Synthesis and evaluation of the cytotoxicities of neoflavenes

Sie Rong Li, Hsing Ming Chen, Po Yuan Chen, Jui Chi Tsai, Liang Yeu Chen, Eng Chi Wang, Yi Ting Huang, Yun Chen Wei, Pei-Jung Lu

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The synthesis of neoflavene and neoflavenes with methoxy substituents at different positions are described. As starting materials, various salicylaldehydes were run through sequential reactions such as O-allylation, Grignard reaction, oxidation, Wittig reaction, and ring-closing metathesis to yield the target neoflavenes in good yield. Among the prepared neoflavenes, 7-methoxy-4′-methoxyneoflavene (6e) and 8-methoxy-4′- methoxyneoflavene (6f) exhibiting potential cell toxicities against various cells were disclosed. In particular, 6f which exhibited an IC50 value of 6.5 ± 2.0 and 5.1 ± 1.1 μM against gastric carcinoma and lung carcinoma cells in vitro was found, respectively. Meanwhile, the structure and activity relationship of our synthesized neoflavenes is further discussed briefly.

Original languageEnglish
Pages (from-to)923-932
Number of pages10
JournalJournal of the Chinese Chemical Society
Volume55
Issue number4
DOIs
Publication statusPublished - 2008 Jan 1

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Allylation
Cytotoxicity
Toxicity
Cells
Oxidation
salicylaldehyde

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Li, S. R., Chen, H. M., Chen, P. Y., Tsai, J. C., Chen, L. Y., Wang, E. C., ... Lu, P-J. (2008). Synthesis and evaluation of the cytotoxicities of neoflavenes. Journal of the Chinese Chemical Society, 55(4), 923-932. https://doi.org/10.1002/jccs.200800137
Li, Sie Rong ; Chen, Hsing Ming ; Chen, Po Yuan ; Tsai, Jui Chi ; Chen, Liang Yeu ; Wang, Eng Chi ; Huang, Yi Ting ; Wei, Yun Chen ; Lu, Pei-Jung. / Synthesis and evaluation of the cytotoxicities of neoflavenes. In: Journal of the Chinese Chemical Society. 2008 ; Vol. 55, No. 4. pp. 923-932.
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abstract = "The synthesis of neoflavene and neoflavenes with methoxy substituents at different positions are described. As starting materials, various salicylaldehydes were run through sequential reactions such as O-allylation, Grignard reaction, oxidation, Wittig reaction, and ring-closing metathesis to yield the target neoflavenes in good yield. Among the prepared neoflavenes, 7-methoxy-4′-methoxyneoflavene (6e) and 8-methoxy-4′- methoxyneoflavene (6f) exhibiting potential cell toxicities against various cells were disclosed. In particular, 6f which exhibited an IC50 value of 6.5 ± 2.0 and 5.1 ± 1.1 μM against gastric carcinoma and lung carcinoma cells in vitro was found, respectively. Meanwhile, the structure and activity relationship of our synthesized neoflavenes is further discussed briefly.",
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Li, SR, Chen, HM, Chen, PY, Tsai, JC, Chen, LY, Wang, EC, Huang, YT, Wei, YC & Lu, P-J 2008, 'Synthesis and evaluation of the cytotoxicities of neoflavenes', Journal of the Chinese Chemical Society, vol. 55, no. 4, pp. 923-932. https://doi.org/10.1002/jccs.200800137

Synthesis and evaluation of the cytotoxicities of neoflavenes. / Li, Sie Rong; Chen, Hsing Ming; Chen, Po Yuan; Tsai, Jui Chi; Chen, Liang Yeu; Wang, Eng Chi; Huang, Yi Ting; Wei, Yun Chen; Lu, Pei-Jung.

In: Journal of the Chinese Chemical Society, Vol. 55, No. 4, 01.01.2008, p. 923-932.

Research output: Contribution to journalArticle

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AU - Li, Sie Rong

AU - Chen, Hsing Ming

AU - Chen, Po Yuan

AU - Tsai, Jui Chi

AU - Chen, Liang Yeu

AU - Wang, Eng Chi

AU - Huang, Yi Ting

AU - Wei, Yun Chen

AU - Lu, Pei-Jung

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N2 - The synthesis of neoflavene and neoflavenes with methoxy substituents at different positions are described. As starting materials, various salicylaldehydes were run through sequential reactions such as O-allylation, Grignard reaction, oxidation, Wittig reaction, and ring-closing metathesis to yield the target neoflavenes in good yield. Among the prepared neoflavenes, 7-methoxy-4′-methoxyneoflavene (6e) and 8-methoxy-4′- methoxyneoflavene (6f) exhibiting potential cell toxicities against various cells were disclosed. In particular, 6f which exhibited an IC50 value of 6.5 ± 2.0 and 5.1 ± 1.1 μM against gastric carcinoma and lung carcinoma cells in vitro was found, respectively. Meanwhile, the structure and activity relationship of our synthesized neoflavenes is further discussed briefly.

AB - The synthesis of neoflavene and neoflavenes with methoxy substituents at different positions are described. As starting materials, various salicylaldehydes were run through sequential reactions such as O-allylation, Grignard reaction, oxidation, Wittig reaction, and ring-closing metathesis to yield the target neoflavenes in good yield. Among the prepared neoflavenes, 7-methoxy-4′-methoxyneoflavene (6e) and 8-methoxy-4′- methoxyneoflavene (6f) exhibiting potential cell toxicities against various cells were disclosed. In particular, 6f which exhibited an IC50 value of 6.5 ± 2.0 and 5.1 ± 1.1 μM against gastric carcinoma and lung carcinoma cells in vitro was found, respectively. Meanwhile, the structure and activity relationship of our synthesized neoflavenes is further discussed briefly.

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