Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives

doi:10.6023/cjoc201604042

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2489-2495.DOI: 10.6023/cjoc201604042 Previous Articles Next Articles

Notes

新型蒎烷基噻唑衍生物的合成及其生物活性研究

孙楠^a, 王欣^b, 丁志彬^a, 张齐^a, 徐徐^a,c,d, 徐海军^a,c, 王石发^a,c,d

a 南京林业大学化学工程学院南京 210037;
b 南京农业大学植物保护学院南京 210095;
c 江苏省生物质绿色燃料与化学品重点实验室南京 210037;
d 广西林产化学与工程重点实验室南宁 530008

收稿日期:2016-04-20 修回日期:2016-05-16 发布日期:2016-06-08
通讯作者: 王石发,E-mail:wsfyyq@njfu.com.cn E-mail:wsfyyq@njfu.com.cn
基金资助:
江苏省高校自然科学研究（No.14KJ220001）、国家自然科学基金（No.31470529）和广西林产化学与工程重点实验室开放基金（No.JSBEM2014010）资助项目.

Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives

Sun Nan^a, Wang Xing^b, Ding Zhibing^a, Zhang Qi^a, Xu Xu^a,c,d, Xu Haijun^a,c, Wang Shifa^a,c,d

a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
b College of Plant Protection, Nanjing Agricultural University, Nanjing 210095;
c Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037;
d Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008

Received:2016-04-20 Revised:2016-05-16 Published:2016-06-08
Supported by:
Project supported by the Natural Science Foundation of the Jiangsu Highter Education Institutions (No.14KJ220001), the National Natural Science Foundation of China (No.31470529), and the Open Funding of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products (No.JSBEM2014010).

1. Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives.PDF(1024KB)

Abstract

Novel pinanyl thiazole derivatives were synthesized from nopinone which was a derivative from β-pinene by con-densation and cyclization, and their bioactivities were also examined in this paper. Nopinone obtained from oxidation of β-pinene was condensed with thiosemicarbazide into nopinone thiosemicarbazone, and thiazole derivatives 2a~2l were prepared via cyclization of nopinone thiosemicarbazone with α-haloketones. The structures of compounds 2a~2l were characterized with ¹H NMR, ¹³C NMR, IR and HRMS, and the antibacterial activity, anti-inflammatory activity on human umbilical vein endothelial cells (HUVECs), and insecticidal activity on crape myrtle aphids of compounds 2a~2l were also examined. Test results showed that compound 2b was a more potent bactericide and fungicide than others because of its good activities against bacteria and fungi, compound 2a had strong anti-inflammatory activity towards HUVECs and had the similar effect to that of aspirin, and compounds 2e, 2h, 2i and 2k had a certain insecticidal activities against crape myrtle aphids.

Key words: nopinone, pinanyl thiazole derivatives, bacteriostatic activity, anti-inflammatory activity, insecticidal activity

Cite this article

Sun Nan, Wang Xing, Ding Zhibing, Zhang Qi, Xu Xu, Xu Haijun, Wang Shifa. Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives[J]. Chin. J. Org. Chem., 2016, 36(10): 2489-2495.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Wu, X. J.; Fassie, M. Mutat. Res. 2005, 589, 81.
[2] Cui, J. G.; Zhao, D. D. Chin. J. Org. Chem. 2016, 36, 630(in Chinese). (崔建国, 赵丹丹, 有机化学, 2016, 36, 630.)
[3] Sriram, D.; Yogeeswari, P.; Dhakla, P. Bioorg. Med. Chem. Lett. 2007, 17, 1881.
[4] Pirrung, M.; Pansare, S.; Sarma, K. Bioorg. Med. Chem. 2005, 48, 3045.
[5] Brousse, B.; Garca, C.; Moglioni, A. Antivitral. Chem. Chemother. 2003, 14(2), 99.
[6] Fuji, N.; Mallari, J. P.; Hansell, E. J. Bioorg. Med. Chem. Lett. 2015, 15, 121.
[7] Saleem, K.; Khan, S. A. Eur. J. Med. Chem. 2008, 43, 2020.
[8] Hutchinson, S. A.; Jennings, B. R.; Vishnuvajjala, A. D. Med. Chem. 2002, 45, 744.
[9] Hargrave, K. D.; Hess, F. K.; Oliver, J. T. J. Med. Chem. 1983, 26, 1158.
[10] Patt, W. C.; Hamilton, H. W.; Taylor, M. D. Med. Chem. 1992, 35, 2562.
[11] Sharma, R. N.; Xavier, F. P.; Vasu, K. K.; Chaturvedi, S. C.; Pancholi, S. S. J. Med. Chem. 2009, 24, 890.
[12] Pasqualotto, A. C.; Thiele, K. O.; Goldani, L. Z. Exp. Opin. Invest. Drugs 2010, 11, 165.
[13] Fox, L. M.; Saravolatz, L. D. Infect. Dis. 2005, 40, 1173.
[14] Ahad, A.; Raish, M. Int. J. Biol. Macromol. 2014, 67, 99.
[15] Foruumadi, A.; Soltani, F.; Moshafi, M. H. Farmaco 2003, 58(10), 1023.
[16] Chandrakantha, B.; Shetty, P.; Nambiyar, V.; Isloor, N. Eur. J. Med. Chem. 2010, 45, 1206.
[17] Kundu, N.; Nandi, B. J. Org. Chem. 2001, 66(13), 4365.
[18] Thmos, L.; Gupta, A.; Gupta, V. J. Fluorine Chem. 2003, 22, 207.
[19] Sawada, Y.; Yanai, T. Pest Manage. Sci. 2003, 59(1), 25.
[20] Nauen, R. U.; Ebbinghaus-Kintscher, U.; Salgado, V. L.; Kaussmann, M. Pestic. Biochem. Physiol. 2003, 76, 55.
[21] Xiao, L. X.; Shi, D. Q. Chin. J. Org. Chem. 2010, 30, 85(in Chinese). (肖琳霞, 石德清, 有机化学, 2010, 30, 85.)
[22] Yan, M; Shi, D. Q. Chin. J. Org. Chem. 2008, 28, 736(in Chi-nese). (严曼, 石德清, 有机化学, 2008, 28, 736.)
[23] Habar, G.; Lepape, A.; Descllsse, C. EP 714786, 1996[Chem. Abstr. 1996, 125, 117645].
[24] Samarasekera, R.; Weerasinghe, I. S.; Hemalal, K. D. P. Pest Manage. Sci. 2008, 64, 290.
[25] Liu, B.; Wang, S. F. J. Nanjing Forestry Univ. 2010, 34(2), 89(in Chinese). (刘兵, 王石发, 南京林业大学学报, 2010, 34(2), 89.)

新型蒎烷基噻唑衍生物的合成及其生物活性研究

Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Mengjia Xiao, Xike Gao. Design, Synthesis and Anti-inflammatory Activity of Azulene Derivatives Containing Benzimidazole Unit [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3246-3256.
[2]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[3]	Zeren Sun, Bingxin Zhai, Guangchao He, Hui Shen, Linya Chen, Shan Zhang, Yi Zou, Qihua Zhu, Yungen Xu. Synthesis and Anti-inflammatory Evaluation of Novel 1,2,3-Triazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2143-2155.
[4]	Zichan Zhang, Yang Sun, Sheng Hua, Baolin Xu, Min Zhang, Qin Zhao, Dandan Zheng, Yang Wang, Jianfeng Ju, Yujun Shi, Hong Dai. Synthesis and Insecticidal Activity of Novel Pyrazole Amides Containing an Isoxazole Moiety [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1435-1443.
[5]	Lei Wang, Shujing Yu, Na Yang, Baolei Wang. Studies on the Synthesis and Biological Activities of Novel Dihydroquinazolinone-Containing Caffeine Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 299-307.
[6]	Wenjuan Li, Rui Zhang, Zhihua Cai, Xiaoqiang Han, Lin He, Bin Dai. Constrution and Insecticidal Activities of Trifluoromethylated Benzocyclicsulfoximine Derivatives by [3+2] Cycloaddition Reaction of Beznyne [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2832-2839.
[7]	Shu Chen, Yingying Shao, Xinhao Fu, Qingwu Chen, Xiaohua Du, Chengxia Tan. Design, Synthesis and Insecticidal Activities of Pyridyl Thiazole Diamide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3870-3879.
[8]	Ali Dai, Renfeng Zhang, Chuanhui Li, Lijiao Yu, Ya Wang, Jian Wu. Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3633-3642.
[9]	Feng He, Shengxin Guo, Ali Dai, Renfeng Zhang, Jian Wu. Synthesis, Characterization, and Biological Activity of Novel Amide Derivatives Containing Trifluoromethylpyridine Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3303-3311.
[10]	Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li, Zewei Mao. Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3292-3296.
[11]	Yangyi Yao, Chaoli Ren, Li Chen, Liangkun Zhong, Tianming Xu, Chengxia Tan. Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2055-2062.
[12]	Hang Liu, Shuyun Zhang, Huan Li, Yan Zhang, Zhengming Li, Baolei Wang. Synthesis and Biological Activities of Novel 8-((3,4,4-Trifluorobut-3-en-1-yl)thio)-substituted Methylxanthines and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2091-2098.
[13]	Weibin Xie, Huangong Li, Xiangde Meng, Zhengming Li, Sha Zhou. Design, Synthesis and Biological Activity Study of Novel N-Phenylpyrazole Anthranilic Diamides Containing Heptafluoroisopropyl Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1722-1727.
[14]	Mingguang Zhang, Mingxin Li, Yiqin Yang, Xu Xu, Jie Song, Zhonglong Wang, Shifa Wang. Synthesis of Nopinone-Based Quinazolin-2-amine Fluorescent Probe for Detection of Cu²⁺ and Its Application Research [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1168-1176.
[15]	Shuyun Zhang, Hang Liu, Lei Wang, Zhengming Li, Baolei Wang. Studies on the Synthesis, Structural Characterization and Biological Activities of Novel Caffeine Derivatives Containing Substituted-Piperazine Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4075-4082.