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5-N-Substituted-2-(substituted benzenesulphonyl) glutamines as antitumor agents. Part II: synthesis, biological activity and QSAR study. | LitMetric

AI Article Synopsis

  • Cancer has been a significant health concern throughout history, and researchers focus on its biology, particularly how tumor cells utilize glutamine for their growth.
  • Glutamine provides essential nitrogen for synthesizing nucleic acids and proteins, prompting the design and synthesis of 17 new glutamine-based compounds as potential anticancer agents.
  • A study analyzing the effectiveness of these compounds using quantitative structure-activity relationship (QSAR) revealed that specific structural features, such as steric effects on the aromatic ring and particular substitutions, enhance their antitumor activity.

Article Abstract

Cancer is a major killer disease throughout human history. Thus, cancer becomes a major point of interest in life science. It was proved that cancer is a nitrogen trap and tumor cells are avid glutamine consumers. The non-essential amino acid glutamine, which is a glutamic acid derivative, supplies its amide nitrogen to tumor cells in the biosynthesis of purine and pyrimidine bases of nucleic acids as well as takes part in protein synthesis. Based on these and in continuation of our composite programme of development of new potential anticancer agents through rational drug design, 17 new 5-N-Substituted-2-(substituted benzenesulphonyl) glutamines were selected for synthesis. These compounds as well as 36 earlier synthesized glutamine analogues were screened for antitumor activity using percentage inhibition of tumor cell count as the activity parameter. QSAR study was performed with 53 compounds in order to design leads with increased effectiveness for antitumor activity using both physicochemical and topological parameters. QSAR study showed that steric effect on the aromatic ring is conducive to the activity. n-butyl substitution on aliphatic side chain and atom no 12 is important for antitumor activity of glutamine analogues.

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Source
http://dx.doi.org/10.1016/j.bmc.2004.01.006DOI Listing

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