Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2H)-ones from Substituted 2′-Aminochalcones,Synthesis

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Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2H)-ones from Substituted 2′-Aminochalcones
Synthesis ( IF 2.2 ) Pub Date : 2020-03-11 , DOI: 10.1055/s-0039-1707985
Alirio Palma ₁ , Angie Meléndez ₁ , Esteban Plata ₁ , Diego Rodríguez ₁ , Diana Ardila ₁ , Sergio A. Guerrero ₁ , Lina M. Acosta ₁ , Justo Cobo ₂ , Manuel Nogueras ₂

Affiliation

An alternative and efficient one-step approach to develop small libraries of polysubstituted 4-styrylquinolines/4-styrylquinolin-2-ones and 9-styryldihydroacridin-1-ones is described. According to this approach, new series of these compounds were straightforwardly synthesized in high yields starting from synthetically available 2′-aminochalcones and 1,3-dicarbonyl compounds in glacial acetic acid as a catalyst via the Friedländer reaction. Our approach also offers an expeditious way to access novel molecular hybrids in whose structures styryl and chalcone fragments are attached at the C4 and C3 positions, respectively, of the quinoline ring. All synthesized compounds were fully characterized by means of IR, HRMS and NMR techniques, and most were screened at the National Cancer Institute, USA, for their antitumor activity.

中文翻译：

从取代的2'-氨基邻苯二酚中直接合成新型4-苯乙烯基喹啉/ 4-苯乙烯基喹啉-2-酮和9-苯乙烯基二氢ac啶-1（2H）-酮

描述了开发多取代的4-苯乙烯基喹啉/ 4-苯乙烯基喹啉-2-酮和9-苯乙烯基二氢ac啶酮-1-酮的小文库的另一种有效的一步方法。根据这种方法，这些新化合物系列是直接从弗里德兰德反应中以冰乙酸为催化剂的合成的2'-氨基查耳酮和1,3-二羰基化合物开始以高收率直接合成的。我们的方法还提供了一种访问新型分子杂化物的快捷方法，在这种杂物中，苯乙烯基和查耳酮片段的结构分别连接在喹啉环的C4和C3位置。所有合成的化合物均通过IR，HRMS和NMR技术进行了充分表征，并且大多数化合物已在美国国家癌症研究所进行了抗肿瘤活性筛选。

更新日期：2020-03-11

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