Bisquinolinone alkaloids from Melicope ptelefolia

Structural Simplification of Bioactive Natural Products with Multicomponent Synthesis. 2. Antiproliferative and Antitubulin Activities of Pyrano[3,2-c]pyridones and Pyrano[3,2-c]quinolones

“…Examples include cytotoxic fusaricide (1) 19 and melicobisquinolinone B (2, Figure 1). 20 In addition, zanthosimuline (3) is active against multidrug resistant KB-VI cancer cells, while huajiaosimuline (4) exhibits a selective cytotoxicity profile showing the greatest activity with estrogen receptor-positive ZR-75-1 breast cancer cells. 21 To develop compound libraries based on this fused heterocyclic scaffold we considered a reaction of 4-hydroxypyridones as well as corresponding quinolones with aldehydes and malononitrile ( Figure 2a).…”

Evaluation and in vivo efficacy study of pyrano[3,2‐c]quinoline analogues as TNF‐α inhibitors

“…It was pre‐established that proinflammatory cytokines like TNF‐α and interleukin‐6 (IL‐6) become attractive targets for adjuvant treatment of cancer as they are master regulators of tumor‐related inflammation and tumorigenesis (Grivennikov & Karin, ). As per showed in Figure , alkaloids with pyrano[3,2‐c]pyridone and pyrano[3,2‐c]quinolone like fusaricide (1, Figure ) (McBrien et al., ), melicobisquinolinone‐B (2, Figure ) (Kamperdick, Van, Van Sung, & Adam, ), zanthosimuline (3, Figure ), and huajiaosimuline (4, Figure ) (Chen et al., ) referred as potential anticancer agents. Additionally, Quinolactin‐A (Sasaki et al., ) (5, Figure )—a 4‐quinolone alkaloid, isolated from the cultured broth of Penicillium sp.…”

Synthesis of Unnatural 1-Methyl-2-quinolone Derivatives

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Since these alkaloids show physiological activities, many researchers have energetically studied the isolation, the structural determination and total syntheses of quinoline alkaloids containing the MeQone skeleton. [4][5][6][7][8][9][10][11][12][13][14][15] From the viewpoint for the drug design, it is also demanded to synthesize hitherto unknown unnatural MeQone derivatives and to develop new methods for functionalization of the MeQone framework.…”

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Since these alkaloids show physiological activities, many researchers have energetically studied the isolation, the structural determination and total syntheses of quinoline alkaloids containing the MeQone skeleton. [4][5][6][7][8][9][10][11][12][13][14][15] From the viewpoint for the drug design, it is also demanded to synthesize hitherto unknown unnatural MeQone derivatives and to develop new methods for functionalization of the MeQone framework. [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32] Especially, modification of the pyridone moiety in the MeQone is highly important because most of the naturally occurring MeQones have substituents at the 3 and/or the 4-position.…”

“…[16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32] Especially, modification of the pyridone moiety in the MeQone is highly important because most of the naturally occurring MeQones have substituents at the 3 and/or the 4-position. Mainly used methods for functionalization of the MeQone involve the activation by the pre-introduced substituents such as hydroxyl, alkoxyl and amino groups, [4][5][6][7][8][9][10][11][12][13][14][15] which compose partial structures of newly constructed skeleton. Meanwhile, direct functionalization methods of MeQone were recently attracted.…”