Syntheses and Biological Activities of V-Shaped Symmetrical Triazolothiazine Oxadiazole Derivatives†

doi:10.7503/cjcu20140918

Abstract

Abstract:

To build V-shaped symmetrical structure thiadiazole derivatives, isophthalic acid and 5-aminoisophthalic acid condensed with 3-aliphatic-1,2,4-triazole(1) respectively. In POCl₃ presence, fourteen symmetrical V-shaped triazolo-thiadiazole derivatives(2a—2g and 3a—3g) were synthesized, wherein thirteen of them were first synthesized, and the structures of compounds 2 and 3 were characterized by infrared(IR), nuclear magnetic resonance(NMR) and high resolution mass spectrometer(HRMS). The inhibitory activities of the target compounds were screened for Cdc25B and PTP1B. The results showed that some compouds exhibited inhibitory activities against Cdc25B, compounds 3b and 3f may be used as potential Cdc25B inhibitors in the treatment of cancer. Compouds 3b—3g exhibited inhibitory activities against PTP1B. Compounds 3b and 3e may be used as potential PTP1B inhibitors in the treatment of diabetes.

Key words: 3-Aliphatic triazole, Drug activity screening, Cell devision cycle B(Cdc25B), Protein tyrosine phosphatase 1B(PTP1B)

CLC Number:

O626.23

TrendMD:

ZHANG Chenglu, WANG Xue, HU Xue, SUN Lijie, QU Ruifeng, GUO Yang, CHAI Jinhua, ZHU Chang’an. Syntheses and Biological Activities of V-Shaped Symmetrical Triazolothiazine Oxadiazole Derivatives^†[J]. Chem. J. Chinese Universities, 2015, 36(3): 463.

Figures/Tables 5

Scheme 1 Synthetic route of the target compounds a. R=C7H15; b. R=C9H19; c. R=C11H23; d. R=C13H27; e. R=C15H31; f. R=C17H35; g. R=Ph

Table 1 Melting points of compounds 1a—1g and 2g

Compd.	m. p.(ref.)/℃	Compd.	m. p.(ref.)/℃
1a	112.0—113.5(112.1—113.7^[19])	1e	108.5—110.0(108.8—110.0^[19])
1b	121.2—122.5(121.6—122.9^[19])	1f	110.0—111.6(110.2—112.1^[19])
1c	120.0—121.5(120.2—122.0^[19])	1g	204.0—205.5(204.0—205.3^[19])
1d	118.1—119.0(118.3—119.5^[19])	2g	>300(>300^[14])

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

Compd.	Appearance	Yield(%)	m. p./℃	IR(KBr), $ν ˙$ /cm^-1	HRMS(positive-SIMS, calcd.)[M+1], m/z
2a	Yellow powder	76.3	145.9—147.1	2914, 2845, 1682, 1618, 1466, 1378, 1237, 724	523.2426(523.2430)
Compd.	Appearance	Yield(%)	m. p./℃	IR(KBr), $ν ˙$ /cm^-1	HRMS(positive-SIMS, calcd.)[M+1], m/z
2b	Yellow powder	75.2	135.5—137.0	2921, 2856, 1642, 1585, 1474, 1317, 1228, 721	579.3052(579.3046)
2c	Yellow powder	71.8	138.7—140.3	2917, 2836, 1681, 1607, 1466, 1317, 1237, 721	635.3678(635.3686)
2d	Yellow powder	74.1	141.6—143.2	2915, 2834, 1642, 1575, 1474, 1335, 1214, 717	691.4304(691.4308)
2e	Yellow powder	70.3	139.7—141.5	2917, 2849, 1656, 1554, 1479, 1277, 1201, 714	747.4930(747.4936)
2f	Yellow powder	65.4	138.5—140.3	2920, 2845, 1652, 1607, 1466, 1306, 1228, 721	803.5556(803.5561)
3a	Yellow powder	65.2	189.9—191.4	3415, 2921, 2834, 1650, 1614, 1469, 1337, 1232, 717	538.2535(538.2530)
3b	Yellow powder	69.7	190.6—192.0	3441, 2920, 2845, 1657, 1607, 1477, 1343, 1248, 701	594.3161(594.3166)
3c	Yellow powder	61.4	192.7—194.2	3441, 2917, 2845, 1671, 1589, 1474, 1317, 1229, 719	650.3787(650.3780)
3d	Yellow powder	64.8	195.6—197.5	3434, 2914, 2856, 1676, 1564, 1466, 1237, 730	706.4413(706.4419)
3e	Yellow powder	60.4	196.8—198.2	3436, 2921, 2856, 1655, 1617, 1474, 1371, 1228, 714	762.5039(762.5037)
3f	Yellow powder	55.2	188.5—190.3	3331, 2908, 2836, 1650, 1607, 1466, 1357, 1177, 707	818.5665(818.5670)
3g	Yellow powder	64.6	280.5—282.2	3345, 2925, 2852, 1685, 1592, 1470, 755	494.0970(494.0979)

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

Compd.	Appearance	Yield(%)	m. p./℃	IR(KBr), $ν ˙$ /cm^-1	HRMS(positive-SIMS, calcd.)[M+1], m/z
2a	Yellow powder	76.3	145.9—147.1	2914, 2845, 1682, 1618, 1466, 1378, 1237, 724	523.2426(523.2430)
Compd.	Appearance	Yield(%)	m. p./℃	IR(KBr), $ν ˙$ /cm^-1	HRMS(positive-SIMS, calcd.)[M+1], m/z
2b	Yellow powder	75.2	135.5—137.0	2921, 2856, 1642, 1585, 1474, 1317, 1228, 721	579.3052(579.3046)
2c	Yellow powder	71.8	138.7—140.3	2917, 2836, 1681, 1607, 1466, 1317, 1237, 721	635.3678(635.3686)
2d	Yellow powder	74.1	141.6—143.2	2915, 2834, 1642, 1575, 1474, 1335, 1214, 717	691.4304(691.4308)
2e	Yellow powder	70.3	139.7—141.5	2917, 2849, 1656, 1554, 1479, 1277, 1201, 714	747.4930(747.4936)
2f	Yellow powder	65.4	138.5—140.3	2920, 2845, 1652, 1607, 1466, 1306, 1228, 721	803.5556(803.5561)
3a	Yellow powder	65.2	189.9—191.4	3415, 2921, 2834, 1650, 1614, 1469, 1337, 1232, 717	538.2535(538.2530)
3b	Yellow powder	69.7	190.6—192.0	3441, 2920, 2845, 1657, 1607, 1477, 1343, 1248, 701	594.3161(594.3166)
3c	Yellow powder	61.4	192.7—194.2	3441, 2917, 2845, 1671, 1589, 1474, 1317, 1229, 719	650.3787(650.3780)
3d	Yellow powder	64.8	195.6—197.5	3434, 2914, 2856, 1676, 1564, 1466, 1237, 730	706.4413(706.4419)
3e	Yellow powder	60.4	196.8—198.2	3436, 2921, 2856, 1655, 1617, 1474, 1371, 1228, 714	762.5039(762.5037)
3f	Yellow powder	55.2	188.5—190.3	3331, 2908, 2836, 1650, 1607, 1466, 1357, 1177, 707	818.5665(818.5670)
3g	Yellow powder	64.6	280.5—282.2	3345, 2925, 2852, 1685, 1592, 1470, 755	494.0970(494.0979)

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

Compd.	¹ H NMR(500 MHz, CDCl₃), δ	¹³ C NMR(125 MHz, CDCl₃ ), δ
2a	8.38(t, J=1.6 Hz, 1H), 8.09(dd, J=1.6 Hz, 7.9 Hz, 2H), 7.76(t, J=7.8 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.99—1.93(m, 4H), 1.50—1.45(m, 4H), 1.42—1.36(m, 4H), 1.33—1.29(m, 8H), 0.89(t, J=6.9 Hz, 6H)	160.04, 155.00, 152.15, 131.96, 130.92, 129.84, 125.43, 32.05, 29.21, 23.28, 22.56, 14.04
2b	8.37(s, 1H), 8.09(d, J=1.4 Hz, 7.8 Hz, 2H), 7.76(t, J=7.8 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.97—1.92(m, 4H), 1.53—1.44(m, 4H), 1.40—1.35(m, 4H), 1.30—1.23(m, 16H), 0.84(t, J=6.5 Hz, 6H).	160.05, 155.04, 152.17, 131.98, 130.93, 129.88, 125.45, 32.06, 29.64, 29.21, 23.20, 22.55, 14.03
2c	8.37(s, 1H), 8.09(dd, J=1.5 Hz, 7.9 Hz, 2H), 7.76(t, J=7.9 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.98—1.92(m, 4H), 1.51—1.44(m, 4H), 1.41—1.35(m, 4H), 1.27—1.25(m, 24H), 0.87(t, J=6.8 Hz, 6H).	160.02, 155.04, 152.10, 132.02, 130.96, 129.88, 125.43, 32.02, 29.65, 29.24, 23.20, 22.55, 14.08
2d	8.37(s, 1H), 8.10(dd, J=1.5 Hz, 7.9 Hz, 2H), 7.75(t, J=7.9 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.97—1.86(m, 4H), 1.50—1.35(m, 4H), 1.27—1.25(m, 36H), 0.88(t, J=6.8 Hz, 6H)	160.04, 155.05, 152.19, 132.01, 130.96, 129.84, 125.45, 32.06, 29.62, 29.21, 23.28, 22.56, 14.08
2e	8.37(s, 1H), 8.09(dd, J=1.4, 7.9 Hz, 2H), 7.65(t, J=7.8 Hz, 1H), 3.17(t, J=7.5 Hz, 4H), 1.95—1.90(m, 4H), 1.52—1.44(m, 4H), 1.34—1.32(m, 4H), 1.30—1.22(m, 40H), 0.87(t, J=6.5 Hz, 6H)	160.06, 155.02, 152.10, 131.98, 130.94, 129.84, 125.47, 32.08, 29.64, 29.25, 23.22, 22.57, 14.07
2f	8.37(d, J=1.6 Hz, 1H), 8.04(dd, J=1.6 Hz, 7.8 Hz, 2H), 7.68(t, J=7.8 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.95—1.92(m, 4H), 1.52—1.50(m, 4H), 1.48—1.34(m, 4H), 1.29—1.25(m, 48H), 0.87(t, J=6.9 Hz, 6H)	160.03, 155.05, 152.16, 132.03, 130.97, 129.84, 125.44, 32.05, 29.62, 29.23, 23.20, 22.55, 14.09
3a	7.46(s, 1H), 7.31(s, 2H), 6.11(s, 2H), 3.07(t, J=7.6 Hz, 4H), 1.75—1.70(m, 4H), 1.52—1.38(m, 4H), 1.36—1.33(m, 4H), 1.25—1.22(m, 8H), 0.86(t, J=6.9 Hz, 6H)	160.22, 155.06, 152.17, 149.55, 134.94, 115.85, 114.49, 31.90, 29.36, 23.27, 22.73, 14.14
Compd.	¹ H NMR(500 MHz, CDCl₃), δ	¹³ C NMR(125 MHz, CDCl₃ ), δ
3b	7.48(s, 1H), 7.34(s, 2H), 6.10(s, 2H), 3.06(t, J=7.6 Hz, 4H), 1.98—1.92(m, 4H), 1.50—1.45(m, 4H), 1.42—1.35(m, 4H), 1.33—1.29(m, 16H), 0.88(t, J=6.9 Hz, 6H)	160.25, 155.04, 152.10, 149.53, 134.95, 115.84, 114.47, 31.96, 29.65, 23.26, 22.73, 14.19
3c	7.49(s, 1H), 7.32(s, 2H), 6.11(s, 2H), 3.05(t, J=7.6 Hz, 4H), 1.98—1.91(m, 4H), 1.52—1.45(m, 4H), 1.36—1.29(m, 28H), 0.87(t, J=6.9 Hz, 6H)	160.26, 155.03, 152.07, 149.56, 134.94, 115.88, 114.46, 31.95, 29.66, 23.22, 22.74, 14.14
3d	7.44(s, 1H), 7.32(s, 2H), 6.10(s, 2H), 3.07(t, J=7.6 Hz, 4H), 1.83—1.60(m, 4H), 1.52—1.45(m, 4H), 1.36—1.29(m, 36H), 0.86(t, J=6.9 Hz, 6H)	160.27, 155.05, 152.03, 149.55, 134.96, 115.86, 114.47, 31.95, 29.65, 29.32, 23.22, 22.74, 14.14
3e	7.43(s, 1H), 7.32(s, 2H), 6.10(s, 2H), 3.06(t, J=7.6 Hz, 4H), 1.84—1.80(m, 4H), 1.65—1.52(m, 4H), 1.42—1.36(m, 4H), 1.34—1.24(m, 40H), 0.89(t, J=6.8 Hz, 6H)	160.25, 155.05, 152.02, 149.55, 134.97, 115.85, 114.46, 31.93, 29.66, 29.38, 23.23, 22.74, 14.13
3f	7.49(s, 1H), 7.33(s, 2H), 6.10(s, 2H), 3.09(t, J=7.6 Hz, 4H), 1.75—1.72(m, 4H), 1.64—1.61(m, 4H), 1.38—1.35(m, 4H), 1.35—1.25(m, 48H), 0.89—0.86(m, 6H)	160.24, 155.05, 152.04, 149.53, 134.96, 115.86, 114.48, 31.97, 29.66, 29.37, 23.23, 22.74, 14.12
3g	8.30—8.10(m, 4H), 7.70—7.55(m, 6H), 7.35(d, J=7.8 Hz, 1H), 7.10(s, 2H), 6.18(s, 2H)	160.46, 155.05, 152.23, 149.54, 134.86, 131.27, 130.67, 129.25, 127.34, 115.94

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

Compd.	¹ H NMR(500 MHz, CDCl₃), δ	¹³ C NMR(125 MHz, CDCl₃ ), δ
2a	8.38(t, J=1.6 Hz, 1H), 8.09(dd, J=1.6 Hz, 7.9 Hz, 2H), 7.76(t, J=7.8 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.99—1.93(m, 4H), 1.50—1.45(m, 4H), 1.42—1.36(m, 4H), 1.33—1.29(m, 8H), 0.89(t, J=6.9 Hz, 6H)	160.04, 155.00, 152.15, 131.96, 130.92, 129.84, 125.43, 32.05, 29.21, 23.28, 22.56, 14.04
2b	8.37(s, 1H), 8.09(d, J=1.4 Hz, 7.8 Hz, 2H), 7.76(t, J=7.8 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.97—1.92(m, 4H), 1.53—1.44(m, 4H), 1.40—1.35(m, 4H), 1.30—1.23(m, 16H), 0.84(t, J=6.5 Hz, 6H).	160.05, 155.04, 152.17, 131.98, 130.93, 129.88, 125.45, 32.06, 29.64, 29.21, 23.20, 22.55, 14.03
2c	8.37(s, 1H), 8.09(dd, J=1.5 Hz, 7.9 Hz, 2H), 7.76(t, J=7.9 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.98—1.92(m, 4H), 1.51—1.44(m, 4H), 1.41—1.35(m, 4H), 1.27—1.25(m, 24H), 0.87(t, J=6.8 Hz, 6H).	160.02, 155.04, 152.10, 132.02, 130.96, 129.88, 125.43, 32.02, 29.65, 29.24, 23.20, 22.55, 14.08
2d	8.37(s, 1H), 8.10(dd, J=1.5 Hz, 7.9 Hz, 2H), 7.75(t, J=7.9 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.97—1.86(m, 4H), 1.50—1.35(m, 4H), 1.27—1.25(m, 36H), 0.88(t, J=6.8 Hz, 6H)	160.04, 155.05, 152.19, 132.01, 130.96, 129.84, 125.45, 32.06, 29.62, 29.21, 23.28, 22.56, 14.08
2e	8.37(s, 1H), 8.09(dd, J=1.4, 7.9 Hz, 2H), 7.65(t, J=7.8 Hz, 1H), 3.17(t, J=7.5 Hz, 4H), 1.95—1.90(m, 4H), 1.52—1.44(m, 4H), 1.34—1.32(m, 4H), 1.30—1.22(m, 40H), 0.87(t, J=6.5 Hz, 6H)	160.06, 155.02, 152.10, 131.98, 130.94, 129.84, 125.47, 32.08, 29.64, 29.25, 23.22, 22.57, 14.07
2f	8.37(d, J=1.6 Hz, 1H), 8.04(dd, J=1.6 Hz, 7.8 Hz, 2H), 7.68(t, J=7.8 Hz, 1H), 3.17(t, J=7.6 Hz, 4H), 1.95—1.92(m, 4H), 1.52—1.50(m, 4H), 1.48—1.34(m, 4H), 1.29—1.25(m, 48H), 0.87(t, J=6.9 Hz, 6H)	160.03, 155.05, 152.16, 132.03, 130.97, 129.84, 125.44, 32.05, 29.62, 29.23, 23.20, 22.55, 14.09
3a	7.46(s, 1H), 7.31(s, 2H), 6.11(s, 2H), 3.07(t, J=7.6 Hz, 4H), 1.75—1.70(m, 4H), 1.52—1.38(m, 4H), 1.36—1.33(m, 4H), 1.25—1.22(m, 8H), 0.86(t, J=6.9 Hz, 6H)	160.22, 155.06, 152.17, 149.55, 134.94, 115.85, 114.49, 31.90, 29.36, 23.27, 22.73, 14.14
Compd.	¹ H NMR(500 MHz, CDCl₃), δ	¹³ C NMR(125 MHz, CDCl₃ ), δ
3b	7.48(s, 1H), 7.34(s, 2H), 6.10(s, 2H), 3.06(t, J=7.6 Hz, 4H), 1.98—1.92(m, 4H), 1.50—1.45(m, 4H), 1.42—1.35(m, 4H), 1.33—1.29(m, 16H), 0.88(t, J=6.9 Hz, 6H)	160.25, 155.04, 152.10, 149.53, 134.95, 115.84, 114.47, 31.96, 29.65, 23.26, 22.73, 14.19
3c	7.49(s, 1H), 7.32(s, 2H), 6.11(s, 2H), 3.05(t, J=7.6 Hz, 4H), 1.98—1.91(m, 4H), 1.52—1.45(m, 4H), 1.36—1.29(m, 28H), 0.87(t, J=6.9 Hz, 6H)	160.26, 155.03, 152.07, 149.56, 134.94, 115.88, 114.46, 31.95, 29.66, 23.22, 22.74, 14.14
3d	7.44(s, 1H), 7.32(s, 2H), 6.10(s, 2H), 3.07(t, J=7.6 Hz, 4H), 1.83—1.60(m, 4H), 1.52—1.45(m, 4H), 1.36—1.29(m, 36H), 0.86(t, J=6.9 Hz, 6H)	160.27, 155.05, 152.03, 149.55, 134.96, 115.86, 114.47, 31.95, 29.65, 29.32, 23.22, 22.74, 14.14
3e	7.43(s, 1H), 7.32(s, 2H), 6.10(s, 2H), 3.06(t, J=7.6 Hz, 4H), 1.84—1.80(m, 4H), 1.65—1.52(m, 4H), 1.42—1.36(m, 4H), 1.34—1.24(m, 40H), 0.89(t, J=6.8 Hz, 6H)	160.25, 155.05, 152.02, 149.55, 134.97, 115.85, 114.46, 31.93, 29.66, 29.38, 23.23, 22.74, 14.13
3f	7.49(s, 1H), 7.33(s, 2H), 6.10(s, 2H), 3.09(t, J=7.6 Hz, 4H), 1.75—1.72(m, 4H), 1.64—1.61(m, 4H), 1.38—1.35(m, 4H), 1.35—1.25(m, 48H), 0.89—0.86(m, 6H)	160.24, 155.05, 152.04, 149.53, 134.96, 115.86, 114.48, 31.97, 29.66, 29.37, 23.23, 22.74, 14.12
3g	8.30—8.10(m, 4H), 7.70—7.55(m, 6H), 7.35(d, J=7.8 Hz, 1H), 7.10(s, 2H), 6.18(s, 2H)	160.46, 155.05, 152.23, 149.54, 134.86, 131.27, 130.67, 129.25, 127.34, 115.94

Table 4 Inhibition of the target compounds for Cdc25B and PTP1B

Compd.	Ar	R	Cdc25B		PTP1B
Compd.	Ar	R	Inhibition(%)	I $C 50 a$ /(μg·mL^-1)	Inhibition(%)	I $C 50 a$ /(μg·mL^-1)
2a	C₆H₅	C₇H₁₅	10.96±1.11	NA^b	11.54±6.85	NA
2b	C₆H₅	C₉H₁₉	38.79±2.25	NA	66.28±7.26	≥5
2c	C₆H₅	C₁₁H₂₃	46.42±0.03	NA	33.57±8.78	NA
2d	C₆H₅	C₁₃H₂₇	43.34±0.64	NA	84.63±3.23	≥5
2e	C₆H₅	C₁₅H₃₁	46.91±3.19	NA	23.40±8.18	NA
2f	C₆H₅	C₁₇H₃₅	11.55±7.14	NA	6.85±3.50	NA
2g	C₆H₅	C₆H₅	10.66±5.19	NA	46.56±2.62	NA
3a	1-H₂NC₆H₄	C₇H₁₅	85.56±0.49	NA	79.72±0.36	≥5
3b	1-H₂NC₆H₄	C₉H₁₉	100.14±0.02	1.34±0.39	99.71±3.41	0.36±0.05
3c	1-H₂NC₆H₄	C₁₁H₂₃	99.55±0.53	2.75±0.41	88.40±2.23	4.55±0.63
3d	1-H₂NC₆H₄	C₁₃H₂₇	99.95±0.06	1.94±0.40	88.72±2.07	3.93±0.79
3e	1-H₂NC₆H₄	C₁₅H₃₁	90.43±0.19	4.40±1.19	95.32±0.91	0.97±0.08
3f	1-H₂NC₆H₄	C₁₇H₃₅	99.94±0.18	0.61±0.09	99.67±0.25	1.61±0.31
3g	1-H₂NC₆H₄	C₆H₅	88.76±0.18	≥5	86.42±5.78	3.25±0.40
Na₃VO₄				1.86±0.24
Oleanolic acid						1.11±0.09

Table 4 Inhibition of the target compounds for Cdc25B and PTP1B

Compd.	Ar	R	Cdc25B		PTP1B
Compd.	Ar	R	Inhibition(%)	I $C 50 a$ /(μg·mL^-1)	Inhibition(%)	I $C 50 a$ /(μg·mL^-1)
2a	C₆H₅	C₇H₁₅	10.96±1.11	NA^b	11.54±6.85	NA
2b	C₆H₅	C₉H₁₉	38.79±2.25	NA	66.28±7.26	≥5
2c	C₆H₅	C₁₁H₂₃	46.42±0.03	NA	33.57±8.78	NA
2d	C₆H₅	C₁₃H₂₇	43.34±0.64	NA	84.63±3.23	≥5
2e	C₆H₅	C₁₅H₃₁	46.91±3.19	NA	23.40±8.18	NA
2f	C₆H₅	C₁₇H₃₅	11.55±7.14	NA	6.85±3.50	NA
2g	C₆H₅	C₆H₅	10.66±5.19	NA	46.56±2.62	NA
3a	1-H₂NC₆H₄	C₇H₁₅	85.56±0.49	NA	79.72±0.36	≥5
3b	1-H₂NC₆H₄	C₉H₁₉	100.14±0.02	1.34±0.39	99.71±3.41	0.36±0.05
3c	1-H₂NC₆H₄	C₁₁H₂₃	99.55±0.53	2.75±0.41	88.40±2.23	4.55±0.63
3d	1-H₂NC₆H₄	C₁₃H₂₇	99.95±0.06	1.94±0.40	88.72±2.07	3.93±0.79
3e	1-H₂NC₆H₄	C₁₅H₃₁	90.43±0.19	4.40±1.19	95.32±0.91	0.97±0.08
3f	1-H₂NC₆H₄	C₁₇H₃₅	99.94±0.18	0.61±0.09	99.67±0.25	1.61±0.31
3g	1-H₂NC₆H₄	C₆H₅	88.76±0.18	≥5	86.42±5.78	3.25±0.40
Na₃VO₄				1.86±0.24
Oleanolic acid						1.11±0.09

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