4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-1-(4-methylphenyl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5.4-c]quinolin-5-one | 1255083-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-1-(4-methylphenyl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5.4-c]quinolin-5-one
• 英文别名: 4-methyl-3,6-bis(5-methyl-1,2-oxazol-3-yl)-1-(4-methylphenyl)-2-sulfanylidene-10bH-pyrimido[5,4-c]quinolin-5-one
• CAS: 1255083-32-9
• 化学式: C₂₇H₂₃N₅O₃S
• 分子量: 497.577
• InChiKey: QKCSILJEBRSBOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氨基-5-甲基异恶唑 、 ethyl 4-(2-chlorophenyl)-6-methyl-1-(5-methylisoxazol-3-yl)-(4-methylphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 以 二苯醚 为溶剂， 反应 10.0h， 以80%的产率得到4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-1-(4-methylphenyl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5.4-c]quinolin-5-one
  参考文献：
  名称：

  Synthesis, antimicrobial, and mosquito larvicidal activity of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones

  摘要：

  A series of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones (6a-h) have been synthesized by cyclization of ethyl-3-aryl-4-(2-chlorophenyl)6-methyl- 1-(5- methylisoxazol-3-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates 4a-h with 3-amino-5-methylisoxazole5. Compounds 4a-h were obtained by Biginelli reaction, by condensation of aromatic aldehyde 1, ethyl acetoacetate 2, and isoxazolyl thioureas 3 in a one-pot reaction catalyzed by ceric ammonium nitrite (CAN). Compounds 6a-h were tested for their antibacterial and antifungal activities against various bacterial and fungal strains. The results showed that these compounds exhibited good antibacterial and antifungal activity compared with that of standard antibiotics. Mosquito larvicidal activity of the newly synthesized compounds 6a-h is also studied against fourth instar larvae Culex quinquefasciatus. Some of the compounds are proved to be lethal for mosquito larvae. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.060

文献信息

• Synthesis, antimicrobial, and mosquito larvicidal activity of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones
  作者：E. Rajanarendar、M. Nagi Reddy、K. Rama Murthy、K. Govardhan Reddy、S. Raju、M. Srinivas、B. Praveen、M. Srinivasa Rao

  DOI：10.1016/j.bmcl.2010.08.060

  日期：2010.10

  A series of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones (6a-h) have been synthesized by cyclization of ethyl-3-aryl-4-(2-chlorophenyl)6-methyl- 1-(5- methylisoxazol-3-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates 4a-h with 3-amino-5-methylisoxazole5. Compounds 4a-h were obtained by Biginelli reaction, by condensation of aromatic aldehyde 1, ethyl acetoacetate 2, and isoxazolyl thioureas 3 in a one-pot reaction catalyzed by ceric ammonium nitrite (CAN). Compounds 6a-h were tested for their antibacterial and antifungal activities against various bacterial and fungal strains. The results showed that these compounds exhibited good antibacterial and antifungal activity compared with that of standard antibiotics. Mosquito larvicidal activity of the newly synthesized compounds 6a-h is also studied against fourth instar larvae Culex quinquefasciatus. Some of the compounds are proved to be lethal for mosquito larvae. (c) 2010 Elsevier Ltd. All rights reserved.