4-methoxy-N-(4-methoxyphenyl)benzohydrazide | 736873-78-2

• 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: 4-methoxy-N-(4-methoxyphenyl)benzohydrazide
• CAS: 736873-78-2
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: MYNKPUSMARVVCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰丙酸 、 4-methoxy-N-(4-methoxyphenyl)benzohydrazide 在 溶剂黄146 作用下， 反应 3.0h， 以403 mg的产率得到2-[5-甲氧基-1-(4-甲氧基苯甲酰基)-2-甲基吲哚-3-基]乙酸
  参考文献：
  名称：

  Development of a prostaglandin D2 receptor antagonist: discovery of a new chemical lead

  摘要：

  A series of N-(p-alkoxy)benzoyl-5-methoxy-2-methylindole-3-acetic acids and N-(p-butoxy)benzoyl-2-methylindole-4-acetic acid were discovered as new chemical leads for a prostaglandin D-2 (PGD(2)) receptor antagonist. Most of them exhibited PGD(2) receptor binding and blocked cyclic adenosine 3',5'-monophosphate (cAMP) formation in vitro. In particular, 2-methylindole-4-acetic acid analog 1 showed markedly increased receptor affinity and cAMP antagonist activity. Chemistry and structure activity relationship (SAR) data are also presented. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.011
• 作为产物：
  描述：

  (4-甲氧基苯基)肼 在 吡啶 、 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.67h， 生成 4-methoxy-N-(4-methoxyphenyl)benzohydrazide
  参考文献：
  名称：

  Development of a prostaglandin D2 receptor antagonist: discovery of a new chemical lead

  摘要：

  A series of N-(p-alkoxy)benzoyl-5-methoxy-2-methylindole-3-acetic acids and N-(p-butoxy)benzoyl-2-methylindole-4-acetic acid were discovered as new chemical leads for a prostaglandin D-2 (PGD(2)) receptor antagonist. Most of them exhibited PGD(2) receptor binding and blocked cyclic adenosine 3',5'-monophosphate (cAMP) formation in vitro. In particular, 2-methylindole-4-acetic acid analog 1 showed markedly increased receptor affinity and cAMP antagonist activity. Chemistry and structure activity relationship (SAR) data are also presented. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.011

文献信息

• Benzoyl 2-methyl indoles as selective PPARγ modulators
  作者：John J. Acton、Regina M. Black、A. Brian Jones、David E. Moller、Lawrence Colwell、Thomas W. Doebber、Karen L. MacNaul、Joel Berger、Harold B. Wood

  DOI：10.1016/j.bmcl.2004.10.068

  日期：2005.1

  Routine screening for human PPAR ligands yielded compounds 1 and 2, both of which were sub-micromolar hPPARgamma agonists. Synthetic modifications of these leads led to a series of potent substituted 3-benzyl-2-methyl indoles, a subset of which were noted to be selective PPARgamma modulators (SPPARgammaMs). SPPARgammaM 24 displayed robust anti-diabetic activity with an improved therapeutic window in comparison to a PPARgamma full agonist in a rodent efficacy model. (C) 2004 Elsevier Ltd. All rights reserved.