5-甲基-1,2,4-三唑-3-硫酮类糖苷化合物的合成及抗菌活性

doi:10.7503/cjcu20150730

摘要/Abstract

摘要：

在KOH/丙酮体系中, 以5-甲基-4-N-取代苯基亚胺/胺基-1,2,4-三唑-3-硫酮为原料, 与溴-α-D-四乙酰葡萄糖进行Kenigs-Knorr反应合成了10个新颖的化合物—5-甲基-4-N-取代苯基亚胺基/胺基-3-S-(2',3',4',6'-四-O-乙酰基-β-D-吡喃葡萄糖基)-1,2,4-三唑(2a~2e, 5a~5e); 并在二氯甲烷/甲醇/甲醇钠混合体系中水解脱除乙酰基, 得到10个新颖的化合物—5-甲基-4-N-取代苯基亚胺基-3-S-(β-D-吡喃葡萄糖基)-1,2,4-三唑(3a~3e)及5-甲基-4-N-取代苯基胺基-3-S-(β-D-吡喃葡萄糖基)-1,2,4-三唑(6a~6e). 化合物的结构均经核磁共振波谱(NMR)、红外光谱(IR)和高分辨质谱(HRMS)分析确证. 生物活性测试结果表明, 目标化合物对大肠杆菌、金黄色葡萄球菌、枯草芽孢杆菌和白色念珠球菌普遍具有较好的抗菌活性. 化合物3d和3e对4种菌株的最小抑菌浓度相对较低, 表现出较强的广谱抗菌活性.

关键词: 5-甲基-4-N-取代苯基亚胺/胺基-1,2,4-三唑-3-硫酮, S-β-D-糖苷, 抗菌活性

Abstract:

Ten novel compounds of 5-methy-4-(N-substituted-phenyl) imino/amido-3-S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranoside)-1,2,4-triazole(2a—2e and 5a—5e) were synthesized via glycosylation of 5-methy-4-(N-substituted-phenyl) imino/amido-1,2,4-triazole-3-thiones with bromo-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in acetone in the presence of potassium hydroxide. Subsequently, ten novel compounds of 5-methy-4-(N-substituted-phenyl) imino/amido-3-S-(β-D-Glucopyranosyl)-1,2,4-triazole(3a—3e and 6a—6e) were generated by deacetylate reaction in the system of sodium methylate, methanol and dichloromethane. The structures of all compounds were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS spectra. The results of preliminary bioassay suggested that nearly all of the new compounds exerted variable inhibitory activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Monilia albican. Especially, compounds 3d and 3e had lower minimum inhibitory concentration values on four tested strains which showed the strong broad-spectrum antimicrobial activity and great development potential.

Key words: 5-Methy-4-(N-substituted-phenyl) imino/amido-1,2,4-triazole-3-thione, S-β-D-Glucoside, Antibacterial activity

中图分类号:

O626.26

TrendMD:

王宏韫, 刘金彪, 卢俊瑞, 应明, 杨旭云, 杨树勋, 马瑶. 5-甲基-1,2,4-三唑-3-硫酮类糖苷化合物的合成及抗菌活性. 高等学校化学学报, 2016, 37(2): 246.

WANG Hongyun, LIU Jinbiao, LU Junrui, YING Ming, YANG Xuyun, YANG Shuxun, MA Yao. Synthesis and Antibacterial Activities of 5-Methyl-1,2,4-triazole-3-thione Glucosides Compounds^†. Chem. J. Chinese Universities, 2016, 37(2): 246.

图/表 4

Scheme 1 Synthetic routes of the target compounds 3a—3e and 6a—6e

Table 1 Appearance, yield, melting point, ESI-TOF-MS and IR data of compounds 2a—2e,3a—3e, 5a—5e and 6a—6e

Compd.	Appearance	Yield(%)	m.p./℃	ESI-TOF-MS(calcd.), m/z [M+H]⁺	IR(KBr), $ν ˙$ /cm^-1
2a	Yellow solid	77.3	131.3—132.9	565.1608(565.1605)	3437, 2927, 1752, 1611, 1226, 1042, 912, 814, 763
2b	White solid	71.0	142.0—143.5	583.1288(583.1265)	2943, 1754, 1610, 1226, 1054, 913, 817, 763
2c	Yellow solid	85.1	134.3—135.9	629.0748(629.0748)	2948, 1751, 1610, 1224, 1046, 911, 815, 762
2d	Yellow solid	84.5	145.1—146.5	599.1214(599.1215)	3439, 2931, 1752, 1610, 1226, 1041, 912, 824, 662
2e	Yellow solid	79.6	101.4—102.9	644.2061(644.2059)	3429, 2940, 1754, 1614, 1227, 1040, 913, 826, 600
3a	White solid	60.4	120.3—121.8	397.1183(397.1170)	3426, 2927, 1614, 1033, 905, 812, 761
3b	Yellow solid	55.7	117.2—118.5	415.0855(415.0843)	3424, 2930, 1614, 1051, 912, 812, 676
3c	Yellow solid	57.0	90.4—91.8	461.0319(461.0318)	3417, 2924, 1614, 1047, 867, 760, 670
3d	Yellow solid	55.1	99.5—100.9	431.0799(431.0792)	3425, 2928, 1616, 1048, 889, 823, 662
3e	Yellow solid	64.3	110.3—111.6	476.0214(476.0210)	3368, 2911, 1614, 1049, 903, 886, 628
5a	Brown solid	72.7	177.3—178.8	565.2129(565.2129)	3320, 2947, 1757, 1609, 1377, 1227, 1061, 913, 821, 679
5b	White solid	85.1	176.2—177.5	582.6536(582.6535)	2942, 1750, 1611, 1377, 1227, 1061, 913, 821, 679
5c	White solid	88.1	155.1—156.4	628.2132(628.2127)	2937, 1755, 1614, 1226, 1041, 913, 819, 762
5d	White solid	82.3	99.6—100.9	600.3156(600.3154)	3334, 2927, 1752, 1609, 1368, 1227, 1042, 998, 841, 653
5e	Yellow solid	75.7	111.2—112.8	644.0922(644.0920)	3421, 2942, 1752, 1608, 1341, 1227, 1047, 938, 901, 763
6a	Yellow solid	55.3	133.0—134.5	397.0649(397.0648)	3282, 2919, 1610, 1049, 880, 811, 758
6b	White solid	53.9	109.2—110.8	415.3352(415.3350)	3415, 2920, 1642, 1050, 794, 701, 657
6c	White solid	55.7	122.0—123.5	460.0145(460.0144)	3451, 2921, 1606, 1046, 883, 758, 664
6d	White solid	45.2	108.2—109.6	429.9244(429.9243)	3441, 2924, 1611, 1042, 986, 858, 798
6e	White solid	40.9	133.2—134.8	476.4221(476.4218)	3442, 2931, 1614, 1049, 883, 698, 601

Table 1 Appearance, yield, melting point, ESI-TOF-MS and IR data of compounds 2a—2e,3a—3e, 5a—5e and 6a—6e

Compd.	Appearance	Yield(%)	m.p./℃	ESI-TOF-MS(calcd.), m/z [M+H]⁺	IR(KBr), $ν ˙$ /cm^-1
2a	Yellow solid	77.3	131.3—132.9	565.1608(565.1605)	3437, 2927, 1752, 1611, 1226, 1042, 912, 814, 763
2b	White solid	71.0	142.0—143.5	583.1288(583.1265)	2943, 1754, 1610, 1226, 1054, 913, 817, 763
2c	Yellow solid	85.1	134.3—135.9	629.0748(629.0748)	2948, 1751, 1610, 1224, 1046, 911, 815, 762
2d	Yellow solid	84.5	145.1—146.5	599.1214(599.1215)	3439, 2931, 1752, 1610, 1226, 1041, 912, 824, 662
2e	Yellow solid	79.6	101.4—102.9	644.2061(644.2059)	3429, 2940, 1754, 1614, 1227, 1040, 913, 826, 600
3a	White solid	60.4	120.3—121.8	397.1183(397.1170)	3426, 2927, 1614, 1033, 905, 812, 761
3b	Yellow solid	55.7	117.2—118.5	415.0855(415.0843)	3424, 2930, 1614, 1051, 912, 812, 676
3c	Yellow solid	57.0	90.4—91.8	461.0319(461.0318)	3417, 2924, 1614, 1047, 867, 760, 670
3d	Yellow solid	55.1	99.5—100.9	431.0799(431.0792)	3425, 2928, 1616, 1048, 889, 823, 662
3e	Yellow solid	64.3	110.3—111.6	476.0214(476.0210)	3368, 2911, 1614, 1049, 903, 886, 628
5a	Brown solid	72.7	177.3—178.8	565.2129(565.2129)	3320, 2947, 1757, 1609, 1377, 1227, 1061, 913, 821, 679
5b	White solid	85.1	176.2—177.5	582.6536(582.6535)	2942, 1750, 1611, 1377, 1227, 1061, 913, 821, 679
5c	White solid	88.1	155.1—156.4	628.2132(628.2127)	2937, 1755, 1614, 1226, 1041, 913, 819, 762
5d	White solid	82.3	99.6—100.9	600.3156(600.3154)	3334, 2927, 1752, 1609, 1368, 1227, 1042, 998, 841, 653
5e	Yellow solid	75.7	111.2—112.8	644.0922(644.0920)	3421, 2942, 1752, 1608, 1341, 1227, 1047, 938, 901, 763
6a	Yellow solid	55.3	133.0—134.5	397.0649(397.0648)	3282, 2919, 1610, 1049, 880, 811, 758
6b	White solid	53.9	109.2—110.8	415.3352(415.3350)	3415, 2920, 1642, 1050, 794, 701, 657
6c	White solid	55.7	122.0—123.5	460.0145(460.0144)	3451, 2921, 1606, 1046, 883, 758, 664
6d	White solid	45.2	108.2—109.6	429.9244(429.9243)	3441, 2924, 1611, 1042, 986, 858, 798
6e	White solid	40.9	133.2—134.8	476.4221(476.4218)	3442, 2931, 1614, 1049, 883, 698, 601

Table 2 1H NMR and 13C NMR data of compounds 2a—2e, 3a—3e, 5a—5e and 6a—6e

Compd.	¹H NMR(400 MHz, DMSO-d₆), δ	¹³C NMR(400 MHz, DMSO-d₆), δ
2a	10.30(s, 1H, OH), 8.86(s, 1H, N=CH), 7.54(t, J=7.6 Hz, 1H, ArH), 7.44(d, 1H, J=7.6 Hz, ArH), 7.04—7.12(m, 2H, ArH), 5.26(d, 1H, J_H1'—H2'=9.6 Hz, H1'), 5.12(t, 1H, J_H3'—H4'=5.6 Hz, J_H3'—H2'=8.2 Hz, H3'), 5.09(t, 1H, J_H2'—H3'=3.6 Hz, J_H2'—H1'=9.2 Hz, H2'), 5.09(t, 1H, J_H4'—H5'=J_H4'—H3'=3.6 Hz, H4'), 4.24(dd, 1H, J_H6'—H6″=4.8 Hz, J_H6'—H5'=4.4 Hz, H6'), 4.02(dd, 1H, J_H6″—H6'=J_H6″—H5'=3.2 Hz, H6″), 3.71(ddd, 1H, J_H5'—H4'=3.2 Hz, J_H5'—H6″=4.8 Hz, J_H5'—H6'=6.4 Hz, H5'), 2.56(s, 3H, CH₃), 2.10, 2.04, 2.02, 2.01(4s, 12H, CH₃CO)	170.33, 169.92, 169.57, 169.42, 169.36, 160.04, 150.97, 142.00, 135.50, 133.48, 120.26, 117.89, 115.82, 85.89, 76.36, 73.52, 70.03, 67.69, 61.52, 20.61, 20.59, 20.56, 20.52, 11.22
2b	9.23(s, 1H, N=CH), 8.16(d, J=8.0 Hz, 1H), 7.52(t, J=5.6 Hz, 2H, ArH), 7.41—7.45(m, 1H, ArH), 5.44(d, 1H, J_H1'—H2'=10.0 Hz, H1'), 5.27(t, 1H, J_H3'—H4'=9.6 Hz, J_H3'—H2'=9.2 Hz, H3'), 5.15(t, 1H, J_H2'—H3'=9.6 Hz, J_H2'—H1'=9.2 Hz, H2'), 5.09(d, 1H, J_H4'—H5'=J_H4'—H3'=9.6 Hz, H4'), 4.21(dd, 1H, J_H6'—H6″=4.8 Hz, J_H6'—H5'=5.2 Hz, H6'), 4.01(dd, 1H, J_H6″—H6'=J_H6″—H5'=1.6 Hz, H6″), 3.76(ddd, 1H, J_H5'—H4'=1.6 Hz, J_H5'—H6″=4.4 Hz, J_H5'—H6'=6.4 Hz, H5'), 2.59(s, 3H, CH₃), 2.08, 2.03, 2.02, 1.99(4s, 12H, CH₃CO)	170.47, 169.97, 169.56, 169.40, 160.06, 151.53, 142.44, 136.50, 133.91, 130.35, 129.51, 128.18, 127.48, 85.03, 76.20, 73.66, 70.09, 67.82, 61.63, 20.67, 20.64, 20.60, 20.55, 11.54
2c	9.18(s, 1H, N=CH), 8.14(d, J=6.4 Hz, 1H, ArH), 7.69(d, 1H, J=6.8 Hz, ArH), 7.45(s, 2H, ArH), 5.44(d, 1H, J_H1'—H2'=10.0 Hz, H1'), 5.26(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.07—5.17(m, 2H, H2', H4'), 4.20(dd, 1H, J_H6'—H6″=4.4 Hz, J_H6'—H5'=4.0 Hz, H6'), 4.02(dd, 1H, J_H6″—H6'=J_H6″—H5'=12.4 Hz, H6″), 3.76(d, 1H, J_H5'—H4'=6.8 Hz, H5'), 2.58(s, 3H, CH₃), 2.06, 2.02, 2.01, 1.98(4s, 12H, CH₃CO)	170.48, 170.11, 169.55, 169.41, 161.97, 151.51, 142.55, 134.06, 133.61, 131.02, 128.55, 128.06, 126.38, 84.96, 76.16, 73.64, 70.04, 67.78, 61.60, 20.65, 20.62, 20.58, 20.57, 11.61
2d	10.32(s, 1H, OH), 8.88(s, 1H, N=CH), 7.47(d, J=2.4 Hz, 1H), 7.43(d, J=2.4 Hz, 1H, ArH), 7.07(d, 1H, J=8.8 Hz, ArH), 5.24—5.29(m, 2H, H1', H3'), 5.13(t, 1H, J_H2'—H3'=J_H2'—H1'=9.6 Hz, H2'), 5.10(t, 1H, J_H4'—H5'=J_H4'—H3'=2.8 Hz, H4')4.26(dd, 1H, J_H6'—H6″=4.8 Hz, J_H6'—H5'=4.4 Hz, H6'), 4.03(dd, 1H, J_H6″—H6'=J_H6″—H5'=12.8 Hz, H6″), 3.70(ddd, 1H, J_H5'—H4'=1.8 Hz, J_H5'—H6″=2.8 Hz, J_H5'—H6'=6.4 Hz, H5'), 2.57(s, 3H, CH₃), 2.12, 2.05, 2.04, 2.03(4s, 12H, CH₃CO)	170.39, 170.01, 169.59, 169.33, 167.73, 158.51, 151.12, 141.94, 135.18, 132.15, 125.06, 119.49, 116.75, 86.17, 76.15, 73.49, 69.99, 67.56, 61.35, 20.65, 20.64, 20.55, 20.51, 11.27
2e	10.34(s, 1H, OH), 8.86(s, 1H, N=CH), 7.57—7.62(m, 2H, ArH), 7.02(d, J=8.8 Hz, 1H, ArH), 7.07(d, 1H, J=8.8 Hz, ArH), 5.24—5.28(m, 2H, H1', H3'), 5.13(t, 1H, J_H2'—H3'=J_H2'—H1'=5.2 Hz, H2'), 5.09(t, 1H, J_H4'—H5'=J_H4'—H3'=3.6	170.40, 170.05, 169.55, 169.40, 169.00, 152.36, 148.30, 134.15, 133.49, 126.64, 120.38, 119.45,
2e	Hz, H4'), 4.24(dd, 1H, J_H6'—H6″=4.8 Hz, J_H6'—H5'=4.4 Hz, H6'), 4.04(dd, 1H, J_H6″—H6'=4.8 Hz, J_H6″—H5'=5.2 Hz, H6″), 3.69—3.75(m, 1H, H5'), 2.57(s, 3H, CH₃), 2.11, 2.06, 2.03, 2.01(4s, 12H, CH₃CO)	116.33, 85.30, 76.33, 73.60, 69.98, 67.54, 61.62, 20.66, 20.63, 20.59, 20.54, 11.55
3a	10.44(s, 1H, OH), 10.14(s, 1H, N=CH), 7.88(d, 1H, J=8.4 Hz, ArH), 7.41—7.49(m, 1H, ArH), 6.95—7.02(m, 1H, ArH), 4.97(d, 1H, J=9.6 Hz, H1'), 4.90(d, 1H, J=3.6 Hz, H3'), 4.51(d, 1H, J=3.6 Hz, H2'), 3.68(d, 1H, J=8.0 Hz, H4'), 3.64—3.65(m, 1H, H6'), 3.58—3.61(m, 1H, H5', H6″), 3.10—3.17(m, 4H, OH), 2.35(s, 3H, CH₃)	168.47, 160.92, 159.94, 148.83, 134.38, 127.69, 120.06, 118.96, 77.48, 73.99, 73.06, 72.38, 61.43, 54.48, 11.24
3b	9.29(s, 1H, N=CH), 8.15(d, 1H, J=7.6 Hz, ArH), 7.56—7.66(m, 2H, ArH), 7.53—7.57(m, 1H, ArH), 5.51(d, 1H, J=9.6 Hz, H1'), 5.19(d, 1H, J=4.8 Hz, H3'), 5.01(d, 1H, J=5.2 Hz, H2'), 4.97(d, 1H, J=9.6 Hz, H4'), 4.38(t, 1H, J=5.6 Hz, H6'), 4.10—4.14(m, 1H, H6″), 3.55—3.59(m, 1H, H5'), 3.09—3.18(m, 4H, OH), 2.47(s, 3H, CH₃)	161.42, 150.61, 143.49, 135.56, 134.64, 130.82, 130.14, 128.89, 128.41, 87.41, 81.92, 78.33, 73.46, 70.08, 61.30, 11.54
3c	9.22(s, 1H, N=CH), 8.13(dd, 1H, J₁=2.8 Hz, J₂=3.2 Hz, ArH), 7.83(dd, 1H, J₁=2.8 Hz, J₂=3.6 Hz, ArH), 7.55—7.60(m, 2H, ArH), 5.50(d, 1H, J=5.6 Hz, H1'), 5.18(d, 1H, J=4.4 Hz, H3'), 4.98—5.01(m, 2H, H2', H4'), 4.37(t, 1H, J=5.6 Hz, H6'), 4.09—4.13(m, 1H, H6″), 3.55—3.59(m, 1H, H5'), 3.10—3.19(m, 4H, OH), 2.42(s, 3H, CH₃)	163.10, 150.75, 143.52, 134.76, 134.16, 131.73, 129.90, 129.23, 125.68, 87.37, 81.91, 78.36, 73.45, 70.07, 61.31, 11.62
3d	10.87(s, 1H, OH), 9.03(s, 1H, N=CH), 7.84(s, 1H, ArH), 7.49(d, 1H, J=6.8 Hz, ArH), 7.03(d, 1H, J=7.2 Hz, ArH), 5.47(d, 1H, J=4.8 Hz, H1'), 5.18(d, 1H, J=1.6 Hz, H3'), 4.86—5.00(m, 2H, H2', H4'), 4.72—4.75(m, 1H, H6'), 4.37—4.51(m, 1H, H6″), 3.58—3.60(m, 1H, H5'), 3.10—3.26(m, 4H, OH), 2.42(s, 3H, CH₃)	161.95, 157.84, 150.27, 143.70, 134.36, 127.27, 123.83, 120.03, 119.07, 87.42, 81.84, 78.34, 73.38, 73.10, 70.03, 11.41
3e	10.76(s, 1H, OH)9.01(s, 1H, N=CH), 7.96(s, 1H, ArH), 7.60(d, 1H, J=8.4 Hz, ArH), 6.97(d, 1H, J=8.8 Hz, ArH), 5.50(d, 1H, J=4.8 Hz, H1'), 5.19(d, 1H, J=2.8 Hz, H3'), 5.01(d, 1H, J=3.6 Hz, H2'), 4.95(d, 1H, J=9.6 Hz, H4'), 4.52—4.61(m, 1H, H6'), 3.49—3.68(m, 2H, H5', H6″), 3.10—3.19(m, 4H, OH), 2.42(s, 3H, CH₃)	161.29, 156.77, 150.44, 134.89, 134.77, 129.01, 124.55, 120.88, 120.19, 87.11, 82.09, 79.45, 73.46, 73.00, 70.91, 11.46
5a	10.37(s, 1H, OH), 7.22(t, 1H, J=7.6 Hz, ArH), 7.08(d, 1H, J=7.6 Hz, ArH), 6.92(d, 1H, J=8.0 Hz, ArH), 6.83(t, 1H, J=8.0 Hz, ArH), 5.64(d, 1H, J_H1'—H2'=10.2 Hz, H1'), 5.23(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.05(t, 1H, J_H2'—H3'=J_H2'—H1'=8.0 Hz, H2'), 4.97(t, 1H, J_H4'—H5'=J_H4'—H3'=10.0 Hz, H4'), 4.25(dd, 1H, J_H6'—H6″=4.4 Hz, J_H6'—H5'=5.2 Hz, H6'), 4.14(s, 2H, CH₂), 4.09(dd, 1H, J_H6″—H6'=J_H6″—H5'=5.2 Hz, H6″), 3.69—3.73(m, 1H, H5'), 2.20(s, 3H, CH₃), 2.12, 2.03, 2.02, 2.00(4s, 12H, CH₃CO)	170.63, 169.94, 169.54, 169.32, 156.04, 154.57, 145.15, 131.11, 130.19, 121.12, 120.31, 116.18, 85.99, 76.20, 73.36, 69.81, 67.75, 61.56, 52.48, 20.77, 20.66, 20.51, 20.41, 10.33
5b	7.43(d, 1H, J=7.6 Hz, ArH), 7.30—7.34(m, 1H, ArH), 7.24(t, 1H, J=7.2 Hz, ArH), 7.16—7.18(m, 1H, ArH), 5.60(d, 1H, J_H1'—H2'=10.4 Hz, H1'), 5.23(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.07(t, 1H, J_H2'—H3'=J_H2'—H1'=3.2 Hz, H2'), 5.03(t, 1H, J_H4'—H5'=J_H4'—H3'=3.6 Hz, H4'), 4.14(s, 2H, CH₂), 4.09(dd, 1H, J_H6'—H6″=J_H6'—H5'=2.0 Hz, H6'), 4.01(dd, 1H, J_H6″—H6'=J_H6″—H5'=6.0 Hz, H6″), 3.66—3.71(m, 1H, H5'), 2.24(s, 3H, CH₃), 2.16, 2.04, 2.03, 1.98(4s, 12H, CH₃CO)	170.44, 169.94, 169.53, 169.38, 160.15, 151.53, 142.42, 136.50, 133.91, 130.34, 129.50, 128.18, 85.00, 76.20, 73.66, 70.11, 67.84, 61.63, 52.57, 20.76, 20.60, 20.56, 20.53, 11.48
5c	7.61(d, 1H, J=1.2 Hz, ArH), 7.24—7.26(m, 1H, ArH), 7.21—7.22(m, 1H, ArH), 7.10—7.18(m, 1H, ArH), 5.52(d, 1H, J_H1'—H2'=9.4 Hz, H1'), 5.22(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.06(t, 1H, J_H2'—H3'=J_H2'—H1'=2.4 Hz, H2'), 5.02(t, 1H, J_H4'—H5'=J_H4'—H3'=2.8 Hz, H4'), 4.32(s, 2H, CH₂), 4.08(dd, 1H, J_H6'—H6″=2.4 Hz, J_H6'—H5'=4.0 Hz, H6'), 4.00(dd, 1H, J_H6″—H6'=8.0 Hz, J_H6″—H5'=6.0 Hz, H6″), 3.67—3.71(m, 1H, H5'), 2.23(s, 3H, CH₃), 2.15, 2.03, 2.02, 1.98(4s, 12H, CH₃CO)	170.22, 169.89, 169.54, 169.32, 154.79, 145.06, 134.58, 133.27, 131.75, 130.33, 127.87, 125.23, 86.09, 75.97, 73.20, 69.72, 67.83, 61.90, 56.20, 20.65, 20.59, 20.50, 20.46, 10.38
5d	10.08(s, 1H, OH), 7.29(s, 1H, ArH), 7.15(d, 1H, J=6.4 Hz, ArH), 6.93(d, 1H, J=9.2 Hz, ArH), 5.36(d, 1H, J_H1'—H2'=6.4 Hz, H1'), 5.23(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.06(t, 1H, J_H2'—H3'=J_H2'—H1'=10.0 Hz, H2'), 4.99(t, 1H,	170.63, 169.97, 169.44, 169.31, 154.98, 154.69, 145.21, 130.87, 129.84, 124.44, 123.01, 117.51,
5d	J_H4'—H5'=J_H4'—H3'=9.2 Hz, H4'), 4.34(s, 2H, CH₂), 4.23(dd, 1H, J_H6'—H6″=3.6 Hz, J_H6'—H5'=6.0 Hz, H6'), 4.12(dd, 1H, J_H6″—H6'=4.8 Hz, J_H6″—H5'=5.2 Hz, H6″), 3.72—3.45(m, 1H, H5'), 2.20(s, 3H, CH₃), 2.12, 2.05, 2.04, 2.02(4s, 12H, CH₃CO)	85.77, 76.35, 73.38, 69.77, 67.68, 61.52, 56.32, 20.80, 20.66, 20.59, 20.52, 10.34
5e	10.21(s, 1H, OH), 7.24(s, 1H, ArH), 7.10(d, 1H, J=6.4 Hz, ArH), 6.49—6.41(m, 1H, ArH), 5.22(d, 1H, J_H1'—H2'=9.4 Hz, H1'), 5.03(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 4.76(t, 1H, J_H2'—H3'=J_H2'—H1'=9.0 Hz, H2'), 4.33(t, 1H, J_H4'—H5'=J_H4'—H3'=8.0 Hz, H4'), 4.30(s, 2H, CH₂), 4.13(dd, 1H, J_H6'—H6″=9.6 Hz, J_H6'—H5'=6.0 Hz, H6'), 4.00(dd, 1H, J_H6″—H6'=6.8 Hz, J_H6″—H5'=4.2 Hz, H6″), 3.77—3.32(m, 1H, H5'), 2.29(s, 3H, CH₃), 2.16, 2.09, 2.04, 2.01(4s, 12H, CH₃CO)	170.24, 169.80, 169.50, 169.33, 154.30, 154.21, 144.39, 131.81, 129.88, 125.40, 124.90, 118.55, 85.30, 77.44, 73.85, 69.51, 67.77, 62.55, 56.30, 20.88, 20.77, 20.54, 20.49, 10.46
6a	9.53(s, 1H, OH), 7.11(t, 1H, J=7.2 Hz, ArH), 7.00(d, 1H, J=7.0 Hz, ArH), 6.75(d, 1H, J=8.0 Hz, ArH), 6.88—6.73(m, 1H, ArH), 5.53(d, 1H, J=2.8 Hz, H1'), 5.18(d, 1H, J=4.8 Hz, H3'), 5.03(d, 1H, J=5.2 Hz, H2'), 4.73(d, 1H, J=10.0 Hz, H4'), 4.54(t, 1H, J=4.8 Hz, H6″), 4.09(s, 2H, CH₂), 3.63(d, 1H, J=7.2 Hz, H6'), 3.10—3.25(m, 4H, OH), 3.03—3.07(m, 1H, H5'), 1.93(s, 3H, CH₃)	156.45, 153.69, 146.88, 131.57, 129.47, 122.95, 119.22, 115.46, 87.60, 81.70, 78.23, 73.35, 70.07, 61.38, 50.17, 10.17
6b	8.15(d, 1H, J=7.2 Hz, ArH), 7.65—6.67(m, 2H, ArH), 7.53—7.57(m, 1H, ArH), 5.50(d, 1H, J=6.0 Hz, H1'), 5.19(d, 1H, J=4.8 Hz, H3'), 4.96—5.02(m, 2H, H2', H4'), 4.38—4.39(m, 1H, H6″), 4.22(s, 2H, CH₂), 4.10—4.14(m, 1H, H6'), 3.55—3.59(m, 1H, H5'), 3.09—3.19(m, 4H, OH), 2.47(s, 3H, CH₃)	159.34, 155.73, 130.03, 129.55, 119.44, 118.04, 113.13, 110.19, 87.66, 82.52, 79.24, 73.30, 71.12, 62.30, 51.12, 10.39
6c	8.17(d, 1H, J=9.0 Hz, ArH), 7.82—7.89(m, 1H, ArH), 7.57—7.67(m, 2H, ArH), 5.51(d, 1H, J=6.4 Hz, H1'), 5.19(d, 1H, J=7.2 Hz, H3'), 4.92—5.05(m, 2H, H2', H4'), 4.38(t, 1H, J=5.2 Hz, H6″), 4.21(s, 2H, CH₂), 4.11—4.13(m, 1H, H6'), 3.56—3.57(m, 1H, H5'), 3.10—3.17(m, 4H, OH), 2.50(s, 3H, CH₃)	159.34, 154.77, 149.15, 144.34, 139.26, 130.18, 129.40, 125.34, 87.66, 82.54, 81.55, 78.25, 73.37, 70.12, 51.45, 10.46
6d	10.29(s, 1H, OH), 8.01(s, 1H, ArH), 7.45(d, 1H, J=8.0 Hz, ArH), 7.00(d, 1H, J=9.0 Hz, ArH), 5.40(d, 1H, J=6.8 Hz, H1'), 5.22(d, 1H, J=7.8 Hz, H3'), 4.88—4.80(m, 2H, H2', H4'), 4.63(t, 1H, J=5.0 Hz, H6″), 4.20(s, 2H, CH₂), 3.88—3.58(m, 2H, H6″, H5'), 3.22—3.07(m, 4H, OH), 1.93(s, 3H, CH₃)	159.66, 158.39, 146.38, 145.39, 139.30, 131.33, 129.46, 123.49, 87.88, 84.36, 82.55, 79.26, 74.30, 71.71, 51.70, 10.56
6e	10.21(s, 1H, OH), 8.35(s, 1H, ArH), 7.30(d, 1H, J=6.4 Hz, ArH), 7.02(d, 1H, J=6.4 Hz, ArH), 5.54(d, 1H, J=6.0 Hz, H1'), 5.24(d, 1H, J=4.8 Hz, H3'), 5.05(t, 2H, J=6.0 Hz, H2', H4'), 4.46(t, 1H, J=5.6 Hz, H6″), 4.21(s, 2H, CH₂), 3.60—3.49(m, 1H, H6″), 3.45—3.41(m, 1H, H5'), 3.20—3.14(m, 4H, OH), 2.21(s, 3H, CH₃)	154.65, 149.70, 143.25, 139.65, 130.45, 129.04, 128.66, 126.41, 87.50, 81.50, 78.39, 73.30, 70.12, 62.44, 52.01, 10.46

Table 2 1H NMR and 13C NMR data of compounds 2a—2e, 3a—3e, 5a—5e and 6a—6e

Compd.	¹H NMR(400 MHz, DMSO-d₆), δ	¹³C NMR(400 MHz, DMSO-d₆), δ
2a	10.30(s, 1H, OH), 8.86(s, 1H, N=CH), 7.54(t, J=7.6 Hz, 1H, ArH), 7.44(d, 1H, J=7.6 Hz, ArH), 7.04—7.12(m, 2H, ArH), 5.26(d, 1H, J_H1'—H2'=9.6 Hz, H1'), 5.12(t, 1H, J_H3'—H4'=5.6 Hz, J_H3'—H2'=8.2 Hz, H3'), 5.09(t, 1H, J_H2'—H3'=3.6 Hz, J_H2'—H1'=9.2 Hz, H2'), 5.09(t, 1H, J_H4'—H5'=J_H4'—H3'=3.6 Hz, H4'), 4.24(dd, 1H, J_H6'—H6″=4.8 Hz, J_H6'—H5'=4.4 Hz, H6'), 4.02(dd, 1H, J_H6″—H6'=J_H6″—H5'=3.2 Hz, H6″), 3.71(ddd, 1H, J_H5'—H4'=3.2 Hz, J_H5'—H6″=4.8 Hz, J_H5'—H6'=6.4 Hz, H5'), 2.56(s, 3H, CH₃), 2.10, 2.04, 2.02, 2.01(4s, 12H, CH₃CO)	170.33, 169.92, 169.57, 169.42, 169.36, 160.04, 150.97, 142.00, 135.50, 133.48, 120.26, 117.89, 115.82, 85.89, 76.36, 73.52, 70.03, 67.69, 61.52, 20.61, 20.59, 20.56, 20.52, 11.22
2b	9.23(s, 1H, N=CH), 8.16(d, J=8.0 Hz, 1H), 7.52(t, J=5.6 Hz, 2H, ArH), 7.41—7.45(m, 1H, ArH), 5.44(d, 1H, J_H1'—H2'=10.0 Hz, H1'), 5.27(t, 1H, J_H3'—H4'=9.6 Hz, J_H3'—H2'=9.2 Hz, H3'), 5.15(t, 1H, J_H2'—H3'=9.6 Hz, J_H2'—H1'=9.2 Hz, H2'), 5.09(d, 1H, J_H4'—H5'=J_H4'—H3'=9.6 Hz, H4'), 4.21(dd, 1H, J_H6'—H6″=4.8 Hz, J_H6'—H5'=5.2 Hz, H6'), 4.01(dd, 1H, J_H6″—H6'=J_H6″—H5'=1.6 Hz, H6″), 3.76(ddd, 1H, J_H5'—H4'=1.6 Hz, J_H5'—H6″=4.4 Hz, J_H5'—H6'=6.4 Hz, H5'), 2.59(s, 3H, CH₃), 2.08, 2.03, 2.02, 1.99(4s, 12H, CH₃CO)	170.47, 169.97, 169.56, 169.40, 160.06, 151.53, 142.44, 136.50, 133.91, 130.35, 129.51, 128.18, 127.48, 85.03, 76.20, 73.66, 70.09, 67.82, 61.63, 20.67, 20.64, 20.60, 20.55, 11.54
2c	9.18(s, 1H, N=CH), 8.14(d, J=6.4 Hz, 1H, ArH), 7.69(d, 1H, J=6.8 Hz, ArH), 7.45(s, 2H, ArH), 5.44(d, 1H, J_H1'—H2'=10.0 Hz, H1'), 5.26(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.07—5.17(m, 2H, H2', H4'), 4.20(dd, 1H, J_H6'—H6″=4.4 Hz, J_H6'—H5'=4.0 Hz, H6'), 4.02(dd, 1H, J_H6″—H6'=J_H6″—H5'=12.4 Hz, H6″), 3.76(d, 1H, J_H5'—H4'=6.8 Hz, H5'), 2.58(s, 3H, CH₃), 2.06, 2.02, 2.01, 1.98(4s, 12H, CH₃CO)	170.48, 170.11, 169.55, 169.41, 161.97, 151.51, 142.55, 134.06, 133.61, 131.02, 128.55, 128.06, 126.38, 84.96, 76.16, 73.64, 70.04, 67.78, 61.60, 20.65, 20.62, 20.58, 20.57, 11.61
2d	10.32(s, 1H, OH), 8.88(s, 1H, N=CH), 7.47(d, J=2.4 Hz, 1H), 7.43(d, J=2.4 Hz, 1H, ArH), 7.07(d, 1H, J=8.8 Hz, ArH), 5.24—5.29(m, 2H, H1', H3'), 5.13(t, 1H, J_H2'—H3'=J_H2'—H1'=9.6 Hz, H2'), 5.10(t, 1H, J_H4'—H5'=J_H4'—H3'=2.8 Hz, H4')4.26(dd, 1H, J_H6'—H6″=4.8 Hz, J_H6'—H5'=4.4 Hz, H6'), 4.03(dd, 1H, J_H6″—H6'=J_H6″—H5'=12.8 Hz, H6″), 3.70(ddd, 1H, J_H5'—H4'=1.8 Hz, J_H5'—H6″=2.8 Hz, J_H5'—H6'=6.4 Hz, H5'), 2.57(s, 3H, CH₃), 2.12, 2.05, 2.04, 2.03(4s, 12H, CH₃CO)	170.39, 170.01, 169.59, 169.33, 167.73, 158.51, 151.12, 141.94, 135.18, 132.15, 125.06, 119.49, 116.75, 86.17, 76.15, 73.49, 69.99, 67.56, 61.35, 20.65, 20.64, 20.55, 20.51, 11.27
2e	10.34(s, 1H, OH), 8.86(s, 1H, N=CH), 7.57—7.62(m, 2H, ArH), 7.02(d, J=8.8 Hz, 1H, ArH), 7.07(d, 1H, J=8.8 Hz, ArH), 5.24—5.28(m, 2H, H1', H3'), 5.13(t, 1H, J_H2'—H3'=J_H2'—H1'=5.2 Hz, H2'), 5.09(t, 1H, J_H4'—H5'=J_H4'—H3'=3.6	170.40, 170.05, 169.55, 169.40, 169.00, 152.36, 148.30, 134.15, 133.49, 126.64, 120.38, 119.45,
2e	Hz, H4'), 4.24(dd, 1H, J_H6'—H6″=4.8 Hz, J_H6'—H5'=4.4 Hz, H6'), 4.04(dd, 1H, J_H6″—H6'=4.8 Hz, J_H6″—H5'=5.2 Hz, H6″), 3.69—3.75(m, 1H, H5'), 2.57(s, 3H, CH₃), 2.11, 2.06, 2.03, 2.01(4s, 12H, CH₃CO)	116.33, 85.30, 76.33, 73.60, 69.98, 67.54, 61.62, 20.66, 20.63, 20.59, 20.54, 11.55
3a	10.44(s, 1H, OH), 10.14(s, 1H, N=CH), 7.88(d, 1H, J=8.4 Hz, ArH), 7.41—7.49(m, 1H, ArH), 6.95—7.02(m, 1H, ArH), 4.97(d, 1H, J=9.6 Hz, H1'), 4.90(d, 1H, J=3.6 Hz, H3'), 4.51(d, 1H, J=3.6 Hz, H2'), 3.68(d, 1H, J=8.0 Hz, H4'), 3.64—3.65(m, 1H, H6'), 3.58—3.61(m, 1H, H5', H6″), 3.10—3.17(m, 4H, OH), 2.35(s, 3H, CH₃)	168.47, 160.92, 159.94, 148.83, 134.38, 127.69, 120.06, 118.96, 77.48, 73.99, 73.06, 72.38, 61.43, 54.48, 11.24
3b	9.29(s, 1H, N=CH), 8.15(d, 1H, J=7.6 Hz, ArH), 7.56—7.66(m, 2H, ArH), 7.53—7.57(m, 1H, ArH), 5.51(d, 1H, J=9.6 Hz, H1'), 5.19(d, 1H, J=4.8 Hz, H3'), 5.01(d, 1H, J=5.2 Hz, H2'), 4.97(d, 1H, J=9.6 Hz, H4'), 4.38(t, 1H, J=5.6 Hz, H6'), 4.10—4.14(m, 1H, H6″), 3.55—3.59(m, 1H, H5'), 3.09—3.18(m, 4H, OH), 2.47(s, 3H, CH₃)	161.42, 150.61, 143.49, 135.56, 134.64, 130.82, 130.14, 128.89, 128.41, 87.41, 81.92, 78.33, 73.46, 70.08, 61.30, 11.54
3c	9.22(s, 1H, N=CH), 8.13(dd, 1H, J₁=2.8 Hz, J₂=3.2 Hz, ArH), 7.83(dd, 1H, J₁=2.8 Hz, J₂=3.6 Hz, ArH), 7.55—7.60(m, 2H, ArH), 5.50(d, 1H, J=5.6 Hz, H1'), 5.18(d, 1H, J=4.4 Hz, H3'), 4.98—5.01(m, 2H, H2', H4'), 4.37(t, 1H, J=5.6 Hz, H6'), 4.09—4.13(m, 1H, H6″), 3.55—3.59(m, 1H, H5'), 3.10—3.19(m, 4H, OH), 2.42(s, 3H, CH₃)	163.10, 150.75, 143.52, 134.76, 134.16, 131.73, 129.90, 129.23, 125.68, 87.37, 81.91, 78.36, 73.45, 70.07, 61.31, 11.62
3d	10.87(s, 1H, OH), 9.03(s, 1H, N=CH), 7.84(s, 1H, ArH), 7.49(d, 1H, J=6.8 Hz, ArH), 7.03(d, 1H, J=7.2 Hz, ArH), 5.47(d, 1H, J=4.8 Hz, H1'), 5.18(d, 1H, J=1.6 Hz, H3'), 4.86—5.00(m, 2H, H2', H4'), 4.72—4.75(m, 1H, H6'), 4.37—4.51(m, 1H, H6″), 3.58—3.60(m, 1H, H5'), 3.10—3.26(m, 4H, OH), 2.42(s, 3H, CH₃)	161.95, 157.84, 150.27, 143.70, 134.36, 127.27, 123.83, 120.03, 119.07, 87.42, 81.84, 78.34, 73.38, 73.10, 70.03, 11.41
3e	10.76(s, 1H, OH)9.01(s, 1H, N=CH), 7.96(s, 1H, ArH), 7.60(d, 1H, J=8.4 Hz, ArH), 6.97(d, 1H, J=8.8 Hz, ArH), 5.50(d, 1H, J=4.8 Hz, H1'), 5.19(d, 1H, J=2.8 Hz, H3'), 5.01(d, 1H, J=3.6 Hz, H2'), 4.95(d, 1H, J=9.6 Hz, H4'), 4.52—4.61(m, 1H, H6'), 3.49—3.68(m, 2H, H5', H6″), 3.10—3.19(m, 4H, OH), 2.42(s, 3H, CH₃)	161.29, 156.77, 150.44, 134.89, 134.77, 129.01, 124.55, 120.88, 120.19, 87.11, 82.09, 79.45, 73.46, 73.00, 70.91, 11.46
5a	10.37(s, 1H, OH), 7.22(t, 1H, J=7.6 Hz, ArH), 7.08(d, 1H, J=7.6 Hz, ArH), 6.92(d, 1H, J=8.0 Hz, ArH), 6.83(t, 1H, J=8.0 Hz, ArH), 5.64(d, 1H, J_H1'—H2'=10.2 Hz, H1'), 5.23(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.05(t, 1H, J_H2'—H3'=J_H2'—H1'=8.0 Hz, H2'), 4.97(t, 1H, J_H4'—H5'=J_H4'—H3'=10.0 Hz, H4'), 4.25(dd, 1H, J_H6'—H6″=4.4 Hz, J_H6'—H5'=5.2 Hz, H6'), 4.14(s, 2H, CH₂), 4.09(dd, 1H, J_H6″—H6'=J_H6″—H5'=5.2 Hz, H6″), 3.69—3.73(m, 1H, H5'), 2.20(s, 3H, CH₃), 2.12, 2.03, 2.02, 2.00(4s, 12H, CH₃CO)	170.63, 169.94, 169.54, 169.32, 156.04, 154.57, 145.15, 131.11, 130.19, 121.12, 120.31, 116.18, 85.99, 76.20, 73.36, 69.81, 67.75, 61.56, 52.48, 20.77, 20.66, 20.51, 20.41, 10.33
5b	7.43(d, 1H, J=7.6 Hz, ArH), 7.30—7.34(m, 1H, ArH), 7.24(t, 1H, J=7.2 Hz, ArH), 7.16—7.18(m, 1H, ArH), 5.60(d, 1H, J_H1'—H2'=10.4 Hz, H1'), 5.23(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.07(t, 1H, J_H2'—H3'=J_H2'—H1'=3.2 Hz, H2'), 5.03(t, 1H, J_H4'—H5'=J_H4'—H3'=3.6 Hz, H4'), 4.14(s, 2H, CH₂), 4.09(dd, 1H, J_H6'—H6″=J_H6'—H5'=2.0 Hz, H6'), 4.01(dd, 1H, J_H6″—H6'=J_H6″—H5'=6.0 Hz, H6″), 3.66—3.71(m, 1H, H5'), 2.24(s, 3H, CH₃), 2.16, 2.04, 2.03, 1.98(4s, 12H, CH₃CO)	170.44, 169.94, 169.53, 169.38, 160.15, 151.53, 142.42, 136.50, 133.91, 130.34, 129.50, 128.18, 85.00, 76.20, 73.66, 70.11, 67.84, 61.63, 52.57, 20.76, 20.60, 20.56, 20.53, 11.48
5c	7.61(d, 1H, J=1.2 Hz, ArH), 7.24—7.26(m, 1H, ArH), 7.21—7.22(m, 1H, ArH), 7.10—7.18(m, 1H, ArH), 5.52(d, 1H, J_H1'—H2'=9.4 Hz, H1'), 5.22(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.06(t, 1H, J_H2'—H3'=J_H2'—H1'=2.4 Hz, H2'), 5.02(t, 1H, J_H4'—H5'=J_H4'—H3'=2.8 Hz, H4'), 4.32(s, 2H, CH₂), 4.08(dd, 1H, J_H6'—H6″=2.4 Hz, J_H6'—H5'=4.0 Hz, H6'), 4.00(dd, 1H, J_H6″—H6'=8.0 Hz, J_H6″—H5'=6.0 Hz, H6″), 3.67—3.71(m, 1H, H5'), 2.23(s, 3H, CH₃), 2.15, 2.03, 2.02, 1.98(4s, 12H, CH₃CO)	170.22, 169.89, 169.54, 169.32, 154.79, 145.06, 134.58, 133.27, 131.75, 130.33, 127.87, 125.23, 86.09, 75.97, 73.20, 69.72, 67.83, 61.90, 56.20, 20.65, 20.59, 20.50, 20.46, 10.38
5d	10.08(s, 1H, OH), 7.29(s, 1H, ArH), 7.15(d, 1H, J=6.4 Hz, ArH), 6.93(d, 1H, J=9.2 Hz, ArH), 5.36(d, 1H, J_H1'—H2'=6.4 Hz, H1'), 5.23(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 5.06(t, 1H, J_H2'—H3'=J_H2'—H1'=10.0 Hz, H2'), 4.99(t, 1H,	170.63, 169.97, 169.44, 169.31, 154.98, 154.69, 145.21, 130.87, 129.84, 124.44, 123.01, 117.51,
5d	J_H4'—H5'=J_H4'—H3'=9.2 Hz, H4'), 4.34(s, 2H, CH₂), 4.23(dd, 1H, J_H6'—H6″=3.6 Hz, J_H6'—H5'=6.0 Hz, H6'), 4.12(dd, 1H, J_H6″—H6'=4.8 Hz, J_H6″—H5'=5.2 Hz, H6″), 3.72—3.45(m, 1H, H5'), 2.20(s, 3H, CH₃), 2.12, 2.05, 2.04, 2.02(4s, 12H, CH₃CO)	85.77, 76.35, 73.38, 69.77, 67.68, 61.52, 56.32, 20.80, 20.66, 20.59, 20.52, 10.34
5e	10.21(s, 1H, OH), 7.24(s, 1H, ArH), 7.10(d, 1H, J=6.4 Hz, ArH), 6.49—6.41(m, 1H, ArH), 5.22(d, 1H, J_H1'—H2'=9.4 Hz, H1'), 5.03(t, 1H, J_H3'—H4'=J_H3'—H2'=9.2 Hz, H3'), 4.76(t, 1H, J_H2'—H3'=J_H2'—H1'=9.0 Hz, H2'), 4.33(t, 1H, J_H4'—H5'=J_H4'—H3'=8.0 Hz, H4'), 4.30(s, 2H, CH₂), 4.13(dd, 1H, J_H6'—H6″=9.6 Hz, J_H6'—H5'=6.0 Hz, H6'), 4.00(dd, 1H, J_H6″—H6'=6.8 Hz, J_H6″—H5'=4.2 Hz, H6″), 3.77—3.32(m, 1H, H5'), 2.29(s, 3H, CH₃), 2.16, 2.09, 2.04, 2.01(4s, 12H, CH₃CO)	170.24, 169.80, 169.50, 169.33, 154.30, 154.21, 144.39, 131.81, 129.88, 125.40, 124.90, 118.55, 85.30, 77.44, 73.85, 69.51, 67.77, 62.55, 56.30, 20.88, 20.77, 20.54, 20.49, 10.46
6a	9.53(s, 1H, OH), 7.11(t, 1H, J=7.2 Hz, ArH), 7.00(d, 1H, J=7.0 Hz, ArH), 6.75(d, 1H, J=8.0 Hz, ArH), 6.88—6.73(m, 1H, ArH), 5.53(d, 1H, J=2.8 Hz, H1'), 5.18(d, 1H, J=4.8 Hz, H3'), 5.03(d, 1H, J=5.2 Hz, H2'), 4.73(d, 1H, J=10.0 Hz, H4'), 4.54(t, 1H, J=4.8 Hz, H6″), 4.09(s, 2H, CH₂), 3.63(d, 1H, J=7.2 Hz, H6'), 3.10—3.25(m, 4H, OH), 3.03—3.07(m, 1H, H5'), 1.93(s, 3H, CH₃)	156.45, 153.69, 146.88, 131.57, 129.47, 122.95, 119.22, 115.46, 87.60, 81.70, 78.23, 73.35, 70.07, 61.38, 50.17, 10.17
6b	8.15(d, 1H, J=7.2 Hz, ArH), 7.65—6.67(m, 2H, ArH), 7.53—7.57(m, 1H, ArH), 5.50(d, 1H, J=6.0 Hz, H1'), 5.19(d, 1H, J=4.8 Hz, H3'), 4.96—5.02(m, 2H, H2', H4'), 4.38—4.39(m, 1H, H6″), 4.22(s, 2H, CH₂), 4.10—4.14(m, 1H, H6'), 3.55—3.59(m, 1H, H5'), 3.09—3.19(m, 4H, OH), 2.47(s, 3H, CH₃)	159.34, 155.73, 130.03, 129.55, 119.44, 118.04, 113.13, 110.19, 87.66, 82.52, 79.24, 73.30, 71.12, 62.30, 51.12, 10.39
6c	8.17(d, 1H, J=9.0 Hz, ArH), 7.82—7.89(m, 1H, ArH), 7.57—7.67(m, 2H, ArH), 5.51(d, 1H, J=6.4 Hz, H1'), 5.19(d, 1H, J=7.2 Hz, H3'), 4.92—5.05(m, 2H, H2', H4'), 4.38(t, 1H, J=5.2 Hz, H6″), 4.21(s, 2H, CH₂), 4.11—4.13(m, 1H, H6'), 3.56—3.57(m, 1H, H5'), 3.10—3.17(m, 4H, OH), 2.50(s, 3H, CH₃)	159.34, 154.77, 149.15, 144.34, 139.26, 130.18, 129.40, 125.34, 87.66, 82.54, 81.55, 78.25, 73.37, 70.12, 51.45, 10.46
6d	10.29(s, 1H, OH), 8.01(s, 1H, ArH), 7.45(d, 1H, J=8.0 Hz, ArH), 7.00(d, 1H, J=9.0 Hz, ArH), 5.40(d, 1H, J=6.8 Hz, H1'), 5.22(d, 1H, J=7.8 Hz, H3'), 4.88—4.80(m, 2H, H2', H4'), 4.63(t, 1H, J=5.0 Hz, H6″), 4.20(s, 2H, CH₂), 3.88—3.58(m, 2H, H6″, H5'), 3.22—3.07(m, 4H, OH), 1.93(s, 3H, CH₃)	159.66, 158.39, 146.38, 145.39, 139.30, 131.33, 129.46, 123.49, 87.88, 84.36, 82.55, 79.26, 74.30, 71.71, 51.70, 10.56
6e	10.21(s, 1H, OH), 8.35(s, 1H, ArH), 7.30(d, 1H, J=6.4 Hz, ArH), 7.02(d, 1H, J=6.4 Hz, ArH), 5.54(d, 1H, J=6.0 Hz, H1'), 5.24(d, 1H, J=4.8 Hz, H3'), 5.05(t, 2H, J=6.0 Hz, H2', H4'), 4.46(t, 1H, J=5.6 Hz, H6″), 4.21(s, 2H, CH₂), 3.60—3.49(m, 1H, H6″), 3.45—3.41(m, 1H, H5'), 3.20—3.14(m, 4H, OH), 2.21(s, 3H, CH₃)	154.65, 149.70, 143.25, 139.65, 130.45, 129.04, 128.66, 126.41, 87.50, 81.50, 78.39, 73.30, 70.12, 62.44, 52.01, 10.46

Table 3 Antibacterial activity data of compounds 2a—2e, 3a—3e, 5a—5e and 6a—6e

Compd.	MIC/(μg·mL^-1)				Compd.	MIC/(μg·mL^-1)
Compd.	B.s.	S.a.	E.c.	M.a.	Compd.	B.s.	S.a.	E.c.	M.a.
2a	64	64	128	32	3a	32	8	32	2
2b	128	64	64	32	3b	32	16	32	8
2c	128	64	64	32	3c	32	16	4	16
2d	32	64	64	16	3d	16	2	4	2
2e	16	32	32	16	3e	2	2	2	8
5a	128	64	64	64	6a	128	8	64	32
5b	128	32	128	64	6b	128	32	64	32
5c	128	32	64	64	6c	128	32	32	16
5d	128	64	64	32	6d	128	32	64	32
5e	128	32	64	32	6e	128	32	32	32
Triclosan	16	4	2	32	Fluconazole	128	16	128	32

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