7-Amino-5-(1H-indol-3-yl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d] pyrimidine-6-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: 7-Amino-5-(1H-indol-3-yl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d] pyrimidine-6-carbonitrile
• 英文别名: 7-amino-5-(1H-indol-3-yl)-2,4-dioxo-1,5-dihydropyrano[2,3-d]pyrimidine-6-carbonitrile
• 化学式: C₁₆H₁₁N₅O₃
• 分子量: 321.295
• InChiKey: DSPJYEITWQLKSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 、 巴比妥酸 、 丙二腈 在 rochelle salt 作用下， 以 neat (no solvent) 为溶剂， 反应 0.1h， 以82%的产率得到7-Amino-5-(1H-indol-3-yl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d] pyrimidine-6-carbonitrile
  参考文献：
  名称：

  无溶剂条件下某些吲哚基衍生物的合成，细胞毒性和DNA裂解研究

  摘要：

  已经在涉及MW辐射的常规且也是无溶剂的条件下进行了一种锅法，快速，简便，绿色且有效的吡喃稠合吲哚基和1，3-二羰基类似物的合成方法。产品的结构已通过光谱数据证实。所有产品均已针对三种肿瘤细胞系进行了DNA切割和体外细胞毒性测试。一些产品具有高活性的特点。

  DOI：

  10.1134/s1070363220010211

文献信息

• Green chemistry approach for rapid synthesis of indol-3-yl-4H-pyran derivatives, biological assessments, and toxicological activities against Cowpea aphid (Aphis craccivora)
  作者：Hany M. Abd El-Lateef、Moumen S. Kamel、Abdullah Yahya Abdullah Alzahrani、Mai M. Khalaf、Mohamed Gouda、Mahmoud Abd El Aleem Ali Ali El-Remaily

  DOI：10.4314/bcse.v38i4.21

  日期：——

  From diverse or indole-3-carbaldehyde, certain unique indol-3-yl-4H-pyran derivatives were generated by condensing with different nucleophiles. IR, 1HNMR, and elemental studies have all confirmed their chemical structures. The green catalyst for the formation of indol-3-yl-4H-pyran derivatives is a zinc-linked amino acid complex [Zn(L-proline)2]. Furthermore, the environmental friendliness of this synthetic technique was investigated by assessing the reusability of the Zn(L-proline)2 complex over five consecutive cycles with no significant loss of catalytic activity. This novel process has showed substantial advantages in terms of safety, simplicity, stability, mild conditions, a short reaction time, excellent yields, and good purity without the use of organic solvents. The antibacterial properties of the compounds produced were investigated and discovered to be promising. To determine whether compounds are appropriate as possible insecticidal agents, the toxicological activity of the synthesized compounds against Cowpea aphid, Aphis craccivora, was tested using leaf dip bioassay technique toxicity studies performed in the laboratory. KEY WORDS: One pot synthesis, Zn(L-proline)2, Indole-3-carbaldehyde, Aqueous media, Microwave irradiation, Cowpea aphid, toxicological activity Bull. Chem. Soc. Ethiop. 2024, 38(4), 1077-1090.                                                     DOI: https://dx.doi.org/10.4314/bcse.v38i4.21