5-[4-(benzyloxy)phenoxy]-2-nitropyridine | 219766-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[4-(benzyloxy)phenoxy]-2-nitropyridine
• 英文别名: 2-(4-benzyloxyphenoxy)-5-nitropyridine；5-nitro-2-(4-phenylmethoxyphenoxy)pyridine
• CAS: 219766-77-5
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: SSWIRWXDAZDCQU-UHFFFAOYSA-N

物化性质

• 沸点：
  476.2±40.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)
• 溶解度：
  <0.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[4-(benzyloxy)phenoxy]-2-nitropyridine 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以100%的产率得到5-amino-(4-hydroxyphenoxy)pyridine
  参考文献：
  名称：

  Design and Synthesis of 4-(4-Benzoylaminophenoxy)phenol Derivatives As Androgen Receptor Antagonists

  摘要：

  We report the design and synthesis of novel 4-(4-benzoylaminophenoxy)phenol derivatives that bind to the androgen receptor (AR) ligand-binding domain and exhibit potent androgen-antagonistic activity. Compound 22 is one of the most potent of these derivatives, inhibiting the dihydrotestosterone-promoted growth of SC-3 cell line bearing wild-type AR (IC50 0.75 mu M), LNCaP cell line bearing T877A-mutated AR (IC50 0.043 mu M), and 22Rv1 cell line bearing H874Y-mutated AR (IC50 0.22 mu M). Structure activity relationship studies confirmed that the pharmacophore of these novel AR antagonists is distinct from the nitro- or cyano-substituted anilide substructure of other nonsteroidal AR antagonists. This novel pharmacophore is expected to provide a basis for designing new antiprostate cancer agents.

  DOI：

  10.1021/ml4001744
• 作为产物：
  描述：

  2-氯-5-硝基吡啶 、 4-苄氧基苯酚 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到5-[4-(benzyloxy)phenoxy]-2-nitropyridine
  参考文献：
  名称：

  苯氧基吡啶衍生物作为钠钙交换剂的新型抑制剂的合成及其构效关系。

  摘要：

  钠钙交换剂（NCX）被称为控制心肌细胞中Ca（2+）浓度的转运蛋白。在心力衰竭和心肌缺血-再灌注的情况下，NCX是导致心律失常的瞬态内向电流的基础，该电流导致心动过速后的去极化和非折返性延迟。NCX是治疗心力衰竭和心肌缺血-再灌注的有吸引力的靶标。我们基于化合物3设计并合成了一系列苯氧基吡啶衍生物。已评估了这些衍生物对CCL39细胞中NCX反向和正向模式的抑制活性。我们发现了几种新型的有效NCX抑制剂（39q，48k），它们对反向NCX抑制活性具有很高的选择性。

  DOI：

  10.1016/j.bmc.2004.07.038

文献信息

• HETEROCYCLIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, MEDICAMENTS COMPRISING THESE COMPOUNDS, AND THE USE THEREOF
  申请人：Zoller Gerhard

  公开号：US20110183998A1

  公开（公告）日：2011-07-28

  Heterocyclic derivatives, processes for their preparation, medicaments comprising these compounds, and the use thereof. The invention relates to compounds of the formula I in which the radicals R1, R2, R3, R4, W, A, B, D, E, G, L, M, R, T and Y have the stated meanings, and to the physiologically tolerated salts thereof. The compounds are suitable for example for the treatment of the metabolic syndrome, insulin resistance, obesity and diabetes.

  杂环衍生物、其制备方法、包含这些化合物的药物和其用途。本发明涉及式I中的化合物，其中基团R1、R2、R3、R4、W、A、B、D、E、G、L、M、R、T和Y具有所述的含义，并且其生理上可耐受的盐。该化合物适用于例如代谢综合征、胰岛素抵抗、肥胖和糖尿病的治疗。
• Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof
  申请人：Zoller Gerhard

  公开号：US08470841B2

  公开（公告）日：2013-06-25

  Heterocyclic derivatives, processes for their preparation, medicaments comprising these compounds, and the use thereof. The invention relates to compounds of the formula I in which the radicals R1, R2, R3, R4, W, A, B, D, E, G, L, M, R, T and Y have the stated meanings, and to the physiologically tolerated salts thereof. The compounds are suitable for example for the treatment of the metabolic syndrome, insulin resistance, obesity and diabetes.

  杂环衍生物，其制备方法，包含这些化合物的药物和其用途。本发明涉及式I的化合物，其中基团R1，R2，R3，R4，W，A，B，D，E，G，L，M，R，T和Y具有所述的含义，并且其生理耐受盐。这些化合物适用于例如治疗代谢综合征，胰岛素抵抗，肥胖和糖尿病。
• [EN] HETEROCYCLIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, MEDICAMENTS COMPRISING THESE COMPOUNDS, AND THE USE THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES, LEURS PROCÉDÉS DE PRÉPARATION, MÉDICAMENTS COMPRENANT LESDITS COMPOSÉS ET LEUR UTILISATION
  申请人：SANOFI AVENTIS

  公开号：WO2010003624A3

  公开（公告）日：2010-04-22
• US8470841B2
  申请人：——

  公开号：US8470841B2

  公开（公告）日：2013-06-25
• Design and Synthesis of 4-(4-Benzoylaminophenoxy)phenol Derivatives As Androgen Receptor Antagonists
  作者：Ayumi Yamada、Shinya Fujii、Shuichi Mori、Hiroyuki Kagechika

  DOI：10.1021/ml4001744

  日期：2013.10.10

  We report the design and synthesis of novel 4-(4-benzoylaminophenoxy)phenol derivatives that bind to the androgen receptor (AR) ligand-binding domain and exhibit potent androgen-antagonistic activity. Compound 22 is one of the most potent of these derivatives, inhibiting the dihydrotestosterone-promoted growth of SC-3 cell line bearing wild-type AR (IC50 0.75 mu M), LNCaP cell line bearing T877A-mutated AR (IC50 0.043 mu M), and 22Rv1 cell line bearing H874Y-mutated AR (IC50 0.22 mu M). Structure activity relationship studies confirmed that the pharmacophore of these novel AR antagonists is distinct from the nitro- or cyano-substituted anilide substructure of other nonsteroidal AR antagonists. This novel pharmacophore is expected to provide a basis for designing new antiprostate cancer agents.