Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid

doi:10.6023/cjoc201610017

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 731-738.DOI: 10.6023/cjoc201610017 Previous Articles Next Articles

Notes

异海松酰(胺)基硫脲类衍生物的合成及其生物活性评价

刘娟娟^a, 卢言菊^a,b, 王婧^a,b, 毕良武^a,b, 赵振东^a,b

a 中国林业科学研究院林产化学工业研究所生物质化学利用国家工程实验室国家林业局林产化学工程重点开放性实验室江苏省生物质能源与材料重点实验室南京 210042;
b 中国林业科学研究院林业新技术研究所北京 100091

收稿日期:2016-10-12 修回日期:2016-12-07 发布日期:2016-12-21
通讯作者: 赵振东,E-mail:zdzhao@189.cn E-mail:zdzhao@189.cn
基金资助:
国家自然科学基金（No.31370575）资助项目.

Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid

Liu Juanjuan^a, Lu Yanju^a,b, Wang Jing^a,b, Bi Liangwu^a,b, Zhao Zhendong^a,b

a Institute of Chemical Industry of Forest Product, Chinese Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, Key and Open Laboratory on Forest Chemical Engineering State Forestry Adminstration, Key Laboratory of Biomass Energy and Material, Nanjing 210042;
b Research Institute of Forestry New Technology, Chinese Academy of Forestry, Beijing 100091

Received:2016-10-12 Revised:2016-12-07 Published:2016-12-21
Contact: 10.6023/cjoc201610017 E-mail:zdzhao@189.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31370575).

1. Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid.PDF(1052KB)

Abstract

To develop isopimaric acid derivatives with high bioactivity, fifteen acyl (amide) thiourea derivatives containing isopimaric acid skeleton were synthesized and confirmed by FT-IR, ¹H NMR, ¹³C NMR and HRMS or elemental analysis. All the compounds were evaluated for their antibacterial and anticancer activity. Most of the compounds showed siginificant inhibitory activity which was higher than that of isopiamric acid against the Candida Albicans. At the concentration of 100 μmol/L, many compounds exhibited pronounced inhibitory effects on human melanoma cells (A375) and prostatic carcinoma (PC-3) cell lines, especially compounds N-isopimaric acyl-N'-(3-methylphenyl)sulfourea (3c) and N-isopimaric acylamino-N'-(4-fluorophenyl) sulfourea (6b) have the best anticancer activity, both with the inhibitory rate of over 90%.

Key words: isopimaric acid, acylthiourea, antibacterial activity, anticancer activity, structure-activity relationship

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Liu Juanjuan, Lu Yanju, Wang Jing, Bi Liangwu, Zhao Zhendong. Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid[J]. Chin. J. Org. Chem., 2017, 37(3): 731-738.

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References

[1] Rabergh, C. M. I.; Lilius, H.; Eriksson, J. E.; Isomaa, B. Aquat. Toxicol. 1999, 46, 55.
[2] Nikinmaa, M.; Wickström, C.; Lilius, H.; Isomaa, B.; Rabergh, C. Environ. Toxicol. Chem. 1999, 18, 993.
[3] Henney, N. C.; Li, B.; Elford, C.; Campbell, A. Am. J. Physiol. Cell Physiol. 2009, 297, C1397.
[4] Wu, C.; Gopal, K. V.; Lukas, T. J.; Gross, G. W.; Moore, E. J. Eur. J. Pharmacology 2014, 732, 68.
[5] Wang, L.; Kang, H.-C.; Li, Y.-Z.; Shui, Y.; Yamamoto, R.; Sugai, T.; Kato, N. Neuropharmacol. 2015, 92, 8.
[6] Sharma, S.; Nagar, V.; Mehta, B. K. Fitoterapia 1993, 64, 476.
[7] Tanaka, R.; Tokuda, H.; Ezaki, Y. Phytomedicine 2008, 15, 985.
[8] Chang, L. C.; Song, L. L.; Park, E. J.; Luyengi, L.; Lee, K. J.; Farnsworth, N. R.; Pezzuto, J. M.; Kinqhorn, A. D. J. Nat. Prod. 2000, 63, 1235.
[9] Adamczyk, S.; Adamczyk, B.; Kitunen, V.; Smolander, A. Soil Biol. Biochem. 2015, 87, 59.
[10] Bisio, A.; Fraternale, D.; Damonte, G.; Millo, E.; Lanteri, A. P.; Russo, E.; Romussi, G.; Parodi, B.; Ricci, D.; De Tommasi, N. Nat. Prod. Commun. 2009, 4, 1621.
[11] Elliger, C. A.; Zinkel, D. F.; Chan, B. G.; Waiss, A. C., Jr. Experientia 1976, 32, 1364.
[12] Perez Gutierrez, R. M.; Garcia, B. E. J. Asian Nat. Prod. Res. 2011, 13, 934.
[13] Cheng, S.-S.; Chang, S.-T. Wood Sci. Technol. 2014, 48, 831.
[14] Xie, Y. S.; Isman, M. B.; Yi, F.; Wong, A. J. Chem. Ecol. 1993, 19, 1075.
[15] Gong, Y.-X.; Wang, Z.-Y.; Zhang, Z.-W.; Chen, C.-B.; Wang, Y.-G. Chin. J. Org. Chem. 2006, 26, 360 (in Chinese).(龚银香, 王子云, 张正文, 陈传兵, 汪炎钢, 有机化学, 2006, 26, 360.)
[16] Zou, X.-J.; Jin, G.-Y.; Yang, Z. Chem. J. Chin. Univ. 2002, 23, 403 (in Chinese). (邹霞娟, 金桂玉, 杨昭, 高等学校化学学报, 2002, 23, 403.)
[17] Su, G.-F.; Huo, L.-N.; Qin, J.-K.; Pan, C.-X.; Guan, Y.-F. Chin. J. Appl. Chem. 2008, 25, 803 (in Chinese).(苏桂发, 霍丽妮, 覃江克, 潘成学, 关一富, 应用化学, 2008, 25, 803.)
[18] Elkholy, S. S.; Salem, H. A.; Eweis, M.; Elsabee, M. Z. Int. J. Biol. Macromol. 2014, 70, 199.
[19] Plutín, A. M.; Mocelo, R.; Alvarez, A.; Ramos, R.; Castellano, E. E.; Cominetti, M. R.; Graminha, A. E.; Ferreira, A. G.; Batista, A. A. J. Inorg. Biochem. 2014, 134, 76.
[20] Koca, ?.; Özgür, A.; Co?kun, K. A.; Tutar, Y. Bioorg. Med. Chem. 2013, 21, 3859.
[21] Wang, Y.-G.; Lu, B.-X.; Ye, W.-F.; Zhao, X.-Y.; Yang, J. Chin. J. Org. Chem. 2002, 22, 862 (in Chinese).(汪焱钢, 卢冰熙, 叶文法, 赵新筠, 杨军, 有机化学, 2002, 22, 862.)
[22] Su, G.-F.; Huo, L.-N.; Chen, R.; Zhao, F.-L.; Guan, Y.-F. Acta Chim. Sinica 2008, 66, 2717 (in Chinese).(苏桂发, 霍丽妮, 陈睿, 赵丰丽, 关一富, 化学学报, 2008, 66, 2717.)
[23] Ulubelen, A.; Oksüz, S.; Topcu, G.; Gören, A. C.; Bozok-Johansson, C.; Celik, C.; Kökdil, G.; Voelter, W. Nat. Pro. Lett. 2001, 15, 307.
[24] Zhao, Z.-D.; Li, X.-D.; Bi, L.-W.; Chen, Y.-X.; Gu, Y.; Li, D.-M.; Wang, J. J. CN 101302151, 2008[Chem. Abstr. 2008, 150, 5919].
[25] Hilliard, N. J.; Duffy, L. B.; Crabb, D. M.; Waites, K. B. J. Microbiol. Methods 2005, 60, 285.
[26] Liu, Z.-J.; Wu, S.-S.; Wang, Y.; Li, R.-J.; Wang, J.; Wang, L.-H.; Zhao, Y.-F.; Gong, P. Eur. J. Med. Chem. 2014, 87, 782.

异海松酰(胺)基硫脲类衍生物的合成及其生物活性评价

Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid

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