Synthesis and Antibacterial Activities of Penta-1,4-dien-3-one Derivatives Containing a Benzotriazin-4(3H)-one Moiety†

doi:10.7503/cjcu20170785

Abstract

Abstract:

To find novel curcumin derivatives with potent biological activities, fourteen new penta-1,4-dien-3-one derivatives containing benzotriazin-4(3H)-one moiety were synthesized by multistep synthetic procedures with two key intermediates penta-1,4-dien-3-one and 3-(chloromethyl)benzo[1,2,3]triazin-4(3H)-one. The structures of target compounds 6 were confirmed by means of nuclear magnetic resonance(NMR), and high resolution mass spectrometer(HRMS). The bioassay data showed that some compounds exhibited good antibacterial activities at the dosage of 100 μg/mL and 50 μg/mL against Xanthomonas axonopodis pv. Citri(Xac) and Ralstonia solanacearum(R. solanacearum). Moreover, compounds 6b, 6j and 6l had 68.8%, 71.0% and 100% antibacterial activity against Xac at 100 μg/mL. Compounds 6a, 6d, 6h and 6i showed 51.8%, 53.0%, 50.7 and 76.9% antibacterial activity against R. solanacearum at 100 μg/mL. Meanwhile, all target compounds displayed excellent antibacterial activity against R. solanacearum at 50 μg/mL, which were superior to that of thiodiazole copper. In addition, compounds 6l and 6i showed wonderful inhibitory activities against Xac and R. solanacearum with the EC₅₀ values of 27.44 and 48.77 μg/mL, respectively. which were better than those of thiodiazole copper(51.35 μg/mL and 87.26 μg/mL, respectively). Those two penta-1,4-dien-3-one derivatives could be considered as useful templates for future development to obtain more potent antibacterial agents.

Key words: Penta-1, 4-dien-3-one, Benzotriazin-4(3H)-one, Antibacterial

CLC Number:

O625

TrendMD:

ZHANG Juping, LI Pu, WANG Yihui, ZHANG Cheng, CHEN Lijuan, TANG Xu, HE Ming, XUE Wei. Synthesis and Antibacterial Activities of Penta-1,4-dien-3-one Derivatives Containing a Benzotriazin-4(3H)-one Moiety^†[J]. Chem. J. Chinese Universities, 2018, 39(7): 1455.

Figures/Tables 6

References 22

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Compd.	¹H NMR(400 MHz, CDCl₃), δ
2a	7.85(dd, J=15.5, 4.4 Hz, 1H), 7.66(d, J=15.9 Hz, 1H), 7.36(dd, J=31.4, 4.2 Hz, 2H), 7.16(dd, J=8.2, 1.6 Hz, 1H), 7.11—7.05(m, 2H), 6.94(t, J=6.3 Hz, 1H), 6.87(dt, J=13.3, 6.5 Hz, 2H), 6.19(s, 1H), 3.93(s, 3H)
2b	7.69(t, J=17.0 Hz, 2H), 7.50(d, J=7.9 Hz, 2H), 7.18(dd, J=20.1, 8.1 Hz, 3H), 7.11—7.00(m, 2H), 6.93(t, J=12.5 Hz, 2H), 3.93(s, 3H), 2.37(s, 3H)
2c	8.84(d, J=2.0 Hz, 1H), 8.62(dd, J=4.8, 1.5 Hz, 1H), 7.93(dt, J=8.0, 1.8 Hz, 1H), 7.75—7.67(m, 2H), 7.37(dd, J=7.9, 4.8 Hz, 1H), 7.17(ddd, J=20.9, 7.4, 1.8 Hz, 3H), 6.95(dd, J=9.5, 6.4 Hz, 2H), 6.90(s, 1H), 3.96(s, 3H)
2d	8.51(s, 1H), 7.84(d, J=23.6 Hz, 2H), 7.48(s, 1H), 7.40(t, J=5.0 Hz, 3H), 7.20(s, 1H), 7.08(s, 1H), 6.98(s, 1H), 6.37(s, 1H), 4.91(s, 1H), 3.83(s, 3H)
2f	8.07(d, J=16.1 Hz, 1H), 7.67(d, J=15.8 Hz, 1H), 7.60(dd, J=7.7, 1.4 Hz, 1H), 7.40—7.32(m, 1H), 7.18—7.08(m, 3H), 7.00—6.89(m, 4H), 6.33(s, 1H), 3.92(s, 3H), 3.89(s, 3H)
2h	7.99(d, J=15.7 Hz, 1H), 7.59(dd, J=55.5, 11.6 Hz, 2H), 7.17—7.02(m, 3H), 6.93(d, J=8.9 Hz, 2H), 6.55—6.39(m, 2H), 6.21(s, 1H), 3.92(s, 3H), 3.87(s, 3H), 3.83(s, 3H)
2i	7.65(dd, J=16.2, 5.1 Hz, 2H), 7.54(dt, J=10.4, 5.2 Hz, 2H), 7.12(t, J=6.6 Hz, 1H), 7.09—7.02(m, 3H), 7.01—6.96(m, 1H), 6.93(dt, J=8.2, 2.1 Hz, 1H), 6.88(dt, J=15.7, 2.4 Hz, 1H), 6.45(s, 1H), 3.89(s, 3H)
Compd.	¹H NMR(400 MHz, CDCl₃), δ
2j	7.82—7.52(m, 3H), 7.40(s, 1H), 7.36(d, J=10.0 Hz, 2H), 7.20(s, 1H), 7.08(s, 1H), 6.93(s, 1H), 6.77(s, 1H), 5.05(s, 1H), 3.87(s, 3H), 3.85(s, 3H), 3.83(s, 3H)
2k	7.85—7.65(m, 3H), 7.64—7.55(m, 2H), 7.39(dd, J=9.9, 7.4 Hz, 3H), 7.22—7.05(m, 3H), 7.00—6.87(m, 2H), 3.92(s, 3H)
2l	8.44(s, 1H), 8.20(d, J=8.1 Hz, 1H), 7.85(d, J=7.6 Hz, 1H), 7.79—7.65(m, 2H), 7.62—7.53(m, 1H), 7.23—7.08(m, 3H), 6.91(dd, J=17.4, 12.0 Hz, 2H), 6.21(s, 1H), 3.93(s, 3H)
2m	7.76(d, J=57.1 Hz, 2H), 7.46(s, 2H), 7.39(d, J=10.0 Hz, 3H), 7.25(s, 1H), 7.20(s, 1H), 7.05(d, J=30.0 Hz, 2H), 6.71(d, J=1.4 Hz, 2H), 6.44(s, 1H), 4.87(s, 1H), 3.83(s, 3H)
2n	7.66(d, J=15.9 Hz, 1H), 7.50(d, J=15.4 Hz, 2H), 7.19—7.08(m, 2H), 6.98(dd, J=28.2, 11.8 Hz, 2H), 6.86(d, J=15.9 Hz, 1H), 6.73—6.47(m, 2H), 6.04(s, 1H), 3.95(s, 3H)
3	14.89(s, 1H), 8.19—7.92(m, 3H), 7.84(t, J=7.5 Hz, 1H)
4	4.89(s, 1H), 8.18—8.05(m, 2H), 8.03—7.95(m, 1H), 7.84(dd, J=11.9, 4.4 Hz, 1H), 6.40(s, 2H)
5	8.38—8.30(m, 1H), 8.15(t, J=9.9 Hz, 1H), 8.00—7.92(m, 1H), 7.85—7.77(m, 1H), 6.15(s, 2H)

Compd.	¹H NMR(400 MHz, CDCl₃), δ
2a	7.85(dd, J=15.5, 4.4 Hz, 1H), 7.66(d, J=15.9 Hz, 1H), 7.36(dd, J=31.4, 4.2 Hz, 2H), 7.16(dd, J=8.2, 1.6 Hz, 1H), 7.11—7.05(m, 2H), 6.94(t, J=6.3 Hz, 1H), 6.87(dt, J=13.3, 6.5 Hz, 2H), 6.19(s, 1H), 3.93(s, 3H)
2b	7.69(t, J=17.0 Hz, 2H), 7.50(d, J=7.9 Hz, 2H), 7.18(dd, J=20.1, 8.1 Hz, 3H), 7.11—7.00(m, 2H), 6.93(t, J=12.5 Hz, 2H), 3.93(s, 3H), 2.37(s, 3H)
2c	8.84(d, J=2.0 Hz, 1H), 8.62(dd, J=4.8, 1.5 Hz, 1H), 7.93(dt, J=8.0, 1.8 Hz, 1H), 7.75—7.67(m, 2H), 7.37(dd, J=7.9, 4.8 Hz, 1H), 7.17(ddd, J=20.9, 7.4, 1.8 Hz, 3H), 6.95(dd, J=9.5, 6.4 Hz, 2H), 6.90(s, 1H), 3.96(s, 3H)
2d	8.51(s, 1H), 7.84(d, J=23.6 Hz, 2H), 7.48(s, 1H), 7.40(t, J=5.0 Hz, 3H), 7.20(s, 1H), 7.08(s, 1H), 6.98(s, 1H), 6.37(s, 1H), 4.91(s, 1H), 3.83(s, 3H)
2f	8.07(d, J=16.1 Hz, 1H), 7.67(d, J=15.8 Hz, 1H), 7.60(dd, J=7.7, 1.4 Hz, 1H), 7.40—7.32(m, 1H), 7.18—7.08(m, 3H), 7.00—6.89(m, 4H), 6.33(s, 1H), 3.92(s, 3H), 3.89(s, 3H)
2h	7.99(d, J=15.7 Hz, 1H), 7.59(dd, J=55.5, 11.6 Hz, 2H), 7.17—7.02(m, 3H), 6.93(d, J=8.9 Hz, 2H), 6.55—6.39(m, 2H), 6.21(s, 1H), 3.92(s, 3H), 3.87(s, 3H), 3.83(s, 3H)
2i	7.65(dd, J=16.2, 5.1 Hz, 2H), 7.54(dt, J=10.4, 5.2 Hz, 2H), 7.12(t, J=6.6 Hz, 1H), 7.09—7.02(m, 3H), 7.01—6.96(m, 1H), 6.93(dt, J=8.2, 2.1 Hz, 1H), 6.88(dt, J=15.7, 2.4 Hz, 1H), 6.45(s, 1H), 3.89(s, 3H)
Compd.	¹H NMR(400 MHz, CDCl₃), δ
2j	7.82—7.52(m, 3H), 7.40(s, 1H), 7.36(d, J=10.0 Hz, 2H), 7.20(s, 1H), 7.08(s, 1H), 6.93(s, 1H), 6.77(s, 1H), 5.05(s, 1H), 3.87(s, 3H), 3.85(s, 3H), 3.83(s, 3H)
2k	7.85—7.65(m, 3H), 7.64—7.55(m, 2H), 7.39(dd, J=9.9, 7.4 Hz, 3H), 7.22—7.05(m, 3H), 7.00—6.87(m, 2H), 3.92(s, 3H)
2l	8.44(s, 1H), 8.20(d, J=8.1 Hz, 1H), 7.85(d, J=7.6 Hz, 1H), 7.79—7.65(m, 2H), 7.62—7.53(m, 1H), 7.23—7.08(m, 3H), 6.91(dd, J=17.4, 12.0 Hz, 2H), 6.21(s, 1H), 3.93(s, 3H)
2m	7.76(d, J=57.1 Hz, 2H), 7.46(s, 2H), 7.39(d, J=10.0 Hz, 3H), 7.25(s, 1H), 7.20(s, 1H), 7.05(d, J=30.0 Hz, 2H), 6.71(d, J=1.4 Hz, 2H), 6.44(s, 1H), 4.87(s, 1H), 3.83(s, 3H)
2n	7.66(d, J=15.9 Hz, 1H), 7.50(d, J=15.4 Hz, 2H), 7.19—7.08(m, 2H), 6.98(dd, J=28.2, 11.8 Hz, 2H), 6.86(d, J=15.9 Hz, 1H), 6.73—6.47(m, 2H), 6.04(s, 1H), 3.95(s, 3H)
3	14.89(s, 1H), 8.19—7.92(m, 3H), 7.84(t, J=7.5 Hz, 1H)
4	4.89(s, 1H), 8.18—8.05(m, 2H), 8.03—7.95(m, 1H), 7.84(dd, J=11.9, 4.4 Hz, 1H), 6.40(s, 2H)
5	8.38—8.30(m, 1H), 8.15(t, J=9.9 Hz, 1H), 8.00—7.92(m, 1H), 7.85—7.77(m, 1H), 6.15(s, 2H)

Compd.	Appearance	Yield(%)	m. p./℃	HRMS, m/z(calcd.)[M+H]⁺
6a	Yellow solid	78	167—168	446.1163(446.1169)
6b	Yellow solid	53	151—152	454.1761(454.1761)
6c	Yellow solid	47	169—170	441.1545(441.1557)
6d	Yellow solid	61	180—182	441.1547(441.1557)
6e	Yellow solid	67	157—158	470.1702(470.1711)
6f	Yellow solid	76	163—165	470.1702(470.1711)
6g	Yellow solid	49	165—166	474.1207(474.1215)
6h	Yellow solid	28	154—155	500.1807(500.1816)
6i	Yellow solid	77	173—174	458.1499(458.1511)
6j	Yellow solid	43	153—154	500.1805(500.1816)
6k	Yellow solid	58	170—172	440.1594(440.1605)
6l	Yellow solid	34	211—212	485.1447(485.1456)
6m	Yellow solid	69	195—196	466.1751(466.1761)
6n	Yellow solid	81	167—168	430.1388(430.1398)

Compd.	Appearance	Yield(%)	m. p./℃	HRMS, m/z(calcd.)[M+H]⁺
6a	Yellow solid	78	167—168	446.1163(446.1169)
6b	Yellow solid	53	151—152	454.1761(454.1761)
6c	Yellow solid	47	169—170	441.1545(441.1557)
6d	Yellow solid	61	180—182	441.1547(441.1557)
6e	Yellow solid	67	157—158	470.1702(470.1711)
6f	Yellow solid	76	163—165	470.1702(470.1711)
6g	Yellow solid	49	165—166	474.1207(474.1215)
6h	Yellow solid	28	154—155	500.1807(500.1816)
6i	Yellow solid	77	173—174	458.1499(458.1511)
6j	Yellow solid	43	153—154	500.1805(500.1816)
6k	Yellow solid	58	170—172	440.1594(440.1605)
6l	Yellow solid	34	211—212	485.1447(485.1456)
6m	Yellow solid	69	195—196	466.1751(466.1761)
6n	Yellow solid	81	167—168	430.1388(430.1398)

Compd.	¹H NMR(500 or 400 MHz), δ	¹³C NMR(125 or 100 MHz), δ
6a	8.27(dd, J=7.9, 1.0 Hz, 1H), 8.21(d, J=7.9 Hz, 1H), 8.12—8.08(m, 1H), 7.96—7.88(m, 2H), 7.73(d, J=5.0 Hz, 1H), 7.66—7.54(m, 2H), 7.43(d, J=1.7 Hz, 1H), 7.31—7.14(m, 4H), 6.93(d, J=15.7 Hz, 1H), 6.26(s, 2H), 3.71(s, 3H)	188.17, 155.40, 150.85, 147.92, 143.88, 142.84, 140.34, 136.65, 135.90, 134.07, 133.14, 130.92, 130.67, 129.31, 128.96, 125.48, 125.21, 125.08, 123.19, 119.85, 118.20, 112.15, 77.33, 56.22
6b	8.38(dd, J=7.9, 1.0 Hz, 1H), 8.16(dd, J=8.1, 0.5 Hz, 1H), 8.00—7.95(m, 1H), 7.84—7.80(m, 1H), 7.73—7.62(m, 2H), 7.51(d, J=8.1 Hz, 2H), 7.21(d, J=8.0 Hz, 2H), 7.15(dd, J=6.4, 4.7 Hz, 3H), 7.06—6.92(m, 2H), 6.38(s, 2H), 3.84(s, 3H), 2.38(s, 3H)	188.83, 155.58, 151.08, 147.80, 143.96, 143.28, 142.68, 141.03, 135.44, 132.83, 132.07, 131.00, 129.73, 128.69, 128.43, 125.50, 124.87, 124.39, 122.30, 119.96, 118.70, 111.38, 77.30, 55.91, 21.57
Compd.	¹H NMR(500 or 400 MHz), δ	¹³C NMR(125 or 100 MHz), δ
6c	8.95(s, 1H), 8.63—8.60(m, 1H), 8.31(d, J=7.9 Hz, 1H), 8.24(t, J=7.4 Hz, 2H), 8.17—8.12(m, 1H), 8.01—7.95(m, 1H), 7.78(dd, J=19.7, 10.7 Hz, 2H), 7.54—7.44(m, 3H), 7.35(dd, J=8.3, 1.4 Hz, 1H), 7.29—7.23(m, 2H), 6.31(s, 2H), 3.76(s, 3H)	188.73, 155.34, 151.36, 150.88, 150.47, 148.02, 143.83, 143.68, 139.44, 136.58, 135.22, 133.99, 131.08, 130.82, 128.90, 127.58, 125.41, 124.45, 123.04, 119.80, 118.31, 112.27, 77.31, 56.19
6d	8.70—8.67(m, 1H), 8.32(dd, J=7.9, 1.0 Hz, 1H), 8.26(d, J=7.6 Hz, 1H), 8.17—8.12(m, 1H), 8.01—7.97(m, 1H), 7.90(td, J=7.7, 1.8 Hz, 1H), 7.81—7.71(m, 3H), 7.63(d, J=15.7 Hz, 1H), 7.51(d, J=1.8 Hz, 1H), 7.44(ddd, J=7.5, 4.7, 1.1 Hz, 1H), 7.40—7.35(m, 2H), 7.26(d, J=8.3 Hz, 1H), 6.31(s, 2H), 3.76(s, 3H)	189.03, 155.35, 153.33, 150.84, 150.52, 148.00, 143.84, 143.55, 141.91, 137.73, 136.61, 134.02, 130.78, 129.16, 128.92, 125.50, 125.43, 125.28, 125.21, 123.25, 119.81, 118.20, 112.29, 77.29, 56.19
6e	8.28(dd, J=25.2, 7.8 Hz, 2H), 8.15(t, J=7.2 Hz, 1H), 7.99(t, J=7.3 Hz, 1H), 7.77—7.68(m, 4H), 7.45(s, 1H), 7.26(ddd, J=29.4, 21.7, 12.1 Hz, 4H), 7.03(d, J=8.6 Hz, 2H), 6.30(s, 2H), 3.82(s, 3H), 3.76(s, 3H)	188.69, 161.71, 155.35, 150.89, 147.79, 143.84, 142.89, 142.54, 136.58, 133.99, 131.03, 130.81, 128.90, 127.79, 125.49, 125.42, 123.92, 122.85, 119.81, 118.38, 114.96, 112.22, 77.36, 56.18, 55.85
6f	8.38(dd, J=8.0, 1.0 Hz, 1H), 8.17—8.14(m, 1H), 8.05(d, J=16.1 Hz, 1H), 7.99—7.95(m, 1H), 7.84—7.80(m, 1H), 7.66—7.59(m, 2H), 7.38—7.34(m, 1H), 7.17—7.10(m, 4H), 7.01—6.91(m, 3H), 6.37(s, 2H), 3.91(s, 3H), 3.84(s, 3H)	188.86, 158.64, 155.32, 150.81, 147.87, 143.80, 142.98, 137.45, 136.54, 133.95, 132.54, 130.88, 128.87, 128.83, 126.10, 125.85, 125.39, 123.44, 122.98, 121.16, 119.77, 118.17, 112.25, 112.14, 77.27, 56.14, 56.13
6g	8.28(dd, J=7.9, 1.3 Hz, 1H), 8.22—8.19(m, 1H), 8.11(td, J=7.9, 1.3 Hz, 1H), 7.97—7.93(m, 1H), 7.79(d, J=8.6 Hz, 2H), 7.72(d, J=2.8 Hz, 1H), 7.68(s, 1H), 7.50—7.48(m, 2H), 7.41(d, J=1.8 Hz, 1H), 7.37(s, 1H), 7.30(dd, J=8.3, 1.8 Hz, 1H), 7.24(d, J=2.0 Hz, 1H), 7.21(d, J=5.7 Hz, 1H), 6.27(s, 2H), 3.72(s, 3H)	188.87, 155.41, 150.94, 148.02, 143.90, 143.44, 141.49, 136.66, 135.44, 134.29, 134.07, 130.93, 130.72, 129.56, 128.97, 126.70, 125.51, 125.48, 123.05, 119.87, 118.38, 112.32, 77.38, 56.25
6h	8.31(dd, J=7.9, 1.3 Hz, 1H), 8.26—8.23(m, 1H), 8.16—8.12(m, 1H), 8.00—7.96(m, 1H), 7.89(d, J=16.0 Hz, 1H), 7.75(d, J=8.5 Hz, 1H), 7.69(d, J=16.0 Hz, 1H), 7.44(d, J=1.9 Hz, 1H), 7.31(dd, J=8.4, 1.8 Hz, 1H), 7.24(dd, J=12.1, 5.0 Hz, 2H), 7.19(d, J=16.0 Hz, 1H), 6.63(dt, J=8.5, 2.3 Hz, 2H), 6.30(s, 2H), 3.90(s, 3H), 3.84(s, 3H), 3.75(s, 3H)	193.51, 168.20, 165.15, 160.16, 155.67, 152.55, 148.65, 147.14, 142.55, 141.50, 138.81, 135.84, 135.31, 133.60, 131.08, 130.35, 128.31, 127.68, 124.62, 123.11, 121.18, 116.94, 111.59, 103.66, 82.15, 61.08, 60.97, 60.82
6i	8.37(dd, J=8.0, 1.2 Hz, 1H), 8.15(d, J=8.0 Hz, 1H), 7.96(ddd, J=8.2, 7.3, 1.4 Hz, 1H), 7.84—7.79(m, 1H), 7.65(t, J=16.2 Hz, 2H), 7.60—7.57(m, 2H), 7.15—7.06(m, 5H), 6.95(dd, J=34.9, 15.9 Hz, 2H), 6.37(s, 2H), 3.83(s, 3H)	186.68, 162.87, 160.40, 153.21, 148.71, 145.77, 141.69, 141.07, 139.54, 134.46, 131.87, 129.75, 129.19, 129.10, 128.74, 126.77, 123.76, 123.29, 120.82, 117.66, 116.13, 114.46, 114.24, 110.07, 75.17, 54.03
6j	8.37—8.34(m, 1H), 8.15—8.13(m, 1H), 7.96(ddd, J=8.1, 6.1, 1.4 Hz, 1H), 7.82—7.79(m, 1H), 7.64(t, J=16.0 Hz, 2H), 7.17(dd, J=8.4, 1.9 Hz, 1H), 7.14—7.10(m, 4H), 6.96—6.85(m, 3H), 6.35(s, 2H), 3.92(s, 3H), 3.90(s, 3H), 3.82(s, 3H)	188.72, 155.66, 151.43, 151.09, 149.28, 147.81, 144.01, 143.41, 142.60, 135.53, 132.92, 131.08, 128.76, 127.81, 125.56, 124.77, 123.63, 123.30, 122.34, 120.00, 118.69, 111.43, 111.14, 109.86, 77.36, 56.09, 56.01, 55.97
6k	8.36(dd, J=7.7, 2.8 Hz, 1H), 8.14(dd, J=8.0, 3.4 Hz, 1H), 7.99—7.91(m, 1H), 7.80(td, J=7.3, 3.2 Hz, 1H), 7.74—7.56(m, 4H), 7.44—7.36(m, 3H), 7.17—7.03(m, 4H), 6.93(dt, J=13.7, 6.9 Hz, 1H), 6.36(s, 2H), 3.82(s, 3H)	188.86, 155.67, 151.12, 147.94, 144.01, 143.28, 143.02, 135.53, 134.88, 132.93, 130.96, 130.57, 129.05, 128.76, 128.48, 125.56, 125.34, 124.86, 122.44, 120.01, 118.69, 111.45, 77.35, 55.98
Compd.	¹H NMR(500 or 400 MHz), δ	¹³C NMR(125 or 100 MHz), δ
6l	8.58(d, J=1.3 Hz, 1H), 8.24(ddd, J=29.7, 9.4, 4.5 Hz, 5H), 8.12—8.08(m, 1H), 7.96—7.92(m, 1H), 7.79(ddd, J=24.7, 16.1, 2.2 Hz, 2H), 7.71(td, J=8.1, 2.6 Hz, 1H), 7.52(dd, J=16.1, 2.6 Hz, 1H), 7.41(s, 1H), 7.31(d, J=8.3 Hz, 1H), 7.23(dd, J=8.4, 2.6 Hz, 1H), 6.26(s, 2H), 3.71(s, 3H)	188.86, 155.41, 150.95, 148.91, 148.12, 143.90, 143.87, 140.43, 137.22, 136.67, 135.04, 134.08, 131.00, 130.86, 128.98, 128.49, 125.48, 125.47, 125.09, 123.31, 123.14, 119.87, 118.36, 112.33, 77.38, 56.26
6m	8.28(d, J=7.9 Hz, 1H), 8.22(d, J=8.0 Hz, 1H), 8.12(t, J=7.7 Hz, 1H), 7.95(t, J=7.6 Hz, 1H), 7.60—7.52(m, 4H), 7.39(dd, J=18.6, 10.7 Hz, 3H), 7.34—7.27(m, 3H), 7.18(dd, J=25.5, 8.6 Hz, 3H), 6.70(d, J=15.2 Hz, 1H), 6.26(s, 2H), 3.72(s, 3H)	188.81, 155.41, 150.96, 147.92, 143.91, 143.71, 142.63, 141.66, 136.66, 136.56, 134.07, 131.01, 130.23, 129.71, 129.46, 128.97, 127.98, 127.82, 125.49, 124.89, 123.11, 119.88, 118.43, 112.30, 77.42, 56.28
6n	8.33—8.29(m, 1H), 8.25(dt, J=6.4, 3.2 Hz, 1H), 8.17—8.11(m, 2H), 8.01—7.95(m, 2H), 7.91(d, J=1.5 Hz, 1H), 7.69—7.56(m, 2H), 7.48(d, J=1.8 Hz, 1H), 7.33(d, J=2.7 Hz, 1H), 7.00(dd, J=11.8, 9.6 Hz, 2H), 6.69(dd, J=3.4, 1.8 Hz, 1H), 6.30(s, 2H), 3.75(s, 3H)	188.20, 155.35, 151.47, 150.84, 147.87, 146.58, 143.83, 142.78, 136.59, 134.01, 130.90, 129.59, 128.90, 125.42, 125.24, 123.32, 123.10, 119.80, 118.26, 117.10, 113.57, 112.20, 77.31, 56.17