Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates

Synthesis and Biological Evaluation of Novel .BETA.-Carbolines as Potent Cytotoxic and DNA Intercalating Agents

“…Recent reports [10][11][12][13][14][15][16][17] have pointed out b-carbolines as a class of potential antitumor agents, which was discovered to function their antitumor activity through multiple mechanisms, such as intercalating into DNA, 11,18) and kinesin Eg5.…”

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901Regular Article b-Carboline alkaloids represent a large number of naturally and synthetic indole alkaloids associated with a broad spectrum of biochemical effects and pharmaceutical properties.1) Previous investigations focused on the effects of b-carboline alkoloids on the central nervous system (CNS).

2-9)Recent reports [10][11][12][13][14][15][16][17] have pointed out b-carbolines as a class of potential antitumor agents, which was discovered to function their antitumor activity through multiple mechanisms, such as intercalating into DNA, 11,18) and kinesin Eg5.

25)Recently, our group investigations 26-31) on the synthesis of a variety of b-carboline derivatives and the evaluation of their antitumor activities unraveled that b-carbolines had potent antitumor activities and the activities were correlated to both the planarity of the molecule and the presence of the ring substituents. Structure-activity relationships (SARs) analysis suggested that the introduction of appropriate substituents into position-2, 3 and 9 played a vital role in determining their antitumor effects, and the n-butyl, benzyl or phenylpropyl substituents at position-9 was suitable pharmacophoric group giving rise to some potent antitumor agents.

In continuing search for novel and effective antitumor agents, we designed and synthesized a series of water-soluble b-carbolines bearing a flexible alkylamino side chain at position-3 and a alkyl or arylated alkyl substituent at position-9, respectively.

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“…1) Previous investigations focused on the effects of b-carboline alkoloids on the central nervous system (CNS). [2][3][4][5][6][7][8][9] Recent reports [10][11][12][13][14][15][16][17] have pointed out b-carbolines as a class of potential antitumor agents, which was discovered to function their antitumor activity through multiple mechanisms, such as intercalating into DNA, 11,18) inhibiting topoisomerase I and II, 13) CDK, [19][20][21] MAPKAP-K2, 22) MK-2, 23) PLK1 24) and kinesin Eg5. 25) Recently, our group investigations [26][27][28][29][30][31] on the synthesis of a variety of b-carboline derivatives and the evaluation of their antitumor activities unraveled that b-carbolines had potent antitumor activities and the activities were correlated to both the planarity of the molecule and the presence of the ring substituents.…”

Synthesis and structure of novel ferrocene-containing β-carbolines including polycondensed derivatives with the elements of planar-, central- and conformational chirality

“…In the recent decades it was also demonstrated that -carboline alkaloids may have a pronounced potential as anti-cancer agents [7][8][9][10][11][12][13][14][15][16], which can act through different mechanisms including eg. DNA-intercalation [17], inhibition of Topoisomerase I and II [18] and CDK (cyclindependent kinases) [19,20].…”

Synthesis of 1,2,3,4-Tetrahydroeudistomin U Derivatives and PreliminaryIn Vitro. Antitumor Evaluation

“…In this paper, based on our previous work on eudistomin U, we synthesized a series of 2-substituted 1,2,3,4-tetrahydroeudistomin U derivatives and tested their inhibitory activities against P. oryzae with the standard method (Kobayashi et al, 1996;Zhao & Zhang, 2005) and Caco-2 cancer cell MTT staining according to the previously reported procedures with a minor modification (AlAllaf & Rashan, 1998;Zhao et al, 2006).…”