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Peng, Fu-Chuo; Cheng, Jur-Shan

doi:10.1023/a:1006845621623

Mycopathologia

1997

DOI: 10.1023/a:1006845621623

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Fu-Chuo Peng

Jur-Shan Cheng

Abstract: 4beta-Methoxymethyl-4beta-demethyl territrem B [5] was synthesized from 4beta-hydroxymethyl-beta-demethyl territrem B [4] by treatment with dimethyl sulfate in methanolic NaOH. The structure of 5 was elucidated by uv, nmr and mass spectra. The IC50 of 5 on acetylcholinesterase (AChE) was 6.30 x 10(-5) M, which indicated 0.4% of the anti-AChE activity of territrem B [2].

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Cited by 3 publications

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Synthesis of A/B Ring Analogs of Territrem B and Evaluation of Their Biological Activities

Zhao

Wang

et al. 2004

Helvetica Chimica Acta

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Two series of territrem B analogs, i.e., 5 ± 10, containing both the 2-en-1-one-A-ring and the aromatic-Ering pharmacophores were designed and synthesized from jujubogenin (4a). The anti-acetylcholinesterase (antiAChE), anti-caspase-3, and other biological activities of these territrem-B analogs and their intermediates were assessed. Compound 9b, 22a, and 24f were shown to be weak inhibitors of AChE. None of the synthesized compounds exhibited significant inhibitory activity on caspase-3. On the other hand, compounds 22e, 24a, 7b, and 8a showed mild cytotoxicity on cultured KB cells, with IC 50 values of 2.0, 3.5, 6.5, and 14 mm, respectively. In addition, compounds 23b and 5f were active against injury arising from oxygen-glucose deprivation.

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Synthesis of A/B Ring Analogs of Territrem B and Evaluation of Their Biological Activities

Zhao

Wang

et al. 2004

Helvetica Chimica Acta

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Synthesis of potentially photoactivatable coumarin derivatives via a 1,3‐dipolar cycloaddition

Chenot¹,

Rodríguez-Domínguez²,

Comel³

et al. 2008

Journal of Heterocyclic Chem

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A copper (1)‐catalyzed 1,3‐dipolar cycloaddition reaction was used to prepare a series of mono and disubstituted 1,2,3‐triazolyl‐coumarins using a 1,3‐cycloaddition (“Click Chemistry”). Starting coumarins were synthesized using classical or modified Pechmann's reaction. The propargyl group was introduced as either propargylether or as a propargylamide. Azides were prepared in a three steps procedure. Cycloaddition products, containing a coumarin and a photoactivatable moiety, were obtained in good yields.

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A computational view on the significance of E-ring in binding of (+)-arisugacin A to acetylcholinesterase

Al‐Rashid¹,

Hsung

2015

Bioorganic & Medicinal Chemistry Letters

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A computational docking study of a series of de novo structural analogs of the highly potent, non-nitrogen containing, acetylcholinesterase inhibitor (+)-arisugacin A is presented. In direct comparison to the recently reported X-ray single-crystal structure of (+)-territrem B bound hAChE, the modeling suggests that there is a unique conformational preference for the E-ring that is responsible for the superior inhibitory activity of (+)-arisugacin A against hAChE relative to (+)-territrem B, and that substitutions on the E-ring also play an important role in the protein-ligand interaction.

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Untitled

Cited by 3 publications

References 5 publications

Synthesis of A/B Ring Analogs of Territrem B and Evaluation of Their Biological Activities

Synthesis of A/B Ring Analogs of Territrem B and Evaluation of Their Biological Activities

Synthesis of potentially photoactivatable coumarin derivatives via a 1,3‐dipolar cycloaddition

A computational view on the significance of E-ring in binding of (+)-arisugacin A to acetylcholinesterase

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