Citation: Sheng-Peng Wang, Yuan-Feng Tong, Dong-Mei Wang, Nan Wang, Zheng Yan, Ping Huang, Song Wu. Synthesis and cytotoxicity evaluation of a novel justicidin G analogue and its phosphate ester[J]. Chinese Chemical Letters, ;2014, 25(7): 1044-1046. doi: 10.1016/j.cclet.2014.05.042 shu

Synthesis and cytotoxicity evaluation of a novel justicidin G analogue and its phosphate ester

1.
a State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China;
2.
b Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China

Corresponding author: Yuan-Feng Tong, Song Wu,
Received Date: 31 March 2014
Available Online: 21 May 2014
Fund Project: the Union Youth Science & Research Fund (No. 3332013074) for financial support. (No. 2012ZX09301002-001)

The novel justicidin G analogue 13 and its phosphate ester 15 were synthesized as potential anticancer agents in several steps starting from commercially available methyl gallate and veratraldehyde. The cytotoxicity of the intermediates was tested against HCT-8, BEL-7402, KETR3, HELA, BGC-823, KB and MCF-7 cell lines by the MTT test, and compound 15 exhibited significant cytotoxicity in HELA and KB cell lines.
- Justicidin G,
- Analogue,
- Phosphate ester,
- Antitumor activity,
- Synthesis
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  [13] Data of compounds 3 and 8. Compound 3: White solid, mp 95-96℃. ¹H NMR (300 MHz, DMSO-d₆): δ 3.74 (s, 3H, -OCH₃), 3.77 (s, 3H, -OCH₃), 3.98-3.89 (m, 2H, C-CH₂-C), 4.14-4.03 (m, 2H, C-CH₂-C), 5.82 (s, 1H, Ar-CH-O), 7.03 (s, 1H, Ar-H), 7.12 (s, 1H, Ar-H). ¹³C NMR (100 MHz, DMSO-d₆):δ190.8, 155.2, 149.3, 126.4, 120.0, 116.6, 111.1, 65.5, 63.5, 57.1, 56.3. HRESIMS Calcd. for C₁₁H₁₄BrO₄ [M+H]⁺: 289.0070, found: 289.0064. Compound 8: White solid, mp 66-68℃. ¹H NMR (400 MHz, DMSO-d₆):δ5.23 (s, 2H, Ar-CH₂-O), 6.14 (s, 2H, O-CH₂-O), 7.09 (s, 1H, Ar-H), 7.61-7.19 (m, 6H, Ar-H×6), 9.75 (s, 1H, -CHO). ¹³CNMR(100 MHz, DMSOd₆):δ191.5, 149.9, 143.2, 141.6, 137.0, 132.1, 129.2, 128.8, 128.6, 113.6, 103.4, 103.1, 71.3. HRESIMS Calcd. for C₁₅H₁₃O₄ [M+H]⁺: 257.0808, found: 257.0799.
14. [14]
  [14] Data of compounds 9-14. Compound 9: White solid, mp 115-116℃. ¹H NMR (400 MHz, DMSO-d₆):δ3.66 (s, 3H, -OCH₃), 3.72 (s, 3H, -OCH₃), 3.97-3.84 (m, 2H, C-CH₂-C), 4.11-3.98 (m, 2H, C-CH₂-C), 5.10 (s, 2H, Ar-CH₂-O), 5.75 (s, 1H, Ar-CH-O), 5.90 (s, 1H, Ar-CH-Ar), 5.92 (s, 2H, O-CH₂-O), 6.47 (s, 1H, Ar-H), 6.70 (s, 1H, Ar-H), 6.92 (s, 1H, Ar-H), 6.97 (s, 1H, Ar-H), 7.48-7.21 (m, 5H, Ar-H×5). ¹³C NMR (125 MHz, DMSO-d₆):δ149.7, 148.8, 147.9, 142.1, 140.5, 137.4, 137.1, 134.2, 128.8, 128.4, 128.2, 126.7, 111.0, 109.9, 108.3, 101.5, 101.2, 100.5, 71.0, 69.3, 65.1, 56.1, 56.0. HRESIMS Calcd. for C26H26NaO8 [M+Na]⁺: 489.1520, found: 489.1512. Compound 10: White solid,mp 162-164℃. ¹H NMR (400 MHz, DMSOd₆):δ0.94 (t, 3H, J=7.1 Hz, -CH₃), 1.25 (t, 3H, J=7.1 Hz, -CH₃), 3.60 (s, 3H-OCH₃), 3.93 (s, 3H, -OCH₃), 3.95 (q, 2H, J=7.1 Hz, C-CH₂-C), 4.33 (q, 3H, J=7.1 Hz, C-CH₂-C), 5.14 (s, 2H, Ar-CH₂-O), 6.06 (s, 1H, O-CH-O), 6.09 (s, 1H, O-CH-O), 6.45 (s, 1H, Ar-H), 6.56 (s, 1H, Ar-H), 6.71 (s, 1H, Ar-H), 7.48-7.27 (m, 5H, Ar-H×5), 7.63 (s, 1H, Ar-H), 11.92 (s, 1H, Ar-OH). ¹³C NMR (125 MHz, DMSO-d₆):δ169.0, 168.6, 157.3, 152.2, 151.5, 149.1, 148.1, 141.6, 136.7, 134.5, 131.4, 130.7, 129.4, 128.4, 127.9, 127.6, 111.7, 105.6, 104.7, 103.2, 102.6, 101.4, 76.9, 70.4, 55.5, 55.2, 52.3, 51.6, 13.6, 13.5. HRESIMS Calcd. for C₃₂H₃₁O₁₀ [M+H]⁺: 575.1912, found: 575.1902. Compound 11: White solid, mp 206-207℃. ¹H NMR (300 MHz, DMSO-d₆):δ3.58 (s, 3H, -OCH₃), 3.92 (s, 3H, -OCH₃), 5.13 (s, 2H, Ar-CH₂-O), 5.36 (s, 2H, Ar-CH₂-O), 6.09 (s, 2H, O-CH₂-O), 6.53 (s, 1H, Ar-H), 6.62 (s, 1H, Ar-H), 6.90 (s, 1H, Ar-H), 7.46-7.24 (m, 5H, Ar-H×5), 7.62 (s, 1H, Ar-H), 10.50 (s, 1H, Ar-OH). ¹³C NMR (150 MHz, DMSO-d₆):δ169.5, 150.5, 149.7, 148.1, 144.9, 141.7, 136.8, 134.7, 129.4, 129.4, 129.3, 128.4, 127.9, 127.7, 123.2, 121.7, 118.7, 111.4, 105.5, 105.0, 101.3, 100.7, 70.4, 66.6, 55.5, 55.1. HRESIMS Calcd. for C₂₈H₂₃O₈
15. [15]
  [M+H]⁺: 487.1387, found: 487.1391. Compound 12: White solid, mp 223-224℃. ¹H NMR (300 MHz, DMSO-d₆):δ3.58 (s, 3H, -OCH₃), 3.93 (s, 3H, -OCH₃), 4.12 (s, 3H, -OCH₃), 5.13 (s, 2H, Ar-CH₂-O), 5.70 (s, 2H, Ar-CH₂-O), 6.10 (s, 2H, O-CH₂-O), 6.54 (s, 1H, Ar-H), 6.62 (s, 1H, Ar-H), 6.89 (s, 1H, Ar-H), 7.45-7.25 (m, 5H, Ar-H×5), 7.50 (s, 1H, Ar-H). ¹³C NMR (125 MHz, acetone-d₆):δ168.9, 151.3, 150.1, 148.3, 147.3, 141.8, 136.9, 134.9, 132.6, 129.5, 129.1, 128.4, 128.0, 127.7, 124.9, 123.9, 119.1, 111.4, 105.7, 104.8, 101.4, 100.6, 70.6, 66.8, 59.2, 55.8, 55.3. HRESIMS Calcd. for C29H25O8 [M+H]⁺: 501.1544, found: 501.1535. Compound 13: White solid, mp 142-143℃. ¹H NMR (300 MHz, DMSO-d₆):δ3.66 (s, 3H, -OCH₃), 3.93 (s, 3H, -OCH₃), 4.12 (s, 3H, -OCH₃), 5.69 (s, 2H, Ar-CH₂-O), 6.03 (s, 2H, O-CH₂-O), 6.32 (s, 1H, Ar-H), 6.35 (s, 1H, Ar-H), 6.97 (s, 1H, Ar-H), 7.50 (s, 1H, Ar-H), 9.73 (s, 1H, Ar-OH). ¹³C NMR (100 MHz, DMSO-d₆):δ169.6, 151.9, 150.6, 148.9, 147.8, 141.2, 134.2, 133.5, 130.1, 129.4, 125.5, 124.4, 119.6, 113.9, 106.3, 103.2, 101.5, 101.2, 67.4, 59.7, 56.3, 55.9. HRESIMS Calcd. for C22H19O8 [M+H]⁺: 411.1074, found: 411.1072. Compound 14: Yellowish solid, mp 157-158℃. ¹H NMR (400 MHz, DMSO-d₆):δ3.60 (s, 3H-OCH₃), 3.95 (s, 3H-OCH₃), 4.14 (s, 3H-OCH₃), 5.14-5.16 (m, 4H, Ar-CH₂-O×2), 5.73 (s, 2H, Ar-CH₂-O), 6.12 (s, 1H, O-CH-O), 6.13 (s, 1H, O-CH-O), 6.68 (s, 1H, Ar-H), 6.81 (s, 1H, Ar-H), 6.92 (s, 1H, Ar-H), 7.39-7.10 (m, 10H, Ar-H 1'), 7.52 (s, 1H, Ar-H). ¹³C NMR (125 MHz, DMSO-d₆)δ169.4, 151.8, 150.3, 150.2, 148.1, 140.1, 139.5, 139.5, 133.3, 133.3, 130.4, 129.7, 129.7, 126.8, 126.8, 119.9, 119.9, 113.2, 110.9, 106.3, 101.7, 101.4, 98.2, 67.0, 60.2, 56.1, 55.8. 31P NMR (200 MHz, DMSO-d₆):δ6.28. HRESIMS Calcd. for C36H31NaO11P [M+Na]⁺: 693.1496, found: 693.1492.
16. [16]
  [15] Compound 15: White solid, mp 212-213℃. The HRESIMS of 15 established a molecular formula of C₂₂H₁₉O₁₁P [m/z 513.0642 (M+Na)⁺, Calcd. for C₂₂H₁₉NaO₁₁P: 513.0640], indicating 14 degrees of unsaturation. ¹H NMR spectrum showed three methoxy groups [δH 3.70 (s, 3H, H-13), 3.94 (s, 3H, H-14), 4.13 (s, 3H, H-15)] and four aromatic protons [δH 7.51 (s, 1H, H-5), 7.05 (s, 1H, H-8), 6.70 (s, 1H, H-20), 6.83 (s, 1H, H-60)]. ¹³C NMR and DEPT spectra exhibited 22 carbons, including three methyls, two methylenes, sixteen quaternary carbons and one carbonyl. 31P NMR spectrum revealed the existence of one phosphate ester. The HMBC correlations of H-5/C-4, C-7, C-9 and H-8/C-1, C-6, C-10 revealed the present of naphthyl (ring A and ring B). The correlations from H-12 to C-2, C-3, C-4 and C-11 suggested the present of ring C. The correlations of H-13/C-7, H-14/ C-6 and H-15/C-4 gave the substituted positions of three methoxy groups. The linkage of ring B and D was elucidated by the HMBC correlations from H-20 and H-60 to C-1 and C-10. The correlations from H-70 to C-40 and C-50 revealed the presence of ring E. The planar structure of 15 was thus established. ¹H NMR (400 MHz, DMSO-d₆):δ7.51 (s, 1H, H-5), 7.05 (s, 1H, H-8), 5.71 (s, 2H, H-12), 3.70 (s, 3H, H-13), 3.94 (s, 3H, H-14), 4.13 (s, 3H, H-15), 6.70 (s, 1H, H-20), 6.83 (s, 1H, H-60), 6.13 (d, 2H, J=4.1 Hz, H-70). ¹³C NMR (125 MHz, DMSO-d₆):δ132.3 (C-1), 116.9 (C-2), 119.4 (C-3), 147.8 (C-4), 101.3 (C-5), 151.7 (C-6), 150.5 (C-7), 106.0 (C-8), 128.6 (C-9), 129.7 (C-1'), 169.4 (C-11), 67.3 (C-12), 55.7 (C-13), 56.1 (C-14), 59.6 (C-15), 125.3 (C-1'), 107.6 (C-2'), 148.9 (C-3'), 137.2 (C-4'), 148.9 (C-5'), 116.9 (C-6'), 102.1 (C-7'). ³¹P NMR (200 MHz, DMSO-d₆):δ5.83.
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