(E)-6-fluoro-2-styrylquinazolin-4(3H)-one | 127033-34-5

• 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: (E)-6-fluoro-2-styrylquinazolin-4(3H)-one
• 英文别名: 6-Fluoro-2-((E)-styryl)-3H-quinazolin-4-one；6-fluoro-2-[(E)-2-phenylethenyl]-3H-quinazolin-4-one
• CAS: 127033-34-5
• 化学式: C₁₆H₁₁FN₂O
• 分子量: 266.275
• InChiKey: TXRNNDHICBASKO-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-fluoro-2-styrylquinazolin-4(3H)-one 、 N-甲基哌嗪 生成 6-fluoro-7-(4-methylpiperazin-1-yl)-2-[2-(4-methylpiperazin-1-yl)-2-phenylethyl]-1H-quinazolin-4-one
  参考文献：
  名称：

  JIANG, J. B.;HESSON, D. P.;DUSAK, B. A.;DEXTER, D. L.;KANG, G. J.;HAMEL, +, J. MED. CHEM., 33,(1990) N, C. 1721-1728

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-5-氟苯甲酸 在 吡啶 、 4-二甲氨基吡啶 、 formamide 作用下， 以 苯 为溶剂， 反应 26.0h， 生成 (E)-6-fluoro-2-styrylquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization

  摘要：

  A novel series of 2-styrylquinazolin-4(3H-ones which inhibited tubulin polymerization and the growth of L1210 murine leukemia cells was discovered. Extensive structure-activity relationship studies suggest that the entire quinazolinone structure was required, but activity was further enhanced by halide or small hydrophobic substituents at position 6. These analogues did not substantially interfere with the binding of radiolabeled colchicine, vinblastine, or GTP to tubulin and weakly stimulated GTP hydrolysis uncoupled from polymerization. Several analogues have shown in vivo tumor growth inhibitory activity in the L1210 leukemia model, with the lead compound 5o exhibiting good antitumor activity against murine solid tumors as well as human tumor xenografts.

  DOI：

  10.1021/jm00168a029

文献信息

• DDQ in mechanochemical C–N coupling reactions
  作者：Shyamal Kanti Bera、Rosalin Bhanja、Prasenjit Mal

  DOI：10.3762/bjoc.18.64

  日期：——

  that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones via the intra- and intermolecular C–N coupling reaction under solvent-free mechanochemical (ball milling) conditions. In the presence of DDQ, the intramolecular C(sp2)–H amidation of N-(2-(arylideneamino)phenyl)-p-toluenesulfonamides leads to 1,2-disubstituted benzimidazoles and the one-pot coupling of 2-aminobenzamides

  2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）是一种众所周知的氧化剂。在此，我们报道DDQ可用于在无溶剂机械化学（球磨）条件下通过分子内和分子间C-N偶联反应合成1,2-二取代苯并咪唑和喹唑啉-4(3 H )-酮。在 DDQ 存在下， N -(2-(亚芳基氨基)苯基)-对甲苯磺酰胺的分子内 C(sp 2 )–H 酰胺化生成 1,2-二取代苯并咪唑，以及 2-氨基苯甲酰胺与芳基/烷基醛以高产率产生取代的喹唑啉-4(3 H )-酮衍生物。
• JIANG, J. B.;HESSON, D. P.;DUSAK, B. A.;DEXTER, D. L.;KANG, G. J.;HAMEL, +, J. MED. CHEM., 33,(1990) N, C. 1721-1728
  作者：JIANG, J. B.、HESSON, D. P.、DUSAK, B. A.、DEXTER, D. L.、KANG, G. J.、HAMEL, +

  DOI：——

  日期：——
• Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization
  作者：Jack B. Jiang、D. P. Hesson、B. A. Dusak、D. L. Dexter、G. J. Kang、E. Hamel

  DOI：10.1021/jm00168a029

  日期：1990.6

  A novel series of 2-styrylquinazolin-4(3H-ones which inhibited tubulin polymerization and the growth of L1210 murine leukemia cells was discovered. Extensive structure-activity relationship studies suggest that the entire quinazolinone structure was required, but activity was further enhanced by halide or small hydrophobic substituents at position 6. These analogues did not substantially interfere with the binding of radiolabeled colchicine, vinblastine, or GTP to tubulin and weakly stimulated GTP hydrolysis uncoupled from polymerization. Several analogues have shown in vivo tumor growth inhibitory activity in the L1210 leukemia model, with the lead compound 5o exhibiting good antitumor activity against murine solid tumors as well as human tumor xenografts.