Synthesis and Antibacterial Activities of Myricetin Derivatives ontaining Acidamide Moiety†

doi:10.7503/cjcu20160654

Abstract

Abstract:

Twelve novel myricetin derivatives containing acidamide moiety were designed and synthesized from myricetin. All the compounds were characterized by ¹H NMR, ¹³C NMR and HRMS. The preliminary bioassay results indicated that all of the title compounds exhibited a certain antibacterial activities in vitro against X. oryzae, X. citri and R. solanacearum. Moreover, These title compounds 3a, 3e, 3f, 3h and 3k displayed good antibacterial activities against the above three plant pathogenic bacteria. Especially, compound 3e displayed 100% inhibition rates against X. oryzae and R. solanacearum at 200 μg/mL, respectively, which is more than the control bismerthiazol(72.85% and 75.86%, repectively).

Key words: Myricetin derivatives, Acidamide, Antibacterial activity

CLC Number:

O625

TrendMD:

XIAO Wei, RUAN Xianghui, LI Qin, ZHANG Juping, ZHONG Xinmin, XIE Yan, WANG Xiaobin, HUANG Minguo, XUE Wei. Synthesis and Antibacterial Activities of Myricetin Derivatives ontaining Acidamide Moiety^†[J]. Chem. J. Chinese Universities, 2017, 38(1): 35.

Figures/Tables 5

References 32

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Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃
1a	128—129(130—131^[19])	1f	102—104(106^[24])	1j	85—87(88—90^[27])
1b	98—100(99—100^[20])	1g	47—49(48—49^[25])	1k	89—90(91—92^[28])
1c	90—91(89—90^[21])	1h	118—120(120—122^[26])	1l	77—79(80—82^[29])
1d	95—97(96.5^[22])	1i	170—171(169^[24])	2	234—235(232—234^[30])
1e	92—93(93.4—94.8^[23])

Compd.	m. p./℃	Compd.	m. p./℃	Compd.	m. p./℃
1a	128—129(130—131^[19])	1f	102—104(106^[24])	1j	85—87(88—90^[27])
1b	98—100(99—100^[20])	1g	47—49(48—49^[25])	1k	89—90(91—92^[28])
1c	90—91(89—90^[21])	1h	118—120(120—122^[26])	1l	77—79(80—82^[29])
1d	95—97(96.5^[22])	1i	170—171(169^[24])	2	234—235(232—234^[30])
1e	92—93(93.4—94.8^[23])

Compd.	R	Appearance	Yield(%)	m. p./℃	HRMS(Calcd.)[M+H]⁺
3a	4-F-Phenyl	White solid	43.2	196—198	540.1664(540.1659)
3b	3-Cl-Phenyl	White solid	46.2	167—169	556.1369(556.1364)
3c	Phenyl	White solid	62.6	183—184	522.1759(522.1751)
3d	n-Butyl	White solid	56.2	181—182	502.2064(502.2072)
3e	Benzyl	White solid	49.3	158—160	536.1915(536.1904)
3f	Cyclohexyl	White solid	56.4	150—151	528.2228(528.2222)
3g	2-OCH₃-Phenyl	White solid	71.8	193—195	552.1864(552.1855)
3h	4-OCH₃-Phenyl	White solid	63.4	117—119	552.1864(552.1856)
3i	4-Cl-Phenyl	White solid	47.2	233—235	556.1369(556.1368)
3j	2-F-Phenyl	White solid	64.7	122—124	540.1664(540.1659)
3k	2-CH₂CH₃-Phenyl	White solid	30.8	199—200	550.2072(550.2063)
3l	Cyclopentyl	White solid	51.6	192—194	514.2072(514.2064)

Compd.	R	Appearance	Yield(%)	m. p./℃	HRMS(Calcd.)[M+H]⁺
3a	4-F-Phenyl	White solid	43.2	196—198	540.1664(540.1659)
3b	3-Cl-Phenyl	White solid	46.2	167—169	556.1369(556.1364)
3c	Phenyl	White solid	62.6	183—184	522.1759(522.1751)
3d	n-Butyl	White solid	56.2	181—182	502.2064(502.2072)
3e	Benzyl	White solid	49.3	158—160	536.1915(536.1904)
3f	Cyclohexyl	White solid	56.4	150—151	528.2228(528.2222)
3g	2-OCH₃-Phenyl	White solid	71.8	193—195	552.1864(552.1855)
3h	4-OCH₃-Phenyl	White solid	63.4	117—119	552.1864(552.1856)
3i	4-Cl-Phenyl	White solid	47.2	233—235	556.1369(556.1368)
3j	2-F-Phenyl	White solid	64.7	122—124	540.1664(540.1659)
3k	2-CH₂CH₃-Phenyl	White solid	30.8	199—200	550.2072(550.2063)
3l	Cyclopentyl	White solid	51.6	192—194	514.2072(514.2064)

Compd.	¹H NMR(DMSO-d₆, 500 MHz), δ	¹³C NMR(DMSO-d₆, 125 MHz), δ
3a	10.40(s, 1H), 7.64(s, 2H), 7.43(s, 2H), 7.15(d, J=8.9 Hz, 2H), 6.87(d, J=2.2 Hz, 1H), 6.51(d, J=2.2 Hz, 1H), 4.55(s, 2H), 3.88(s, 3H), 3.83(d, J=4.9 Hz, 9H), 3.70(s, 3H)	172.94, 167.14, 164.61, 160.90, 159.71, 158.78, 157.80, 153.34, 152.43, 140.18, 140.12, 135.29, 125.67, 121.76, 115.97, 108.74, 106.50, 96.72, 93.76, 71.46, 60.71, 60.30, 56.76, 56.65
3b	10.52(s, 1H), 7.80(s, 1H), 7.51(t, J=9.9 Hz, 1H), 7.41(s, 2H), 7.32(d, J=8.2 Hz, 1H), 7.16—7.10(m, 1H), 6.86(s, 1H), 6.50(s, 1H), 4.57(s, 2H), 3.88(s, 3H), 3.83(s, 9H), 3.70(d, J=0.7 Hz, 3H)	172.96, 167.70, 164.62, 160.89, 158.77, 153.33, 152.44, 140.36, 140.17, 140.12, 133.59, 131.03, 125.64, 123.92, 119.44, 118.40, 108.71, 106.50, 96.71, 93.75, 71.53, 60.70, 56.74, 56.64, 56.36
3c	10.34(s, 1H), 7.61(d, J=8.1 Hz, 2H), 7.44(s, 2H), 7.29(t, J=7.7 Hz, 2H), 7.05(dd, J=10.7, 4.1 Hz, 1H), 6.87(d, J=1.5 Hz, 1H), 6.50(d, J=1.5 Hz, 1H), 4.55(s, 2H), 3.88(s, 3H), 3.83(d, J=2.9 Hz, 9H), 3.71(d, J=0.7 Hz, 3H)	172.99, 167.20, 164.61, 160.89, 158.78, 153.34, 152.42, 140.20, 138.88, 129.31, 125.68, 124.21, 119.98, 108.73, 106.49, 96.72, 93.75, 71.56, 60.71, 56.76, 56.65
3d	8.21(t, J=5.6 Hz, 1H), 7.38(s, 2H), 6.83(d, J=2.1 Hz, 1H), 6.48(d, J=2.1 Hz, 1H), 4.32(s, 2H), 3.87(s, 3H), 3.83(d, J=7.5 Hz, 9H), 3.72(s, 3H), 3.07(dd, J=13.1, 6.7 Hz, 2H), 1.39—1.33(m, 2H), 1.22(dd, J=14.9, 7.4 Hz, 2H), 0.83(t, J=7.3 Hz, 3H)	172.65, 167.99, 164.51, 160.86, 158.74, 153.34, 152.42, 140.13, 139.80, 125.70, 108.79, 106.41, 96.64, 93.72, 70.92, 60.71, 56.70, 56.65, 38.45, 31.70, 20.05, 14.19
3e	8.80(t, J=5.9 Hz, 1H), 7.39(s, 2H), 7.24(tt, J=14.1, 7.2 Hz, 5H), 6.84(s, 1H), 6.49(s, 1H), 4.43(s, 2H), 4.30(d, J=5.9 Hz, 2H), 3.87(s, 3H), 3.82(s, 3H), 3.78(s, 6H), 3.71(d, J=0.8 Hz, 3H)	172.62, 168.29, 164.52, 160.86, 158.73, 153.33, 152.39, 140.12, 139.74, 139.68, 128.76, 127.81, 127.33, 125.69, 108.79, 106.39, 96.65, 93.72, 70.72, 60.71, 56.70, 56.65, 56.61, 42.30
3f	7.96(d, J=7.9 Hz, 1H), 7.38(d, J=1.4 Hz, 2H), 6.81(s, 1H), 6.47(s, 1H), 4.30(s, 2H), 3.87(d, J=1.3 Hz, 3H), 3.84(d, J=1.3 Hz, 6H), 3.82(s, 3H), 3.72(d, J=1.5 Hz, 3H), 1.64(d, J=8.0 Hz, 4H), 1.51(d, J=11.9 Hz, 1H), 1.25—1.03(m, 6H)	172.65, 167.07, 164.48, 160.85, 158.72, 153.35, 152.39, 140.10, 139.93, 125.72, 108.79, 106.44, 96.63, 93.68, 70.99, 60.68, 56.68, 56.62, 47.83, 32.73, 25.67, 25.13
3g	9.49(s, 1H), 8.05(d, J=7.8 Hz, 1H), 7.33(d, J=1.4 Hz, 2H), 7.04(dd, J=17.6, 7.8 Hz, 2H), 6.90(t, J=7.5 Hz, 1H), 6.84(s, 1H), 6.50(s, 1H), 4.59(d, J=0.7 Hz, 2H), 3.88(d, J=1.6 Hz, 3H), 3.82(d, J=1.4 Hz, 3H), 3.80(d, J=1.5 Hz, 6H), 3.75(d, J=1.5 Hz, 3H), 3.70(d, J=1.7 Hz, 3H)	172.65, 166.94, 164.57, 160.88, 158.81, 153.37, 152.70, 149.52, 140.11, 139.94, 127.11, 125.65, 125.06, 121.03, 120.94, 111.64, 108.77, 106.35, 96.69, 93.75, 71.65, 60.70, 56.71, 56.65, 56.55, 56.29
3h	10.21(s, 1H), 7.52(d, J=9.0 Hz, 2H), 7.43(s, 2H), 6.86(dd, J=5.5, 3.3 Hz, 3H), 6.50(d, J=2.0 Hz, 1H), 4.51(s, 2H), 3.88(s, 3H), 3.83(d, J=3.7 Hz, 9H), 3.71(s, 3H), 3.69(s, 3H)	172.95, 166.65, 164.60, 160.89, 158.78, 156.01, 153.34, 152.43, 140.16, 131.99, 125.68, 121.54, 114.40, 108.73, 106.48, 96.71, 93.75, 71.51, 60.72, 56.75, 56.65, 55.69
3i	10.48(s, 1H), 7.66(s, 1H), 7.65(s, 1H), 7.43(s, 2H), 7.36(d, J=8.8 Hz, 2H), 6.87(d, J=2.2 Hz, 1H), 6.51(d, J=2.2 Hz, 1H), 4.56(s, 2H), 3.88(s, 3H), 3.83(d, J=4.5 Hz, 9H), 3.70(s, 3H)	172.96, 167.42, 164.63, 160.89, 158.78, 153.33, 152.45, 140.11, 137.87, 132.08, 129.23, 127.79, 125.66, 121.54, 108.71, 106.49, 96.72, 93.76, 71.49, 65.57, 60.71, 56.78, 56.64
3j	8.40(s, 1H), 7.39(s, 2H), 7.23(dd, J=14.0, 6.6 Hz, 2H), 7.14—7.02(m, 2H), 6.85(s, 1H), 6.49(s, 1H), 4.33(s, 2H), 3.88(s, 3H), 3.83(s, 9H), 3.71(d, J=0.9 Hz, 3H)	172.62, 168.23, 164.53, 162.17, 160.87, 158.74, 153.34, 152.37, 140.13, 139.75, 131.62, 128.83, 124.86, 115.72, 115.54, 108.79, 106.41, 96.66, 93.73, 70.80, 60.71, 56.72, 56.66
3k	9.84(s, 1H), 7.40(d, J=11.4 Hz, 3H), 7.24—7.19(m, 1H), 7.18—7.10(m, 2H), 6.87(d, J=2.2 Hz, 1H), 6.51(d, J=2.1 Hz, 1H), 4.57(s, 2H), 3.88(s, 3H), 3.83(d, J=4.9 Hz, 9H), 3.71(s, 3H), 2.58—2.52(m, 2H), 1.07(t, J=7.5 Hz, 3H)	173.00, 167.48, 164.63, 160.91, 158.82, 153.39, 152.62, 140.31, 140.18, 137.87, 135.46, 129.10, 126.57, 126.24, 125.70, 108.73, 106.51, 96.73, 93.76, 71.77, 60.71, 56.75, 56.68, 24.15, 14.59
Compd.	¹H NMR(DMSO-d₆, 500 MHz), δ	¹³C NMR(DMSO-d₆, 125 MHz), δ
3l	8.11(d, J=7.3 Hz, 1H), 7.39(s, 2H), 6.84(d, J=1.6 Hz, 1H), 6.49(d, J=1.7 Hz, 1H), 4.30(s, 2H), 3.99(dd, J=14.0, 6.9 Hz, 1H), 3.87(s, 3H), 3.83(d, J = 10.0 Hz, 9H), 3.72(s, 3H), 1.74(d, J=6.3 Hz, 2H), 1.59(s, 2H), 1.45(d, J=4.3 Hz, 2H), 1.38—1.29(m, 2H)	172.73, 167.55, 164.52, 160.87, 158.74, 153.35, 152.39, 140.12, 140.02, 125.73, 108.80, 106.46, 96.67, 93.72, 71.10, 60.70, 56.69, 50.51, 32.59, 23.93