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Keywords = 2-(2-phenylethenyl)chromone derivative

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18 pages, 2251 KiB  
Review
Development of Newly Synthesized Chromone Derivatives with High Tumor Specificity against Human Oral Squamous Cell Carcinoma
by Yoshiaki Sugita, Koichi Takao, Yoshihiro Uesawa, Junko Nagai, Yosuke Iijima, Motohiko Sano and Hiroshi Sakagami
Medicines 2020, 7(9), 50; https://doi.org/10.3390/medicines7090050 - 26 Aug 2020
Cited by 15 | Viewed by 5340
Abstract
Since many anticancer drugs show severe adverse effects such as mucositis, peripheral neurotoxicity, and extravasation, it was crucial to explore new compounds with much reduced adverse effects. Comprehensive investigation with human malignant and nonmalignant cells demonstrated that derivatives of chromone, back-bone structure of [...] Read more.
Since many anticancer drugs show severe adverse effects such as mucositis, peripheral neurotoxicity, and extravasation, it was crucial to explore new compounds with much reduced adverse effects. Comprehensive investigation with human malignant and nonmalignant cells demonstrated that derivatives of chromone, back-bone structure of flavonoid, showed much higher tumor specificity as compared with three major polyphenols in the natural kingdom, such as lignin-carbohydrate complex, tannin, and flavonoid. A total 291 newly synthesized compounds of 17 groups (consisting of 12 chromones, 2 esters, and 3 amides) gave a wide range of the intensity of tumor specificity, possibly reflecting the fitness for the optimal 3D structure and electric state. Among them, 7-methoxy-3-[(1E)-2-phenylethenyl]-4H-1-benzopyran-4-one (compound 22), which belongs to 3-styrylchromones, showed the highest tumor specificity. 22 induced subG1 and G2 + M cell population in human oral squamous cell carcinoma cell line, with much less keratinocyte toxicity as compared with doxorubicin and 5-FU. However, 12 active compounds selected did not necessarily induce apoptosis and mitotic arrest. This compound can be used as a lead compound to manufacture more active compound. Full article
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8 pages, 495 KiB  
Article
2-(2-Phenylethyl)chromone Derivatives of Agarwood Originating from Gyrinops salicifolia
by Hang Shao, Wen-Li Mei, Wen-Hua Dong, Cui-Juan Gai, Wei Li, Guo-Peng Zhu and Hao-Fu Dai
Molecules 2016, 21(10), 1313; https://doi.org/10.3390/molecules21101313 - 3 Oct 2016
Cited by 21 | Viewed by 5118
Abstract
Three new2-(2-phenylethyl)chromone derivatives (1–3) and a new2-(2-phenylethenyl)chromone derivative (4), together with two known 2-(2-phenylethyl)chromone derivatives (5–6), were isolated from agarwood originating from Gyrinops salicifolia Ridl. The structures of compounds 1–4 were elucidated by comprehensive spectroscopic techniques (UV, IR, 1D and 2D-NMR) and MS [...] Read more.
Three new2-(2-phenylethyl)chromone derivatives (1–3) and a new2-(2-phenylethenyl)chromone derivative (4), together with two known 2-(2-phenylethyl)chromone derivatives (5–6), were isolated from agarwood originating from Gyrinops salicifolia Ridl. The structures of compounds 1–4 were elucidated by comprehensive spectroscopic techniques (UV, IR, 1D and 2D-NMR) and MS analysis, as well as by comparison with the literature. Compounds 1, 2, and 5 showed moderate cytotoxicity against human tumor K562, BEL-7402, and SGC-7901 cell lines with IC50 values of 5.76 to 20.1 µM. Full article
(This article belongs to the Section Natural Products Chemistry)
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