N-[4-(4-benzyloxyphenoxy)-phenyl]-5-fluoro-2-nitrobenzamide | 496064-28-9

• 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: N-[4-(4-benzyloxyphenoxy)-phenyl]-5-fluoro-2-nitrobenzamide
• 英文别名: N-(4-(4-(Benzyloxy)phenoxy)phenyl)-5-fluoro-2-nitrobenzamide；5-fluoro-2-nitro-N-[4-(4-phenylmethoxyphenoxy)phenyl]benzamide
• CAS: 496064-28-9
• 化学式: C₂₆H₁₉FN₂O₅
• 分子量: 458.446
• InChiKey: CWPSIDSRGSZXDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[4-(4-benzyloxyphenoxy)-phenyl]-5-fluoro-2-nitrobenzamide 在 sodium hydride 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-[4-(4-benzyloxyphenoxy)-phenyl]-5-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propoxy]-2-nitrobenzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of anthranilamide-based non-peptide mimetics of ω-conotoxin GVIA

  摘要：

  Non-peptide mimetics based on an anthranilamide 'scaffold' possessing fragments that mimic Lys2, Tyr13 and Arg17 in omega-conotoxin GVIA have been prepared. Compounds were assayed for binding to the voltage-gated calcium channels Ca(v)2.2 ('N-type') and Ca(v)2.1 'P/Q-type') in rat brain. The primary synthetic target, 2-(6-amino-hexanoylamino)-5-(3-guanidino-propoxy)-N-[4-(4-hydroxyphenoxy)phenyll -benzamide (2a), exhibited low mu M binding to Ca(v)2.2 and was more than 30-fold selective for Ca(v)2.2 over Cav2. 1. Crown Copyright (c) 2006 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.041
• 作为产物：
  描述：

  间氟苯甲酸 在 硫酸 、 硝酸 、 phosphorus pentoxide 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-[4-(4-benzyloxyphenoxy)-phenyl]-5-fluoro-2-nitrobenzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of anthranilamide-based non-peptide mimetics of ω-conotoxin GVIA

  摘要：

  Non-peptide mimetics based on an anthranilamide 'scaffold' possessing fragments that mimic Lys2, Tyr13 and Arg17 in omega-conotoxin GVIA have been prepared. Compounds were assayed for binding to the voltage-gated calcium channels Ca(v)2.2 ('N-type') and Ca(v)2.1 'P/Q-type') in rat brain. The primary synthetic target, 2-(6-amino-hexanoylamino)-5-(3-guanidino-propoxy)-N-[4-(4-hydroxyphenoxy)phenyll -benzamide (2a), exhibited low mu M binding to Ca(v)2.2 and was more than 30-fold selective for Ca(v)2.2 over Cav2. 1. Crown Copyright (c) 2006 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.041

文献信息

• Synthesis and biological evaluation of anthranilamide-based non-peptide mimetics of ω-conotoxin GVIA
  作者：Jonathan B. Baell、Peter J. Duggan、Stewart A. Forsyth、Richard J. Lewis、Y. Phei Lok、Christina I. Schroeder、Nicholas E. Shepherd

  DOI：10.1016/j.tet.2006.05.041

  日期：2006.7

  Non-peptide mimetics based on an anthranilamide 'scaffold' possessing fragments that mimic Lys2, Tyr13 and Arg17 in omega-conotoxin GVIA have been prepared. Compounds were assayed for binding to the voltage-gated calcium channels Ca(v)2.2 ('N-type') and Ca(v)2.1 'P/Q-type') in rat brain. The primary synthetic target, 2-(6-amino-hexanoylamino)-5-(3-guanidino-propoxy)-N-[4-(4-hydroxyphenoxy)phenyll -benzamide (2a), exhibited low mu M binding to Ca(v)2.2 and was more than 30-fold selective for Ca(v)2.2 over Cav2. 1. Crown Copyright (c) 2006 Published by Elsevier Ltd. All rights reserved.