cytotoxic Ortho-Aryl Chalcones as New Scaffold Targeting Tubulin and Mitosis with Affinity-Based Fluorescence

  摘要：

  A series of new ortho-aryl chalcones have been designed and synthesized. Many of these compounds were found to exhibit significant antiproliferation activity toward a panel of cancer cell lines. Selected compounds show potent cytotoxicity against several drug resistant cell lines including paclitaxel (Taxol) resistant human ovarian carcinoma cells, vincristine resistant human ileocecum carcinoma cells, and doxorubicin resistant human breast carcinoma cells. Further investigation revealed that active analogues could inhibit the microtubule polymerization by binding to colchicine site and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. Furthermore, affinity-based fluorescence enhancement was observed during the binding of active compounds with tubulin, which greatly facilitated the determination of tubulin binding site of the compounds. Finally, selected compound 26 was found to exhibit obvious in vivo antitumor activity in A549 tumor xenografts model. Our systematic studies implied a new scaffold targeting tubulin and mitosis for novel antitumor drug discovery.

  DOI：

  10.1021/jm500024v

文献信息

• Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US10227304B2

  公开（公告）日：2019-03-12

  The present disclosure provides compounds of formula (I) that function as modulators of mitochondrial aldehyde dehydrogenase-2 (ALDH2) activity, and methods of preparing these compounds.

  本公开提供了作为线粒体醛脱氢酶-2（ALDH2）活性调节剂的式(I)化合物，以及制备这些化合物的方法。
• MITOCHONDRIAL ALDEHYDE DEHYDROGENASE-2 MODULATORS AND METHODS OF USE THEREOF
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：EP2126574B1

  公开（公告）日：2015-12-23
• Mitochondrial Aldehyde Dehydrogenase-2 Modulators and Methods of Use Thereof
  申请人：MOCHLY-ROSEN DARIA

  公开号：US20110105602A2

  公开（公告）日：2011-05-05

  The present invention provides compounds that function as modulators of mitochondrial aldehyde dehydrogenase-2 (ALDH2) activity; and pharmaceutical compositions comprising the compounds. The present invention provides therapeutic methods involving administering a subject compound, or a subject pharmaceutical composition. The present invention further provides assays for identifying agonists of ALDH2.
• Mitochondrial Aldehyde Dehyrogenase-2 Modulators and Methods of Use Thereof
  申请人：THE BOARD OF TRUSTEES OF THE LE-LAND STANFORD JUNIOR UNIVERSITY

  公开号：US20160107996A1

  公开（公告）日：2016-04-21

  The present disclosure provides compounds of formula (I) that function as modulators of mitochondrial aldehyde dehydrogenase-2 (ALDH2) activity, and methods of preparing these compounds.
• US9102651B2
  申请人：——

  公开号：US9102651B2

  公开（公告）日：2015-08-11