异海松酰基噻吩类磺酰胺的制备及其抗肿瘤活性研究

doi:10.3969/j.issn.0253-2417.2020.05.008

Abstract

Abstract:

Isopimaric chloride(compound 2) was synthesized by using isopimaric acid as raw material. Then four new isopimaric thiophene sulfonamides derivatives:isopimaric acid acyl-4-bromo-2, 5-dichlorothiophene-3-sulfonamide(5a), isopimaric acid acyl-5-bromothiophene-2-sulfonamide(5b), isopimaric acid acyl-5-chloro-4-nitro-sulfonamide (5c), and isopimaric acid acyl-thiophene-2-sulfonamide(5d) were prepared by aminolysis reaction from compound 2 and thiophere sulfonamides which were connected with p-phenylenediamine. The structures of the compound were confirmed by FT-IR, ¹H NMR, ¹³C NMR, and ESI-MS. In addition, the cell proliferation inhibition assay (MTT method) was used to study the in vitro inhibitory activity of 5a-5d on four human tumor cells. The results showed that compound 5b had inhibition rates of 91.36%, 94.06% and 92.26% against Hela, MDA-MB-231 and Hep G-2 at the concentration of 100 μmol/L, besides, the inhibition rate against PC-3 was 86.93%, which was close to 90%, indicating that compound 5b had good antitumor activity. Through the determination of IC₅₀ value, it was further concluded that the inhibition effect of compound 5b was better than that of 5-fluorouracil (5-FU), a widely used anticancer agent in clinic.

Key words: isopimaric acid, thiophene, sulfonamides, synthesis, characterization, biological activity

CLC Number:

TQ351

Yanju LU,Zhendong ZHAO,Liangwu BI,Yuxiang CHEN,Jing WANG,Yan GU. Synthesis and Antitumor Activity of Isopimaric Thiophene Sulfonamides Derivatives[J]. Chemistry and Industry of Forest Products, 2020, 40(5): 57-62.

Figures/Tables 3

References 15

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肿瘤细胞 cancer cell	10 μmol/L时的抑制率/% inhibitory rates under 10 μmol/L				100 μmol/L时的抑制率/% inhibitory rates under 100 μmol/L
肿瘤细胞 cancer cell	5a	5b	5c	5d	5a	5b	5c	5d
宫颈癌Hela	1.56	1.65	5.96	1.56	15.67	91.36	9.50	10.35
乳腺癌MDA-MB-231	2.13	3.44	0.91	3.35	19.10	94.06	21.04	4.57
前列腺癌PC-3	0.58	0.87	2.32	0.19	11.32	86.93	9.86	18.57
肝癌Hep G2	0.71	2.81	5.90	9.08	17.92	92.26	13.21	19.46

化合物 compound	半数抑制浓度median inhibitory concentration (IC₅₀)/(μmol·L^-1)
化合物 compound	Hela	MDA-MB-231	PC-3	Hep G2
5b	28.53	32.54	32.93	29.22
紫杉醇taxol	133.16	3.22	5.52	11.31
5-FU	52.60	76.30	36.36	31.70

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Synthesis and Antitumor Activity of Isopimaric Thiophene Sulfonamides Derivatives

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