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Synthesis and antitumor activity of fluoroquinolone C-3 arylidene thiazolone derivatives from ciprofloxacin
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Na WANG1, Hui-li ZHANG2, Chao-ran CHEN3, *, Wen-long HUANG4, Guo-qiang HU1, *
Acta Pharmaceutica Sinica | 2019, 54(4) : 687 - 691
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Acta Pharmaceutica Sinica | 2019, 54(4): 687-691
• Original Articles •
Synthesis and antitumor activity of fluoroquinolone C-3 arylidene thiazolone derivatives from ciprofloxacin
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Na WANG1, Hui-li ZHANG2, Chao-ran CHEN3, *, Wen-long HUANG4, Guo-qiang HU1, *
Affiliations
  • 1. Institute of Drugs, Henan University, Kaifeng 475001, China
  • 2. School of Pharmacy, Zhengzhou University of Industrial Technology, Zhengzhou 451150, China
  • 3. Institute of Nursing and Health, Henan University, Kaifeng 475004, China
  • 4. Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China
Published: 2019-04-12 doi: 10.16438/j.0513-4870.2019-0036
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To expand an efficient strategy for the conversion of antibacterial activity of fluoroquinolones into an antitumor activity, sixteen new compounds, 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-3-(5-arylidene-thiazol-4(5H)-one-2-yl)-quinolon-4(1H)-ones (7a-7p), were designed and synthesized with a thiazolone ring and an arylidene moiety as an isostere and modified group, respectively, from ciprofloxacin. Their structures were characterized by elemental analysis and spectral data. The in vitro antitumor activity of the synthesized compounds were measured using Hep-3B, Capan-1 and HL60 cell lines and were found to be more potent than ciprofloxacin. Meanwhile, the SAR revealed that the halogenated phenyl compounds such as fluorophenyl (7h, 7i), chlorophenyl (7j, 7k) or bromophenyl compounds (7l, 7m), and aromatic heterocyclic substitution such as furyl (6n) or pyridyl compounds (6o, 6p) displayed better activity than the control compounds, especially the IC50 values of pyridyl compounds 6o and 6p against Capan-1 cell growth was comparable to doxorubicin. Thus, an arylidene-modified thiazolone scaffold as the replacement of the C-3 carboxylic acid group appears to be an alternative route for an improved antitumor activity of fluoroquinolones.

fluoroquinolone  /  thiazole  /  unsaturated ketone  /  bioisostere  /  antitumor activity
Na WANG, Hui-li ZHANG, Chao-ran CHEN, Wen-long HUANG, Guo-qiang HU. Synthesis and antitumor activity of fluoroquinolone C-3 arylidene thiazolone derivatives from ciprofloxacin[J]. Acta Pharmaceutica Sinica, 2019 , 54 (4) : 687 -691 . DOI: 10.16438/j.0513-4870.2019-0036
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Year 2019 volume 54 Issue 4
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Article Info
doi: 10.16438/j.0513-4870.2019-0036
  • Receive Date：2019-01-11
  • Online Date：2026-01-26
  • Published：2019-04-12
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History
  • Received：2019-01-11
  • Revised：2019-02-10
Funding
Affiliations
    1. Institute of Drugs, Henan University, Kaifeng 475001, China
    2. School of Pharmacy, Zhengzhou University of Industrial Technology, Zhengzhou 451150, China
    3. Institute of Nursing and Health, Henan University, Kaifeng 475004, China
    4. Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China
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表12种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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