2-(5H-dibenzo[b,f]azepin-5-yl)ethanol | 14769-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2-(5H-dibenzo[b,f]azepin-5-yl)ethanol
• 英文别名: 2-Dibenzo[b,f]azepin-5-yl-ethanol；2-benzo[b][1]benzazepin-11-ylethanol
• CAS: 14769-40-5
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: IJOPFAOVLBCPMP-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  417.2±34.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5H-dibenzo[b,f]azepin-5-yl)ethanol 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 19.0h， 生成 3-(4-(2-(Dibenzo[b,f]azepin-5-yl)-ethoxy)-phenyl)-2-ethoxy-propionic acid
  参考文献：
  名称：

  Novel Tricyclic-α-alkyloxyphenylpropionic Acids:  Dual PPARα/γ Agonists with Hypolipidemic and Antidiabetic Activity

  摘要：

  Synthesis and structure-activity relationships of tricyclic alpha-ethoxy-phenylpropionic acid derivatives guided by in vitro PPARalpha and PPARgamma transactivation data and computer modeling led to the identification of the novel carbazole analogue, 3q, with dual PPARalpha (EC50 = 0.36 muM) and PPARgamma (EC50 = 0.17 muM) activity in vitro. Ten days treatment of db/db mice with 3q improved the insulin sensitivity, as measured by OGTT, better than that seen with both pioglitazone and rosiglitazone treatment, suggesting in vivo PPARgamma activity. Likewise, 3q lowered plasma triglycerides and cholesterol in high cholesterol fed rats after 4 days treatment, indicating in vivo PPARalpha activity. Investigations of the pharmacokinetics of selected compounds suggested that extended drug exposure improved the in vivo activity of in vitro active compounds.

  DOI：

  10.1021/jm010964g

文献信息

• Design, synthesis, biological evaluation and computational investigation of novel inhibitors of dihydrofolate reductase of opportunistic pathogens
  作者：Seema Bag、Nilesh R. Tawari、Mariam S. Degani、Sherry F. Queener

  DOI：10.1016/j.bmc.2010.03.031

  日期：2010.5

  with design, synthesis and biological evaluation of novel, diverse compounds as potential inhibitors of dihydrofolate reductase (DHFR) from opportunistic microorganisms; Pneumocystis carinii (pc), Toxoplasma gondii (tg) and Mycobacterium avium (ma). A set of 14 structurally diverse compounds were designed with varying key pharmacophoric features of DHFR inhibitors, bulky distal substitutions and different

  目前的工作涉及新型，多样的化合物的设计，合成和生物学评估，这些化合物可作为机会微生物中二氢叶酸还原酶（DHFR）的潜在抑制剂。卡氏肺孢子虫（pc），弓形虫（tg）和鸟分枝 杆菌（嘛）。设计了一组14种结构多样的化合物，这些化合物具有DHFR抑制剂的关键药理学特征，远侧大体积取代以及连接远侧部分和2,4-二氨基嘧啶核的不同桥。合成了设计的化合物，并在酶分析中针对pc，tg和ma DHFR进行了评估。大鼠肝脏（rI）DHFR被用作哺乳动物标准品。作为该项目的下一个逻辑步骤，进行了灵活的分子对接研究，以预测这些化合物在pcDHFR活性位点的结合方式，并使用MM-GBSA协议对获得的对接位姿进行后处理，以预测相对结合亲和力。在大多数情况下，预测的结合模式能够使实验结果合理化。特别令人感兴趣的是，对接分数和MM-GBSA预测的ΔG结合能够区分活性化合物和低活性化合物。此外，在IC 50值和MM-GBSA预测的ΔG结合之间获得了0
• Novel compounds, their preparation and use
  申请人：——

  公开号：US20030055076A1

  公开（公告）日：2003-03-20

  Novel compounds of the general formula (I), the use of these compounds as medicaments, pharmaceuticaly compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR). The compounds exert their effects by modulating the PPAR&ggr; response in a partial agonist manner.

  本发明涉及一般式（I）的新化合物，这些化合物作为药物的用途，包括这些化合物的制药组合物和使用这些化合物和组合物的治疗方法。这些化合物可能在治疗和/或预防由核受体介导的疾病方面有用，特别是过氧化物酶体增殖物激活受体（PPAR）。这些化合物通过以部分激动剂方式调节PPAR&ggr;反应来发挥作用。
• NOVEL VINYL N-(2-BENZOYLPHENYL)-L-TYROSINE DERIVATIVES AND THEIR USE AS ANTIDIABETICS ETC
  申请人：NOVO NORDISK A/S

  公开号：EP1414806A1

  公开（公告）日：2004-05-06
• [EN] NOVEL VINYL N-(2-BENZOYLPHENYL)-L-TYROSINE DERIVATIVES AND THEIR USE AS ANTIDIABETICS ETC<br/>[FR] NOUVEAUX DERIVES DE VINYL N-(2-BENZOYLPHENYL)-L-TYROSINE ET LEUR UTILISATION EN TANT QU'ANTIDIABETIQUES ETC.
  申请人：NOVO NORDISK AS

  公开号：WO2003011834A1

  公开（公告）日：2003-02-13

  Novel compounds of the general formula (I), the use of these compounds as medicaments, pharmaceutical compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR). The compounds exert their effects by modulating the PPARη response in a partial agonist manner.
• Novel Tricyclic-α-alkyloxyphenylpropionic Acids:  Dual PPARα/γ Agonists with Hypolipidemic and Antidiabetic Activity
  作者：Per Sauerberg、Ingrid Pettersson、Lone Jeppesen、Paul S. Bury、John P. Mogensen、Karsten Wassermann、Christian L. Brand、Jeppe Sturis、Helle F. Wöldike、Jan Fleckner、Anne-Sofie T. Andersen、Steen B. Mortensen、L. Anders Svensson、Hanne B. Rasmussen、Søren V. Lehmann、Zdenek Polivka、Karel Sindelar、Vladimira Panajotova、Lars Ynddal、Erik M. Wulff

  DOI：10.1021/jm010964g

  日期：2002.2.1

  Synthesis and structure-activity relationships of tricyclic alpha-ethoxy-phenylpropionic acid derivatives guided by in vitro PPARalpha and PPARgamma transactivation data and computer modeling led to the identification of the novel carbazole analogue, 3q, with dual PPARalpha (EC50 = 0.36 muM) and PPARgamma (EC50 = 0.17 muM) activity in vitro. Ten days treatment of db/db mice with 3q improved the insulin sensitivity, as measured by OGTT, better than that seen with both pioglitazone and rosiglitazone treatment, suggesting in vivo PPARgamma activity. Likewise, 3q lowered plasma triglycerides and cholesterol in high cholesterol fed rats after 4 days treatment, indicating in vivo PPARalpha activity. Investigations of the pharmacokinetics of selected compounds suggested that extended drug exposure improved the in vivo activity of in vitro active compounds.