ethyl 3-(4-(2-(β-carbolin-9-yl)ethoxy)phenyl)-2-ethoxypropionate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 3-(4-(2-(β-carbolin-9-yl)ethoxy)phenyl)-2-ethoxypropionate
• 英文别名: Ethyl 2-ethoxy-3-[4-(2-pyrido[3,4-b]indol-9-ylethoxy)phenyl]propanoate
• 化学式: C₂₆H₂₈N₂O₄
• 分子量: 432.519
• InChiKey: BEKNPMOLLVBFHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-(2-(β-carbolin-9-yl)ethoxy)phenyl)-2-ethoxypropionate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以30%的产率得到3-(4-(2-(Betacarbolin-9-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
• 作为产物：
  描述：

  9-(2-Hydroxyethyl)-β-carbolin 、 2-乙氧基-3-对羟基苯基丙酸乙酯 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以76%的产率得到ethyl 3-(4-(2-(β-carbolin-9-yl)ethoxy)phenyl)-2-ethoxypropionate
  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

• 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.