2-(2-thienyl)-6-iodo-3-amino-quinazolin-4-one | 958804-04-1

• 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-(2-thienyl)-6-iodo-3-amino-quinazolin-4-one
• 英文别名: 3-Amino-6-iodo-2-(2-thienyl)-3H-quinazolin-4-one；3-amino-6-iodo-2-thiophen-2-ylquinazolin-4-one
• CAS: 958804-04-1
• 化学式: C₁₂H₈IN₃OS
• 分子量: 369.186
• InChiKey: SFONERNWMJBQJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  86.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四溴苯酐 、 2-(2-thienyl)-6-iodo-3-amino-quinazolin-4-one 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以70%的产率得到4,5,6,7-Tetrabromo-2-(6-iodo-4-oxo-2-thiophen-2-ylquinazolin-3-yl)isoindole-1,3-dione
  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-(2-thienylcarbonylamino)-5-iodo-benzoic acid 在 hydrazine hydrate 作用下， 以 乙酸酐 为溶剂， 生成 2-(2-thienyl)-6-iodo-3-amino-quinazolin-4-one
  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

• Substituted quinazolines, part 3. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs☆
  作者：Abdulrahman M. Al-Obaid、Sami G. Abdel-Hamide、Hassan A. El-Kashef、Alaa A.-M. Abdel-Aziz、Adel S. El-Azab、Hamad A. Al-Khamees、Hussein I. El-Subbagh

  DOI：10.1016/j.ejmech.2008.09.015

  日期：2009.6

  2-thieno-4(3H)-quinazolinone derivatives and their biological evaluation as antitumor agents using the National Cancer Institute (NCI) disease oriented antitumor screen protocol are investigated. Compounds 2-(2-thienylcarbonylamino)-5-iodo-N-(4-hydroxyphenyl)-benzamide (16), 2-(2-thieno)-6-iodo-3-phenylamino-3,4-dihydro-quina-zolin-4-one (26), and 2-(2-thieno)-4-[4-sulfonamidobenzylamino]-6-iodo-quinazoline

  研究了一些新的2-thieno-4（3 H）-喹唑啉酮衍生物的合成及其使用美国国家癌症研究所（NCI）疾病导向的抗肿瘤筛选方案作为抗肿瘤剂的生物学评估。化合物2-（2-噻吩基羰基氨基）-5-碘-N-（4-羟基苯基）-苯甲酰胺（16），2-（2-噻吩基）-6-碘-3-苯基氨基-3,4-二氢-喹啉-唑啉-4-酮（26）和2-（2-噻吩基）-4- [4-磺酰胺基苄基氨基] -6-碘-喹唑啉（42），GI 50与已知药物5-FU相比，该值分别为12.7、10.3和16.9μM是最活跃的成员。使用分子建模和QSAR技术对活性最高的分子进行构象分析，有助于理解2-硫代喹唑啉酮衍生物作为抗肿瘤药的药效学要求。这三个喹唑啉酮类似物（16，26，42）可被视为有用的模板，为未来的发展，以获得更有效的抗肿瘤药物。