Semi-synthesis and anti-proliferative activity evaluation of novel analogues of Honokiol

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 16, 2009, Pages 4702-4705

  Luo, Youfu ^a,b   Xu, Yongbin ^a   Chen, Lijuan ^a   Hu, Jia ^a   Peng, Cheng ^c   Xie, DaChun ^a   Shi, Jianyou ^a   Huang, Wencai ^b   Xu, Guobin ^a   Peng, Ming ^a   Han, Jing ^a   Li, Rui ^a   Yang, Shengyong ^a   Wei, Yuquan ^a  

^a SICHUAN UNIVERSITY   (China)

^b SICHUAN UNIVERSITY   (China)

^c CHENGDU UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

Analogue; Anti drug resistance effect; Anti proliferative activity; Honokiol; Semi synthesis

Indexed keywords

3' FORMYLHONOKIOL; 5 FORMYLHONOKIOL; HONOKIOL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL PROLIFERATION; CELL STRAIN; CELL STRAIN A 2780; CELL STRAIN A 549; CELL STRAIN K 562; CELL STRAIN SPC A1; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIPHENYL COMPOUNDS; CELL LINE, TUMOR; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LIGNANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67651171563     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.06.071     Document Type: Article

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15. Typical procedure for the synthesis of the oxime derivatives 3a-c: Compound 3a was prepared as follows. The solution of 3′-formylhonokiol (2a) (0.1 mmol), methanol (2 mL), and hydroxylammonium chloride (0.5 mmol) was bufferd to a pH of 8 with triethylamine and then heated under reflux for 3 h. The mixture was poured into distilled water (10 mL), filtered, washed with distilled water (3 × 5 mL), and dried in vacuo at 50 °C for 24 h. The product was yellowish white solid with a yield of 90% in purity of 99%.
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18. Typical procedure for the synthesis of compounds 5a-c: 3′-Formylhonokiol (2a) (0.1 mmol) was dissolved in 2 mL acetic acid. 2,4-Thiazolidinedione (0.2 mmol) and β-alanine (0.2 mmol) were added and left the mixture to stir at 100 °C for 12 h. The reaction mixture was poured into distilled water (5 mL), filtered, washed with distilled water (10 × 5 mL), and dried in vacuo at 50 °C for 24 h. The product was yellow solid with a yield of 92% in purity of 99%.
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23. 3), δ (ppm), 8.55 (s, 1H), 7.49 (d, J = 2.0 Hz, 1H), 7.35 (m, 1H), 7.33 (d, J = 2.0 Hz, 1H), 7.31 (d, J = 2.0 Hz, 1H), 6.90 (d, J = 8.4 Hz, 1H)