2-amino-4-(1H-indol-3-yl)pyrimidine-5-carbonitrile | 928203-38-7

• 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: 2-amino-4-(1H-indol-3-yl)pyrimidine-5-carbonitrile
• 英文别名: 5'-cyanomeridianin G
• CAS: 928203-38-7
• 化学式: C₁₃H₉N₅
• 分子量: 235.248
• InChiKey: JTESHWHFRHLIFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(1H-indol-3-yl)pyrimidine-5-carbonitrile 在 sodium hydroxide 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 [4-(1H-吲哚-3-基)嘧啶-2-基]胺
  参考文献：
  名称：

  Synthesis and antitumor activity of indolylpyrimidines: Marine natural product meridianin D analogues

  摘要：

  Marine indole alkaloid meridianin D analogues have been synthesized starting from the appropriate 3-cyanoacetyl indole. A facile two-step conversion of 3-cyanoacetyl indole to the corresponding cyano meridianin D analogue by treatment with dimethylformamide-dimethylacetal and further cyclization of the resulting enaminonitrile with antinoguanidine is described. Then, alkaline hydrolysis of cyano meridianin D afforded the carboxylic acid analogue. The treatment of acid with 75% H2SO4 afforded the desired 6-debromomeridianin D. Simply treatment of cyano meridianin D analogue with hydrazine hydrate afforded the amidrazone analogue. The biological evaluation indicated that cyano analogue showed good cytotoxic activity with IC50 values of 0.85 and 2.65 g (against MCF7 and HeLa, respectively), but acid and amidrazone analogues showed high cytotoxicity with IC50 values of 0.75 and 0.25 mu g, respectively (against MCF7). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.023
• 作为产物：
  描述：

  3-(1H-吲哚-3-基)-3-氧丙腈 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 7.08h， 生成 2-amino-4-(1H-indol-3-yl)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  由吲哚基烯氨基腈合成 3-吲哚基唑和经络苷衍生物

  摘要：

  吲哚衍生物与氰基乙酸反应，然后用 DMFDMA 处理得到中间体吲哚烯氨基腈 3。与氨基胍进一步反应产生 5'-氰基花青素类似物 4。相同的中间体与对甲氧基苯肼反应得到吡唑基衍生物 8. ( 2E)-3-二甲氨基-2-(1H-吲哚-3-基)-丙烯酸酯3a与盐酸羟胺在碱性介质中得到(5-氨基-异恶唑-4-基)-(1H-吲哚-3-基)-分别在短时间或长时间加热后得到甲酮 5 和丙烯酸衍生物 6。后一种化合物的明确结构说明是通过单晶 X 射线衍射研究实现的。

  DOI：

  10.3998/ark.5550190.0012.b11

文献信息

• Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles
  作者：Ana M. F. Oliveira-Campos、Abdellatif M. Salaheldin、Filipe A. Almeida Paz、Ligia M. Rodrigues

  DOI：10.3998/ark.5550190.0012.b11

  日期：——

  The reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles 3. Further reaction with aminoguanidine yielded 5´-cyanomeridianin analogues 4. The same intermediate reacted with p-methoxyphenylhydrazine to give the pyrazolyl derivative 8. Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate 3a with hydroxylamine hydrochloride

  吲哚衍生物与氰基乙酸反应，然后用 DMFDMA 处理得到中间体吲哚烯氨基腈 3。与氨基胍进一步反应产生 5'-氰基花青素类似物 4。相同的中间体与对甲氧基苯肼反应得到吡唑基衍生物 8. ( 2E)-3-二甲氨基-2-(1H-吲哚-3-基)-丙烯酸酯3a与盐酸羟胺在碱性介质中得到(5-氨基-异恶唑-4-基)-(1H-吲哚-3-基)-分别在短时间或长时间加热后得到甲酮 5 和丙烯酸衍生物 6。后一种化合物的明确结构说明是通过单晶 X 射线衍射研究实现的。
• Synthesis and antitumor activity of indolylpyrimidines: Marine natural product meridianin D analogues
  作者：Mohamed A.A. Radwan、Mahmoud El-Sherbiny

  DOI：10.1016/j.bmc.2006.11.023

  日期：2007.2.1

  Marine indole alkaloid meridianin D analogues have been synthesized starting from the appropriate 3-cyanoacetyl indole. A facile two-step conversion of 3-cyanoacetyl indole to the corresponding cyano meridianin D analogue by treatment with dimethylformamide-dimethylacetal and further cyclization of the resulting enaminonitrile with antinoguanidine is described. Then, alkaline hydrolysis of cyano meridianin D afforded the carboxylic acid analogue. The treatment of acid with 75% H2SO4 afforded the desired 6-debromomeridianin D. Simply treatment of cyano meridianin D analogue with hydrazine hydrate afforded the amidrazone analogue. The biological evaluation indicated that cyano analogue showed good cytotoxic activity with IC50 values of 0.85 and 2.65 g (against MCF7 and HeLa, respectively), but acid and amidrazone analogues showed high cytotoxicity with IC50 values of 0.75 and 0.25 mu g, respectively (against MCF7). (c) 2006 Elsevier Ltd. All rights reserved.