3,5-dimethyl-4-(4'-hydroxyphenoxy)nitrobenzene | 112556-09-9

• 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: 3,5-dimethyl-4-(4'-hydroxyphenoxy)nitrobenzene
• 英文别名: 4-(2,6-dimethyl-4-nitrophenoxy)phenol；4-(4-nitro-2,6-dimethylphenoxy)-phenol
• CAS: 112556-09-9
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: KRZOQVXMLPZQFL-UHFFFAOYSA-N

物化性质

• 沸点：
  400.3±45.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-4-(4'-hydroxyphenoxy)nitrobenzene 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以90%的产率得到4-(4-amino-2,6-dimethylphenoxy)phenol
  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-氟-1,3-二甲基硝基苯 、 对苯二酚 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 5.25h， 以55%的产率得到3,5-dimethyl-4-(4'-hydroxyphenoxy)nitrobenzene
  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

文献信息

• Thyromimetic organic compounds
  申请人：——

  公开号：US20020045751A1

  公开（公告）日：2002-04-18

  Compounds of the present invention of the formula 1 are thyromimetic agents which can be used to prevent and/or treat diseases associated with an imbalance of thyroid hormones, such as hypo- and hyper-thyroidism, obesity, osteoporosis and depression. The compounds of the invention are, in particular, hypolipedemic agents which enhance the clearance of cholesterol from circulation, particularly the clearance of cholesterol in the form of low density lipoproteins (LDL). The compounds are useful for reducing total cholesterol plasma levels in mammals, in particular for reducing levels of LDL-cholesterol. Furthermore, such compounds also lower elevated lipoprotein (a) [Lp(a)] levels, an independent cardiovascular risk factor, in mammals. The compounds of the invention can therefore be used for the prevention and/or treatment of occlusive cardiovascular conditions in which hyperlipidemia and hyperlipoproteinemia are implicated, such as atherosclerosis and coronary heart disease in mammals.

  本发明的化合物具有以下公式的甲型甲状腺模拟剂，可用于预防和/或治疗与甲状腺激素失衡相关的疾病，如甲状腺功能减退和亢进、肥胖、骨质疏松症和抑郁症。本发明的化合物特别是降脂剂，可增强胆固醇从循环中的清除，特别是以低密度脂蛋白（LDL）形式的胆固醇的清除。这些化合物可用于减少哺乳动物的总胆固醇血浆水平，特别是减少LDL胆固醇水平。此外，这些化合物还可以降低哺乳动物体内独立的心血管风险因子脂蛋白（a）[Lp(a)]水平。因此，本发明的化合物可用于预防和/或治疗与高脂血症和高脂蛋白血症有关的闭塞性心血管疾病，如动脉粥样硬化和冠心病等。
• Verfahren zur Herstellung von Halogenalkoxy-diphenylethern
  申请人：BAYER AG

  公开号：EP0238792A1

  公开（公告）日：1987-09-30

  Die Erfindung betrifft ein neues mehrstufiges Verfahren zur Herstellung von Halogenalkoxy-diphenylethern der Formel (1) in welcher R1 für Wasserstoff, Halogen, Alkyl, Alkoxy oder Alkylthio steht, R2 für Wasserstoff, Halogen, Alkyl, Alkoxy oder Alkylthio steht, R3 für Wasserstoff, Chlor oder Brom steht, R4 für Wasserstoff oder Alkyl steht und X für Wasserstoff, Fluor, Chlor oder die Reste -CH2Cl, -CHF2, -CHCl2 und -CHFCI steht.

  本发明涉及一种制备式（1）卤代烷氧基二苯醚的多级新工艺，其中 R1 是氢、卤素、烷基、烷氧基或烷基硫代物，R2 是氢、卤素、烷基、烷氧基或烷基硫代物，R3 是氢、氯或溴，R4 是氢或烷基，X 是氢、氟、氯或自由基 -CH2Cl、-CHF2、-CHCl2 和 -CHFCI。
• Verfahren zur Herstellung von Difluorchlormethoxybenzolen
  申请人：BAYER AG

  公开号：EP0239726A1

  公开（公告）日：1987-10-07

  Difluorchlormethoxybenzole werden hergestellt, in dem man Phenole mit Trichlormethyl-kohlensäure-esterchlorid (= Di­phosgen) in Gegenwart von Fluorwasserstoff umsetzt.

  二氟氯甲氧基苯是由苯酚与三氯甲基碳酸酯氯化物（=二光气）在氟化氢存在下反应生成的。
• GALLENKAMP, BERND;MARHOLD, ALBRECHT;SIRRENBERG, WILHELM
  作者：GALLENKAMP, BERND、MARHOLD, ALBRECHT、SIRRENBERG, WILHELM

  DOI：——

  日期：——
• DIARYL DERIVATIVES AND THEIR USE AS MEDICAMENTS
  申请人：Novartis AG

  公开号：EP1165502A1

  公开（公告）日：2002-01-02