trifluoromethanesulfonic acid 1-nitrodibenzofuran-4-yl ether | 912824-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: trifluoromethanesulfonic acid 1-nitrodibenzofuran-4-yl ether
• 英文别名: trifluoro-methanesulfonic acid 1-nitro-dibenzofuran-4-yl ester；(1-nitrodibenzofuran-4-yl) trifluoromethanesulfonate
• CAS: 912824-66-9
• 化学式: C₁₃H₆F₃NO₆S
• 分子量: 361.255
• InChiKey: FDMHSTUQWWBHGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 1-nitrodibenzofuran-4-yl ether 、 联硼酸频那醇酯 在 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以87%的产率得到1-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzofuran
  参考文献：
  名称：

  WO2006/109081

  摘要：

  公开号：
• 作为产物：
  描述：

  二苯并呋喃 在 正丁基锂 、 硝酸 、 吡啶盐酸盐 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 生成 trifluoromethanesulfonic acid 1-nitrodibenzofuran-4-yl ether
  参考文献：
  名称：

  DNA-Dependent Protein Kinase (DNA-PK) Inhibitors. Synthesis and Biological Activity of Quinolin-4-one and Pyridopyrimidin-4-one Surrogates for the Chromen-4-one Chemotype

  摘要：

  Following the discovery of dibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (NU7441) (Leahy, J. J. J.; Golding, B. T.; Griffin, R. J.; Hardcastle, I. R.; Richardson, C.; Rigoreau, L.; Smith, G. C. M. Bioorg. Med. Chem. Lett. 2004, 14, 6083-6087) as a potent inhibitor (IC50 = 30 nM) of DNA-dependent protein kinase (DNA-PK), we have investigated analogues in which the chromen-4-one core template has been replaced by aza-heterocyclic systems: 9-substituted 2-morpholin-4-ylpyrido[1,2-a]-pyrimidin-4-ones and 8-substituted 2-morpholin-4-yl-1 H-quinolin-4-ones. The 8- and 9-substituents were either dibenzothiophen-4-yl or dibenzofuran-4-yl, which were each further substituted at the 1-position with water-solubilizing groups [NHCO(CH2)(n) NR1 R-2, where n = 1 or 2 and the moiety (RRN)-R-1-N-2 was derived from a library of primary and secondary amines (e.g., morpholine)]. The inhibitors were synthesized by employing a multiple-parallel approach in which the two heterocyclic components were assembled by Suzuki-Miyaura cross-coupling. Potent DNA-PK inhibitory activity was generally observed across the compound series, with structure activity studies indicating that optimal potency resided in pyridopyrimidin-4-ones bearing a substituted dibenzothiophen-4-yl group. Several of the newly synthesized compounds (e.g., 2-morpholin-4-yl-N-[4-(2-morpholin-4-yl-4-oxo-4H-pyrido[1,2-a]-pyrimidin-9-yl)dibenzothiophen-1-yl]acetamide) combined high potency against the target enzyme (DNA-PK IC50 = 8 nM) with promising activity as potentiators of ionizing radiation-induced cytotoxicity in vitro.

  DOI：

  10.1021/jm100608j

文献信息

• DNA-PK inhibitors
  申请人：Smith Cameron Murray Graeme

  公开号：US20060264427A1

  公开（公告）日：2006-11-23

  Compounds of formula I: wherein A, B and D are respectively selected from the group consisting of: (i) CH, NH, C; (ii) CH, N, N;and (iii) CH, O, C; the dotted lines represent two double bonds in the appropriate locations; and where Z is selected from S, O, C(═O), CH 2 and NH are disclosed for use in inhibiting DNA-PK.

  式I的化合物： 其中A、B和D分别从以下组中选择：(i) CH、NH、C；(ii) CH、N、N；和(iii) CH、O、C；虚线表示适当位置上的两个双键；Z从S、O、C(═O)、CH2和NH中选择，用于抑制DNA-PK。
• DNA-PK INHIBITORS
  申请人：Kudos Pharmaceuticals Ltd

  公开号：EP1869021A1

  公开（公告）日：2007-12-26
• US7696203B2
  申请人：——

  公开号：US7696203B2

  公开（公告）日：2010-04-13
• [EN] DNA-PK INHIBITORS<br/>[FR] INHIBITEURS D'ADN-PK
  申请人：KUDOS PHARM LTD

  公开号：WO2006109081A1

  公开（公告）日：2006-10-19

  [EN] Compounds of formula: (I) wherein A, B and D are respectively selected from the group consisting of: (i) CH, NH, C; (ii) CH, N, N; and (iii) CH, O, C; the dotted lines represent two double bonds in the appropriate locations; and where Z is selected from S, O, C(=O), CH₂ and NH are disclosed for use in inhibiting DNA-PK.
  [FR] Composés de formule: (I) dans laquelle A, B et D sont respectivement choisis parmi le groupe composé de: (i) CH, NH, C; (ii) CH, N, N; et (iii) CH, O, C; les lignes pointillées représentent deux doubles liaisons dans les emplacements appropriés; et Z est choisi parmi S, O, C(=O), CH₂ et NH. Les composés sont décrits pour une utilisation dans l'inhibition de l'ADN-PK.