Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines

doi:10.15302/J-FASE-2015079

Frontiers of Agricultural Science and Engineering

2015, Vol. 2

Issue (4): 335-340 https://doi.org/10.15302/J-FASE-2015079

本期目录

Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines

Shengliang LIAO¹,Shibin SHANG¹,Minggui SHEN¹,Xiaoping RAO¹,Hongyan SI¹,Jie SONG²,Zhanqian SONG^1,^*(

)

1. Institute of Chemical Industry of Forest Products, China Academy of Forestry; National Engineering Laboratory for Biomass Chemical Utilization; State Forestry Administration’s Key and Open Laboratory for Forest Chemical Engineering; Jiangsu Provincial Key Laboratory for Biomass Energy and Material, Nanjing 210042, China
2. Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint MI 48502, USA

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Abstract：

Twelve (+)-nopinone-based 2-amino-3-cyanopyridines 4a–l were synthesized from (–)-β-pinene. The structures of these compounds were characterized by FT-IR, ¹H NMR, and ESI-MS. All the compounds were tested for their anticancer activity against lung cancer cell line A549, gastric cancer cell line MKN45 and breast cancer cell line MCF7 by MTT method, respectively. The results showed that compounds 4f, 4j and 4k had promising anticancer activity against these cancer cell lines, in particular, compound 4f exhibited broad-spectrum and highly efficient anticancer activity against cell lines A549, MKN45 and MCF7 with IC₅₀ of 23.78, 67.61 and 53.87 µmol·L⁻¹, respectively. The preliminary analysis of the structure activity relationship implied that the Br or Cl substituted group of the benzene ring in these derivatives significantly contributed to the anticancer activity.

Key words： b-pinene nopinone synthesis 2-amino-3-cyanopyridine anticancer

收稿日期: 2015-09-30 出版日期: 2016-01-19

Corresponding Author(s): Zhanqian SONG

引用本文:

. [J]. Frontiers of Agricultural Science and Engineering, 2015, 2(4): 335-340.
Shengliang LIAO,Shibin SHANG,Minggui SHEN,Xiaoping RAO,Hongyan SI,Jie SONG,Zhanqian SONG. Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines. Front. Agr. Sci. Eng. , 2015, 2(4): 335-340.

链接本文:

https://academic.hep.com.cn/fase/CN/10.15302/J-FASE-2015079
https://academic.hep.com.cn/fase/CN/Y2015/V2/I4/335

Fig.1

Compound	Characterization data
2	Yield 82%, GC purity 90.35%, [α]_D¹⁸ + 33.9° (c 1.0 CHCl₃), FT-IR v (cm⁻¹): 2948, 2874 (C–H stretching vibration), 1705 (C= O stretching vibration), 1459, 1386 (C–H bending vibration). ¹H NMR (300 MHz, CDCl₃) d: 2.56 (pd, J= 12.4, 5.0 Hz, 3H, –CH– and–CH₂–), 2.41–2.19 (m, 2H, –CH₂–), 2.12–1.88 (m, 2H, –CH₂–), 1.59 (d, J= 9.9 Hz, 1H, –CH–), 1.33 (s, 3H, –CH₃), 0.86 (s, 3H, –CH₃). ESI-MS: m/z 138.1 [M]⁺
4a	Yield 75%, HPLC purity= 91.46%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 209–210°C; FT-IR v (cm⁻¹): 3409, 3305, 3150 (N–H), 2949, 2925, 2842(C–H), 2203(C≡N), 1641, 1557, 1497, 1466 (phenyl), 1376 (C–H); ¹H NMR (300 MHz, CDCl₃) d: 7.60–7.43 (m, 3H, phenyl), 7.34 (dd, J= 7.7, 1.7 Hz, 2H, phenyl), 5.40 (s, 2H, –NH₂), 2.92 (t, J= 5.5 Hz, 1H, –CH–), 2.69 (dt, J= 9.9, 5.7 Hz, 1H, –CH₂–), 2.58 (d, J= 2.9 Hz, 2H, –CH₂–), 2.34–2.18 (m, 1H, –CH–), 1.41 (s, 3H, –CH₃), 1.32 (d, J= 9.8 Hz, 1H, –CH₂–), 0.76 (s, 3H, –CH₃); ESI-MS: m/z 290.4 [M+ 1]⁺; 312.4 [M+ 23]⁺
4b	Yield 60%, HPLC purity= 98.23%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 205–206°C; FT-IR v (cm⁻¹): 3382, 3306, 3184 (N–H), 2950, 2917, 2840 (C–H), 2211 (C≡N), 1640, 1598, 1561, 1483, 1463 (phenyl), 1378 (C–H); ¹H NMR (300 MHz, CDCl₃) d: 7.63 (dd, J= 6.3, 2.9 Hz, 1H, phenyl), 7.58–7.45 (m, 2H, phenyl), 7.457.27 (m, 1H, phenyl), 6.66 (s, 2H, –NH₂), 3.28 (s, 1H, –CH–), 2.73 (t, J= 5.5 Hz, 1H, –CH₂–), 2.68–2.58 (m, 1H, –CH₂–), 2.35–2.22 (m, 2H, –CH₂–), 2.19 (d, J= 2.8 Hz, 1H, –CH–), 1.35 (s, 3H, –CH₃), 1.24 (d, J= 9.6 Hz, 1H, –CH₂–), 0.69 (d, J= 5.1 Hz, 3H, –CH₃); ESI-MS: m/z 324.8 [M+ 1]⁺; 346.8 [M+ 23]⁺
4c	Yield 77%, HPLC purity= 99.12%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 207–208°C; FT-IR v (cm⁻¹): 3388, 3304, 3173 (N–H), 2935, 2839 (C–H), 2208 (C≡N), 1640, 1605, 1561, 1498, 1459 (phenyl), 1379 (C–H); ¹H NMR (300?MHz, CDCl₃) d: 7.54–7.36 (m, 1H, phenyl), 7.24–7.12 (m, 2H, phenyl), 7.06 (t, J = 7.4 Hz, 1H, phenyl), 6.46 (s, 2H, –NH₂), 3.93–3.56 (m, 3H, –CH₃), 3.26 (d, J = 11.9 Hz, 1H, –CH–), 2.70 (t, J = 5.5 Hz, 1H, –CH₂–), 2.60 (dt, J = 11.3, 5.5 Hz, 1H, –CH–), 2.40–2.24 (m, 1H, –CH₂–), 2.17 (d, J = 2.8 Hz, 1H, –CH–), 1.34 (s, 3H, –CH₃), 1.18 (dd, J = 17.5, 9.5 Hz, 1H, –CH₂–), 0.67 (d, J = 14.0 Hz, 3H, –CH₃); ESI-MS: m/z 320.4 [M+ 1]⁺; 342.4 [M+ 23]⁺
4d	Yield 55%, HPLC purity= 99.58%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 264–265°C; FT-IR v (cm⁻¹): 3459(O–H), 3442, 3232 (N–H), 2922 (C–H), 2217 (C≡N), 1631, 1560, 1499, 1439 (phenyl), 1370 (C–H); ¹H NMR (300 MHz, CDCl₃) d: 9.60 (s, 1H, –OH), 7.29 (t, J = 7.8 Hz, 1H, phenyl), 6.84 (dd, J = 8.1, 1.8 Hz, 1H, phenyl), 6.72 (d, J = 7.4 Hz, 1H, phenyl), 6.68 (s, 1H, phenyl), 6.53 (s, 2H, –NH₂), 3.28 (s, 1H, –CH–), 2.71 (t, J = 5.5 Hz, 1H, –CH₂–), 2.65–2.56 (m, 1H, –CH–), 2.42 (dd, J = 29.5, 8.6 Hz, 2H, –CH₂–), 2.20 (s, 1H–CH–), 1.34 (s, 3H, –CH₃), 1.21 (d, J = 9.5 Hz, 1H, –CH–), 0.66 (s, 3H, –CH₃); ESI-MS: m/z 306.4 [M+ 1]⁺; 328.4 [M+ 23]⁺
4e	Yield 87%, HPLC purity= 94.58%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 145–146°C; FT-IR v (cm⁻¹): 3390, 3306, 3171 (N–H), 2933 (C–H), 2207 (C≡N), 1641, 1610, 1560, 1492, 1463 (phenyl), 1370 (C–H); ¹H NMR (300 MHz, DMSO-d6) d: 7.42 (t, J= 8.0 Hz, 1H, phenyl), 7.08–6.98 (m, 1H, phenyl), 6.89 (s, 2H, phenyl), 6.55 (s, 2H, –NH₂), 3.80 (s, 3H, –CH₃), 3.30 (s, 1H, –CH–), 2.72 (t, J= 5.5 Hz, 1H, –CH₂–), 2.67–2.56 (m, 1H, –CH–), 2.37 (dd, J= 16.5, 1.9 Hz, 1H, –CH₂–), 2.26–2.15 (m, 1H, –CH–), 1.34 (s, 3H, –CH₃), 1.23 (d, J= 9.5 Hz, 1H, –CH₂–), 0.67 (s, 3H, –CH₃); ESI-MS: m/z 320.4 [M+ 1]⁺; 342.4 [M+ 23]⁺
4f	Yield 79%, HPLC purity= 98.93%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 242–243°C; FT-IR v (cm⁻¹): 3432, 3330 (N–H), 2978, 2929 (C–H), 2211 (C≡N), 1628, 1553, 1478, 1450 (phenyl), 1368 (C–H); ¹H NMR (300 MHz, DMSO-d6) d: 7.67 (d, J = 8.0 Hz, 1H, phenyl), 7.60 (s, 1H, phenyl), 7.48 (t, J = 7.8 Hz, 1H, phenyl), 7.37 (d, J = 7.6 Hz, 1H, phenyl), 6.62 (s, 2H, –NH₂), 3.28 (s, 1H, –CH–), 2.72 (t, J = 5.5 Hz, 1H, –CH₂–), 2.66–2.57 (m, 1H, –CH–), 2.34 (d, J = 16.3 Hz, 1H, –CH₂–), 2.20 (s, 1H, –CH–), 1.34 (s, 3H, –CH₃), 1.24 (d, J = 9.4 Hz, 1H, –CH₂–), 0.67 (s, 3H, –CH₃); ESI-MS: m/z 369.3 [M+ 1]⁺; 390.3, 392.3 [M+ 23]⁺
4g	Yield 52%, HPLC purity= 94.94%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 174–175°C; FT-IR v (cm⁻¹): 3406, 3300, 3161 (N–H), 2924, 2837 (C–H), 2207 (C≡N), 1638, 1589, 1562, 1480, 1465 (phenyl), 1385 (C–H). ¹H NMR (300?MHz, DMSO-d6) d: 7.67–7.49 (m, 2H, phenyl), 7.24 (d, J = 4.3 Hz, 1H, phenyl), 6.63 (s, 2H, –NH₂), 3.27 (s, 1H, –CH–), 2.72 (t, J = 5.5 Hz, 1H, –CH₂–), 2.68–2.57 (m, 1H, –CH–), 2.36 (d, J = 16.5 Hz, 1H, –CH₂–), 2.28–2.11 (m, 1H, –CH–), 1.34 (s, 3H, –CH₃), 1.23 (d, J = 9.5 Hz, 1H, –CH₂–), 0.67 (s, 3H, –CH₃); ESI-MS: m/z 326.4 [M+ 1]⁺; 348.1 [M+ 23]⁺
4h	Yield 73%, HPLC purity= 99.47%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 195–196°C; FT-IR v (cm⁻¹): 3416, 3305, 3180 (N–H), 2952, 2935, 2835 (C–H), 2203 (C≡N), 1637, 1603, 1556, 1514, 1461 (phenyl), 1370 (C–H); ¹H NMR (300?MHz, DMSO-d6) d: 7.06 (d, J = 8.2 Hz, 1H, phenyl), 6.94 (s, 1H, phenyl), 6.88 (d, J = 8.1 Hz, 1H, phenyl), 6.49 (s, 2H, –NH₂), 3.78 (t, J = 17.4 Hz, 6H,, –CH₃), 3.27 (s, 1H, –CH–), 2.71 (t, J = 5.5 Hz, 1H, –CH₂–), 2.66–2.57 (m, 1H, –CH–), 2.41 (d, J = 16.5 Hz, 1H, –CH₂–), 2.21 (s, 1H, –CH–), 1.34 (s, 3H, –CH₃), 1.24 (d, J = 9.5 Hz, 1H, –CH₂–), 0.66 (s, 3H, –CH₃); ESI-MS: m/z 350.2 [M+ 1]⁺; 372.2 [M+ 23]⁺
4i	Yield 71%, HPLC purity= 99.30%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 212–213°C; FT-IR v (cm⁻¹): 3461, 3292, 3161 (N–H), 2963 (C–H), 2202 (C≡N), 1625, 1607, 1564, 1511, 1456 (phenyl), 1379 (C–H); ¹H NMR (300 MHz, DMSO-d6) d: 7.42 (dd, J= 8.5, 5.6 Hz, 2H, phenyl), 7.33 (t, J= 8.9 Hz, 2H, phenyl), 6.58 (s, 2H, –NH₂), 3.27 (s, 1H, –CH–), 2.72 (t, J= 5.5 Hz, 1H, –CH₂–), 2.65–2.56 (m, 1H, –CH–), 2.36 (dd, J= 16.4, 2.2 Hz, 1H, –CH₂–), 2.24–2.16 (m, 1H, –CH–), 1.34 (s, 3H, –CH₃), 1.22 (d, J= 9.5 Hz, 1H, –CH₂–), 0.67 (s, 3H, –CH₃); ESI-MS: m/z 308.2 [M+ 1]⁺; 330.2 [M+ 23]⁺
4j	Yield 78%, HPLC purity= 96.37%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 167–168°C; FT-IR v (cm⁻¹): 3379, 3311, 3189 (N–H), 2954, 2933 (C–H), 2205 (C≡N), 1639, 1603, 1574, 1556, 1494, 1462 (phenyl), 1369 (C–H); ¹H NMR (300?MHz, DMSO-d6) d: 7.57 (d, J = 8.4 Hz, 2H, phenyl), 7.40 (d, J = 8.3 Hz, 2H, phenyl), 6.61 (s, 2H, –NH₂), 3.29 (d, J = 19.9 Hz, 1H, –CH–), 2.72 (t, J = 5.5 Hz, 1H, –CH₂–), 2.36 (d, J= 16.7 Hz, 2H, –CH₂–), 2.20 (s, 1H, –CH–), 1.35 (d, J = 3.8 Hz, 3H, –CH₃), 1.22 (d, J = 9.5 Hz, 1H, –CH₂–), 0.67 (s, 3H, –CH₃); ESI-MS: m/z 325.1 [M+ 1]⁺; 346.1, 348.1 [M+ 23]⁺
4k	Yield 74%, HPLC purity= 97.76%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 209–210°C; FT-IR v (cm⁻¹): 3453, 3299, 3149 (N–H), 2954, 2925 (C–H), 2211 (C≡N), 1636, 1592, 1555, 1491, 1458 (phenyl), 1370 (C–H); ¹H NMR (300 MHz, DMSO-d6) d: 7.71 (d, J = 8.4 Hz, 2H, phenyl), 7.34 (d, J = 8.3 Hz, 2H, phenyl), 6.61 (s, 2H, –NH₂), 3.29 (d, J = 19.9 Hz, 1H, –CH–), 2.74 (t, J = 5.5 Hz, 1H, –CH₂–), 2.61 (dt, J = 22.3, 8.6 Hz, 1H, –CH₂–), 2.36 (d, J = 16.6 Hz, 1H–CH₂–), 2.20 (s, 1H, –CH–), 1.34 (s, 3H, –CH₃), 1.23 (d, J = 9.6 Hz, 1H, –CH₂–), 0.67 (s, 3H, –CH₃); ESI-MS: m/z 369.1 [M+ 1]⁺; 390.1, 392.1, 393.1 [M+ 23]⁺
4l	Yield 73%, HPLC purity= 94.72%, (XDB-C-18 column; MeOH:H₂O/80:20), t_r = 12 min; pale yellow crystals, m.p. 182–183°C; FT-IR v (cm⁻¹): 3405, 3311, 3189 (N–H), 2931(C–H), 2204 (C≡N), 1687, 1637, 1599, 1556, 1515, 1461 (phenyl), 1371 (C–H); ¹H NMR (300 MHz, DMSO-d6) d: 7.31 (d, J = 7.9 Hz, 2H, phenyl), 7.23 (d, J = 7.9 Hz, 2H, phenyl), 6.52 (s, 2H, –NH₂), 3.27 (s, 1H, –CH–), 2.71 (t, J = 5.5 Hz, 1H, –CH₂–), 2.41–2.33 (m, 5H, –CH₃ and–CH₂–), 2.19 (s, 1H, –CH–), 1.34 (d, J = 3.4 Hz, 3H, –CH₃), 1.21 (d, J = 9.5 Hz, 1H, –CH₂–), 0.66 (s, 3H, –CH₃); ESI-MS: m/z 304.2 [M+ 1]⁺; 326.2 [M+ 23]⁺

Tab.1

Tab.2

Fig.2

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