The convenient synthesis and evaluation of the anticancer activities of new resveratrol derivatives

Hyung-In MoonDepartment of Neuroscience and, Inam Neuroscience Research Center, Sanbon Medical Center, Wonkwang University, Kyunggido 435-040, South Korea

Ill-Min ChungDepartment of Applied Life science, Kon Kuk University, Seoul 143-701, South Korea

Jae-Chul JungDepartment of Neuroscience and Medical Research Institute, School of Medicine, Ewha Womans University, Seoul 158-710, South Korea

Eunyoung LimDepartment of Chemistry, Yonsei University, Seoul, 120-749 South Korea

Yongnam LeeDepartment of Chemistry, Yonsei University, Seoul, 120-749 South Korea

Seikwan OhDepartment of Neuroscience and Medical Research Institute, School of Medicine, Ewha Womans University, Seoul 158-710, South KoreaCorrespondence[email protected]

Mankil JungDepartment of Chemistry, Yonsei University, Seoul, 120-749 South KoreaCorrespondence[email protected]

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Figures & data

Figure 1. Chemical structures of trans-stilbene and its analogues.

Scheme 1. Reagents and conditions: (a) P(OEt)₃, 160 °C, 3 h, 85%; (b) 7, n-BuLi (1.3 equiv), THF, − 20 °C, 1 h; then rt, 12 h, 86%, or 7, NaH (1.3 equiv), CH₂Cl₂, 0 °C, 16 h, 80% (E:Z = 25:1); (c) DIBAL-H (2.5equiv), CH₂Cl₂, − 78 °C, 1 h, 77%; (d) DMSO, (COCl)₂, TEA, CH₂Cl₂, − 78 °C, 1 h, 89% or TPAP (5 mol %), NMO, THF, rt 30 min, 90%, then NaClO₂ (3.0 equiv), NaH₂PO₄ (3.0 equiv), 2-methyl-2-butene, t-BuOH, 0 °C, 16 h, 96%; (e) HATU (1.5 equiv), CH₂Cl₂, rt, 16 h, 50%–91%; (f) 20% TFA, CH₂Cl₂, rt, 1 h, 50–80%, or TBAF (2.5 equiv), THF, 0 °C, 30 min, (64%–73%).

Scheme 1. Reagents and conditions: (a) P(OEt)3, 160 °C, 3 h, 85%; (b) 7, n-BuLi (1.3 equiv), THF, − 20 °C, 1 h; then rt, 12 h, 86%, or 7, NaH (1.3 equiv), CH2Cl2, 0 °C, 16 h, 80% (E:Z = 25:1); (c) DIBAL-H (2.5equiv), CH2Cl2, − 78 °C, 1 h, 77%; (d) DMSO, (COCl)2, TEA, CH2Cl2, − 78 °C, 1 h, 89% or TPAP (5 mol %), NMO, THF, rt 30 min, 90%, then NaClO2 (3.0 equiv), NaH2PO4 (3.0 equiv), 2-methyl-2-butene, t-BuOH, 0 °C, 16 h, 96%; (e) HATU (1.5 equiv), CH2Cl2, rt, 16 h, 50%–91%; (f) 20% TFA, CH2Cl2, rt, 1 h, 50–80%, or TBAF (2.5 equiv), THF, 0 °C, 30 min, (64%–73%).

Table I. In vitro anticancer activity of new stilbene derivatives 13–22.

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The convenient synthesis and evaluation of the anticancer activities of new resveratrol derivatives

Table I. In vitro anticancer activity of new stilbene derivatives 13–22.

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The convenient synthesis and evaluation of the anticancer activities of new resveratrol derivatives

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Table I. In vitro anticancer activity of new stilbene derivatives 13–22.

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