(E)-6-bromo-2-styrylquinazolin-4(3H)-one | 127033-32-3

• 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: (E)-6-bromo-2-styrylquinazolin-4(3H)-one
• 英文别名: 6-bromo-2-styrylquinazolin-4(3H)-one；6-bromo-2-[(E)-2-phenylethenyl]-3H-quinazolin-4-one
• CAS: 127033-32-3
• 化学式: C₁₆H₁₁BrN₂O
• 分子量: 327.18
• InChiKey: GZYFJIWNVOVZTF-RMKNXTFCSA-N

物化性质

• 熔点：
  334-338 °C
• 沸点：
  488.7±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-bromo-2-styrylquinazolin-4(3H)-one 在 三乙胺 、 三氯氧磷 作用下， 以78%的产率得到(E)-6-bromo-4-chloro-2-styrylquinazoline
  参考文献：
  名称：

  9-取代的5-苯乙烯基四唑并[1,5-c]喹唑啉衍生物的合成、细胞毒性和分子对接研究

  摘要：

  在本文中，我们描述了 5-苯乙烯基四唑并 [1,5-c] 喹唑啉在 9 位被 4-氟苯环直接或通过共轭 π-间隔（C=C 或 C≡C 键）取代的合成) 基于 6-bromo-4-chloro-2-styrylquinazoline 支架。合成化合物的结构基于 1H-NMR、13C-NMR、IR 和高分辨率质谱数据以及微量分析的组合进行表征。评估了四唑并喹唑啉对人乳腺癌 (MCF-7) 和宫颈癌 (HeLa) 细胞的潜在体外细胞毒性。抗增殖试验表明，9-溴-5-苯乙烯基四唑并[1,5-c]喹唑啉3a和9-溴-5-(4-氟苯乙烯基)四唑并[1,5-c]喹唑啉3b对两种细胞系。除了 5,9-双((E)-4-氟苯乙烯基)四唑并[1,5-c]喹唑啉 4e 外，9 位的碳基取代基导致对两种细胞系的细胞毒性完全丧失。发现对 MCF-7 细胞系具有与美法仑 (IC50 = 61 μM) 相当的细胞毒性，IC50

  DOI：

  10.3390/molecules22111719
• 作为产物：
  描述：

  5-bromo-2-[[(E)-3-phenylprop-2-enoyl]amino]benzoic acid 在 formamide 作用下， 反应 6.0h， 生成 (E)-6-bromo-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

• Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones
  作者：Emmanuel Agbo、Tshepiso Makhafola、Yee Choong、Malose Mphahlele、Ponnadurai Ramasami

  DOI：10.3390/molecules21010028

  日期：——

  Suzuki-Miyaura cross-coupling of 6-bromo-2-styrylquinazolin-4(3H)-ones with arylboronic acids afforded a series of novel 6-aryl-2-styrylquinazolin-4(3H)-ones. These compounds were evaluated for potential anticancer properties against the human renal (TK-10), melanoma (UACC-62) and breast cancer (MCF-7) cell lines. Their antimicrobial properties were also evaluated against six Gram-positive and four Gram-negative bacteria, as well as two strains of fungi. Molecular docking studies (in silico) were conducted on compounds 5a, b, d and 6a, b, d–f to recognize the hypothetical binding motif of the title compounds within the active site of the dihydrofolate reductase and thymidylate synthase enzymes.

  采用Suzuki-Miyaura交叉偶联反应，以6-溴-2-苯乙烯基喹唉-4(3H)-酮与芳基硼酸为原料，制得了一系列新型6-芳基-2-苯乙烯基喹唉-4(3H)-酮。这些化合物对人肾癌（TK-10细胞系）、黑色素瘤（UACC-62细胞系）和乳腺癌（MCF-7细胞系）进行了潜在抗癌活性的评估。同时，针对六种革兰氏阳性菌、四种革兰氏阴性菌及两种真菌菌株，评价了这些化合物的抗菌活性。对化合物5a, b, d 和6a, b, d–f进行了分子对接研究（计算机模拟），以识别目标化合物在二氢叶酸还原酶和胸苷酸合酶活性位点的假定结合模式。
• 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.
• Synthesis, Cytotoxicity and Molecular Docking Studies of the 9-Substituted 5-Styryltetrazolo[1,5-c]quinazoline Derivatives
  作者：Malose Mphahlele、Samantha Gildenhuys、Nishal Parbhoo

  DOI：10.3390/molecules22111719

  日期：——

  demonstrated that the 9-bromo-5-styryltetrazolo[1,5-c]quinazoline 3a and 9-bromo-5-(4-fluorostyryl)tetrazolo[1,5-c]quinazoline 3b exhibit significant cytotoxicity against both cell lines. A carbon-based substituent at the 9-position resulted in complete loss of cytotoxicity against both cell lines except for the 5,9-bis((E)-4-fluorostyryl)tetrazolo[1,5-c]quinazoline 4e, which was found to exhibit comparable

  在本文中，我们描述了 5-苯乙烯基四唑并 [1,5-c] 喹唑啉在 9 位被 4-氟苯环直接或通过共轭 π-间隔（C=C 或 C≡C 键）取代的合成) 基于 6-bromo-4-chloro-2-styrylquinazoline 支架。合成化合物的结构基于 1H-NMR、13C-NMR、IR 和高分辨率质谱数据以及微量分析的组合进行表征。评估了四唑并喹唑啉对人乳腺癌 (MCF-7) 和宫颈癌 (HeLa) 细胞的潜在体外细胞毒性。抗增殖试验表明，9-溴-5-苯乙烯基四唑并[1,5-c]喹唑啉3a和9-溴-5-(4-氟苯乙烯基)四唑并[1,5-c]喹唑啉3b对两种细胞系。除了 5,9-双((E)-4-氟苯乙烯基)四唑并[1,5-c]喹唑啉 4e 外，9 位的碳基取代基导致对两种细胞系的细胞毒性完全丧失。发现对 MCF-7 细胞系具有与美法仑 (IC50 = 61 μM) 相当的细胞毒性，IC50