Designed, Synthesis and Herbicidal Activity of Novel 2-Alkylthio-thieno[2,3-d]pyrimidin-4-ones

doi:10.6023/cjoc201612048

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1877-1882.DOI: 10.6023/cjoc201612048 Previous Articles Next Articles

Notes

新型2-烷硫基-噻吩并[2,3-d]嘧啶-4-酮衍生物的设计、合成与除草活性

赵安林^a, 刘姝^a, 朱咏梅^b, 王涛^a, 罗劲^a,b

a. 江西省化学生物学重点实验室江西师范大学化学化工学院南昌 330022;
b. 江西师范大学分析测试中心南昌 330022

收稿日期:2019-12-19 修回日期:2017-02-19 发布日期:2017-03-03
通讯作者: 王涛, 罗劲 E-mail:wangtao@jxnu.edu.cn;jinluo@jxnu.edu.cn
基金资助:
国家自然科学基金（Nos.21262018，21562026）、江西省自然科学基金（Nos.20161BAB203085，20161BAB213072）资助项目.

Designed, Synthesis and Herbicidal Activity of Novel 2-Alkylthio-thieno[2,3-d]pyrimidin-4-ones

Zhao Anlin^a, Liu Shu^a, Zhu Yongmei^b, Wang Tao^a, Luo Jin^a,b

a. Jiangxi Province Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022;
b. Analytical & Testing Center, Jiangxi Normal University, Nanchang 330022

Received:2019-12-19 Revised:2017-02-19 Published:2017-03-03
Contact: 10.6023/cjoc201612048 E-mail:wangtao@jxnu.edu.cn;jinluo@jxnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21262018,21562026) and the Natural Science Foundation of Jiangxi Province (Nos.20161BAB203085,20161BAB213072).

1. Designed, Synthesis and Herbicidal Activity of Novel 2-Alkylthio-thieno[2,3-d]pyrimidin-4-ones.PDF(1080KB)

Abstract

In an attempt to discover novel fuse heterocyclic compound with high herbicidal activity, sixteen newly 2-alkythio-thieno[2,3-d]pyrimidin-4(3H)-ones have been designed and synthesized by the reaction of 3-propyl-6-ethylthieno[2,3-d]pyrimidine-2-thione with halo-hydrocarbon. Their structures were clearly verified by ¹H NMR, IR, LC-MS and elemental analysis. Preliminary bioassay results indicate that some target compounds have excellent inhibitory activities on barnyard grass and rape. 2-Cyclopentylthio-3-n-propyl-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one (4e) and 2-n-hexdecylthio-3-n-propyl-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one (4o) show 100% inhibition rate to barnyard grass at the concentration of 100 mg/L.

Key words: thieno[2,3-d]pyrimidin-4(3H)-ones, synthesis, herbicidal activitiess

Cite this article

Zhao Anlin, Liu Shu, Zhu Yongmei, Wang Tao, Luo Jin. Designed, Synthesis and Herbicidal Activity of Novel 2-Alkylthio-thieno[2,3-d]pyrimidin-4-ones[J]. Chin. J. Org. Chem., 2017, 37(7): 1877-1882.

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[1] Ravindr, V. C.; Barsu, G. K.; Anil, S. B.; Rajesh, H. B. Eur. J Med. Chem. 2003, 34, 89.
[2] Temple, D. L. US 4054656, 1977[Chem. Abstr. 1977, 88, 37830].
[3] Panico, A. M.; Santagati, A.; Cardile, V. Colloids Surf. B 2003, 28, 77.
[4] Zeng, G. P.; Zheng, P. Acta Chim. Sinica 2012, 70, 759(in Chinese). (曾国平, 郑平, 化学学报, 2012, 70, 759.)
[5] Crespo, M. l.; Pages, L. L; Vega, A.; Segarra, V.; Lopez, M.; Domenech, T.; Miralpeix, M.; Beleta, J.; Ryder, H.; Palacios, J. M. J. Med. Chem. 1998, 41, 4021.
[6] Samsonova, N. V.; Kharizomenova, L. A.; Givenv, A. N.; Kaplina, E. K. Pharm. Chem. J. 1981, 15, 645.
[7] Tokio, O.; Katsutoshi, F.; Isamu, N. EP 0356158, 1990[Chem. Abst. 1990, 113, 59210].
[8] Rosowsky, A.; Chaykovsk, M.; Chen, K. K. N.; Lin, M.; Modest, E. J. J. Med. Chem. 1973, 16, 185.
[9] Perspicace, E.; Ragno, R.; Ballante, F.; Hesse, S. Eur. J. Med. Chem. 2013, 63, 765.
[10] Chen, Y.; Bai, S.; He, W. H.; Yang, G. Z. Chin. J. Org. Chem. 2014, 34, 2362(in Chinese). (陈玉, 柏舜, 贺红武, 杨光忠, 有机化学, 2014, 34, 2362.)
[11] Bozorov, K.; Zhao, J. Y.; Elmuradov, B.; Pataer, a.; Aisa, H. A. Eur. J. Med. Chem. 2015, 102, 552.
[12] John, G. R.; Joanne, L.; Elizabeth, D. C. WO 02055524, 2002[Chem. Abstr. 2002, 137, 109287].
[13] Leistner, S.; Wagner, G.; Guetscharo, M.; Glusa, E. Pharmazie, 1986, 41, 54.
[14] Wang, H. M.; Guo, S. B.; Hu, Y. G.; Zeng, X. H.; Yang, G. Y. Chin. J. Org. Chem. 2015, 35, 1075(in Chinese). (王红梅, 郭树兵, 胡扬根, 曾小华, 杨光义, 有机化学, 2015, 35, 1075.)
[15] Liu, H.; Wang, H. Q.; Liu, Z. J. Bioorg. Med. Chem. Lett. 2007, 38, 2203.
[16] Shield, M. Eur. J. Rheumatol. Inflammation 1993, 13, 7.
[17] Palmoski, M. J.; Brandt, K. D. Arthritis Rheum. 1983, 26, 528.
[18] Hess, E. V.; Herman, J. H. Am. J. Med. 1986, 81, 36.
[19] Redini, F.; Mauviel, A.; Loyau, G.; Pujol, J. P. Agents Actions 1990, 31, 358.
[20] Rainsford, K. D. Am. J. Med. 1999, 107, S27.
[21] Krell, R. D.; Aharony, D.; Buckner, C. K.; Keith, R. A.; Kusner, E.J.; Snyder, D. W.; Bernstein, P. R.; Matassa, V. G.; Yee, Y. K.; Gilles, R. E. Am. Rev. Respir. Dis. 1990, 141, 978.
[22] Jarvis, B.; Markham, A. Drugs 2000, 59, 891
[23] Krell, R. D.; Aharony, D.; Buckner, C. K; Keith, R. A.; Kusner, E. J.; Snyder, D. W.; Bernstein, P. R.; Matassa, V. G.; Yee, Y. K; Brown, F. J.; Hesp, B.; Giles, R. E. Am. Rev. Respir. Dis. 1990, 141, 978.
[24] Wang, T.; Zheng, C. H.; Liu, S.; Chen, H. Z. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 1543.
[25] Wang, T. Ph.D. Dissertation, Central China Normal University, Wuhan, 2004(in Chinese). (王涛, 博士论文, 华中师范大学, 武汉, 2004.)
[26] Guo, Y. C.; Li, J.; Ma, J. L.; Yu, Z. R.; Wang, H. W.; Zhu, W. J.; Liao, X. C.; Zhao, Y. F. Chin. Chem. Lett. 2015, 26, 755.

新型2-烷硫基-噻吩并[2,3-d]嘧啶-4-酮衍生物的设计、合成与除草活性

Designed, Synthesis and Herbicidal Activity of Novel 2-Alkylthio-thieno[2,3-d]pyrimidin-4-ones

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