Tert-butyl 4-[2-[2-[3-(2-ethoxy-2-oxoethoxy)-4-methoxyphenyl]-5-hydroxy-4-oxochromen-7-yl]oxyacetyl]piperazine-1-carboxylate | 930774-56-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: Tert-butyl 4-[2-[2-[3-(2-ethoxy-2-oxoethoxy)-4-methoxyphenyl]-5-hydroxy-4-oxochromen-7-yl]oxyacetyl]piperazine-1-carboxylate
• CAS: 930774-56-4
• 化学式: C₃₁H₃₆N₂O₁₁
• 分子量: 612.634
• InChiKey: YOAGXPYCSXOROP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-[2-[2-[3-(2-ethoxy-2-oxoethoxy)-4-methoxyphenyl]-5-hydroxy-4-oxochromen-7-yl]oxyacetyl]piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and antimalarial evaluation of a series of piperazinyl flavones

  摘要：

  A series of 27 flavonoid derivatives containing a piperazinyl chain have been synthesized and tested for their antiplasmodial activity. Diverse substitution patterns on piperazinyl and flavone moieties were examined and found to affect the activity differently. The most active compounds, which have a 2,3,4-trimethoxybenzylpiperazinyl chain attached to the flavone at the 7-phenol group, showed in vitro activity against chloroquine-sensitive (Thai) and -resistant (FcB1,K1) Plasmodium falciparum strains in the micromolar to submicromolar range. One of them was active when given orally in a Plasmodium yoelii nigeriensis infected mouse model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.051
• 作为产物：
  描述：

  4-氯乙酰基哌嗪-1-羧酸叔丁酯 、 5,7-dihydroxy-3'-(ethoxycarbonylmethoxy)-4'-methoxyflavone 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 Tert-butyl 4-[2-[2-[3-(2-ethoxy-2-oxoethoxy)-4-methoxyphenyl]-5-hydroxy-4-oxochromen-7-yl]oxyacetyl]piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis and antimalarial evaluation of a series of piperazinyl flavones

  摘要：

  A series of 27 flavonoid derivatives containing a piperazinyl chain have been synthesized and tested for their antiplasmodial activity. Diverse substitution patterns on piperazinyl and flavone moieties were examined and found to affect the activity differently. The most active compounds, which have a 2,3,4-trimethoxybenzylpiperazinyl chain attached to the flavone at the 7-phenol group, showed in vitro activity against chloroquine-sensitive (Thai) and -resistant (FcB1,K1) Plasmodium falciparum strains in the micromolar to submicromolar range. One of them was active when given orally in a Plasmodium yoelii nigeriensis infected mouse model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.051

文献信息

• Synthesis and antimalarial evaluation of a series of piperazinyl flavones
  作者：Gwenola Auffret、Mehdi Labaied、François Frappier、Philippe Rasoanaivo、Philippe Grellier、Guy Lewin

  DOI：10.1016/j.bmcl.2006.11.051

  日期：2007.2

  A series of 27 flavonoid derivatives containing a piperazinyl chain have been synthesized and tested for their antiplasmodial activity. Diverse substitution patterns on piperazinyl and flavone moieties were examined and found to affect the activity differently. The most active compounds, which have a 2,3,4-trimethoxybenzylpiperazinyl chain attached to the flavone at the 7-phenol group, showed in vitro activity against chloroquine-sensitive (Thai) and -resistant (FcB1,K1) Plasmodium falciparum strains in the micromolar to submicromolar range. One of them was active when given orally in a Plasmodium yoelii nigeriensis infected mouse model. (c) 2006 Elsevier Ltd. All rights reserved.