Synthesis and Antitumor Activities of α-2,7,11-Cembratriene-4,6-diol Derivatives †

doi:10.7503/cjcu20190446

Abstract

Abstract:

Twenty eight α-2,7,11-cembratriene-4,6-diol derivatives were prepared by the modification at C6 position via introduction of acyl and ether groups. Their structures were confirmed by nuclear magnetic resonance spectroscopy(NMR) and high resolution mass spectrometry(HRMS). The synthesized compounds were screened for their in vitro biological activity. The results of 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfopheny)-2H-tetrazolium(MTS) assay indicated that some of them showed the same anticancer activity as cisplatin(DDP) did. Among them, α-2,7,11-cembratriene-4-ol-6-phenylacetate(1i) showed cytotoxicity against MCF-7 with an IC₅₀ value of 15.45 μmol/L, and α-2,7,11-cembratriene-4-ol-6-(2-F)phenylacetate(1t) showed cytotoxicity against SMMC-7721 with an IC₅₀ value of 11.44 μmol/L, respectively. Structure-activity relationship revealed that the phenylacetate substituents at C6 position played an important role in inhibition activity.

Key words: Cembratriene derivative, Antitumor, Tobacco

CLC Number:

O629.9

TrendMD:

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 ^†[J]. Chem. J. Chinese Universities, 2020, 41(3): 481.

Figures/Tables 5

References 27

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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.	[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

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)
Compound	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)
Compound	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