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Design, synthesis and antitumor activity of 3-arylidene-4-fluoroquinolin-4-ones as ciprofloxacin derivatives
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Hui-li ZHANG1, Ya-ling JIANG1, Hui ZHAO2, *, Wen-long HUANG3, Guo-qiang HU2, *
Acta Pharmaceutica Sinica | 2020, 55(9) : 2170 - 2175
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Acta Pharmaceutica Sinica | 2020, 55(9): 2170-2175
• Original Articles •
Design, synthesis and antitumor activity of 3-arylidene-4-fluoroquinolin-4-ones as ciprofloxacin derivatives
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Hui-li ZHANG1, Ya-ling JIANG1, Hui ZHAO2, *, Wen-long HUANG3, Guo-qiang HU2, *
Affiliations
  • 1. Water Environment and Health of Henan Engineering Technology Research Center, Zhengzhou University of Industrial Technology, Zhengzhou 451150, China
  • 2. Institute of Drugs, Henan University, Kaifeng 475001, China
  • 3. Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China
Published: 2020-09-12 doi: 10.16438/j.0513-4870.2020-0879
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To identify an effective structural modification strategy for improving the antitumor activity of fluoroquinolones, sixteen new 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-3-arylidene-2, 3-dihydroquinolin-4(1H)-ones compounds (4a-4p), were designed and synthesized by a condensation reaction of dihydroquinolin-4-one (3) and aromatic aldehydes, based on the structure of ciprofloxacin (1). Their structures were characterized by elemental analysis and spectral data, and anti-cell proliferative activities against Hep-3B, Capan-1 and HL60 cell lines were measured by an MTT assay. Preliminary pharmacological results indicated that the synthesized target compounds had greater potency than ciprofloxacin (1). SAR revealed that the halophenyl compounds such as fluorophenyl (4h, 4i), chlorophenyl (4j, 4k) or bromophenyl compounds (4l, 4m) and aromatic heterocyclic compounds such as furanly (4n) or pyridyl compounds (4o, 4p) demonstrated better activity than the control compounds, and the IC50 values of the chlorophenyl compounds 4j and 4k against Capan-1 cell growth were comparable to that of doxorubicin. Thus, a 3-arylidene as an isostere of the C-3 carboxylic acid group appears to be beneficial in improving the antitumor activity of fluoroquinolone. Furthermore, an α, β-unsaturated ketone fragment used as a potential bioisostere of C-3 carboxylic acid group may warrant further study.

fluoroquinolone  /  dihydroquinolinone  /  unsaturated ketone  /  bioisostere  /  antitumor activity
Hui-li ZHANG, Ya-ling JIANG, Hui ZHAO, Wen-long HUANG, Guo-qiang HU. Design, synthesis and antitumor activity of 3-arylidene-4-fluoroquinolin-4-ones as ciprofloxacin derivatives[J]. Acta Pharmaceutica Sinica, 2020 , 55 (9) : 2170 -2175 . DOI: 10.16438/j.0513-4870.2020-0879
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Year 2020 volume 55 Issue 9
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Article Info
doi: 10.16438/j.0513-4870.2020-0879
  • Receive Date：2020-06-01
  • Online Date：2026-01-23
  • Published：2020-09-12
Article Data
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History
  • Received：2020-06-01
  • Revised：2020-06-15
Funding
Affiliations
    1. Water Environment and Health of Henan Engineering Technology Research Center, Zhengzhou University of Industrial Technology, Zhengzhou 451150, China
    2. Institute of Drugs, Henan University, Kaifeng 475001, China
    3. 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
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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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