高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (3): 481.doi: 10.7503/cjcu20190446
白冰,王龙,徐改改,杨鹏飞,张改红,毛多斌
收稿日期:
2019-08-09
出版日期:
2020-02-26
发布日期:
2019-12-31
通讯作者:
毛多斌
作者简介:
毛多斌, 男, 博士, 教授, 主要从事烟草活性成分研究. E-mail: maoduobin@sohu.com
基金资助:
BAI Bing,WANG Long,XU Gaigai,YANG Pengfei,ZHANG Gaihong,MAO Duobin
Received:
2019-08-09
Online:
2020-02-26
Published:
2019-12-31
Contact:
Duobin MAO
Supported by:
摘要:
以烟草中含量丰富的大环二萜类化合物2,7,11-西柏三烯-4,6-二醇(CBT)为母体, 其C6位羟基经酯化/醚化, 合成了28个西柏三烯-4-醇-6-羧酸酯及西柏三烯-4-醇-6-烷氧类化合物. 采用核磁共振波谱(NMR)和高分辨质谱(HRMS)对目标化合物进行了结构表征, 并初步评价了其生物活性. 细胞毒活性测试结果表明, 部分化合物对肿瘤细胞的抑制作用与阳性对照顺铂相当, 其中α-2,7,11-西柏三烯-4-醇-6-O-苯乙酸酯(1i)对乳腺癌细胞株MCF-7的IC50值为15.45 μmol/L, α-2,7,11-西柏三烯-4-醇-6-O-(2-氟)苯乙酸酯(1t)对肺癌细胞株SMMC-7721的IC50值为11.44 μmol/L.
中图分类号:
TrendMD:
白冰,王龙,徐改改,杨鹏飞,张改红,毛多斌. 西柏三烯-4,6-二醇衍生物的合成及抗肿瘤活性. 高等学校化学学报, 2020, 41(3): 481.
BAI Bing,WANG Long,XU Gaigai,YANG Pengfei,ZHANG Gaihong,MAO Duobin. Synthesis and Antitumor Activities of α-2,7,11-Cembratriene-4,6-diol Derivatives . Chem. J. Chinese Universities, 2020, 41(3): 481.
Compd. | [α]D(CHCl3) | Yield(%) | HRMS, m/z, calcd.(found) |
---|---|---|---|
1a | +119.9°(c 0.14) | 86 | [M+NH4]+366.3003(366.3003) |
1b | +125.3°(c 0.16) | 86 | [M+NH4]+380.3159(380.3153) |
1c | +109.1°(c 0.20) | 80 | [M+NH4]+394.3316(394.3317) |
1d | +98.5°(c 0.14) | 77 | [M+NH4]+394.3316(394.3317) |
1e | +106.5°(c 0.18) | 78 | [M+NH4]+408.3472(408.3472) |
1f | +101.1°(c 0.18) | 75 | [M+NH4]+408.3472(408.3474) |
1g | +87.3°(c 0.24) | 70 | [M+Na]+397.2713(397.2698) |
1h | +95.5°(c 0.22) | 55 | [M+Na]+ 433.2713(433.2709) |
1i | +100.9°(c 0.16) | 45 | [M+NH4]+442.3316(442.3317) |
1j | +83.5°(c 0.24) | 49 | [M+NH4]+ 456.3472(456.3468) |
1k | +18.2°(c 0.32) | 43 | [M+Na]+ 459.2870(459.2865) |
1l | +79.0°(c 0.15) | 55 | [M+Na]+ 465.2776(465.2763) |
1m | +28.1°(c 0.18) | 61 | [M+Na]+515.2744(515.2735) |
1n | +56.6°(c 0.16) | 62 | [M+NH4]+478.3127(478.3122) |
1o | +104.6°(c 0.21) | 58 | [M+NH4]+ 502.3527(502.3518) |
1p | +124.1°(c 0.22) | 54 | [M+NH4]+ 487.3167(487.3165) |
1q | +85.9°(c 0.16) | 51 | [M+NH4]+ 499.3530(499.3528) |
Compd. | [α]D(CHCl3) | Yield(%) | HRMS, m/z, calcd.(found) |
1r | +42.2°(c 0.10) | 53 | [M+NH4]+ 583.2617(583.2602) |
1s | +82.1°(c 0.24) | 66 | [M+Na]+ 481.2480(481.2471) |
1t | +80.6°(c 0.14) | 59 | [M+NH4]+ 460.3222(460.3213) |
1u | +92.2°(c 0.17) | 58 | [M+Na]+ 515.2090(515.2068) |
1v | +105.5°(c 0.20) | 53 | [M+Na]+ 483.2681(483.2667) |
1w | +86.5°(c 0.21) | 59 | [M+NH4]+ 456.3472(456.3469) |
2a | +114.0°(c 0.26) | 78 | [M+Na]+ 343.2608(343.2589) |
2b | +97.3°(c 0.18) | 74 | [M+Na]+ 357.2764(357.2761) |
2c | +125.8°(c 0.14) | 69 | [M+Na]+ 371.2921(371.2922) |
2d | +112.2°(c 0.15) | 68 | [M+Na]+ 385.3077(385.3077) |
2e | +101.9°(c 0.20) | 54 | [M+Na]+ 397.3077(397.3072) |
Table 1 Appearance, yields and HRMS data of compounds 1a—1w, 2a—2e
Compd. | [α]D(CHCl3) | Yield(%) | HRMS, m/z, calcd.(found) |
---|---|---|---|
1a | +119.9°(c 0.14) | 86 | [M+NH4]+366.3003(366.3003) |
1b | +125.3°(c 0.16) | 86 | [M+NH4]+380.3159(380.3153) |
1c | +109.1°(c 0.20) | 80 | [M+NH4]+394.3316(394.3317) |
1d | +98.5°(c 0.14) | 77 | [M+NH4]+394.3316(394.3317) |
1e | +106.5°(c 0.18) | 78 | [M+NH4]+408.3472(408.3472) |
1f | +101.1°(c 0.18) | 75 | [M+NH4]+408.3472(408.3474) |
1g | +87.3°(c 0.24) | 70 | [M+Na]+397.2713(397.2698) |
1h | +95.5°(c 0.22) | 55 | [M+Na]+ 433.2713(433.2709) |
1i | +100.9°(c 0.16) | 45 | [M+NH4]+442.3316(442.3317) |
1j | +83.5°(c 0.24) | 49 | [M+NH4]+ 456.3472(456.3468) |
1k | +18.2°(c 0.32) | 43 | [M+Na]+ 459.2870(459.2865) |
1l | +79.0°(c 0.15) | 55 | [M+Na]+ 465.2776(465.2763) |
1m | +28.1°(c 0.18) | 61 | [M+Na]+515.2744(515.2735) |
1n | +56.6°(c 0.16) | 62 | [M+NH4]+478.3127(478.3122) |
1o | +104.6°(c 0.21) | 58 | [M+NH4]+ 502.3527(502.3518) |
1p | +124.1°(c 0.22) | 54 | [M+NH4]+ 487.3167(487.3165) |
1q | +85.9°(c 0.16) | 51 | [M+NH4]+ 499.3530(499.3528) |
Compd. | [α]D(CHCl3) | Yield(%) | HRMS, m/z, calcd.(found) |
1r | +42.2°(c 0.10) | 53 | [M+NH4]+ 583.2617(583.2602) |
1s | +82.1°(c 0.24) | 66 | [M+Na]+ 481.2480(481.2471) |
1t | +80.6°(c 0.14) | 59 | [M+NH4]+ 460.3222(460.3213) |
1u | +92.2°(c 0.17) | 58 | [M+Na]+ 515.2090(515.2068) |
1v | +105.5°(c 0.20) | 53 | [M+Na]+ 483.2681(483.2667) |
1w | +86.5°(c 0.21) | 59 | [M+NH4]+ 456.3472(456.3469) |
2a | +114.0°(c 0.26) | 78 | [M+Na]+ 343.2608(343.2589) |
2b | +97.3°(c 0.18) | 74 | [M+Na]+ 357.2764(357.2761) |
2c | +125.8°(c 0.14) | 69 | [M+Na]+ 371.2921(371.2922) |
2d | +112.2°(c 0.15) | 68 | [M+Na]+ 385.3077(385.3077) |
2e | +101.9°(c 0.20) | 54 | [M+Na]+ 397.3077(397.3072) |
Compd | 1H NMR, δ(600 MHz, CDCl3) | 13C NMR, δ(150 MHz, CDCl3) |
---|---|---|
1a | 5.53(t, J=8.4 Hz, 1H), 5.34—5.28(m, 2H), 5.23(d, J=9.8 Hz, 1H), 5.00(s, 1H), 2.15(ddd, J=35.4, 13.7, 6.4 Hz, 4H), 2.02(s, 3H), 2.02—1.90(m, 4H), 1.71(s, 3H), 1.62—1.54(m, 3H), 1.51(s, 3H), 1.49—1.42(m, 1H), 1.37(s, 3H), 1.31—1.25(m, 1H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 169.6, 138.8, 136.7, 133.0, 127.4, 126.2, 123.9, 71.8, 68.3, 50.2, 45.9, 38.4, 36.2, 32.4, 29.2, 22.7, 21.0, 20.2, 18.9, 15.7, 14.3 |
1b | 5.53(t, J=8.3 Hz, 1H), 5.31(dd, J=10.3, 5.0 Hz, 2H), 5.23(d, J=9.6 Hz, 1H), 5.01(s, 1H), 2.29(q, J=7.5 Hz, 2H), 2.25—2.06(m, 4H), 2.04—1.94(m, 4H), 1.72(s, 3H), 1.63—1.53(m, 3H), 1.51(s, 3H), 1.50 — 1.43(m, 1H), 1.38(s, 3H), 1.32—1.24(m, 1H), 1.12(t, J=7.6 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 173.3, 139.0, 137.0, 133.2, 127.6, 126.5, 124.2, 72.1, 68.4, 50.5, 46.1, 38.6, 36.4, 32.7, 29.4, 27.7, 27.6, 23.0, 20.5, 19.2, 16.0, 14.6, 8.9 |
1c | 5.54(t, J=8.3 Hz, 1H), 5.32(d, J=7.1 Hz, 2H), 5.23(d, J=9.8 Hz, 1H), 5.00(d, J=5.5 Hz, 1H), 2.27—2.09(m, 6H), 2.06—1.94(m, 4H), 1.72(s, 3H), 1.67—1.54(m, 5H), 1.51(s, 3H), 1.49—1.42(m, 1H), 1.38(s, 3H), 1.31—1.18(m, 1H), 0.93(t, J=7.4 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 172.1, 138.6, 136.6, 132.9, 127.2, 126.1, 123.8, 71.7, 67.9, 50.2, 45.8, 38.2, 36.1, 35.9, 32.3, 29.1, 27.3, 22.6, 20.1, 18.8, 17.9, 15.6, 14.2, 13.0 |
1d | 5.57—5.46(m, 1H), 5.38—5.27(m, 2H), 5.23(d, J=9.7 Hz, 1H), 5.01(s, 1H), 2.58—2.43(m, 1H), 2.32—2.05(m, 4H), 2.05—1.87(m, 4H), 1.71(s, 3H), 1.66—1.53(m, 3H), 1.51(s, 3H), 1.50—1.40(m, 1H), 1.38(s, 3H), 1.32—1.24(m, 1H), 1.14(dd, J=9.1, 7.0 Hz, 6H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 176.1, 139.0, 137.1, 133.3, 127.7, 126.5, 124.3, 72.2, 68.4, 50.6, 46.2, 38.7, 36.5, 34.0, 32.8, 29.5, 27.7, 23.1, 20.6, 19.3, 18.9, 18.7, 16.7, 14.7 |
1e | 5.53(t, J=8.4 Hz, 1H), 5.37—5.29(m, 2H), 5.23(d, J=9.8 Hz, 1H), 5.01(s, 1H), 2.38—2.05(m, 6H), 2.06—1.89(m, 4H), 1.72(s, 3H), 1.65—1.53(m, 5H), 1.51(s, 3H), 1.50—1.42(m, 1H), 1.38(s, 3H), 1.36—1.19(m, 3H), 0.91(t, J=7.4 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 172.9, 139.2, 137.2, 133.4, 127.8, 126.7, 124.4, 72.3, 68.5, 50.7, 46.3, 38.8, 36.7, 34.4, 32.9, 29.7, 27.8, 27.1, 23.2, 22.2, 20.7, 19.4, 16.2, 14.8, 13.8 |
1f | 5.54(t, J=8.3 Hz, 1H), 5.32(d, J=7.0 Hz, 2H), 5.23(d, J=9.8 Hz, 1H), 4.99(d, J=5.6 Hz, 1H), 2.22—2.07(m, 7H), 2.04—1.93(m, 4H), 1.72(s, 3H), 1.60—1.53(m, 3H), 1.51(s, 3H), 1.49—1.45(m, 1H), 1.38(s, 3H), 1.33—1.21(m, 1H), 0.94(d, J=0.7 Hz, 3H), 0.93(d, J=0.5 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 171.9, 139.0, 137.0, 133.2, 127.6, 126.5, 124.2, 72.1, 68.2, 50.6, 46.1, 43.6, 38.6, 36.4, 32.7, 29.4, 27.6, 25.6, 23.0, 22.2, 22.1, 20.5, 19.2, 15.9, 14.6 |
1g | 6.08(s, 1H), 5.61—5.47(m, 2H), 5.38—5.19(m, 3H), 5.02(s, 1H), 2.21—2.10(m, 3H), 2.06—1.97(m, 5H), 1.93(s, 3H), 1.74(s, 3H), 1.63—1.54(m, 4H), 1.51(s, 3H), 1.39(s, 3H), 1.33—1.25(m, 1H), 0.83(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 165.5, 138.3, 136.3, 135.8, 132.4, 126.9, 125.6, 124.2, 123.4, 71.3, 68.1, 49.7, 45.4, 37.9, 35.7, 31.9, 28.7, 26.8, 22.2, 19.7, 18.4, 17.4, 15.2, 13.8 |
1h | 8.09—7.98(m, 2H), 7.61—7.50(m, 1H), 7.45—7.36(m, 2H), 5.78(t, J=8.7 Hz, 1H), 5.43—5.30(m, 3H), 5.04(s, 1H), 2.27—2.16(m, 3H), 2.12(ddd, J=13.1, 8.0, 3.9 Hz, 3H), 2.08—1.96(m, 2H), 1.80(s, 3H), 1.64—1.55(m, 3H), 1.53(s, 3H), 1.51—1.45(m, 1H), 1.43(s, 3H), 1.34—1.26(m, 1H), 0.85(d, J=6.7 Hz, 3H), 0.81(d, J=6.8 Hz, 3H) | 165.1, 139.0, 136.6, 132.9, 132.2, 130.2, 129.0, 127.7, 127.4, 126.0, 123.9, 71.8, 68.9, 50.2, 45.8, 38.3, 36.1, 32.4, 29.1, 27.3, 22.6, 20.1, 18.9, 15.7, 14.2 |
Compd. | 1H NMR, δ(600 MHz, CDCl3) | 13C NMR, δ(150 MHz, CDCl3) |
1i | 7.38—7.29(m, 2H), 7.26(d, J=7.1 Hz, 3H), 5.60—5.46(m, 1H), 5.36—5.29(m, 2H), 5.24(d, J=9.8 Hz, 1H), 5.00(s, 1H), 3.59(s, 2H), 2.23—2.08(m, 4H), 2.05—1.94(m, 4H), 1.70(s, 3H), 1.62—1.52(m, 3H), 1.51(s, 3H), 1.47(d, J=6.2 Hz, 1H), 1.34(s, 3H), 1.31—1.25(m, 1H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.7, 139.6, 137.2, 134.2, 133.5, 129.3, 128.6, 127.9, 127.0, 126.4, 124.4, 72.3, 69.4, 50.5, 46.4, 41.6, 38.8, 36.7, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1j | 7.31—7.24(m, 2H), 7.22—7.15(m, 3H), 5.58—5.48(m, 1H), 5.33—5.27(m, 2H), 5.20(d, J=9.8 Hz, 1H), 4.99(s, 1H), 2.94(t, J=7.8 Hz, 2H), 2.64—2.53(m, 2H), 2.27—2.06(m, 4H), 2.04—1.96(m, 2H), 1.96—1.91(m, 2H), 1.71(s, 3H), 1.64—1.58(m, 1H), 1.58—1.52(m, 2H), 1.51(s, 3H), 1.36(s, 3H), 1.32—1.20(m, 2H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 171.9, 140.5, 139.3, 137.1, 133.5, 128.5, 128.3, 127.9, 126.6, 126.2, 124.4, 72.3, 68.8, 50.7, 46.4, 38.8, 36.6, 36.2, 32.9, 31.0, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1k | 7.67(d, J=16.0 Hz, 1H), 7.57—7.46(m, 2H), 7.43—7.32(m, 3H), 6.42(d, J=16.0 Hz, 1H), 5.67(t, J=8.7 Hz, 1H), 5.39—5.22(m, 3H), 5.03(s, 1H), 3.72(q, J=7.0 Hz, 1H), 2.29—2.18(m, 2H), 2.17—2.09(m, 3H), 2.08—1.97(m, 3H), 1.77(s, 3H), 1.64—1.55(m, 3H), 1.52(s, 3H), 1.42(s, 3H), 1.33—1.27(m, 1H), 1.24(t, J=7.0 Hz, 1H), 0.84(d, J=6.7 Hz, 3H), 0.81(d, J=6.8 Hz, 3H) | 166.1, 144.7, 139.5, 137.2, 134.5, 133.5, 130.2, 128.9, 128.1, 127.9, 126.7, 124.4, 118.6, 72.4, 68.9, 50.8, 46.4, 38.9, 36.7, 32.9, 29.7, 27.9, 23.2, 20.7, 19.4, 16.2, 14.8 |
1l | 7.24—7.19(m, 2H), 7.00(t, J=8.7 Hz, 2H), 5.55—5.50(m, 1H), 5.30(d, J=5.0 Hz, 2H), 5.22(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.56(s, 2H), 2.25—2.19(m, 1H), 2.19—2.15(m, 1H), 2.15—2.08(m, 2H), 2.02(d, J=14.0 Hz, 1H), 1.99—1.94(m, 3H), 1.69(s, 3H), 1.62—1.53(m, 3H), 1.50(s, 3H), 1.34(s, 3H), 1.27(d, J=13.9 Hz, 2H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.5, 162.0(d, J=245.2 Hz), 139.6, 137.1, 133.5, 130.8, 130.8, 129.8, 127.9, 126.3, 124.3, 115.5, 115.3, 72.2, 69.5, 50.5, 46.3, 40.7, 38.8, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1m | 7.52(s, 2H), 7.48—7.41(m, 2H), 5.57—5.52(m, 1H), 5.33—5.29(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.65(s, 2H), 2.23—2.15(m, 2H), 2.15—2.08(m, 2H), 2.03—2.00(m, 1H), 2.00—1.98(m, 2H), 1.98—1.94(m, 1H), 1.70(s, 3H), 1.60—1.53(m, 3H), 1.51(s, 3H), 1.49—1.43(m, 1H), 1.35(s, 3H), 1.33—1.23(m, 2H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.9, 139.9, 137.0, 135.0, 133.5, 132.7, 130.9, 130.7, 129.0, 128.0, 126.1, 126.0, 124.3, 123.9, 72.2, 69.7, 50.4, 46.3, 41.2, 38.8, 36.6, 32.9, 29.6, 27.8, 23.1, 20.7, 19.4, 16.2, 14.8 |
1n | 7.25—7.19(m, 1H), 6.87—6.78(m, 2H), 5.54(t, J=8.2 Hz, 1H), 5.32—5.29(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.60(s, 2H), 2.23—2.15(m, 2H), 2.15—2.08(m, 2H), 2.02—1.98(m, 2H), 1.98—1.96(m, 1H), 1.70(s, 3H), 1.60—1.56(m, 2H), 1.50(s, 3H), 1.48—1.45(m, 1H), 1.35(s, 3H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.58, 162.2(d, J=248.0 Hz), 161.0(d, J=249.1 Hz), 139.7, 137.0, 133.5, 132.0, 127.9, 126.2, 124.3, 117.5, 111.3, 103.9, 72.2, 69.7, 50.4, 46.3, 38.8, 36.6, 34.2, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1o | 6.82—6.78(m, 3H), 5.56—5.51(m, 1H), 5.32—5.29(m, 2H), 5.24(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.87(s, 3H), 3.86(s, 3H), 3.52(s, 2H), 2.18—2.08(m, 3H), 2.01(s, 1H), 1.98(s, 1H), 1.97—1.94(m, 1H), 1.69(s, 3H), 1.57—1.52(m, 2H), 1.50(s, 3H), 1.48—1.43(m, 1H), 1.34(s, 3H), 1.32—1.23(m, 2H), 0.90—0.82(m, 2H), 0.81(d, J=6.7 Hz, 3H), 0.77(d, J=6.8 Hz, 3H) | 170.9, 148.8, 148.0, 139.6, 137.1, 133.5, 127.9, 126.6, 126.4, 124.3, 121.4, 112.2, 111.1, 72.2, 69.3, 55.9, 55.8, 50.5, 46.3, 41.1, 38.8, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1p | 7.59(t, J=7.5 Hz, 1H), 7.47(t, J=7.8 Hz, 1H), 7.35(d, J=7.5 Hz, 1H), 5.55(t, J=9.4 Hz, 1H), 5.30(d, J=7.3 Hz, 2H), 5.24(d, J=9.7 Hz, 1H), 4.98(s, 1H), 3.98(d, J=35.9 Hz, 2H), 2.23—2.16(m, 2H), 2.16—2.09(m, 2H), 2.05(d, J=13.1 Hz, 1H), 2.02—1.93(m, 3H), 1.69(s, 3H), 1.62—1.52(m, 4H), 1.50(s, 3H), 1.47—1.43(m, 1H), 1.36(s, 3H), 1.29—1.25(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.77(d, J=6.7 Hz, 3H) | 169.1, 148.8, 139.9, 137.0, 133.6, 133.6, 133.5, 130.4, 128.6, 127.9, 126.2, 125.4, 124.4, 72.3, 70.0, 50.5, 46.3, 40.2, 38.8, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.1, 14.8 |
1q | 7.44(d, J=8.4 Hz, 2H), 7.22(d, J=8.4 Hz, 2H), 7.16(s, 1H), 5.56—5.49(m, 1H), 5.30(d, J=4.5 Hz, 2H), 5.22(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.55(s, 2H), 2.24—2.18(m, 1H), 2.17(s, 3H), 2.15—2.04(m, 3H), 2.04—1.93(m, 4H), 1.69(s, 3H), 1.60—1.55(m, 4H), 1.50(s, 3H), 1.48—1.42(m, 1H), 1.34(s, 3H), 1.30—1.24(m, 2H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.6, 168.2, 139.6, 137.1, 136.8, 133.5, 130.0, 129.8, 127.8, 126.3, 124.3, 119.9, 72.2, 69.4, 50.5, 46.3, 41.0, 38.8, 36.6, 32.9, 29.6, 27.8, 24.7, 23.2, 20.7, 19.4, 16.2, 14.8 |
Compd. | 1H NMR, δ(600 MHz, CDCl3) | 13C NMR, δ(150 MHz, CDCl3) |
1r | 7.82—7.72(m, 3H), 5.59—5.53(m, 1H), 5.33—5.29(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.98(s, 1H), 3.72(s, 2H), 2.25—2.16(m, 2H), 2.15—2.08(m, 2H), 2.05—1.96(m, 4H), 1.70(s, 3H), 1.60—1.55(m, 3H), 1.51(s, 3H), 1.36(s, 3H), 1.31—1.23(m, 2H), 0.82(d, J=6.7 Hz, 3H), 0.79(t, J=6.4 Hz, 3H) | 169.0, 140.3, 136.9, 136.4, 133.6, 131.8, 131.6, 129.6, 128.1, 125.9, 124.2, 122.3, 121.2, 72.1, 70.2, 50.4, 46.3, 40.9, 38.8, 36.6, 32.9, 29.6, 27.8, 23.1, 20.7, 19.4, 16.2, 14.8 |
1s | 7.31—7.27(m, 2H), 7.20(d, J=8.4 Hz, 2H), 5.55—5.50(m, 1H), 5.31—5.29(m, 3H), 5.22(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.55(s, 2H), 2.24—2.15(m, 2H), 2.14—2.06(m, 2H), 2.05—2.00(m, 1H), 2.00—1.94(m, 3H), 1.69(s, 3H), 1.61—1.56(m, 2H), 1.50(s, 3H), 1.48—1.43(m, 1H), 1.34(s, 3H), 1.30—1.25(m, 1H), 0.82(t, J=7.5 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.2, 139.7, 137.0, 133.5, 133.0, 132.5, 130.6, 128.7, 127.9, 126.2, 124.3, 72.2, 69.6, 50.4, 46.3, 40.8, 38.8, 36.6, 32.9, 29.6, 27.8, 23.1, 20.7, 19.4, 16.2, 14.8 |
1t | 7.26—7.23(m, 2H), 7.12—7.02(m, 2H), 5.55(t, J=8.4 Hz, 1H), 5.30(d, J=5.2 Hz, 3H), 5.24(d, J=9.7 Hz, 1H), 4.99(s, 1H), 3.68—3.60(m, 2H), 2.23—2.08(m, 4H), 2.04—1.92(m, 4H), 1.70(s, 3H), 1.61—1.55(m, 2H), 1.50(s, 3H), 1.48—1.43(m, 1H), 1.36(s, 3H), 1.31—1.24(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.8, 161.0(d, J=246.4 Hz), 139.6, 137.1, 133.5, 131.4, 129.0, 127.8, 126.3, 124.4, 124.1, 121.6, 115.4, 72.3, 69.6, 50.4, 46.3, 38.8, 36.6, 34.8, 34.8, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1u | 7.40(s, 1H), 7.21(s, 2H), 5.55(t, J=10.5 Hz, 1H), 5.32—5.28(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.98(s, 1H), 3.73—3.65(m, 2H), 2.25—2.16(m, 2H), 2.15—2.07(m, 2H), 2.06—2.00(m, 2H), 1.99—1.90(m, 2H), 1.70(s, 3H), 1.62—1.57(m, 2H), 1.57—1.52(m, 2H), 1.50(s, 3H), 1.48—1.43(m, 1H), 1.36(s, 3H), 1.29—1.23(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.3, 139.8, 137.0, 135.2, 133.3, 133.5, 132.2, 131.2, 129.3, 127.9, 127.2, 126.2, 124.3, 72.2, 69.8, 50.4, 46.3, 38.9, 38.8, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1v | 6.86—6.78(m, 2H), 6.71(t, J=9.0 Hz, 1H), 5.58—5.50(m, 1H), 5.34—5.27(m, 2H), 5.23(d, J=9.7 Hz, 1H), 4.99(s, 1H), 3.56(s, 2H), 2.32—2.16(m, 2H), 2.16—2.06(m, 2H), 2.04—1.93(m, 4H), 1.70(s, 3H), 1.61—1.54(m, 3H), 1.51(s, 3H), 1.48—1.44(m, 1H), 1.35(s, 3H), 1.30—1.25(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.4, 163.8, 162.1, 139.9, 137.5, 136.9, 133.5, 128.0, 126.1, 124.3, 112.4, 112.2, 102.7, 72.2, 69.9, 50.4, 46.3, 41.1, 38.8, 36.6, 32.9, 29.6, 27.8, 23.1, 20.7, 19.4, 16.2, 14.8 |
1w | 7.20—7.12(m, 4H), 5.54(t, J=10.5 Hz, 1H), 5.33—5.26(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.64—3.57(m, 2H), 2.29(s, 3H), 2.23—2.15(m, 2H), 2.14—2.07(m, 2H), 2.04—1.94(m, 4H), 1.70(s, 3H), 1.63—1.52(m, 3H), 1.51(s, 3H), 1.48—1.44(m, 1H), 1.34(s, 3H), 1.30—1.25(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.6, 139.5, 137.1, 136.7, 133.4, 132.9, 130.3, 130.1, 127.8, 127.3, 126.4, 126.1, 124.3, 72.3, 69.3, 50.5, 46.3, 39.5, 38.78, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.6, 19.4, 16.2, 14.8 |
2a | 5.36—5.25(m, 2H), 5.12(d, J=9.6 Hz, 1H), 5.03(s, 1H), 3.90(t, J=9.7 Hz, 1H), 3.22(s, 3H), 2.25—2.18(m, 2H), 2.18—2.12(m, 2H), 2.06—1.95(m, 3H), 1.88(dd, J=13.2, 8.6 Hz, 1H), 1.66(s, 3H), 1.61—1.57(m, 1H), 1.51(s, 3H), 1.46(dd, J=12.4, 6.6 Hz, 1H), 1.34(s, 3H), 1.25(s, 3H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 138.1, 137.8, 133.3, 128.4, 127.5, 124.5, 74.7, 72.4, 55.2, 51.2, 46.4, 38.8, 26.8, 33.0, 29.7, 28.0, 23.3, 20.7, 19.4, 16.1, 14.8 |
2b | 5.32—5.28(m, 2H), 5.16(d, J=9.5 Hz, 1H), 5.04(t, J=5.2 Hz, 1H), 4.08—3.97(m, 1H), 3.55—3.42(m, 1H), 3.39—3.27(m, 1H), 2.24—2.09(m, 5H), 2.08—1.97(m, 3H), 1.89(dd, J=13.3, 8.5 Hz, 1H), 1.64(s, 3H), 1.61—1.56(m, 2H), 1.51(s, 3H), 1.33(s, 3H), 1.31—1.22(m, 2H), 1.18(t, J=7.0 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 137.9, 137.2, 133.3, 129.0, 127.5, 124.6, 73.0, 72.4, 62.6, 51.2, 46.4, . 38.8, 36.8, 33.1, 29.8, 28.0, 23.4, 20.7, 19.4, 16.1, 15.4, 14.8 |
2c | 5.32—5.28(m, 2H), 5.16(d, J=9.5 Hz, 1H), 5.04(s, 1H), 4.04—3.91(m, 1H), 3.37(dd, J=15.9, 6.8 Hz, 1H), 3.26—3.12(m, 1H), 2.23—2.16(m, 2H), 2.16—2.10(m, 2H), 2.05—1.98(m, 3H), 1.93—1.81(m, 2H), 1.64(s, 3H), 1.60—1.54(m, 4H), 1.51(s, 3H), 1.49—1.44(m, 1H), 1.32(s, 3H), 1.28—1.24(m, 1H), 0.90(t, J=7.4 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 138.0, 137.1, 133.2, 129.0, 127.5, 124.6, 73.2, 72.4, 69.2, 51.1, 56.5, 38.8, 36.9, 33.1, 29.8, 28.0, 23.4, 23.1, 20.7, 19.4, 16.2, 14.9, 10.7 |
Compd. | 1H NMR, δ(600 MHz, CDCl3) | 13C NMR, δ(150 MHz, CDCl3) |
2d | 5.34—5.24(m, 2H), 5.16(d, J=9.5 Hz, 1H), 5.04(t, J=5.3 Hz, 1H), 3.99(t, J=8.3 Hz, 1H), 3.47—3.36(m, 1H), 3.33—3.18(m, 1H), 2.22—2.16(m, 2H), 2.16—2.10(m, 2H), 2.05—1.98(m, 3H), 1.94—1.84(m, 2H), 1.64(s, 3H), 1.58(dd, J=8.5, 5.0 Hz, 1H), 1.53(d, J=7.0 Hz, 2H), 1.51(s, 3H), 1.48—1.45(m, 1H), 1.38—1.33(m, 2H), 1.32(s, 3H), 1.29—1.26(m, 1H), 0.90(t, J=7.4 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 138.0, 137.1, 133.3, 129.0, 127.5, 124.6, 73.2, 72.5, 67.3, 51.1, 46.5, 38.8, 36.9, 33.1, 32.0, 29.8, 28.0, 23.4, 20.7, 19.5, 16.2, 14.9, 13.9 |
2e | 5.36—5.24(m, 3H), 5.16(d, J=9.6 Hz, 1H), 5.03(s, 1H), 4.04(t, J=8.4 Hz, 1H), 3.97—3.88(m, 1H), 3.86—3.76(m, 1H), 2.22—2.17(m, 2H), 2.17—2.12(m, 2H), 2.08—1.97(m, 3H), 1.92—1.85(m, 1H), 1.73(s, 3H), 1.65—1.62(m, 6H), 1.62—1.56(m, 2H), 1.51(s, 5H), 1.33(s, 3H), 1.27—1.23(m, 1H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H). | 137.9, 137.4, 136.7, 133.3, 129.0, 127.4, 124.5, 121.6, 72.4,72.3, 63.8, 51.4, 46.4, 38.8, 36.8, 33.1, 29.6, 28.0, 25.8, 23.3, 20.7, 19.4, 18.1, 16.4, 14.8 |
Table 2 1H NMR and 13C NMR data of compounds 1a—1w, 2a—2e
Compd | 1H NMR, δ(600 MHz, CDCl3) | 13C NMR, δ(150 MHz, CDCl3) |
---|---|---|
1a | 5.53(t, J=8.4 Hz, 1H), 5.34—5.28(m, 2H), 5.23(d, J=9.8 Hz, 1H), 5.00(s, 1H), 2.15(ddd, J=35.4, 13.7, 6.4 Hz, 4H), 2.02(s, 3H), 2.02—1.90(m, 4H), 1.71(s, 3H), 1.62—1.54(m, 3H), 1.51(s, 3H), 1.49—1.42(m, 1H), 1.37(s, 3H), 1.31—1.25(m, 1H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 169.6, 138.8, 136.7, 133.0, 127.4, 126.2, 123.9, 71.8, 68.3, 50.2, 45.9, 38.4, 36.2, 32.4, 29.2, 22.7, 21.0, 20.2, 18.9, 15.7, 14.3 |
1b | 5.53(t, J=8.3 Hz, 1H), 5.31(dd, J=10.3, 5.0 Hz, 2H), 5.23(d, J=9.6 Hz, 1H), 5.01(s, 1H), 2.29(q, J=7.5 Hz, 2H), 2.25—2.06(m, 4H), 2.04—1.94(m, 4H), 1.72(s, 3H), 1.63—1.53(m, 3H), 1.51(s, 3H), 1.50 — 1.43(m, 1H), 1.38(s, 3H), 1.32—1.24(m, 1H), 1.12(t, J=7.6 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 173.3, 139.0, 137.0, 133.2, 127.6, 126.5, 124.2, 72.1, 68.4, 50.5, 46.1, 38.6, 36.4, 32.7, 29.4, 27.7, 27.6, 23.0, 20.5, 19.2, 16.0, 14.6, 8.9 |
1c | 5.54(t, J=8.3 Hz, 1H), 5.32(d, J=7.1 Hz, 2H), 5.23(d, J=9.8 Hz, 1H), 5.00(d, J=5.5 Hz, 1H), 2.27—2.09(m, 6H), 2.06—1.94(m, 4H), 1.72(s, 3H), 1.67—1.54(m, 5H), 1.51(s, 3H), 1.49—1.42(m, 1H), 1.38(s, 3H), 1.31—1.18(m, 1H), 0.93(t, J=7.4 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 172.1, 138.6, 136.6, 132.9, 127.2, 126.1, 123.8, 71.7, 67.9, 50.2, 45.8, 38.2, 36.1, 35.9, 32.3, 29.1, 27.3, 22.6, 20.1, 18.8, 17.9, 15.6, 14.2, 13.0 |
1d | 5.57—5.46(m, 1H), 5.38—5.27(m, 2H), 5.23(d, J=9.7 Hz, 1H), 5.01(s, 1H), 2.58—2.43(m, 1H), 2.32—2.05(m, 4H), 2.05—1.87(m, 4H), 1.71(s, 3H), 1.66—1.53(m, 3H), 1.51(s, 3H), 1.50—1.40(m, 1H), 1.38(s, 3H), 1.32—1.24(m, 1H), 1.14(dd, J=9.1, 7.0 Hz, 6H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 176.1, 139.0, 137.1, 133.3, 127.7, 126.5, 124.3, 72.2, 68.4, 50.6, 46.2, 38.7, 36.5, 34.0, 32.8, 29.5, 27.7, 23.1, 20.6, 19.3, 18.9, 18.7, 16.7, 14.7 |
1e | 5.53(t, J=8.4 Hz, 1H), 5.37—5.29(m, 2H), 5.23(d, J=9.8 Hz, 1H), 5.01(s, 1H), 2.38—2.05(m, 6H), 2.06—1.89(m, 4H), 1.72(s, 3H), 1.65—1.53(m, 5H), 1.51(s, 3H), 1.50—1.42(m, 1H), 1.38(s, 3H), 1.36—1.19(m, 3H), 0.91(t, J=7.4 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 172.9, 139.2, 137.2, 133.4, 127.8, 126.7, 124.4, 72.3, 68.5, 50.7, 46.3, 38.8, 36.7, 34.4, 32.9, 29.7, 27.8, 27.1, 23.2, 22.2, 20.7, 19.4, 16.2, 14.8, 13.8 |
1f | 5.54(t, J=8.3 Hz, 1H), 5.32(d, J=7.0 Hz, 2H), 5.23(d, J=9.8 Hz, 1H), 4.99(d, J=5.6 Hz, 1H), 2.22—2.07(m, 7H), 2.04—1.93(m, 4H), 1.72(s, 3H), 1.60—1.53(m, 3H), 1.51(s, 3H), 1.49—1.45(m, 1H), 1.38(s, 3H), 1.33—1.21(m, 1H), 0.94(d, J=0.7 Hz, 3H), 0.93(d, J=0.5 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 171.9, 139.0, 137.0, 133.2, 127.6, 126.5, 124.2, 72.1, 68.2, 50.6, 46.1, 43.6, 38.6, 36.4, 32.7, 29.4, 27.6, 25.6, 23.0, 22.2, 22.1, 20.5, 19.2, 15.9, 14.6 |
1g | 6.08(s, 1H), 5.61—5.47(m, 2H), 5.38—5.19(m, 3H), 5.02(s, 1H), 2.21—2.10(m, 3H), 2.06—1.97(m, 5H), 1.93(s, 3H), 1.74(s, 3H), 1.63—1.54(m, 4H), 1.51(s, 3H), 1.39(s, 3H), 1.33—1.25(m, 1H), 0.83(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 165.5, 138.3, 136.3, 135.8, 132.4, 126.9, 125.6, 124.2, 123.4, 71.3, 68.1, 49.7, 45.4, 37.9, 35.7, 31.9, 28.7, 26.8, 22.2, 19.7, 18.4, 17.4, 15.2, 13.8 |
1h | 8.09—7.98(m, 2H), 7.61—7.50(m, 1H), 7.45—7.36(m, 2H), 5.78(t, J=8.7 Hz, 1H), 5.43—5.30(m, 3H), 5.04(s, 1H), 2.27—2.16(m, 3H), 2.12(ddd, J=13.1, 8.0, 3.9 Hz, 3H), 2.08—1.96(m, 2H), 1.80(s, 3H), 1.64—1.55(m, 3H), 1.53(s, 3H), 1.51—1.45(m, 1H), 1.43(s, 3H), 1.34—1.26(m, 1H), 0.85(d, J=6.7 Hz, 3H), 0.81(d, J=6.8 Hz, 3H) | 165.1, 139.0, 136.6, 132.9, 132.2, 130.2, 129.0, 127.7, 127.4, 126.0, 123.9, 71.8, 68.9, 50.2, 45.8, 38.3, 36.1, 32.4, 29.1, 27.3, 22.6, 20.1, 18.9, 15.7, 14.2 |
Compd. | 1H NMR, δ(600 MHz, CDCl3) | 13C NMR, δ(150 MHz, CDCl3) |
1i | 7.38—7.29(m, 2H), 7.26(d, J=7.1 Hz, 3H), 5.60—5.46(m, 1H), 5.36—5.29(m, 2H), 5.24(d, J=9.8 Hz, 1H), 5.00(s, 1H), 3.59(s, 2H), 2.23—2.08(m, 4H), 2.05—1.94(m, 4H), 1.70(s, 3H), 1.62—1.52(m, 3H), 1.51(s, 3H), 1.47(d, J=6.2 Hz, 1H), 1.34(s, 3H), 1.31—1.25(m, 1H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.7, 139.6, 137.2, 134.2, 133.5, 129.3, 128.6, 127.9, 127.0, 126.4, 124.4, 72.3, 69.4, 50.5, 46.4, 41.6, 38.8, 36.7, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1j | 7.31—7.24(m, 2H), 7.22—7.15(m, 3H), 5.58—5.48(m, 1H), 5.33—5.27(m, 2H), 5.20(d, J=9.8 Hz, 1H), 4.99(s, 1H), 2.94(t, J=7.8 Hz, 2H), 2.64—2.53(m, 2H), 2.27—2.06(m, 4H), 2.04—1.96(m, 2H), 1.96—1.91(m, 2H), 1.71(s, 3H), 1.64—1.58(m, 1H), 1.58—1.52(m, 2H), 1.51(s, 3H), 1.36(s, 3H), 1.32—1.20(m, 2H), 0.82(d, J=6.7 Hz, 3H), 0.79(d, J=6.8 Hz, 3H) | 171.9, 140.5, 139.3, 137.1, 133.5, 128.5, 128.3, 127.9, 126.6, 126.2, 124.4, 72.3, 68.8, 50.7, 46.4, 38.8, 36.6, 36.2, 32.9, 31.0, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1k | 7.67(d, J=16.0 Hz, 1H), 7.57—7.46(m, 2H), 7.43—7.32(m, 3H), 6.42(d, J=16.0 Hz, 1H), 5.67(t, J=8.7 Hz, 1H), 5.39—5.22(m, 3H), 5.03(s, 1H), 3.72(q, J=7.0 Hz, 1H), 2.29—2.18(m, 2H), 2.17—2.09(m, 3H), 2.08—1.97(m, 3H), 1.77(s, 3H), 1.64—1.55(m, 3H), 1.52(s, 3H), 1.42(s, 3H), 1.33—1.27(m, 1H), 1.24(t, J=7.0 Hz, 1H), 0.84(d, J=6.7 Hz, 3H), 0.81(d, J=6.8 Hz, 3H) | 166.1, 144.7, 139.5, 137.2, 134.5, 133.5, 130.2, 128.9, 128.1, 127.9, 126.7, 124.4, 118.6, 72.4, 68.9, 50.8, 46.4, 38.9, 36.7, 32.9, 29.7, 27.9, 23.2, 20.7, 19.4, 16.2, 14.8 |
1l | 7.24—7.19(m, 2H), 7.00(t, J=8.7 Hz, 2H), 5.55—5.50(m, 1H), 5.30(d, J=5.0 Hz, 2H), 5.22(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.56(s, 2H), 2.25—2.19(m, 1H), 2.19—2.15(m, 1H), 2.15—2.08(m, 2H), 2.02(d, J=14.0 Hz, 1H), 1.99—1.94(m, 3H), 1.69(s, 3H), 1.62—1.53(m, 3H), 1.50(s, 3H), 1.34(s, 3H), 1.27(d, J=13.9 Hz, 2H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.5, 162.0(d, J=245.2 Hz), 139.6, 137.1, 133.5, 130.8, 130.8, 129.8, 127.9, 126.3, 124.3, 115.5, 115.3, 72.2, 69.5, 50.5, 46.3, 40.7, 38.8, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1m | 7.52(s, 2H), 7.48—7.41(m, 2H), 5.57—5.52(m, 1H), 5.33—5.29(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.65(s, 2H), 2.23—2.15(m, 2H), 2.15—2.08(m, 2H), 2.03—2.00(m, 1H), 2.00—1.98(m, 2H), 1.98—1.94(m, 1H), 1.70(s, 3H), 1.60—1.53(m, 3H), 1.51(s, 3H), 1.49—1.43(m, 1H), 1.35(s, 3H), 1.33—1.23(m, 2H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.9, 139.9, 137.0, 135.0, 133.5, 132.7, 130.9, 130.7, 129.0, 128.0, 126.1, 126.0, 124.3, 123.9, 72.2, 69.7, 50.4, 46.3, 41.2, 38.8, 36.6, 32.9, 29.6, 27.8, 23.1, 20.7, 19.4, 16.2, 14.8 |
1n | 7.25—7.19(m, 1H), 6.87—6.78(m, 2H), 5.54(t, J=8.2 Hz, 1H), 5.32—5.29(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.60(s, 2H), 2.23—2.15(m, 2H), 2.15—2.08(m, 2H), 2.02—1.98(m, 2H), 1.98—1.96(m, 1H), 1.70(s, 3H), 1.60—1.56(m, 2H), 1.50(s, 3H), 1.48—1.45(m, 1H), 1.35(s, 3H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.58, 162.2(d, J=248.0 Hz), 161.0(d, J=249.1 Hz), 139.7, 137.0, 133.5, 132.0, 127.9, 126.2, 124.3, 117.5, 111.3, 103.9, 72.2, 69.7, 50.4, 46.3, 38.8, 36.6, 34.2, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1o | 6.82—6.78(m, 3H), 5.56—5.51(m, 1H), 5.32—5.29(m, 2H), 5.24(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.87(s, 3H), 3.86(s, 3H), 3.52(s, 2H), 2.18—2.08(m, 3H), 2.01(s, 1H), 1.98(s, 1H), 1.97—1.94(m, 1H), 1.69(s, 3H), 1.57—1.52(m, 2H), 1.50(s, 3H), 1.48—1.43(m, 1H), 1.34(s, 3H), 1.32—1.23(m, 2H), 0.90—0.82(m, 2H), 0.81(d, J=6.7 Hz, 3H), 0.77(d, J=6.8 Hz, 3H) | 170.9, 148.8, 148.0, 139.6, 137.1, 133.5, 127.9, 126.6, 126.4, 124.3, 121.4, 112.2, 111.1, 72.2, 69.3, 55.9, 55.8, 50.5, 46.3, 41.1, 38.8, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1p | 7.59(t, J=7.5 Hz, 1H), 7.47(t, J=7.8 Hz, 1H), 7.35(d, J=7.5 Hz, 1H), 5.55(t, J=9.4 Hz, 1H), 5.30(d, J=7.3 Hz, 2H), 5.24(d, J=9.7 Hz, 1H), 4.98(s, 1H), 3.98(d, J=35.9 Hz, 2H), 2.23—2.16(m, 2H), 2.16—2.09(m, 2H), 2.05(d, J=13.1 Hz, 1H), 2.02—1.93(m, 3H), 1.69(s, 3H), 1.62—1.52(m, 4H), 1.50(s, 3H), 1.47—1.43(m, 1H), 1.36(s, 3H), 1.29—1.25(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.77(d, J=6.7 Hz, 3H) | 169.1, 148.8, 139.9, 137.0, 133.6, 133.6, 133.5, 130.4, 128.6, 127.9, 126.2, 125.4, 124.4, 72.3, 70.0, 50.5, 46.3, 40.2, 38.8, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.1, 14.8 |
1q | 7.44(d, J=8.4 Hz, 2H), 7.22(d, J=8.4 Hz, 2H), 7.16(s, 1H), 5.56—5.49(m, 1H), 5.30(d, J=4.5 Hz, 2H), 5.22(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.55(s, 2H), 2.24—2.18(m, 1H), 2.17(s, 3H), 2.15—2.04(m, 3H), 2.04—1.93(m, 4H), 1.69(s, 3H), 1.60—1.55(m, 4H), 1.50(s, 3H), 1.48—1.42(m, 1H), 1.34(s, 3H), 1.30—1.24(m, 2H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.6, 168.2, 139.6, 137.1, 136.8, 133.5, 130.0, 129.8, 127.8, 126.3, 124.3, 119.9, 72.2, 69.4, 50.5, 46.3, 41.0, 38.8, 36.6, 32.9, 29.6, 27.8, 24.7, 23.2, 20.7, 19.4, 16.2, 14.8 |
Compd. | 1H NMR, δ(600 MHz, CDCl3) | 13C NMR, δ(150 MHz, CDCl3) |
1r | 7.82—7.72(m, 3H), 5.59—5.53(m, 1H), 5.33—5.29(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.98(s, 1H), 3.72(s, 2H), 2.25—2.16(m, 2H), 2.15—2.08(m, 2H), 2.05—1.96(m, 4H), 1.70(s, 3H), 1.60—1.55(m, 3H), 1.51(s, 3H), 1.36(s, 3H), 1.31—1.23(m, 2H), 0.82(d, J=6.7 Hz, 3H), 0.79(t, J=6.4 Hz, 3H) | 169.0, 140.3, 136.9, 136.4, 133.6, 131.8, 131.6, 129.6, 128.1, 125.9, 124.2, 122.3, 121.2, 72.1, 70.2, 50.4, 46.3, 40.9, 38.8, 36.6, 32.9, 29.6, 27.8, 23.1, 20.7, 19.4, 16.2, 14.8 |
1s | 7.31—7.27(m, 2H), 7.20(d, J=8.4 Hz, 2H), 5.55—5.50(m, 1H), 5.31—5.29(m, 3H), 5.22(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.55(s, 2H), 2.24—2.15(m, 2H), 2.14—2.06(m, 2H), 2.05—2.00(m, 1H), 2.00—1.94(m, 3H), 1.69(s, 3H), 1.61—1.56(m, 2H), 1.50(s, 3H), 1.48—1.43(m, 1H), 1.34(s, 3H), 1.30—1.25(m, 1H), 0.82(t, J=7.5 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.2, 139.7, 137.0, 133.5, 133.0, 132.5, 130.6, 128.7, 127.9, 126.2, 124.3, 72.2, 69.6, 50.4, 46.3, 40.8, 38.8, 36.6, 32.9, 29.6, 27.8, 23.1, 20.7, 19.4, 16.2, 14.8 |
1t | 7.26—7.23(m, 2H), 7.12—7.02(m, 2H), 5.55(t, J=8.4 Hz, 1H), 5.30(d, J=5.2 Hz, 3H), 5.24(d, J=9.7 Hz, 1H), 4.99(s, 1H), 3.68—3.60(m, 2H), 2.23—2.08(m, 4H), 2.04—1.92(m, 4H), 1.70(s, 3H), 1.61—1.55(m, 2H), 1.50(s, 3H), 1.48—1.43(m, 1H), 1.36(s, 3H), 1.31—1.24(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.8, 161.0(d, J=246.4 Hz), 139.6, 137.1, 133.5, 131.4, 129.0, 127.8, 126.3, 124.4, 124.1, 121.6, 115.4, 72.3, 69.6, 50.4, 46.3, 38.8, 36.6, 34.8, 34.8, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1u | 7.40(s, 1H), 7.21(s, 2H), 5.55(t, J=10.5 Hz, 1H), 5.32—5.28(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.98(s, 1H), 3.73—3.65(m, 2H), 2.25—2.16(m, 2H), 2.15—2.07(m, 2H), 2.06—2.00(m, 2H), 1.99—1.90(m, 2H), 1.70(s, 3H), 1.62—1.57(m, 2H), 1.57—1.52(m, 2H), 1.50(s, 3H), 1.48—1.43(m, 1H), 1.36(s, 3H), 1.29—1.23(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.3, 139.8, 137.0, 135.2, 133.3, 133.5, 132.2, 131.2, 129.3, 127.9, 127.2, 126.2, 124.3, 72.2, 69.8, 50.4, 46.3, 38.9, 38.8, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.4, 16.2, 14.8 |
1v | 6.86—6.78(m, 2H), 6.71(t, J=9.0 Hz, 1H), 5.58—5.50(m, 1H), 5.34—5.27(m, 2H), 5.23(d, J=9.7 Hz, 1H), 4.99(s, 1H), 3.56(s, 2H), 2.32—2.16(m, 2H), 2.16—2.06(m, 2H), 2.04—1.93(m, 4H), 1.70(s, 3H), 1.61—1.54(m, 3H), 1.51(s, 3H), 1.48—1.44(m, 1H), 1.35(s, 3H), 1.30—1.25(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 169.4, 163.8, 162.1, 139.9, 137.5, 136.9, 133.5, 128.0, 126.1, 124.3, 112.4, 112.2, 102.7, 72.2, 69.9, 50.4, 46.3, 41.1, 38.8, 36.6, 32.9, 29.6, 27.8, 23.1, 20.7, 19.4, 16.2, 14.8 |
1w | 7.20—7.12(m, 4H), 5.54(t, J=10.5 Hz, 1H), 5.33—5.26(m, 2H), 5.23(d, J=9.8 Hz, 1H), 4.99(s, 1H), 3.64—3.57(m, 2H), 2.29(s, 3H), 2.23—2.15(m, 2H), 2.14—2.07(m, 2H), 2.04—1.94(m, 4H), 1.70(s, 3H), 1.63—1.52(m, 3H), 1.51(s, 3H), 1.48—1.44(m, 1H), 1.34(s, 3H), 1.30—1.25(m, 1H), 0.81(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 170.6, 139.5, 137.1, 136.7, 133.4, 132.9, 130.3, 130.1, 127.8, 127.3, 126.4, 126.1, 124.3, 72.3, 69.3, 50.5, 46.3, 39.5, 38.78, 36.6, 32.9, 29.6, 27.8, 23.2, 20.7, 19.6, 19.4, 16.2, 14.8 |
2a | 5.36—5.25(m, 2H), 5.12(d, J=9.6 Hz, 1H), 5.03(s, 1H), 3.90(t, J=9.7 Hz, 1H), 3.22(s, 3H), 2.25—2.18(m, 2H), 2.18—2.12(m, 2H), 2.06—1.95(m, 3H), 1.88(dd, J=13.2, 8.6 Hz, 1H), 1.66(s, 3H), 1.61—1.57(m, 1H), 1.51(s, 3H), 1.46(dd, J=12.4, 6.6 Hz, 1H), 1.34(s, 3H), 1.25(s, 3H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 138.1, 137.8, 133.3, 128.4, 127.5, 124.5, 74.7, 72.4, 55.2, 51.2, 46.4, 38.8, 26.8, 33.0, 29.7, 28.0, 23.3, 20.7, 19.4, 16.1, 14.8 |
2b | 5.32—5.28(m, 2H), 5.16(d, J=9.5 Hz, 1H), 5.04(t, J=5.2 Hz, 1H), 4.08—3.97(m, 1H), 3.55—3.42(m, 1H), 3.39—3.27(m, 1H), 2.24—2.09(m, 5H), 2.08—1.97(m, 3H), 1.89(dd, J=13.3, 8.5 Hz, 1H), 1.64(s, 3H), 1.61—1.56(m, 2H), 1.51(s, 3H), 1.33(s, 3H), 1.31—1.22(m, 2H), 1.18(t, J=7.0 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 137.9, 137.2, 133.3, 129.0, 127.5, 124.6, 73.0, 72.4, 62.6, 51.2, 46.4, . 38.8, 36.8, 33.1, 29.8, 28.0, 23.4, 20.7, 19.4, 16.1, 15.4, 14.8 |
2c | 5.32—5.28(m, 2H), 5.16(d, J=9.5 Hz, 1H), 5.04(s, 1H), 4.04—3.91(m, 1H), 3.37(dd, J=15.9, 6.8 Hz, 1H), 3.26—3.12(m, 1H), 2.23—2.16(m, 2H), 2.16—2.10(m, 2H), 2.05—1.98(m, 3H), 1.93—1.81(m, 2H), 1.64(s, 3H), 1.60—1.54(m, 4H), 1.51(s, 3H), 1.49—1.44(m, 1H), 1.32(s, 3H), 1.28—1.24(m, 1H), 0.90(t, J=7.4 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 138.0, 137.1, 133.2, 129.0, 127.5, 124.6, 73.2, 72.4, 69.2, 51.1, 56.5, 38.8, 36.9, 33.1, 29.8, 28.0, 23.4, 23.1, 20.7, 19.4, 16.2, 14.9, 10.7 |
Compd. | 1H NMR, δ(600 MHz, CDCl3) | 13C NMR, δ(150 MHz, CDCl3) |
2d | 5.34—5.24(m, 2H), 5.16(d, J=9.5 Hz, 1H), 5.04(t, J=5.3 Hz, 1H), 3.99(t, J=8.3 Hz, 1H), 3.47—3.36(m, 1H), 3.33—3.18(m, 1H), 2.22—2.16(m, 2H), 2.16—2.10(m, 2H), 2.05—1.98(m, 3H), 1.94—1.84(m, 2H), 1.64(s, 3H), 1.58(dd, J=8.5, 5.0 Hz, 1H), 1.53(d, J=7.0 Hz, 2H), 1.51(s, 3H), 1.48—1.45(m, 1H), 1.38—1.33(m, 2H), 1.32(s, 3H), 1.29—1.26(m, 1H), 0.90(t, J=7.4 Hz, 3H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H) | 138.0, 137.1, 133.3, 129.0, 127.5, 124.6, 73.2, 72.5, 67.3, 51.1, 46.5, 38.8, 36.9, 33.1, 32.0, 29.8, 28.0, 23.4, 20.7, 19.5, 16.2, 14.9, 13.9 |
2e | 5.36—5.24(m, 3H), 5.16(d, J=9.6 Hz, 1H), 5.03(s, 1H), 4.04(t, J=8.4 Hz, 1H), 3.97—3.88(m, 1H), 3.86—3.76(m, 1H), 2.22—2.17(m, 2H), 2.17—2.12(m, 2H), 2.08—1.97(m, 3H), 1.92—1.85(m, 1H), 1.73(s, 3H), 1.65—1.62(m, 6H), 1.62—1.56(m, 2H), 1.51(s, 5H), 1.33(s, 3H), 1.27—1.23(m, 1H), 0.82(d, J=6.7 Hz, 3H), 0.78(d, J=6.8 Hz, 3H). | 137.9, 137.4, 136.7, 133.3, 129.0, 127.4, 124.5, 121.6, 72.4,72.3, 63.8, 51.4, 46.4, 38.8, 36.8, 33.1, 29.6, 28.0, 25.8, 23.3, 20.7, 19.4, 18.1, 16.4, 14.8 |
Compound | IC50/(μmol·L-1) | ||||
---|---|---|---|---|---|
HL-60 | A-549 | SMMC-7721 | MCF-7 | SW480 | |
1a | >40 | >40 | >40 | >40 | >40 |
1b | >40 | >40 | >40 | >40 | >40 |
1c | >40 | >40 | >40 | 28.02±0.62 | >40 |
1d | 15.84±0.80 | >40 | >40 | 23.30±2.05 | >40 |
1e | >40 | >40 | >40 | 22.49±0.61 | >40 |
1f | >40 | >40 | >40 | 16.57±1.16 | >40 |
1g | >40 | >40 | >40 | >40 | >40 |
1h | >40 | >40 | >40 | 26.16±0.19 | >40 |
1i | >40 | 32.34±0.99 | >40 | 15.45±0.82 | 16.62±0.45 |
1j | >40 | >40 | >40 | 19.11±1.90 | >40 |
1k | 14.72±0.17 | >40 | >40 | 17.42±1.66 | >40 |
1l | >40 | >40 | 22.93±0.38 | >40 | >40 |
1m | >40 | 28.22±1.65 | 21.51±0.91 | >40 | >40 |
1n | >40 | >40 | 13.26±0.82 | >40 | >40 |
1o | >40 | >40 | 35.35±1.80 | >40 | >40 |
1p | >40 | 23.14±0.29 | 18.21±0.75 | 34.38±0.89 | >40 |
1q | >40 | >40 | >40 | >40 | >40 |
1r | >40 | >40 | 16.15±1.23 | 29.42±1.03 | >40 |
1s | >40 | >40 | 20.11±1.12 | >40 | >40 |
1t | >40 | >40 | 11.44±0.85 | >40 | >40 |
1u | >40 | >40 | 27.52±1.49 | >40 | >40 |
Compound | IC50/(μmol·L-1) | ||||
HL-60 | A-549 | SMMC-7721 | MCF-7 | SW480 | |
1v | >40 | >40 | >40 | >40 | >40 |
1w | >40 | >40 | 21.36±0.58 | >40 | >40 |
2a | >40 | >40 | >40 | >40 | >40 |
2b | >40 | 32.34±1.56 | >40 | >40 | >40 |
2c | >40 | >40 | >40 | >40 | >40 |
2d | >40 | >40 | >40 | >40 | >40 |
2e | >40 | 31.48±2.07 | >40 | >40 | >40 |
3a | >40 | >40 | >40 | >40 | >40 |
3b | >40 | >40 | >40 | >40 | >40 |
DPP | 1.35±0.10 | 14.74±0.39 | 11.64±0.89 | 23.32±1.15 | 11.82±0.47 |
Table 3 Inhibition activity against five human cancer cell lines by MTS assay
Compound | IC50/(μmol·L-1) | ||||
---|---|---|---|---|---|
HL-60 | A-549 | SMMC-7721 | MCF-7 | SW480 | |
1a | >40 | >40 | >40 | >40 | >40 |
1b | >40 | >40 | >40 | >40 | >40 |
1c | >40 | >40 | >40 | 28.02±0.62 | >40 |
1d | 15.84±0.80 | >40 | >40 | 23.30±2.05 | >40 |
1e | >40 | >40 | >40 | 22.49±0.61 | >40 |
1f | >40 | >40 | >40 | 16.57±1.16 | >40 |
1g | >40 | >40 | >40 | >40 | >40 |
1h | >40 | >40 | >40 | 26.16±0.19 | >40 |
1i | >40 | 32.34±0.99 | >40 | 15.45±0.82 | 16.62±0.45 |
1j | >40 | >40 | >40 | 19.11±1.90 | >40 |
1k | 14.72±0.17 | >40 | >40 | 17.42±1.66 | >40 |
1l | >40 | >40 | 22.93±0.38 | >40 | >40 |
1m | >40 | 28.22±1.65 | 21.51±0.91 | >40 | >40 |
1n | >40 | >40 | 13.26±0.82 | >40 | >40 |
1o | >40 | >40 | 35.35±1.80 | >40 | >40 |
1p | >40 | 23.14±0.29 | 18.21±0.75 | 34.38±0.89 | >40 |
1q | >40 | >40 | >40 | >40 | >40 |
1r | >40 | >40 | 16.15±1.23 | 29.42±1.03 | >40 |
1s | >40 | >40 | 20.11±1.12 | >40 | >40 |
1t | >40 | >40 | 11.44±0.85 | >40 | >40 |
1u | >40 | >40 | 27.52±1.49 | >40 | >40 |
Compound | IC50/(μmol·L-1) | ||||
HL-60 | A-549 | SMMC-7721 | MCF-7 | SW480 | |
1v | >40 | >40 | >40 | >40 | >40 |
1w | >40 | >40 | 21.36±0.58 | >40 | >40 |
2a | >40 | >40 | >40 | >40 | >40 |
2b | >40 | 32.34±1.56 | >40 | >40 | >40 |
2c | >40 | >40 | >40 | >40 | >40 |
2d | >40 | >40 | >40 | >40 | >40 |
2e | >40 | 31.48±2.07 | >40 | >40 | >40 |
3a | >40 | >40 | >40 | >40 | >40 |
3b | >40 | >40 | >40 | >40 | >40 |
DPP | 1.35±0.10 | 14.74±0.39 | 11.64±0.89 | 23.32±1.15 | 11.82±0.47 |
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