Synthesis and antiproliferative evaluations of certain 2-phenylvinylquinoline (2-styrylquinoline) and 2-furanylvinylquinoline derivatives

Bioorganic & Medicinal Chemistry
Feng-Shuo ChangYeh-Long Chen

Abstract

The present study describes the synthesis of 2-phenylvinylquinoline (styrylquinoline) and 2-furanylvinylquinoline derivatives and evaluation for their antiproliferative activities. (E)-2-Styrylquinolin-8-ol (14a) was inactive against a 3-cell line panel consisting of MCF-7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Replacement of the phenyl ring with 5-nitrofuran-2-yl group significantly enhanced antiproliferative activity in which (E)-2-(2-(5-nitrofuran-2-yl)vinyl)quinolin-8-ol (14i) and its 4-substituted derivatives 15-19 exhibited strong inhibitory effects against the growth of all three cancer cells. These compounds were further evaluated for their IC(50) against the growth of MCF-7, LNCaP, and PC3. Results indicated that a hydrogen bond donating oxime derivative 19a was more active than its hydrogen bond accepting methyloxime derivative 19b. For the inhibition of LNCaP, the potency decreased in an order 14i>19a>19b>15>18>16. Compound 14i is the most active with an IC(50) value of 0.35 and 0.14 microM, respectively, against the growth of LNCaP and PC3 cancer cells. Therefore, compound 14i was evaluated by flow cytometric analysis for its effects on cell cycle distributions. Results indicated that 14i effectively induced c...Continue Reading

References

Feb 25, 2005·Nature Reviews. Drug Discovery·Yves PommierChristophe Marchand

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Citations

Apr 15, 2014·European Journal of Medicinal Chemistry·Chih-Hua TsengJin-Ching Lee
Jan 24, 2017·Organic Letters·Zhenhao ZhangYangjie Wu
Dec 19, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Magda A-A El-SayedAlaa A-M Abdel-Aziz
Jun 5, 2019·Medicinal Chemistry·Robert Musiol
Mar 23, 2011·Organic & Biomolecular Chemistry·Chih-Hua TsengCherng-Chyi Tzeng
Mar 21, 2019·Drug Development Research·Joshua O OdingoTanya Parish
Jul 16, 2011·The Journal of Organic Chemistry·Yizhe YanZhiyong Wang
Jan 10, 2020·Organic Letters·Jiajin ZhaoZhan Lu

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