Synthesis and anti-neuroinflammatory activity of N-heterocyclic analogs based on natural biphenyl-neolignan honokiol

Bioorg Med Chem Lett. 2019 Jan 15;29(2):329-333. doi: 10.1016/j.bmcl.2018.11.014.

Yue Yuan ¹, Lalita Subedi ¹, Daesung Lim ¹, Jae-Kyung Jung ², Sun Yeou Kim ³, Seung-Yong Seo ⁴

Affiliations

1 College of Pharmacy, and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Republic of Korea.
2 College of Pharmacy, Chungbuk National University, Cheongju, Chungbuk 28644, Republic of Korea.
3 College of Pharmacy, and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Republic of Korea. Electronic address: sunnykim@gachon.ac.kr.
4 College of Pharmacy, and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Republic of Korea. Electronic address: syseo@gachon.ac.kr.

PMID: 30472026 DOI: 10.1016/j.bmcl.2018.11.014

Abstract

Novel isoxazole and pyrazole analogs based on natural biphenyl-neolignan honokiol were synthesized and evaluated for their inhibitory activities against nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells. The isoxazole skeleton was constructed via nitrile oxide cycloaddition from oxime 3 and pyrazole was generated by condensation of 4-chromone and alkylhydrazine. Among the analogs, 13b and 14a showed stronger inhibitory activities with IC₅₀ values of 8.9 and 1.2 µM, respectively, than honokiol.

Keywords

Anti-neuroinflammatory activity; Biphenyl-neolignan; Honokiol; Isoxazole; Pyrazole.

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