(S)-ethyl 3-(4-(2-(carbazol-9-yl)ethoxy)phenyl)-2-ethoxypropionate | 265301-19-7

• 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: (S)-ethyl 3-(4-(2-(carbazol-9-yl)ethoxy)phenyl)-2-ethoxypropionate
• 英文别名: ethyl (2S)-3-[4-(2-carbazol-9-ylethoxy)phenyl]-2-ethoxypropanoate
• CAS: 265301-19-7
• 化学式: C₂₇H₂₉NO₄
• 分子量: 431.532
• InChiKey: XZDGZEZYSUUKRB-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 3-(4-(2-(carbazol-9-yl)ethoxy)phenyl)-2-ethoxypropionate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以100%的产率得到(S)-3-(4-(2-carbazol-9-ylethoxy)phenyl)-2-ethoxypropionic 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-咔唑乙醇 、 (S)-2-乙氧基-3-(4-羟基苯基)丙酸乙酯 在 三丁基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 苯 为溶剂， 反应 2.0h， 以89%的产率得到(S)-ethyl 3-(4-(2-(carbazol-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

• Substituted hetero-polycyclic compounds as PPARalpha and PPARgamma activators
  申请人：——

  公开号：US20020111344A1

  公开（公告）日：2002-08-15

  The present invention relates to compounds of the general formula (I) 1 The compounds are useful in the treatment and/or prevention of conditions mediated by nu-clear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).

  本发明涉及一般式（I）的化合物。这些化合物在治疗和/或预防由核受体介导的疾病方面具有用途，特别是过氧化物酶体增殖物激活受体（PPAR）。
• Substituted hetero-polycyclic compounds as PPARalpha and PPARgamma
  申请人：——

  公开号：US20020115657A1

  公开（公告）日：2002-08-22

  The present invention relates to compounds of the general formula (I) 1 The compounds are useful in the treatment and/or prevention of conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).

  本发明涉及一般式（I）的化合物。这些化合物在治疗和/或预防由核受体介导的疾病中有用，特别是过氧化物酶体增殖物激活受体（PPAR）。
• NEW COMPOUNDS, THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP1123279A1

  公开（公告）日：2001-08-16
• US6468996B1
  申请人：——

  公开号：US6468996B1

  公开（公告）日：2002-10-22
• [EN] NEW COMPOUNDS, THEIR PREPARATION AND USE<br/>[FR] NOUVEAUX COMPOSES, PREPARATION ET UTILISATION CORRESPONDANTES
  申请人：NOVO NORDISK AS

  公开号：WO2000023425A1

  公开（公告）日：2000-04-27

  The present invention relates to compounds of general formula (Ia). The compounds are useful in the treatment and/or preventionof conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).