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Synthesis and anti-inflammatory activities of 4H-chromene and chromeno[2,3-b]pyridine derivatives

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Abstract

Several derivatives of 4H-chromene and chromeno[2,3-b]pyridine were efficiently prepared under microwave irradiation in a one-pot reaction, and their anti-inflammatory activities were evaluated. Six synthetic products (1b, 1c, 1h, 2d, 2j, and 2l) exhibited more powerfully inhibited the production of tumor necrosis factor-α-induced nitric oxide (NO) than quercetin and exhibited comparable cell viability in both human and porcine chondrocytes. In particular, 2d at dosages of 10 and 20 mg/kg had a very potent anti-inflammatory effect by suppressing the formation of carrageenan-induced rat paw edema and prostaglandin E2. The results herein suggest that these compounds may have potential as structural templates in the design and development of new anti-inflammatory drugs.

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Acknowledgments

We gratefully acknowledge the research grant, NSC 103-2320-B-016-009, supported from the National Science Council of the Republic of China. The authors would like to thank Professor Ted Knoy for his editorial assistance.

Conflict of interest

The authors declare no conflicts of interest.

Ethical standard

This study was performed in accordance with the criteria of the National Academy of Sciences, and approved by the Institutional Animal Care and Use Committee of National Defense Medical Center, Taipei, Taiwan (Approval Number: IACUC-13-178). All patients enrolled with informed consent in this study were purposively sampled under Tri-Service General Hospital Institution Review Board approval (Approval Number: 1-102-05-091).

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Authors and Affiliations

  1. Graduate Institute of Medical Sciences, National Defense Medical Center, Taipei, Taiwan

    Shu-Ting Chung, Wen-Hsin Huang & An-Rong Lee

  2. School of Pharmacy, National Defense Medical Center, Taipei, Taiwan

    Wen-Hsin Huang, Chih-Kuo Huang & An-Rong Lee

  3. Division of Rheumatology/Immunology and Allergy, Tri-Service General Hospital, National Defense Medical Center, Taipei, Taiwan

    Feng-Cheng Liu

  4. Department of Periodontology, School of Dentistry, Tri-Service General Hospital, National Defense Medical Center, Taipei, Taiwan

    Ren-Yeong Huang

  5. Department of Pharmacology, National Defense Medical Center, Taipei, Taiwan

    Chin-Chen Wu

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  1. Shu-Ting Chung
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Correspondence to An-Rong Lee.

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Chung, ST., Huang, WH., Huang, CK. et al. Synthesis and anti-inflammatory activities of 4H-chromene and chromeno[2,3-b]pyridine derivatives. Res Chem Intermed 42, 1195–1215 (2016). https://doi.org/10.1007/s11164-015-2081-7

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