NSC 382468 | 35834-17-4

• 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: NSC 382468
• 英文别名: 2-benzyl-6-chloroquinazolin-4(3H)-one；6-Chlor-2-benzyl-3(H)-4-ketochinazolin；2-benzyl-6-chloro-3H-quinazolin-4-one；2-benzyl-6-chloro-3H-quinazolin-4-one
• CAS: 35834-17-4
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: WWZHDYWCEFFEAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  色酮-3-甲醛 、 NSC 382468 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 以89%的产率得到2-chloro-8-(2-hydroxybenzoyl)-6-phenyl-11H-pyrido[2,1-b]quinazolin-11-one
  参考文献：
  名称：

  用于构建吡啶并稠合杂环的微波辅助环化及其作为光致发光化学传感器的应用

  摘要：

  开发了一种用于制备具有生物学意义的吡啶并稠合喹唑啉酮和吡啶并[1,2- a ]苯并咪唑的无催化剂微波辅助环化方案。该反应涉及各种喹唑啉酮或苯并咪唑与 3-甲酰基色酮的 [3 + 3] 环化，生成官能化的 11 H-吡啶并[ 2,1- b ]喹唑啉-11-酮和吡啶并[1,2- a ]苯并咪唑衍生物。该方法成功地扩展到构建各种吡唑并[4,3 - d ]pyrido[1,2 - a ]pyrimidin-10(1 H）-那些。本方法是对现有合成方法的补充，并提供了一种快速简便的方法，具有广泛的底物范围、良好的收率、无催化剂条件和高官能团耐受性。最佳合成化合物也可用作“开关”光致发光探针，用于选择性检测 Fe 3+和 Ag +金属离子。

  DOI：

  10.1039/d2ob00257d
• 作为产物：
  描述：

  N-(4-Chloro-2-cyano-phenyl)-2-phenyl-acetamide 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 NSC 382468
  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

• A novel, one-pot, solvent-, and catalyst-free synthesis of 2-aryl/alkyl-4(3H)-quinazolinones
  作者：Mehdi Adib、Samira Ansari、Ali Mohammadi、Hamid Reza Bijanzadeh

  DOI：10.1016/j.tetlet.2009.06.034

  日期：2010.1

  A novel and one-pot synthesis of 2-aryl/alkyl-4(3H)-quinazolinones is described. The in situ prepared amidoximes from the reaction between nitriles and hydroxylamine are condensed with anthranilic acids under solvent- and catalyst-free conditions to produce the title compounds in excellent yields.

  描述了一种新颖的一锅合成2-芳基/烷基-4（3 H）-喹唑啉酮的方法。在无溶剂和无催化剂的条件下，将腈和羟胺之间的反应原位制备的a胺肟与邻氨基苯甲酸缩合，以优异的收率生产标题化合物。
• A Direct Method for Synthesis of Quinoxalines and Quinazolinones Using Epoxides as Alkyl Precursor
  作者：Xueyan Lv、Lili Lv、Shichen Li、Chengcheng Ding、Bingchuan Yang、Chen Ma

  DOI：10.3390/molecules28217391

  日期：——

  An iodine-mediated one-pot synthesis of pyrrolo/indolo [1,2-a]quinoxalines and quinazolin-4-one via utilizing epoxides as alkyl precursors under metal-free conditions has been described. Both 1-(2-aminophenyl)-pyrrole and 2-aminobenzamide could be applied to this protocol. A total of 33 desired products were obtained with moderate to good yields. This methodology was suitable for wide-scale preparation

  描述了在无金属条件下利用环氧化物作为烷基前体，碘介导的吡咯并/吲哚[1,2-a]喹喔啉和喹唑啉-4-酮的一锅法合成。1-(2-氨基苯基)-吡咯和2-氨基苯甲酰胺都可以应用于该方案。总共获得了 33 种所需产物，收率中等至良好。该方法适合大规模制备，所得产品可以进一步修饰为有前景的药物活性试剂。
• 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.
• Microwave-assisted annulation for the construction of pyrido-fused heterocycles and their application as photoluminescent chemosensors
  作者：Ei Seul Yun、Muhammad Saeed Akhtar、Sonaimuthu Mohandoss、Yong Rok Lee

  DOI：10.1039/d2ob00257d

  日期：——

  3-formylchromones to yield functionalized 11H-pyrido[2,1-b]quinazolin-11-one and pyrido[1,2-a] benzimidazole derivatives. This approach is successfully extended to the construction of various pyrazolo[4,3-d]pyrido[1,2-a]pyrimidin-10(1H)-ones. The present approach is complementary to the existing synthetic methodologies and offers a rapid and facile approach with a broad substrate scope, good yields, catalyst-free

  开发了一种用于制备具有生物学意义的吡啶并稠合喹唑啉酮和吡啶并[1,2- a ]苯并咪唑的无催化剂微波辅助环化方案。该反应涉及各种喹唑啉酮或苯并咪唑与 3-甲酰基色酮的 [3 + 3] 环化，生成官能化的 11 H-吡啶并[ 2,1- b ]喹唑啉-11-酮和吡啶并[1,2- a ]苯并咪唑衍生物。该方法成功地扩展到构建各种吡唑并[4,3 - d ]pyrido[1,2 - a ]pyrimidin-10(1 H）-那些。本方法是对现有合成方法的补充，并提供了一种快速简便的方法，具有广泛的底物范围、良好的收率、无催化剂条件和高官能团耐受性。最佳合成化合物也可用作“开关”光致发光探针，用于选择性检测 Fe 3+和 Ag +金属离子。