Synthesis and Antibacterial Activities of 5-Methyl-1,2,4-triazole-3-thione Glucosides Compounds†

doi:10.7503/cjcu20150730

Abstract

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

CLC Number:

O626.26

TrendMD:

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^†[J]. Chem. J. Chinese Universities, 2016, 37(2): 246.

Figures/Tables 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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