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

✍ Scribed by Jinhao Zhao; Feng Zhao; Yanguang Wang; Haibo Li; Qijun Zhang; Daniel Guénard; Qiufu Ge; Erqing Wei; Hao Jiang; Yihang Wu; Lin Wang; Hualiang Jiang; Françoise Guéritte; Xiumei Wu; Christopher H. K. Cheng; Shoei-Sheng Lee; Yu Zhao

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
535 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Two series of territrem B analogs, i.e., 5–10, containing both the 2‐en‐1‐one‐A‐ring and the aromatic‐E‐ring pharmacophores were designed and synthesized from jujubogenin (4a). The anti‐acetylcholinesterase (anti‐AChE), 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 μM, respectively. In addition, compounds 23b and 5f were active against injury arising from oxygen‐glucose deprivation.

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