7-氟-5-苯基-1,3-二氢-1,4-苯并二氮杂卓-2-酮 | 2648-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 7-氟-5-苯基-1,3-二氢-1,4-苯并二氮杂卓-2-酮
• 英文名称: 7-fluoro-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
• 英文别名: 7-Fluoro-5-phenyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one；7-fluoro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
• CAS: 2648-00-2
• 化学式: C₁₅H₁₁FN₂O
• 分子量: 254.264
• InChiKey: BHRKXOYRRFPATI-UHFFFAOYSA-N

物化性质

• 沸点：
  421.6±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-氟-5-苯基-1,3-二氢-1,4-苯并二氮杂卓-2-酮 在 劳森试剂 作用下， 以 乙二醇二甲醚 为溶剂， 生成 7-fluoro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione
  参考文献：
  名称：

  Pyrazolobenzodiazepines: Part I. Synthesis and SAR of a potent class of kinase inhibitors

  摘要：

  A novel series of pyrazolobenzodiazepines 3 has been identified as potent inhibitors of cyclin-dependent kinase 2 (CDK2). Their synthesis and structure-activity relationships (SAR) are described. Representative compounds from this class reversibly inhibit CDK2 activity in vitro, and block cell cycle progression in human tumor cell lines. Further exploration has revealed that this class of compounds inhibits several kinases that play critical roles in cancer cell growth and division as well as tumor angiogenesis. Together, these properties suggest a compelling basis for their use as antitumor agents. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.079
• 作为产物：
  描述：

  2-氨基-5-氟苯甲酸 在 哌啶 、 吡啶 、 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 7-氟-5-苯基-1,3-二氢-1,4-苯并二氮杂卓-2-酮
  参考文献：
  名称：

  苯胺衍生的二芳基碘鎓盐的热解和放射性氟化†

  摘要：

  通过明智地利用吸电子保护基团，可以合成苯胺衍生的二芳基碘鎓盐并以良好至极好的收率进行官能化。这种简单的方法为在相对复杂的分子（如氟替莫尔）中对氨基芳烃进行放射性标记开辟了另一条途径。

  DOI：

  10.1039/c7ob00253j

文献信息

• Structure–Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin
  作者：Hajer Abdelkafi、Aurélien Michau、Valérie Pons、Flora Ngadjeua、Alexandra Clerget、Lilia Ait Ouarab、David-Alexandre Buisson、David Montoir、Lucie Caramelle、Daniel Gillet、Julien Barbier、Jean-Christophe Cintrat

  DOI：10.1021/acs.jmedchem.0c00298

  日期：2020.8.13

  High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.
• FLUORINE CONTAINING COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Ritter Tobias

  公开号：US20120095217A1

  公开（公告）日：2012-04-19

  Fluorinated compounds and methods of making fluorinated compounds are described herein.
• [EN] FLUORINE CONTAINING COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS FLUORÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：HARVARD COLLEGE

  公开号：WO2010081036A2

  公开（公告）日：2010-07-15

  Fluorinated compounds and methods of making fluorinated compounds are described herein.
• Thermolysis and radiofluorination of diaryliodonium salts derived from anilines
  作者：Ethan J. Linstad、Amy L. Vāvere、Bao Hu、Jayson J. Kempinger、Scott E. Snyder、Stephen G. DiMagno

  DOI：10.1039/c7ob00253j

  日期：——

  Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.

  通过明智地利用吸电子保护基团，可以合成苯胺衍生的二芳基碘鎓盐并以良好至极好的收率进行官能化。这种简单的方法为在相对复杂的分子（如氟替莫尔）中对氨基芳烃进行放射性标记开辟了另一条途径。
• Pyrazolobenzodiazepines: Part I. Synthesis and SAR of a potent class of kinase inhibitors
  作者：Jin-Jun Liu、Irena Daniewski、Qingjie Ding、Brian Higgins、Grace Ju、Kenneth Kolinsky、Fred Konzelmann、Christine Lukacs、Giacomo Pizzolato、Pamela Rossman、Amy Swain、Kshitij Thakkar、Chung-Chen Wei、Dorota Miklowski、Hong Yang、Xuefeng Yin、Peter M. Wovkulich

  DOI：10.1016/j.bmcl.2010.08.079

  日期：2010.10

  A novel series of pyrazolobenzodiazepines 3 has been identified as potent inhibitors of cyclin-dependent kinase 2 (CDK2). Their synthesis and structure-activity relationships (SAR) are described. Representative compounds from this class reversibly inhibit CDK2 activity in vitro, and block cell cycle progression in human tumor cell lines. Further exploration has revealed that this class of compounds inhibits several kinases that play critical roles in cancer cell growth and division as well as tumor angiogenesis. Together, these properties suggest a compelling basis for their use as antitumor agents. (c) 2010 Elsevier Ltd. All rights reserved.