2-(ethoxycarbonylmethyl)-thio-3-phenyl-4-oxo-6-nitro-3H-quinazoline | 1412904-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(ethoxycarbonylmethyl)-thio-3-phenyl-4-oxo-6-nitro-3H-quinazoline
• 英文别名: Ethyl 2-(6-nitro-4-oxo-3-phenylquinazolin-2-yl)sulfanylacetate；ethyl 2-(6-nitro-4-oxo-3-phenylquinazolin-2-yl)sulfanylacetate
• CAS: 1412904-48-3
• 化学式: C₁₈H₁₅N₃O₅S
• 分子量: 385.4
• InChiKey: KWVKUNAPCFXKBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(ethoxycarbonylmethyl)-thio-3-phenyl-4-oxo-6-nitro-3H-quinazoline 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以60%的产率得到2-hydrazino-6-nitro-3-phenyl-4-oxo-3H-quinazoline
  参考文献：
  名称：

  Novel 4(3H)-quinazolinone analogs: synthesis and anticonvulsant activity

  摘要：

  A new series of quinazoline analogs was designed, synthesized, and evaluated for their anticonvulsant activity. Compounds 6, 12, 21, 36, 37, and 38 showed 70-100 % protection against PTZ-induced seizures acting as GABA(A) receptor agonists. Compound N-(3,4,5,6-tetrachloro-phthalimido)-2-[(3-phenyl-4-oxo-6-methyl-3H-quinazolin-2-yl)-thio]acetamide (12) representing the moderate active compounds and 2-[6-iodo-4-oxo-2-(thiophen-2-yl)-quinazolin-3(4H)-yl]-isoindoline-1,3-dione (38) representing the remarkably active compounds in this stud, showed ED50 values of 457 and 251 mg/kg; TD50 values of 562 and 447 mg/kg; PI values of 1.22 and 1.78, LD50 values of 1,288 and 1,380 mg/kg, and TI values of 2.82 and 5.50, respectively. Compound 38 proved to be almost twofold more active than the standard drug sodium valproate.

  DOI：

  10.1007/s00044-012-0280-y
• 作为产物：
  描述：

  2-mercapto-3-phenyl-4-oxo-6-nitro-3H-quinazoline 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以75%的产率得到2-(ethoxycarbonylmethyl)-thio-3-phenyl-4-oxo-6-nitro-3H-quinazoline
  参考文献：
  名称：

  Novel 4(3H)-quinazolinone analogs: synthesis and anticonvulsant activity

  摘要：

  A new series of quinazoline analogs was designed, synthesized, and evaluated for their anticonvulsant activity. Compounds 6, 12, 21, 36, 37, and 38 showed 70-100 % protection against PTZ-induced seizures acting as GABA(A) receptor agonists. Compound N-(3,4,5,6-tetrachloro-phthalimido)-2-[(3-phenyl-4-oxo-6-methyl-3H-quinazolin-2-yl)-thio]acetamide (12) representing the moderate active compounds and 2-[6-iodo-4-oxo-2-(thiophen-2-yl)-quinazolin-3(4H)-yl]-isoindoline-1,3-dione (38) representing the remarkably active compounds in this stud, showed ED50 values of 457 and 251 mg/kg; TD50 values of 562 and 447 mg/kg; PI values of 1.22 and 1.78, LD50 values of 1,288 and 1,380 mg/kg, and TI values of 2.82 and 5.50, respectively. Compound 38 proved to be almost twofold more active than the standard drug sodium valproate.

  DOI：

  10.1007/s00044-012-0280-y

文献信息

• Novel 4(3H)-quinazolinone analogs: synthesis and anticonvulsant activity
  作者：Adel S. El-Azab、Sami G. Abdel-Hamide、Mohamed M. Sayed-Ahmed、Ghada S. Hassan、Tariq M. El-Hadiyah、Othman A. Al-Shabanah、Omar A. Al-Deeb、Hussein I. El-Subbagh

  DOI：10.1007/s00044-012-0280-y

  日期：2013.6

  A new series of quinazoline analogs was designed, synthesized, and evaluated for their anticonvulsant activity. Compounds 6, 12, 21, 36, 37, and 38 showed 70-100 % protection against PTZ-induced seizures acting as GABA(A) receptor agonists. Compound N-(3,4,5,6-tetrachloro-phthalimido)-2-[(3-phenyl-4-oxo-6-methyl-3H-quinazolin-2-yl)-thio]acetamide (12) representing the moderate active compounds and 2-[6-iodo-4-oxo-2-(thiophen-2-yl)-quinazolin-3(4H)-yl]-isoindoline-1,3-dione (38) representing the remarkably active compounds in this stud, showed ED50 values of 457 and 251 mg/kg; TD50 values of 562 and 447 mg/kg; PI values of 1.22 and 1.78, LD50 values of 1,288 and 1,380 mg/kg, and TI values of 2.82 and 5.50, respectively. Compound 38 proved to be almost twofold more active than the standard drug sodium valproate.