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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 02: 332 - 338

DOI: https://doi.org/10.6023/cjoc201208035

Articles

Synthesis and Antitumor Activities of β-Carboline Derivatives

  • Guo Liang ,
  • Fan Wenxi ,
  • Chen Xuemei ,
  • Ma Qin ,
  • Cao Rihui
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  • a Xinjiang Huashidan Pharmaceutical Research Co., Ltd., Urumqi 830011;
    b School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275

Received date: 2012-08-30

  Revised date: 2012-11-01

  Online published: 2012-11-14

Supported by

Project supported by the National Key Program for New Drug Development (No. 2009ZX09401-007).

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Abstract

In search of more effective antitumor agents, based on the previous results of computer aided drug design. The starting material L-tryptophan reacted with formaldehyde via Pictet-Spengler condensation and followed by oxidation and decarboxylation to afford the intermediate β-carboline. The intermediate was further reacted with halogenated hydrocarbon by N9-alkylation and N2-quaternarization to obtain new β-carboline derivatives. Fourteennovel β-carboline derivatives were synthesized and characterized by 1H NMR, IR, MS and elemental analysis. Compound 5h was further studied by X-ray single crystal diffraction analysis. The antitumor activity of the target compounds was studied by MTT method. The results demonstrated that N2-quaternarized compounds (5a～5n) had more remarkable cytotoxic activities in vitro than 9-phenylpropyl-β-carboline (4). The tumor inhibition rates of the selected compounds 5e and 5h in mice bearing Lewis lung cancer. The compound 9 showed inhibition activity on transplanting-tumor growth of Lewis lung cancer.

Key words： β-carboline; synthesis; antitumor activity; structure-activity relationship

Cite this article

Guo Liang , Fan Wenxi , Chen Xuemei , Ma Qin , Cao Rihui . Synthesis and Antitumor Activities of β-Carboline Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 332 -338 . DOI: 10.6023/cjoc201208035

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