ethyl 3-(4-(N-methyl-N-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)aminoethoxy)phenyl)-2-ethoxypropionate | 264881-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: ethyl 3-(4-(N-methyl-N-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)aminoethoxy)phenyl)-2-ethoxypropionate
• 英文别名: 3-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid ethyl ester；ethyl 2-ethoxy-3-[4-[2-[methyl(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)amino]ethoxy]phenyl]propanoate
• CAS: 264881-88-1
• 化学式: C₃₁H₃₇NO₄
• 分子量: 487.639
• InChiKey: UFUQQFDCWXZIOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-(N-methyl-N-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)aminoethoxy)phenyl)-2-ethoxypropionate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 144.0h， 以1.15 g的产率得到3-(4-{2-[(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-methyl-amino]-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：

  2-乙氧基-3-对羟基苯基丙酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 53.0h， 生成 ethyl 3-(4-(N-methyl-N-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)aminoethoxy)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

• Compounds, their preparation and use
  申请人：Novo Nordisk A/S

  公开号：US06214820B1

  公开（公告）日：2001-04-10

  The present invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, A, X, T, Q, Z, U, Y, Ar, p and n are as defined in the specification. These compounds are useful in the treatment and/or prevention of conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).

  本发明涉及式（I）的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、A、X、T、Q、Z、U、Y、Ar、p和n如规范中定义。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激活受体（PPAR）。
• Compounds useful in the treatment of conditions mediated by peroxisome proliferator-activated receptors (PPAR)
  申请人：Novo Nordisk A/S

  公开号：US06248781B1

  公开（公告）日：2001-06-19

  The present invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, Ar, X, Q, A, Y and Z are as defined in the specification. These compounds are useful in the treatment and/or prevention of conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).

  本发明涉及式(I)的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、Ar、X、Q、A、Y和Z如规范中所定义。这些化合物在治疗和/或预防由核受体介导的疾病中具有用途，特别是过氧化物酶体增殖激活受体（PPAR）。
• New compounds, their preparation and use
  申请人：——

  公开号：US20010029256A1

  公开（公告）日：2001-10-11

  The present invention relates to compounds of formula (I) 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , A, X, T, Q, Z, U, Y, Ar, p and n are as defined in the specification. These compounds are useful in the treatment and/or prevention of conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).

  本发明涉及式(I)1的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、A、X、T、Q、Z、U、Y、Ar、p和n的定义如规范中所述。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）。
• Compounds useful in the treatment of conditions mediated by peroxisome proliferator-activated receptors(PPAR)
  申请人：——

  公开号：US20010031764A1

  公开（公告）日：2001-10-18

  The present invention relates to compounds of formula (I) 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Ar, X, Q, A, Y and Z are as defined in the specification. These compounds are useful in the treatment and/or prevention of conditions mediated by nuclear receptors, in particular the Peroxisome Proliferator-Activated Receptors (PPAR).

  本发明涉及式(I)化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、Ar、X、Q、A、Y和Z的定义如规范中所述。这些化合物在治疗和/或预防通过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：EP1123268A1

  公开（公告）日：2001-08-16