2-[4-[3-(4-Methoxyphenyl)-3-oxoprop-1-enyl]phenoxy]acetic acid | 139877-56-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-[4-[3-(4-Methoxyphenyl)-3-oxoprop-1-enyl]phenoxy]acetic acid
• CAS: 139877-56-8
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: QAPTYDCXRZEIMB-UHFFFAOYSA-N

物化性质

• 沸点：
  539.3±50.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氨基-1-苄基哌啶 、 2-[4-[3-(4-Methoxyphenyl)-3-oxoprop-1-enyl]phenoxy]acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以46.69%的产率得到(E)-N-(1-benzylpiperidin-4-yl)-2-(4-(3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl)phenoxy)acetamide
  参考文献：
  名称：

  Design, synthesis chalcone derivatives as AdipoR agonist for type 2 diabetes

  摘要：

  Two structurally novel series of chalcone derivatives were designed and synthesized as potential agents against type 2 diabetes. As a result of the antidiabetic biological evaluation in streptozotocin (STZ)‐induced type 2 diabetes animal model, 13e, 13g, and 19f showed more significant reduction in serum Glu, TG, TC levels by contrast to the positive control AdipoRon. In addition to upregulating the expression of AdipoR1 and AdipoR2, 13e and 19f treatment also increased expression of AMPK and PPAR‐α. Taken together, these results suggested that 13e and 19f might be a promising compound for type 2 diabetes treatment.

  DOI：

  10.1111/cbdd.13319
• 作为产物：
  描述：

  4-(乙氧基羰基甲氧基)苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 30.0h， 生成 2-[4-[3-(4-Methoxyphenyl)-3-oxoprop-1-enyl]phenoxy]acetic acid
  参考文献：
  名称：

  Design, synthesis chalcone derivatives as AdipoR agonist for type 2 diabetes

  摘要：

  Two structurally novel series of chalcone derivatives were designed and synthesized as potential agents against type 2 diabetes. As a result of the antidiabetic biological evaluation in streptozotocin (STZ)‐induced type 2 diabetes animal model, 13e, 13g, and 19f showed more significant reduction in serum Glu, TG, TC levels by contrast to the positive control AdipoRon. In addition to upregulating the expression of AdipoR1 and AdipoR2, 13e and 19f treatment also increased expression of AMPK and PPAR‐α. Taken together, these results suggested that 13e and 19f might be a promising compound for type 2 diabetes treatment.

  DOI：

  10.1111/cbdd.13319

文献信息

• Synthesis and Hypolipidemic Activity of Novel 2-(4-(2-Amino-6-(4-Substituted Phenyl) Pyrimidin-4-yl)-2-Substituted Phenoxy) Acetic Acid Derivatives
  作者：Santosh N. Mokale、Maheshwari T. Shete、Sameer I. Shaikh、Devanand B. Shinde

  DOI：10.1111/j.1747-0285.2012.01319.x

  日期：2012.4

  A novel series of 2‐(4‐(2‐amino‐6‐(4‐substituted phenyl) pyrimidin‐4‐yl)‐2‐substituted phenoxy) acetic acid derivatives were efficiently synthesized. The synthesized compounds were evaluated for their in vivo hypolipidemic activity, using high‐fat‐diet‐induced hyperlipidemia in rats. Some of these compounds showed significant antihyperlipidemic activity.

  一种新颖的一系列2-（4-（2-氨基-6-（4-取代的苯基）嘧啶-4-基）- 2 -取代的苯氧基）乙酸衍生物有效地合成。使用高脂饮食诱导的高脂血症大鼠对合成的化合物的体内降血脂活性进行了评估。这些化合物中的一些显示出显着的抗高血脂活性。
• Synthesis and in vitro antiplasmodial evaluation of 7-chloroquinoline–chalcone and 7-chloroquinoline–ferrocenylchalcone conjugates
  作者：Raghu Raj、Anu Saini、Jiri Gut、Philip J. Rosenthal、Vipan Kumar

  DOI：10.1016/j.ejmech.2015.03.045

  日期：2015.5

  The manuscript describes the synthesis of novel amide tethered 7-chloroquinoline chalcone and 7-chloroquinoline-ferrocenylchalcone bifunctional hybrids and their evaluation as antimalarial agents against W2 resistant strain of Plasmodium falciparum. The antiplasmodial activity of 7-chloroquinoline-ferrocenylchalcones was found to be less than their corresponding simple chalcone conjugates. The presence of a methoxy substituent at para position of ring B on chalcones and longer alkyl chain length markedly improved the antiplasmodial profiles of the synthesized scaffolds with the most potent of the test compound exhibiting an IC50 value of 17.8 nM. (C) 2015 Elsevier Masson SAS. All rights reserved.