N-(α-桐酸酰基)三唑类化合物的制备及其生物活性

doi:10.3969/j.issn.0253-2417.2022.03.004

Abstract

Abstract:

A series of N-(α-eleostearic acyl) triazole compounds derived from α-eleostearic acid were synthesized: N-(α-eleostearic acyl)-3, 5-dibromo-1, 2, 4-triazole(3a), N-(α-eleostearic acyl)-1, 2, 4-triazole(3b), N-(α-eleostearic acyl)-3-sulfhydryl-1, 2, 4-triazole(3c), N-(α-eleostearic acyl)-5-nitro-1, 2, 4-triazole(3d), N-(α-eleostearic acyl)-1, 2, 3-benzotriazole(3e), 3-(α-eleostearic acyl)-1, 2, 4-triazole(3f), 4-(α-eleostearic acyl)-1, 2, 4-triazole(3g). The products were confirmed by FT-IR, ¹H NMR, ¹³C NMR and MS. The results of biological activity experiments showed that compound 3a and 3e had inhibitory effect on hepatocarcinoma cells Hep G2, rectal carcinoma cells DLD-1 and breast cancer cells MCF-7. The 50% inhibition concentration(IC₅₀) of compound 3d on MCF-7 was 25.12 μmol/L, which was better than the IC₅₀ of 5-fluorouracil(5-Fu). All compounds had good inhibitory activity against Candida albicans, and inhibitory activities on against Escherichia coli and Staphylococcus aureus were not significant. The IC₅₀ of compound 3e against Candida albicans was 22.96 mg/L, which was similar to 5-flucytosine and indicated that it had the potential of drug development.

Key words: α-eleostearic acid, triazole, biological activity, derivatives

CLC Number:

TQ35

Jiang CHENG, Pujun XIE, Lixin HUANG, Caihong ZHANG, Lujie LIU. Synthesis and Biological Activity of N-(α-Eleostearic Acyl) Triazole Derivatives[J]. Chemistry and Industry of Forest Products, 2022, 42(3): 27-33.

Figures/Tables 4

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Table 1

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References 16

1	ZHANG X , ZHANG H . 3D-QSAR studies on 1, 2, 4-triazolyl 5-azaspiro[2.4]-heptanes as D₃R antagonists[J]. Chemical Physics Letters, 2018, 704, 11- 20. doi: 10.1016/j.cplett.2018.05.022
2	VENEPALLY V , REDDY JALA R C . An insight into the biological activities of heterocyclic-fatty acid hybrid molecules[J]. European Journal of Medicinal Chemistry, 2017, 141, 113- 137. doi: 10.1016/j.ejmech.2017.09.069
3	RAUF A , GANGAL S . Facile one-pot synthesis of N-acyl-1H-1, 2, 3benzotriazoles from internal and terminal olefinic fatty acids and their antimicrobial screening[J]. Journal of Oleo Science, 2008, 57 (8): 453- 457. doi: 10.5650/jos.57.453
4	AHMAD A , VARSHNEY H , RAUF A , et al. Synthesis and anticancer activity of long chain substituted 1, 3, 4-oxadiazol-2-thione, 1, 2, 4-triazol-3-thione and 1, 2, 4-triazolo[3, 4-b]-1, 3, 4-thiadiazine derivatives[J]. Arabian Journal of Chemistry, 2017, 10, S3347- S3357. doi: 10.1016/j.arabjc.2014.01.015
5	SHARMA S , GANGAL S , RAUF A , et al. Synthesis, antibacterial and antifungal activity of some novel 3, 5-disubstituted-1H-1, 2, 4-triazoles[J]. Archiv Der Pharmazie, 2008, 341 (11): 714- 720. doi: 10.1002/ardp.200800005
6	CHEN G C , CHEN W H , TSENG K T , et al. The anti-adiposity effect of bitter melon seed oil is solely attributed to its fatty acid components[J]. Lipids in Health and Disease, 2017, 16, 1- 10. doi: 10.1186/s12944-016-0392-3
7	YOO Y , YOUNGBLOOD J P . Tung oil wood finishes with improved weathering, durability, and scratch performance by addition of cellulose nanocrystals[J]. ACS Applied Materials and Interfaces, 2017, 9 (29): 24936- 24946. doi: 10.1021/acsami.7b04931
8	ZHOU J , LIU Y , HU Y , et al. Synthesis of novel urushiol-like compounds from tung oil using silica-supported phosphotungstic heteropoly acid catalyst[J]. Industrial Crops and Products, 2016, 94, 424- 430. doi: 10.1016/j.indcrop.2016.09.013
9	CHEN G C , SU H M , LIN Y S , et al. A conjugated fatty acid present at high levels in bitter melon seed favorably affects lipid metabolism in hepatocytes by increasing NAD(+)/NADH ratio and activating PPAR alpha, AMPK and SIRT1 signaling pathway[J]. Journal of Nutritional Biochemistry, 2016, 33, 28- 35. doi: 10.1016/j.jnutbio.2016.03.009
10	SAHA S S , DASGUPTA P , SENGUPTA S , et al. Synergistic effect of conjugated linolenic acid isomers against induced oxidative stress, inflammation and erythrocyte membrane disintegrity in rat model[J]. Biochimica et Biophysica Acta, 2012, 1820 (12): 1951- 1970. doi: 10.1016/j.bbagen.2012.08.021
11	ZHUO R J , WANG F , ZHANG X H , et al. α-Eleostearic acid inhibits growth and induces apoptosis in breast cancer cells via HER2/HER3 signaling[J]. Molecular Medicine Reports, 2014, 9 (3): 993- 998. doi: 10.3892/mmr.2014.1892
12	CHENG J , LIU L , HUANG L X , et al. Mass transfer modeling of α-eleostearic acid from tung oil concentration by low-temperature crystallization[J]. Chemistryselect, 2020, 5 (15): 4715- 4721. doi: 10.1002/slct.202000206
13	FARAG A B , EWIDA H A , AHMED M S . Design, synthesis, and biological evaluation of novel amide and hydrazide based thioether analogs targeting Histone deacteylase(HDAC) enzymes[J]. European Journal of Medicinal Chemistry, 2018, 148, 73- 85. doi: 10.1016/j.ejmech.2018.02.011
14	卢言菊, 赵振东, 毕良武, 等. 异海松酰基噻吩类磺酰胺的制备及其抗肿瘤活性研究[J]. 林产化学与工业, 2019, 40 (5): 57- 62.
	LU Y J , ZHAO Z D , BI L W , et al. Synthesis and antitumor activity of isopimaric thiophene sulfonamides derivatives[J]. Chemistry and Industry of Forest Products, 2019, 40 (5): 57- 62.
15	MANEEDAENG A , PHOEMBOON S , CHANTHASENA P , et al. Synthesis, interfacial properties, and antimicrobial activity of a new cationic gemini surfactant[J]. Korean Journal of Chemical Engineering, 2018, 35 (11): 2313- 2320. doi: 10.1007/s11814-018-0133-6
16	VENENPALLY V , PRASAD R B N , POORNACHANDRA Y , et al. Synthesis of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1, 4-dihydro-4-oxoquinoline-3-carboxylate derivatives and their biological evaluation[J]. Bioorganic & Medicinal Chemistry Letters, 2016, 26 (2): 613- 617.

化合物 compound	抑制率inhibition rates(20 μmol/L)/%			抑制率inhibition rates(200 μmol/L)/%
化合物 compound	人肝癌Hep G2	人直肠癌DLD-1	人乳腺癌MCF-7	人肝癌Hep G2	人直肠癌DLD-1	人乳腺癌MCF-7
3a	8.64	7.57	5.99	82.53	91.07	86.69
3b	0.23	0.82	0.07	1.54	7.01	2.89
3c	1.77	0.96	3.33	2.93	8.74	7.35
3d	4.33	5.31	35.06	5.72	14.88	92.83
3e	6.08	7.31	6.49	85.85	93.88	92.18
3f	1.98	3.38	1.47	9.83	3.45	4.05
3g	1.97	2.17	1.45	6.36	3.89	3.37
5-Fu	10.67	25.75	13.16	94.43	96.38	92.76

化合物 compound	IC₅₀/(μmol·L^-1)
化合物 compound	人肝癌细胞 Hep G2	人直肠癌细胞 DLD-1	人乳腺癌细胞 MCF-7
3a	112.76	101.22	97.99
3d	＞200	＞200	25.12
3e	115.00	104.39	107.89
5-Fu	42.23	29.89	40.70

化合物 compounds	IC₅₀/(mg·L^-1)
化合物 compounds	大肠杆菌E. coli	白色念珠菌C. albicans	金黄色葡萄球菌S. aureus
3a	＞500	120.21	＞500
3b	＞500	111.5	＞500
3c	＞500	49.16	＞500
3d	＞500	53.94	＞500
3e	148.20	22.69	457.83
3f	＞500	108.01	＞500
3g	＞500	384.20	＞500
氨苄青霉素钠ampicillin sodium	57.51	—	3.71
5-氟胞嘧啶5-fluorocytosine	—	19.35	—

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Synthesis and Biological Activity of N-(α-Eleostearic Acyl) Triazole Derivatives

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