6-(furan-2-ylmethyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione | 950259-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-(furan-2-ylmethyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione
• 英文别名: 6-(Furan-2-ylmethyl)pyrrolo[3,4-b]pyrazine-5,7-dione
• CAS: 950259-92-4
• 化学式: C₁₁H₇N₃O₃
• 分子量: 229.195
• InChiKey: VPDXZMCKHGADIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-吡嗪二羧酸 、 2-呋喃甲胺 反应 0.08h， 以88%的产率得到6-(furan-2-ylmethyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione
  参考文献：
  名称：

  Microwave-assisted synthesis of N-substituted cyclic imides and their evaluation for anticancer and anti-inflammatory activities

  摘要：

  A number of N-substituted cyclic imides 3a-e, 5a-e, 7a-d, and 9a-e have been synthesized in very high yields, by condensation of various diacids 2, 4, 6, and 8 with different amines under microwave irradiation. These compounds were screened for anticancer and anti-inflammatory activities, and compounds 3c, 3e, 5c, 9c, and 9d exhibited anticancer activity against colon (COLO 205) cancer better than 5-fluorouracil and mitomycin-C, and compound 9b exhibited anti-inflammatory activity better than standard drug phenyl butazone. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.07.048

文献信息

• Preparation of Pyrazine Carboxamides: A Reaction Involving <i>N</i>-Heterocyclic Carbene (NHC) Intermediates
  作者：Rajasekhar Reddy Naredla、Barada P. Dash、Douglas A. Klumpp

  DOI：10.1021/ol402200x

  日期：2013.9.20

  In the reactions of 2,3-pyrazinedicarboxylic anhydride with amines and anilines, pyrazine carboxamides are formed in good to excellent yields. A mechanism is proposed involving ring opening of the anhydride and decarboxylation of the heterocyclic ring. Based on other similar heterocyclic decarboxylations, this suggests the involvement of an N-heterocyclic carbene intermediate leading to the product

  在2，3-吡嗪二羧酸酐与胺和苯胺的反应中，形成吡嗪羧酰胺的产率高至优异。提出了涉及酸酐的开环和杂环的脱羧的机理。基于其他类似的杂环脱羧，这表明涉及N-杂环卡宾中间体导致产物。
• Microwave-assisted synthesis of N-substituted cyclic imides and their evaluation for anticancer and anti-inflammatory activities
  作者：Sham M. Sondhi、Reshma Rani、Partha Roy、S.K. Agrawal、A.K. Saxena

  DOI：10.1016/j.bmcl.2008.07.048

  日期：2009.3

  A number of N-substituted cyclic imides 3a-e, 5a-e, 7a-d, and 9a-e have been synthesized in very high yields, by condensation of various diacids 2, 4, 6, and 8 with different amines under microwave irradiation. These compounds were screened for anticancer and anti-inflammatory activities, and compounds 3c, 3e, 5c, 9c, and 9d exhibited anticancer activity against colon (COLO 205) cancer better than 5-fluorouracil and mitomycin-C, and compound 9b exhibited anti-inflammatory activity better than standard drug phenyl butazone. (C) 2009 Published by Elsevier Ltd.