AI Article Synopsis
- A series of new arylidene N-alkoxydiketopiperazines were created using specific chemical processes, leading to a focus on their properties and effectiveness.
- The study highlighted potential mechanisms for how these compounds could rearrange and fragment, supported by crystal structure analysis.
- Several compounds showed strong antitumor activity, particularly against the enzyme caspase-3, with certain variants demonstrating promising selectivity and potency in low micromolar concentrations.
Article Abstract
A series of arylidene N-alkoxydiketopiperazines was designed and stereoselectively synthesized via oxime-ether formation and intramolecular acylation. Possible cyclization and acid-catalyzed rearrangement-fragmentation mechanisms were discussed. The crystal structure of the novel diketopiperazine further confirmed the rearrangement mechanism. Most compounds exhibited antitumor activity. Several compounds were more potent against caspase-3. Specifically, compounds 6e, 6g, and 6f inhibited caspase-3 at IC values lying within the low micromolar range and demonstrated good selectivity. The binding modes of alkoxydiketopiperazines in the active center of caspase-3 were also discussed based on the molecular docking results.
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| http://dx.doi.org/10.1016/j.bmc.2016.08.038 | DOI Listing |
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Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.
Bioorg Med Chem
November 2016
State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China. Electronic address:
Article Synopsis
- A series of new arylidene N-alkoxydiketopiperazines were created using specific chemical processes, leading to a focus on their properties and effectiveness.
- The study highlighted potential mechanisms for how these compounds could rearrange and fragment, supported by crystal structure analysis.
- Several compounds showed strong antitumor activity, particularly against the enzyme caspase-3, with certain variants demonstrating promising selectivity and potency in low micromolar concentrations.
Stereoselective synthesis and rearrangement-fragmentation of arylidene N-alkoxydiketopiperazines.
Org Biomol Chem
November 2011
State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China.
A stereoselective synthesis of arylidene N-alkoxydiketopiperazines via oxime-ether formation and intramolecular acylation is described, followed by an acid-catalysed rearrangement-fragmentation to give novel diketopiperazine hemiaminal derivatives with useful bioactivity against certain tumour cell lines.
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