Citation: You-An Xiao, Zhi-Qiang Wang, Xue-Min Wang, Yi Hui, Yong Ling, Xin-Yang Wang, Li-Qin He. Synthesis and in vitro biological evaluation of novel 2-aminoimidazolone derivatives as anti-tumor agents[J]. Chinese Chemical Letters, ;2013, 24(8): 727-730. shu

Synthesis and in vitro biological evaluation of novel 2-aminoimidazolone derivatives as anti-tumor agents

You-An Xiao ^a,b ,
Zhi-Qiang Wang ^b,c ,
Xue-Min Wang ^b ,
Yi Hui ^b ,
Yong Ling ^b,, ,
Xin-Yang Wang ^b ,
Li-Qin He ^a,,

1.
a Anhui University of Traditional Chinese Medicine, Anhui Key Laboratory of Modernized Chinese Material Medical, Hefei 230031, China;
2.
b Medical College, Nantong University, Nantong 226001, China;
3.
c Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China

Corresponding author: Yong Ling, Li-Qin He,
Received Date: 13 March 2013
Available Online: 26 April 2013

Novel 2-aminoimidazolone derivatives were synthesized. Most compounds displayed strong anticancer activities against human carcinoma cells in vitro. Compounds 8a, 8b and 8j exhibited optimal activity superior to 5-FU in most cancer cells tested. Especially, the IC₅₀s of 8b (12.6-21.5 μmol/L) against five tumor cells were 1-4 fold less than those of 5-FU (18.4-56.1 μmol/L) in vitro. Furthermore, compound 8b could induce SMMC-7721 cell apoptosis in a dose-dependent manner. Therefore, our novel findingsmay provide a new framework for the design of new 2-aminoimidazolone derivatives for the treatment of cancer.
- Synthesis,
- 2-Aminoimidazolone,
- Anti-tumor agents,
- Cytotoxic activities,
- Cell apoptosis
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  [15] The data of selected compounds: 8a: Yield 75%, mp > 250℃. MS (ESI): m/z 270[M+1]⁺. ¹H NMR (300 MHz, CDC_l3): δ 7.60 (s, 1H), 7.33 (s, 1H), 7.11 (s, 1H), 7.02 (m, 1H), 6.74 (m, 1H). Anal. calcd. for C₁₁H₉F₂N₃O₃: C 49.02, H 3.38, N 15.56; Found: C 49.08, H 3.37, N 15.61. 8b: Yield 71%,mp > 250℃. MS (ESI): m/z 284[M+1]⁺. 1 3): δ 7.80 (s, 1H), 7.43 (s, 1H), 7.26 (S, 1H), 7.01 (m, 1H), 6.82 (m, 1H), 2.48-2.47 (d, 3H, J = 9.0 Hz). Anal. calcd. forC₁₂H₁₁F₂N₃O₃: C 50.82, H 3.98, N 14.82; Found: C 50.89, H 3.91, N 14.84. 8j: Yield 70%, mp > 250℃. MS (ESI): m/z 358 [M+1]⁺. ¹H NMR (300MHz, CDC_l3): 7.41-7.30 (s, 1H, C=CH), 7.21 (s, 1H, CF₂H), 7.09-7.04 (m, 2H, Ar-H), 6.46 (d, 1H, Ar-H), 3.72-3.60 (m, 3H, HOCH₂, HOCH), 3.07(d, 3H, CH₃), 2.80-2.72 (m, 2H, NHCH₂). Anal. calcd. for C₁₅H₁₇F₂N₃O₅: C 50.35, H 4.88, N 11.68; Found: C 50.42, H 4.80, N 11.76.
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