2-amino-7-methyl-4-(3-methyl-2-thienyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile | 414899-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-amino-7-methyl-4-(3-methyl-2-thienyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile
• 英文别名: 2-amino-7-methyl-4-(3-methylthiophen-2-yl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile；2-amino-7-methyl-4-(3-methylthiophen-2-yl)-5-oxo-4H-pyrano[3,2-c]pyran-3-carbonitrile
• CAS: 414899-69-7
• 化学式: C₁₅H₁₂N₂O₃S
• 分子量: 300.338
• InChiKey: KZORLJGPNUQHJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲基噻吩醛 、 4-羟基-6-甲基-2-吡喃酮 、 丙二腈 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.2h， 以93%的产率得到2-amino-7-methyl-4-(3-methyl-2-thienyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile
  参考文献：
  名称：

  Solvent-free, green and efficient synthesis of pyrano[4, 3-b]pyrans by grinding and their biological evaluation as antitumor and antioxidant agents

  摘要：

  A facile, green, and efficient method has been developed for the synthesis of pyrano[4, 3-b]pyrans via a one-pot reaction of aromatic aldehydes, malononitrile, and 4-hydroxy-6-methyl-pyran-2-one in the presence of ammonium acetate under solvent-free conditions using grinding method. The experimental simplicity, short reaction time, easy work-up, avoidance of organic solvents, and utilization of an inexpensive and readily available catalyst make this new methodology practical and economically attractive. The antitumor activity of the compounds was tested against human breast cancer cell line MCF-7. Compounds 4l, 4o, and 4p showed good cytotoxic activity comparable with standard drug Doxorubicin. On the other hand, compounds 4q and 4r exhibited potent growth inhibitory activity. Furthermore, the synthesized compounds were screened for in vitro antioxidant activity by DPPH assay. All the compounds assayed showed moderate to good free radical scavenging activity.

  DOI：

  10.1007/s00044-013-0586-4

文献信息

• Alum [KAl(SO4)2·12H2O]: a green and efficient catalyst for synthesis of pyrano[4,3-b]pyrans in water under conventional and microwave conditions
  作者：Deepika Rajguru、Balwant S. Keshwal、Shubha Jain、Vasant W. Bhagwat

  DOI：10.1007/s00706-013-0975-x

  日期：2013.9

  One-pot synthesis of pyrano[4,3-b]pyrans by condensation of 4-hydroxy-6-methylpyran-2-one, aromatic aldehydes, and malononitrile or cyanoacetates in water using alum as a non-toxic, readily available, and reusable catalyst at 80 A degrees C under conventional conditions and also under microwave irradiation is described.
• Solvent-free, green and efficient synthesis of pyrano[4, 3-b]pyrans by grinding and their biological evaluation as antitumor and antioxidant agents
  作者：Deepika Rajguru、Balwant S. Keshwal、Shubha Jain

  DOI：10.1007/s00044-013-0586-4

  日期：2013.12

  A facile, green, and efficient method has been developed for the synthesis of pyrano[4, 3-b]pyrans via a one-pot reaction of aromatic aldehydes, malononitrile, and 4-hydroxy-6-methyl-pyran-2-one in the presence of ammonium acetate under solvent-free conditions using grinding method. The experimental simplicity, short reaction time, easy work-up, avoidance of organic solvents, and utilization of an inexpensive and readily available catalyst make this new methodology practical and economically attractive. The antitumor activity of the compounds was tested against human breast cancer cell line MCF-7. Compounds 4l, 4o, and 4p showed good cytotoxic activity comparable with standard drug Doxorubicin. On the other hand, compounds 4q and 4r exhibited potent growth inhibitory activity. Furthermore, the synthesized compounds were screened for in vitro antioxidant activity by DPPH assay. All the compounds assayed showed moderate to good free radical scavenging activity.