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

doi:10.1002/jccs.200800137

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

Institute of Clinical Medicine

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	923-932
Number of pages	10
Journal	Journal of the Chinese Chemical Society
Volume	55
Issue number	4
DOIs	https://doi.org/10.1002/jccs.200800137
Publication status	Published - 2008 Jan 1

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1002/jccs.200800137

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@article{08f388dfa37a489aa40760a71d3beb2c,

title = "Synthesis and evaluation of the cytotoxicities of neoflavenes",

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.",

author = "Li, {Sie Rong} and Chen, {Hsing Ming} and Chen, {Po Yuan} and Tsai, {Jui Chi} and Chen, {Liang Yeu} and Wang, {Eng Chi} and Huang, {Yi Ting} and Wei, {Yun Chen} and Lu, {Pei Jung}",

year = "2008",

month = jan,

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doi = "10.1002/jccs.200800137",

language = "English",

volume = "55",

pages = "923--932",

journal = "Journal of the Chinese Chemical Society",

issn = "0009-4536",

publisher = "Chinese Chemical Society",

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TY - JOUR

T1 - Synthesis and evaluation of the cytotoxicities of neoflavenes

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

PY - 2008/1/1

Y1 - 2008/1/1

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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DO - 10.1002/jccs.200800137

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JO - Journal of the Chinese Chemical Society

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