N-tert-butyl-2-(1,4-dioxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-2-(3,4,5-trimethoxyphenyl)acetamide | 1404118-21-3

• 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: N-tert-butyl-2-(1,4-dioxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-2-(3,4,5-trimethoxyphenyl)acetamide
• 英文别名: N-tert-butyl-2-(1,4-dioxo-3H-pyrazino[1,2-a]indol-2-yl)-2-(3,4,5-trimethoxyphenyl)acetamide
• CAS: 1404118-21-3
• 化学式: C₂₆H₂₉N₃O₆
• 分子量: 479.533
• InChiKey: HDNYOOSDCKEIKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-2-(1,4-dioxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-2-(3,4,5-trimethoxyphenyl)acetamide 、 3,4-二氯苄胺 以 乙醇 为溶剂， 以78%的产率得到N-(2-(tert-butylamino)-2-oxo-1-(3,4,5-trimethoxyphenyl)ethyl)-N-(2-(3,4-dichlorobenzyl amino)-2-oxoethyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  鉴定多种吲哚-2-羧酰胺为有效的抗疟药化学型

  摘要：

  利用基于异氰化物的多组分反应（IMCR）-后修饰方法合成了一系列高度多样化的新型吲哚-2-羧酰胺，并被确定为潜在的无前趋性化学型。在合成的18种类似物中，与标准药物miltefosine和stibogluconate钠相比，有12种类似物对利什曼原虫的胞内变形虫表现出更好的抗疟疾活性（IC 50值为0.6–7.5μM）。该化合物对Vero细胞也无毒。化合物2b中，2米和2P用显著体外然后活性评价它们在体内腹膜内途径的疗效。在内脏利什曼病的仓鼠模型中，在治疗后第7天，浓度为50 mg / kg / day的这三种化合物连续5天分别显示出对羊膜利什曼原虫的抑制率为70.0％，63.5％和63.4％。

  DOI：

  10.1016/j.ejmech.2016.01.028
• 作为产物：
  描述：

  吲哚-2-羧酸 、 异氰酸叔丁酯 、 甘氨酸甲酯盐酸盐 、 3,4,5-三甲氧基苯甲醛 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.17h， 以82%的产率得到N-tert-butyl-2-(1,4-dioxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-2-(3,4,5-trimethoxyphenyl)acetamide
  参考文献：
  名称：

  Access to Indole- And Pyrrole-Fused Diketopiperazines via Tandem Ugi-4CR/Intramolecular Cyclization and Its Regioselective Ring-Opening by Intermolecular Transamidation

  摘要：

  An efficient approach for the synthesis of indole- and pyrrole-fused diketopiperazines has been developed. This protocol involves the Ugi four-component reaction (U-4CR) followed by an intramolecular cyclization of the Ugi products at room temperature to afford the desired products in good to excellent yields. In addition, it is interesting to report the subsequent regioselective ring-opening of diketopiperazine unit occurring via an intermolecular transamidation reaction under mild condition, resulting in the formation of highly functionalized indole-2-carboxamides and pyrrole-2-carboxamides.

  DOI：

  10.1021/jo3018704

文献信息

• Identification of a diverse indole-2-carboxamides as a potent antileishmanial chemotypes
  作者：Shashi Pandey、Shikha S. Chauhan、Rahul Shivahare、Abhisheak Sharma、Swati Jaiswal、Suman Gupta、Jawahar Lal、Prem M.S. Chauhan

  DOI：10.1016/j.ejmech.2016.01.028

  日期：2016.3

  potential antileishmanial chemotype. Among the synthesized 18 analogues, 12 analogues exhibited better antileishmanial activity against intracellular amastigotes form of Leishmania donovani (IC50 values of 0.6–7.5 μM) as compared to standard drugs miltefosine and sodium stibogluconate. The compounds were also non-toxic towards Vero cells. Compounds 2b, 2m and 2p with significant in vitro activity were

  利用基于异氰化物的多组分反应（IMCR）-后修饰方法合成了一系列高度多样化的新型吲哚-2-羧酰胺，并被确定为潜在的无前趋性化学型。在合成的18种类似物中，与标准药物miltefosine和stibogluconate钠相比，有12种类似物对利什曼原虫的胞内变形虫表现出更好的抗疟疾活性（IC 50值为0.6–7.5μM）。该化合物对Vero细胞也无毒。化合物2b中，2米和2P用显著体外然后活性评价它们在体内腹膜内途径的疗效。在内脏利什曼病的仓鼠模型中，在治疗后第7天，浓度为50 mg / kg / day的这三种化合物连续5天分别显示出对羊膜利什曼原虫的抑制率为70.0％，63.5％和63.4％。
• Access to Indole- And Pyrrole-Fused Diketopiperazines via Tandem Ugi-4CR/Intramolecular Cyclization and Its Regioselective Ring-Opening by Intermolecular Transamidation
  作者：Shashi Pandey、Shahnawaz Khan、Awantika Singh、Harsh M. Gauniyal、Brijesh Kumar、Prem M. S. Chauhan

  DOI：10.1021/jo3018704

  日期：2012.11.16

  An efficient approach for the synthesis of indole- and pyrrole-fused diketopiperazines has been developed. This protocol involves the Ugi four-component reaction (U-4CR) followed by an intramolecular cyclization of the Ugi products at room temperature to afford the desired products in good to excellent yields. In addition, it is interesting to report the subsequent regioselective ring-opening of diketopiperazine unit occurring via an intermolecular transamidation reaction under mild condition, resulting in the formation of highly functionalized indole-2-carboxamides and pyrrole-2-carboxamides.