Synthesis and Bioactivity of 1,4-Bis[3-aliphatic/aryl -1,2,4-triazole[3,4-b]-1,3,4-thiatriazole-6-yl] Aryl Derivatives†

doi:10.7503/cjcu20131194

Abstract

Abstract:

Fourteen new bis-1,2,4-triazole[3,4-b]-[1,3,4]thiadiazol-6-yl derivatives(2 and 3) were synthesized in high yields through the reactions of six 3-aliphatic-1,2,4-triazole derivatives(1a—1f) and 3-phe-nyl-1,2,4-triazole(1g) with terephthalic acid and 2-aminoterephthalic acid, respectively, in the presence of phosphorus oxychloride. The structures of target compounds were characterized and the inhibitory properties of Cdc25B and PTP1B were studied. The results showed that compounds 2f, 3a and 3g exhibited high inhibitory activity against Cdc25B enzyme with IC₅₀ values of (3.45±0.60), (0.69±0.10) and (1.52±0.19) μg/mL, respectively. Compounds 3a and 3b showed high inhibitory activity against PTP1B with IC₅₀ values of (0.98±0.13) and (2.00±0.16) μg/mL.

Key words: 3-Aliphatic-1, 2, 4-triazole [3, 4-b]-1, 3, 4-thiatriazole, Cell division cycle 25B(Cdc25B), Protein tyrosine phosphatases 1B(PTP1B)

CLC Number:

O626.23

TrendMD:

ZHANG Chenglu, SUN Lijie, WU Feiyu, QU Ruifeng, ZHU Chang’an, WANG Xue, CHAI Jinhua, GUO Yang, HU Xue. Synthesis and Bioactivity of 1,4-Bis[3-aliphatic/aryl -1,2,4-triazole[3,4-b]-1,3,4-thiatriazole-6-yl] Aryl Derivatives^†[J]. Chem. J. Chinese Universities, 2014, 35(7): 1445.

Figures/Tables 5

Table 1 Appearance, yields, melting points, 1H NMR and IR data for compounds 1

Compd.	Appearance	Yield(%)	m. p./℃	¹ H NMR(500 MHz, DMSO-d₆), δ	IR(KBr), $ν ˙$ /cm^-1
1a	White solid	85.0	112.1—113.7	13.39(s, 1H), 5.50(s, 2H), 2.62(t, J=7.5 Hz, 2H), 1.65—1.60(m, 2H), 1.30—1.25(m, 8H), 0.87(t, J=6.8 Hz, 3H)	3292, 2915, 2750, 1921, 1605, 1562, 1384, 1234, 1138, 1016, 942, 769, 532
1b	White solid	83.7	121.6—122.9	13.40(s, 1H), 5.50(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.61(m, 2H), 1.29—1.25(m, 12H), 0.85(t, J=6.7 Hz, 3H)	3448, 2932, 2824, 1679, 1583, 1434, 1248, 1227, 1185, 1057, 954, 778, 524
1c	White solid	79.3	120.2—122.0	13.39(s, 1H), 5.42(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.59(m, 2H), 1.28—1.24(m, 16H), 0.79(t, J=6.6 Hz, 3H)	3386, 2901, 2846, 2587, 1621, 1578, 1447, 1368, 1304, 1215, 1131, 1076, 815
1d	White solid	81.8	118.3—119.5	13.38(s, 1H), 5.48(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.60(m, 2H), 1.29—1.24(m, 20H), 0.86(t, J=6.5 Hz, 3H)	3401, 2935, 2825, 2446, 1624, 1427, 1325, 1247, 1164, 1025, 964, 805, 653
1e	White solid	78.0	108.8—110.0	13.40(s, 1H), 5.46(s, 2H), 2.56(t, J=7.5 Hz, 2H), 1.63—1.60(m, 2H), 1.28—1.23(m, 24H), 0.86(t, J=6.5 Hz, 3H)	3378, 2834, 2815, 2545, 1621, 1454, 1425, 1326, 1314, 1224, 1152, 1034, 852
1f	White solid	75.3	110.2—112.1	13.32(s, 1H), 5.45(s, 2H), 2.56(t, J=7.4 Hz, 2H), 1.65—1.60(m, 2H), 1.29—1.23(m, 28H), 0.85(t, J=6.8 Hz, 3H)	3443, 2852, 2625, 1615, 1545, 1434, 1326, 1232, 1215, 1105, 946, 775
1g	White solid	84.5	204.0—205.3^*	14.61(s, 1H), 7.89(d, J=7.4 Hz, 2H), 7.66—7.58(m, 3H), 5.51(s, 2H)	3425, 3320, 3114, 1659, 1598, 1460, 1356, 1425, 1108, 956, 855, 767, 700

Table 1 Appearance, yields, melting points, 1H NMR and IR data for compounds 1

Compd.	Appearance	Yield(%)	m. p./℃	¹ H NMR(500 MHz, DMSO-d₆), δ	IR(KBr), $ν ˙$ /cm^-1
1a	White solid	85.0	112.1—113.7	13.39(s, 1H), 5.50(s, 2H), 2.62(t, J=7.5 Hz, 2H), 1.65—1.60(m, 2H), 1.30—1.25(m, 8H), 0.87(t, J=6.8 Hz, 3H)	3292, 2915, 2750, 1921, 1605, 1562, 1384, 1234, 1138, 1016, 942, 769, 532
1b	White solid	83.7	121.6—122.9	13.40(s, 1H), 5.50(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.61(m, 2H), 1.29—1.25(m, 12H), 0.85(t, J=6.7 Hz, 3H)	3448, 2932, 2824, 1679, 1583, 1434, 1248, 1227, 1185, 1057, 954, 778, 524
1c	White solid	79.3	120.2—122.0	13.39(s, 1H), 5.42(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.59(m, 2H), 1.28—1.24(m, 16H), 0.79(t, J=6.6 Hz, 3H)	3386, 2901, 2846, 2587, 1621, 1578, 1447, 1368, 1304, 1215, 1131, 1076, 815
1d	White solid	81.8	118.3—119.5	13.38(s, 1H), 5.48(s, 2H), 2.60(t, J=7.5 Hz, 2H), 1.65—1.60(m, 2H), 1.29—1.24(m, 20H), 0.86(t, J=6.5 Hz, 3H)	3401, 2935, 2825, 2446, 1624, 1427, 1325, 1247, 1164, 1025, 964, 805, 653
1e	White solid	78.0	108.8—110.0	13.40(s, 1H), 5.46(s, 2H), 2.56(t, J=7.5 Hz, 2H), 1.63—1.60(m, 2H), 1.28—1.23(m, 24H), 0.86(t, J=6.5 Hz, 3H)	3378, 2834, 2815, 2545, 1621, 1454, 1425, 1326, 1314, 1224, 1152, 1034, 852
1f	White solid	75.3	110.2—112.1	13.32(s, 1H), 5.45(s, 2H), 2.56(t, J=7.4 Hz, 2H), 1.65—1.60(m, 2H), 1.29—1.23(m, 28H), 0.85(t, J=6.8 Hz, 3H)	3443, 2852, 2625, 1615, 1545, 1434, 1326, 1232, 1215, 1105, 946, 775
1g	White solid	84.5	204.0—205.3^*	14.61(s, 1H), 7.89(d, J=7.4 Hz, 2H), 7.66—7.58(m, 3H), 5.51(s, 2H)	3425, 3320, 3114, 1659, 1598, 1460, 1356, 1425, 1108, 956, 855, 767, 700

Scheme 1 Syntheses of the target compounds 2 and 3

Table 2 Appearance, yields, melting points and HRMS data for compounds 2 and 3

Compd.	Appearance	Yield(%)	m. p. /℃	HRMS(positive-SIMS)[M+H]⁺, m/z(calcd.)
2a	Yellow solid	68.9	160.0—161.5	523.2421(523.2426)
2b	Yellow solid	82.1	159.4—161.1	579.3058(579.3052)
2c	Yellow solid	74.2	156.3—158.2	635.3674(635.3678)
2d	Yellow solid	64.6	157.4—160.0	691.4300(691.4304)
2e	Yellow solid	68.7	161.6—163.1	747.4933(747.4930)
2f	Yellow solid	70.8	162.7—164.5	803.5559(803.5556)
2g	Yellow solid	70.3	240.2—242.0	479.0852(479.0860)
3a	Yellow solid	63.4	210.3—212.0	538.2538(538.2535)
3b	Yellow solid	65.3	208.6—210.8	594.3158(594.3161)
3c	Yellow solid	67.9	205.5—207.0	650.3782(650.3787)
3d	Yellow solid	58.1	209.0—212.0	706.4410(706.4413)
3e	Yellow solid	55.0	210.1—211.5	762.5035(762.5039)
3f	Yellow solid	63.0	212.3—214.2	818.5669(818.5665)
3g	Yellow solid	60.3	250.3—251.7	494.0974(494.0970)

Table 3 1H NMR, 13C NMR and IR data for compounds 2 and 3

Compd.	¹ H NMR(500 MHz, DMSO-d₆), δ	¹³ C NMR(125 MHz, DMSO-d₆ ), δ	IR(KBr), $ν ˙$ /cm^-1
2a	8.06(s, 4H), 3.18(t, J=7.6 Hz, 4H), 1.98—1.92(m, 4H), 1.51—1.44(m, 4H), 1.38—1.35(m, 4H), 1.29—1.25(m, 8H), 0.88(t, J=7.1 Hz, 6H)	161.32, 155.39, 145.31, 132.50, 127.02, 31.78, 29.20, 23.21, 22.66, 22.46, 14.05	3426, 3322, 3158, 2936, 2846, 1673, 1599, 1465, 1391, 1153, 1063, 959, 841
2b	8.06(s, 4H), 3.15(t, J=7.6 Hz, 4H), 1.96—1.91(m, 4H), 1.50—1.44(m, 4H), 1.42—1.34(m, 4H), 1.27—1.22(m, 16H), 0.87(t, J=7.1 Hz, 6H)	161.17, 155.38, 145.20, 132.28, 127.14, 31.77, 29.23, 23.19, 22.73, 22.28, 14.01	3420, 3322, 3138, 2924, 2835, 1646, 1578, 1452, 1401, 1156, 959, 852
2c	8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.96—1.91(m, 4H), 1.51—1.41(m, 4H), 1.32—1.26(m, 28H), 0.87(t, J=6.6 Hz, 6H)	161.21, 155.36, 145.31, 132.03, 126.96, 31.78, 29.12, 23.23, 22.76, 22.51, 14.10	3423, 3330, 3117, 2920, 2856, 1647, 1569, 1456, 1415, 1148, 1067, 944, 827
2d	8.06(s, 4H), 3.15(t, J=7.1 Hz, 4H), 1.94—1.90(m, 4H), 1.48—1.45(m, 4H), 1.36—1.35(m, 4H), 1.27—1.25(m, 32H), 0.87(t, J=6.5 Hz, 6H)	161.28, 155.37, 145.29, 132.72, 127.79, 31.71, 29.23, 23.38, 22.68, 22.45, 14.17	3438, 3222, 3131, 2921, 2842, 1648, 1607, 1459, 1386, 1165, 1064, 942, 832
2e	8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.97—1.91(m, 4H), 1.53—1.44(m, 4H), 1.37—1.26(m, 44H), 0.87(t, J=6.6 Hz, 6H)	161.14, 155.16, 144.97, 132.52, 127.42, 31.78, 29.16, 23.21, 22.68, 22.46, 14.11	3437, 3304, 3117, 2920, 2842, 1653, 1589, 1456, 1375, 1154, 1015, 937, 825
2f	8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.97—1.91(m, 4H), 1.52—1.44(m, 4H), 1.38—1.35(m, 4H), 1.29—1.25(m, 48H), 0.88(t, J=6.7 Hz, 6H)	160.47, 155.37, 145.92, 132.32, 127.20, 31.81, 29.14, 23.22, 22.76, 22.53, 14.04	3441, 3323, 3145, 2927, 2847, 1652, 1458, 1387, 1168, 1057, 948, 857, 714
2g	8.30(m, 4H), 7.85(d, J=7.4 Hz, 4H), 7.50—7.45(m, 6H)	160.59, 155.13, 143.31, 133.47, 130.62, 129.16, 128.03, 127.45	3410, 3218, 2845, 2820, 1630, 1550, 1500, 1438, 1215, 944, 885, 765, 655
3a	7.68(d, J=8.3 Hz, 1H), 7.56(s, 1H), 7.21(d, J=8.2 Hz, 1H), 7.09(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.84—1.79(m, 4H), 1.38—1.25(m, 16H), 0.87—0.83(m, 6H)	171.13, 160.32, 155.36, 145.73, 145.13, 134.32, 128.81, 123.09, 118.02, 114.56, 31.69, 29.22, 23.27, 22.68, 22.37, 14.04	3424, 3335, 3178, 2935, 2841, 1608, 1456, 1378, 1156, 1057, 935, 846
3b	7.66(d, J=8.3 Hz, 1H), 7.55(s, 1H), 7.19(d, J=8.2 Hz, 1H), 7.08(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.83—1.79(m, 4H),1.39—1.26(m, 24H), 0.87—0.82(m, 6H)	171.04, 160.26, 155.36, 145.81, 145.13, 134.34, 128.82, 123.23, 118.01, 114.58, 31.71, 29.20, 23.38, 22.71, 22.41, 14.04	3413, 3320, 3154, 2933, 2865, 1617, 1456, 1390, 1160, 1063, 905, 850
3c	7.72(d, J=8.3 Hz, 1H), 7.58(s, 1H), 7.23(d, J=10.0 Hz, 1H), 7.08(s, 1H), 3.09(t, J=7.5 Hz, 2H), 3.04(t, J=7.4 Hz, 2H), 1.83—1.78(m, 4H), 1.35—1.21(m, 32H), 0.85—0.83(m, 6H)	171.36, 160.33, 155.41, 145.71, 144.95, 134.28, 128.76, 123.12, 118.41, 114.59, 31.72, 29.17, 23.28, 22.71, 22.30, 14.16	3434, 3307, 3125, 2935, 2805, 1614, 1456, 1414, 1161, 1026, 934, 851
3d	7.68(d, J=8.3 Hz, 1H), 7.50(s, 1H), 7.20(d, J=8.2 Hz, 1H), 7.08(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.85—1.79(m, 4H), 1.38—1.26(m, 40H), 0.87—0.82(m, 6H)	171.18, 160.31, 155.27, 145.68, 145.12, 134.19, 128.81, 123.13, 118.00, 114.62, 31.67, 29.14, 23.31, 22.69, 22.51, 14.03	3438, 3325, 2917, 2837, 1645, 1608, 1458, 1378, 1198, 1057, 915, 847
3e	7.72(d, J=8.3 Hz, 1H), 7.57(s, 1H), 7.24(d, J=10.0 Hz, 1H), 7.08(s, 1H), 3.09(t, J=7.5 Hz, 2H), 3.05(t, J=7.4 Hz, 2H), 1.84—1.78(m, 4H), 1.37—1.25(m, 48H), 0.83—0.81(m, 6H)	171.21, 160.28, 155.41, 145.67, 145.30, 134.31, 128.73, 123.13, 117.98, 114.63, 31.71, 29.16, 23.31, 22.80, 22.45, 14.15	3437, 3298, 3078, 2914, 2784, 1654, 1605, 1434, 1154, 1034, 951, 838
3f	7.68(d, J=8.3 Hz, 1H), 7.55(s, 1H), 7.17(d, J=8.3 Hz, 1H), 7.08(s, 2H), 3.09(t, J=7.4 Hz, 2H), 3.04(t, J=7.4 Hz, 2H), 1.81—1.79(m, 4H), 1.35—1.26(m, 56H), 0.86—0.82(m, 6H)	171.26, 160.31, 155.24, 145.63, 145.14, 134.29, 128.78, 123.30, 118.12, 114.58, 31.71, 29.12, 23.26, 22.72, 22.46, 14.03	3324, 3152, 2921, 2845, 1672, 1598, 1452, 1168, 1058, 949, 848, 718
3g	8.25—8.15(m, 4H), 7.75(d, J=7.1 Hz, 1H), 7.63(d, J=7.5 Hz, 1H), 7.51—7.45(m, 7H), 6.27(s, 2H)	171.13, 161.61, 155.08, 145.73, 143.31, 134.28, 131.08, 130.62, 129.23, 128.80, 127.47, 123.12, 118.07, 114.65	3320, 3120, 2923, 2856, 1658, 1599, 1480, 1410, 1205, 955, 845, 766, 680

Table 3 1H NMR, 13C NMR and IR data for compounds 2 and 3

Compd.	¹ H NMR(500 MHz, DMSO-d₆), δ	¹³ C NMR(125 MHz, DMSO-d₆ ), δ	IR(KBr), $ν ˙$ /cm^-1
2a	8.06(s, 4H), 3.18(t, J=7.6 Hz, 4H), 1.98—1.92(m, 4H), 1.51—1.44(m, 4H), 1.38—1.35(m, 4H), 1.29—1.25(m, 8H), 0.88(t, J=7.1 Hz, 6H)	161.32, 155.39, 145.31, 132.50, 127.02, 31.78, 29.20, 23.21, 22.66, 22.46, 14.05	3426, 3322, 3158, 2936, 2846, 1673, 1599, 1465, 1391, 1153, 1063, 959, 841
2b	8.06(s, 4H), 3.15(t, J=7.6 Hz, 4H), 1.96—1.91(m, 4H), 1.50—1.44(m, 4H), 1.42—1.34(m, 4H), 1.27—1.22(m, 16H), 0.87(t, J=7.1 Hz, 6H)	161.17, 155.38, 145.20, 132.28, 127.14, 31.77, 29.23, 23.19, 22.73, 22.28, 14.01	3420, 3322, 3138, 2924, 2835, 1646, 1578, 1452, 1401, 1156, 959, 852
2c	8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.96—1.91(m, 4H), 1.51—1.41(m, 4H), 1.32—1.26(m, 28H), 0.87(t, J=6.6 Hz, 6H)	161.21, 155.36, 145.31, 132.03, 126.96, 31.78, 29.12, 23.23, 22.76, 22.51, 14.10	3423, 3330, 3117, 2920, 2856, 1647, 1569, 1456, 1415, 1148, 1067, 944, 827
2d	8.06(s, 4H), 3.15(t, J=7.1 Hz, 4H), 1.94—1.90(m, 4H), 1.48—1.45(m, 4H), 1.36—1.35(m, 4H), 1.27—1.25(m, 32H), 0.87(t, J=6.5 Hz, 6H)	161.28, 155.37, 145.29, 132.72, 127.79, 31.71, 29.23, 23.38, 22.68, 22.45, 14.17	3438, 3222, 3131, 2921, 2842, 1648, 1607, 1459, 1386, 1165, 1064, 942, 832
2e	8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.97—1.91(m, 4H), 1.53—1.44(m, 4H), 1.37—1.26(m, 44H), 0.87(t, J=6.6 Hz, 6H)	161.14, 155.16, 144.97, 132.52, 127.42, 31.78, 29.16, 23.21, 22.68, 22.46, 14.11	3437, 3304, 3117, 2920, 2842, 1653, 1589, 1456, 1375, 1154, 1015, 937, 825
2f	8.06(s, 4H), 3.15(t, J=7.5 Hz, 4H), 1.97—1.91(m, 4H), 1.52—1.44(m, 4H), 1.38—1.35(m, 4H), 1.29—1.25(m, 48H), 0.88(t, J=6.7 Hz, 6H)	160.47, 155.37, 145.92, 132.32, 127.20, 31.81, 29.14, 23.22, 22.76, 22.53, 14.04	3441, 3323, 3145, 2927, 2847, 1652, 1458, 1387, 1168, 1057, 948, 857, 714
2g	8.30(m, 4H), 7.85(d, J=7.4 Hz, 4H), 7.50—7.45(m, 6H)	160.59, 155.13, 143.31, 133.47, 130.62, 129.16, 128.03, 127.45	3410, 3218, 2845, 2820, 1630, 1550, 1500, 1438, 1215, 944, 885, 765, 655
3a	7.68(d, J=8.3 Hz, 1H), 7.56(s, 1H), 7.21(d, J=8.2 Hz, 1H), 7.09(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.84—1.79(m, 4H), 1.38—1.25(m, 16H), 0.87—0.83(m, 6H)	171.13, 160.32, 155.36, 145.73, 145.13, 134.32, 128.81, 123.09, 118.02, 114.56, 31.69, 29.22, 23.27, 22.68, 22.37, 14.04	3424, 3335, 3178, 2935, 2841, 1608, 1456, 1378, 1156, 1057, 935, 846
3b	7.66(d, J=8.3 Hz, 1H), 7.55(s, 1H), 7.19(d, J=8.2 Hz, 1H), 7.08(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.83—1.79(m, 4H),1.39—1.26(m, 24H), 0.87—0.82(m, 6H)	171.04, 160.26, 155.36, 145.81, 145.13, 134.34, 128.82, 123.23, 118.01, 114.58, 31.71, 29.20, 23.38, 22.71, 22.41, 14.04	3413, 3320, 3154, 2933, 2865, 1617, 1456, 1390, 1160, 1063, 905, 850
3c	7.72(d, J=8.3 Hz, 1H), 7.58(s, 1H), 7.23(d, J=10.0 Hz, 1H), 7.08(s, 1H), 3.09(t, J=7.5 Hz, 2H), 3.04(t, J=7.4 Hz, 2H), 1.83—1.78(m, 4H), 1.35—1.21(m, 32H), 0.85—0.83(m, 6H)	171.36, 160.33, 155.41, 145.71, 144.95, 134.28, 128.76, 123.12, 118.41, 114.59, 31.72, 29.17, 23.28, 22.71, 22.30, 14.16	3434, 3307, 3125, 2935, 2805, 1614, 1456, 1414, 1161, 1026, 934, 851
3d	7.68(d, J=8.3 Hz, 1H), 7.50(s, 1H), 7.20(d, J=8.2 Hz, 1H), 7.08(s, 2H), 3.10(t, J=7.4 Hz, 2H), 3.05(t, J=7.5 Hz, 2H), 1.85—1.79(m, 4H), 1.38—1.26(m, 40H), 0.87—0.82(m, 6H)	171.18, 160.31, 155.27, 145.68, 145.12, 134.19, 128.81, 123.13, 118.00, 114.62, 31.67, 29.14, 23.31, 22.69, 22.51, 14.03	3438, 3325, 2917, 2837, 1645, 1608, 1458, 1378, 1198, 1057, 915, 847
3e	7.72(d, J=8.3 Hz, 1H), 7.57(s, 1H), 7.24(d, J=10.0 Hz, 1H), 7.08(s, 1H), 3.09(t, J=7.5 Hz, 2H), 3.05(t, J=7.4 Hz, 2H), 1.84—1.78(m, 4H), 1.37—1.25(m, 48H), 0.83—0.81(m, 6H)	171.21, 160.28, 155.41, 145.67, 145.30, 134.31, 128.73, 123.13, 117.98, 114.63, 31.71, 29.16, 23.31, 22.80, 22.45, 14.15	3437, 3298, 3078, 2914, 2784, 1654, 1605, 1434, 1154, 1034, 951, 838
3f	7.68(d, J=8.3 Hz, 1H), 7.55(s, 1H), 7.17(d, J=8.3 Hz, 1H), 7.08(s, 2H), 3.09(t, J=7.4 Hz, 2H), 3.04(t, J=7.4 Hz, 2H), 1.81—1.79(m, 4H), 1.35—1.26(m, 56H), 0.86—0.82(m, 6H)	171.26, 160.31, 155.24, 145.63, 145.14, 134.29, 128.78, 123.30, 118.12, 114.58, 31.71, 29.12, 23.26, 22.72, 22.46, 14.03	3324, 3152, 2921, 2845, 1672, 1598, 1452, 1168, 1058, 949, 848, 718
3g	8.25—8.15(m, 4H), 7.75(d, J=7.1 Hz, 1H), 7.63(d, J=7.5 Hz, 1H), 7.51—7.45(m, 7H), 6.27(s, 2H)	171.13, 161.61, 155.08, 145.73, 143.31, 134.28, 131.08, 130.62, 129.23, 128.80, 127.47, 123.12, 118.07, 114.65	3320, 3120, 2923, 2856, 1658, 1599, 1480, 1410, 1205, 955, 845, 766, 680

Table 4 Inhibition of target compounds against Cdc25B and PTP1B

Compd.	Cdc25B^a		PTP1B^b
Compd.	Inhibition(%)^c	IC₅₀/(μg·mL^-1)^d	Inhibition(%)^c	IC₅₀/(μg·mL^-1)^d
2a	98.68±0.15	NA	84.39±4.91	NA
2b	95.43±0.67	NA	62.49±3.71	NA
2c	24.77±1.33	NA	34.16±1.87	NA
2d	95.93±0.04	NA	40.98±0.48	NA
2e	77.86±0.10	NA	9.68±7.30	NA
2f	73.64±6.99	3.45±0.60	3.93±3.78	NA
2g	7.29±9.63	NA	60.44±8.95	NA
3a	99.90±0.03	0.69±0.10	88.85±4.41	0.98±0.13
3b	1.98±0.28	NA	76.73±1.75	2.00±0.16
3c	2.51±1.28	NA	82.89±2.30	NA
3d	8.02±1.34	NA	74.48±0.10	NA
3e	9.18±2.45	NA	61.77±4.98	NA
3f	6.70±2.47	NA	62.89±0.64	NA
3g	99.88±0.03	1.52±0.19	84.57±3.66	NA

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