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Novel 2-(E)-substituted benzylidene-6-(N-substituted aminomethyl)cyclohexanones and cyclohexanols as analgesic and anti-inflammatory agents

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Abstract

Twenty-two new 2-(E)-substituted benzylidene-6-(N-substituted aminomethyl)cyclohexanones (6a–6j) and cyclohexanols (7a–7l) were designed and synthesized. Target compounds were obtained through Stork enamine, Mannich, and Grignard reactions taking cyclohexanone as starting material. The structures were confirmed by the application of IR, 1H NMR, MS, and HR-MS data. The analgesic activities were evaluated by acetic acid-induced writhing test and hot plate method. The anti-inflammatory activities were assayed by xylene-induced ear swelling and carrageenan-induced paw edema in mice model. All tested compounds showed analgesic and anti-inflammatory capacities in oral administration. Some compounds (6a, 6c, 6h, 6i, 7c, 7h, and 7i) displayed the moderate analgesic activity compared with positive control ibuprofen, and some compounds (6a, 6b, 6d, 6h, 7a, and 7d) exhibited more anti-inflammatory activity than ibuprofen. Among them, compound 6a could be a potential nonsteroidal anti-inflammatory agent with significant analgesic activities and remarkable anti-inflammatory activities. Further research is being conducted.

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Acknowledgments

This work was supported by a grant from the National Natural Science Foundation of China (No. 81028015).

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Authors and Affiliations

  1. Key Laboratory of Structure-Based Drugs Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang, 110016, Liaoning, People’s Republic of China

    Dan Liu, Weishe Yu, Jingjing Li, Cong Pang & Linxiang Zhao

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  1. Dan Liu
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  2. Weishe Yu
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  3. Jingjing Li
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  4. Cong Pang
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  5. Linxiang Zhao
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Correspondence to Linxiang Zhao.

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Liu, D., Yu, W., Li, J. et al. Novel 2-(E)-substituted benzylidene-6-(N-substituted aminomethyl)cyclohexanones and cyclohexanols as analgesic and anti-inflammatory agents. Med Chem Res 22, 3779–3786 (2013). https://doi.org/10.1007/s00044-012-0362-x

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  • DOI: https://doi.org/10.1007/s00044-012-0362-x

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