Synthesis and Anti-mycobacterial Activities of Heterocyclic Hydrazones and Their Bioisosteric Compounds

doi:10.6023/cjoc201412011

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1310-1319.DOI: 10.6023/cjoc201412011 Previous Articles Next Articles

Articles

杂环酮腙与类似物的合成及其对结核杆菌的抑制活性

李忠洲^a, 赵升^a, 李新军^a, 王翠翠^a, 姚璐璐^a, 金瑞良^b, 邹新琢^a

a 华东师范大学化学系上海 200241;
b 同济大学附属上海肺科医院上海市结核病(肺)重点实验室上海 200433

收稿日期:2014-12-04 修回日期:2015-01-21 发布日期:2015-02-02
通讯作者: 邹新琢 E-mail:xzzou@chem.ecnu.edu.cn

Synthesis and Anti-mycobacterial Activities of Heterocyclic Hydrazones and Their Bioisosteric Compounds

Li Zhongzhou^a, Zhao Sheng^a, Li Xinjun^a, Wang Cuicui^a, Yao Lulu^a, Jin Ruiliang^b, Zou Xinzhuo^a

a Department of Chemistry, East China Normal University, Shanghai 200241;
b Shanghai Key Laboratory of Tuberculosis, Shanghai Pulmonary Hospital, Tongji University, Shanghai 200433

Received:2014-12-04 Revised:2015-01-21 Published:2015-02-02

1. Synthesis and Anti-mycobacterial Activities of Heterocyclic Hydrazones and Their Bioisosteric Compounds.PDF(17816KB)

Abstract

A total of 22 new heterocyclic hydrazones and their bioisosteric compounds were synthesized and evaluated for their activity against Mycobacterium tuberculosis, strain H37Rv. All newly synthesized compounds showed inhibitory activities. Among these compounds, (1E,4E)-1,5-bis(5-bromo-2-thiophenyl)-1,4-pentadiene-3-one-(1,4,5,6-tetrahydro-2-pyrimi- dimyl)-hydrazone (1d) showed the most effective anti-tubercular activity with MIC₉₀ value of 2 μg/mL, and exhibited an excellent inhibitory activity against isoniazid-resistant strain 242, multidrug-resistant strain 2312, and extensively drug-resistant strain 1220 with MIC₉₀ values of 0.25, 1.0 and 0.5 μg/mL, respectively.

Key words: heterocyclic hydrazone analogs, synthesis, Mycobacterium tuberculosis, anti-mycobacterial activity

Cite this article

Li Zhongzhou, Zhao Sheng, Li Xinjun, Wang Cuicui, Yao Lulu, Jin Ruiliang, Zou Xinzhuo. Synthesis and Anti-mycobacterial Activities of Heterocyclic Hydrazones and Their Bioisosteric Compounds[J]. Chin. J. Org. Chem., 2015, 35(6): 1310-1319.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Boogaard, J.; Kibiki, G. S.; Kisanga, E. R.; Boeree, M. J.; Aarnoutse, R. E. Antimicrob. Agents Chemother. 2009, 53, 849.
[2] Palmer, B. D.; Thomposon, A. M.; Sutherland, H. S.; Blaser, A.; Kmentova, I.; Franzblau, S. G.; Wan, B. J.; Wang, Y. H.; Ma, Z. K.,; Denny, W. A. J. Med. Chem. 2010, 53, 282.
[3] Sethi, A.; Yadav, S.; Sharma, R. K. Int. J. Pharm. Sci. Rev. Res. 2010, 6, 117.
[4] Zhang, J.; Angala, S. K.; Pramanik, P. K.; Li. K.; Crick, D. C.; Liav, A.; Jozwiak, A.; Swiezewska, E.; Jackson, M.; Chatterjee, D. ACS Chem. Biol. 2011, 6, 819.
[5] Liu, Y. X.; Xiao, C. L.; Wang, Y. X.; Li, Y. H.; Yang, Y. H.; Li, Y. B.; Bi, C. W.; Gao, L. M.; Jiang, J. D.; Song, D. Q. Eur. J. Med. Chem. 2012, 52, 151.
[6] Oliveira, K. N.; Chiaradia, L. D.; Martins, P. G.; Mascarello, A.; Cordeiro, M. N.; Guido, R. V.; Andricopula, A. D.; Yunes, R. A.; Nunes, R. J.; Vernal, J.; Terenzi, H. Med. Chem. Commun. 2011, 2, 500.
[7] Srivastav, M. K.; Shantakumar, S. M. Chem. Sci. Trans. 2013, 2, 1056.
[8] Torres, E.; Moreno, E.; Ancizu, S.; Barea, C.; Galiano, S.; Aldana, I.; Monge, A.; Perez-Silanes, S. Bioorg. Med. Chem. Lett. 2011, 21, 3699.
[9] Sasaki, H.; Haraguchi, Y.; Itotani, M.; Kuroda, H.; Hashizume, H.; Tomishige, T.; Kawasaki, M.; Masumoto, M.; Komatsu, M.; Tsubouchi, H. J. Med. Chem. 2006, 49, 7854.
[10] WHO Global Tuberculosis Report 2012. Available at: http://www.who.int/tb/publications/global_report/en/.
[11] Servusova, B.; Vobickova, J.; Paterova, P.; Kubicek, V.; kunes, J.; Dolezal, M.; Zitko, J. Bioorg. Med. Chem. Lett. 2013, 23, 3589.
[12] Ahsan, M. J.; Samy, J. G.; Khalilullah, H.; Bakht, M. A.; Hassan, M. Z. Eur. J. Med. Chem. 2011, 46, 5694.
[13] Manvar, A.; Bavishi, A.; Radadiya, A.; Patel, J.; Vora, V.; Dodia, N.; Rawal, K.; Shah, A. Bioorg. Med. Chem. Lett. 2011, 21, 4728.
[14] Simone, P. M.; Starke, J. R.; Vernon, A. A. Am. J. Respir. Crit. Care Med. 2003, 167, 62.
[15] Saquib, M.; Gupta, M. K.; Sagar, R.; Prabhakar, Y. S.; Shaw, A. K.; Kumar, R.; Maulik, P. R.; Gaikwad, A. N.; Sinha, S.; Srivastava, A. K.; Chaturvedi, V.; Srivastava, R.; Srivastava, B. S. J. Med. Chem. 2007, 50, 2942.
[16] Huang, X.; Huang, H.; Li, H.; Sun, X.; Huang, H.; Lu, Y.; Long, Y.; She, Z. Org. Lett. 2013, 15, 721.
[17] Koul, A.; Vranckx, L.; Dendouga, N.; Balmans, W.; Wyngaert, I.; Vergauwen, K.; Gohlmann, H.; Willebrords, R.; Poncelet, A.; Guillemont, J.; Bald, D.; Andries, K. J. Biol. Chem. 2008, 283, 25273.
[18] Dixit, P. P.; Patial, V. J.; Nait, P. S.; Jain, S.; Sinha, N.; Arora, S. K. Eur. J. Med. Chem. 2006, 41, 423.
[19] Pieter, C.; Davie, C.; Blaise, M. M.; Jan, J.; Birgit, M.; Vanessa, M.; Luc, V.; Kris, H.; Norbert, D. K. Eur. J. Med. Chem. 2013, 67, 98.
[20] Hwang, J.; Oh, T.; Kaneko, T.; Upton, A.; Franzblau, S.; Ma, Z.; Cho, S.; Kim, P. J. Nat. Prod. 2013, 76, 354.
[21] Ma, Z.; Lienhardt, C.; Mcllleron, H.; Nunn, A. J.; Wang, X. Lancet 2010, 275, 2100.
[22] Chen, S.-J.; Cui, J.-G.; Li, Y.; Fan, L.-H. Chin. J. Org. Chem. 2011, 31, 187 (in Chinese). (陈思静, 崔建国, 李莹, 范良华, 有机化学, 2011, 31, 187.)
[23] Bo, Z.-S.; Wang, D.-X. The Research Development of New Heterocyclic Pesticides and Synthetic Method, Chemical Industry Press, Beijing, 2004, pp. 179～184 (in Chinese) (柏再苏, 王大翔, 新杂环农药的研究发展及合成方法, 化学工业出版社, 北京, 2004, pp. 179～184.)
[24] Zhao, S. M.S. Thesis, East China Normal University, Shanghai, 2008 (in Chinese). (赵升, 硕士论文, 华东师范大学, 上海, 2008.)
[25] Zhang W.-S.; Li, A.-L. Medicinal Chemistry, Higher Education Press, Beijing, 1999, pp. 555～556 (in Chinese). (仉文升, 李安良, 药物化学, 高等教育出版社, 北京, 1999, pp. 555～556.)
[26] Merz, K. W.; Rauchle, K. Arch. Pharm. 1960, 16, 968.
[27] Okamoto, O.; Kobayashi, K.; Kawamoto, H.; Ito, S.; Satoh, A.; Kato, T.; Yamamoto, I.; Mizutani, S.; Hashimoto, M.; Shimizu, A.; Sakoh, H.; Nagatomi, Y.; Iwasawa, Y.; Takahashi, H.; Ishii, Y.; Ozaki, S.; Ohta, H. Bioorg. Med. Chem. Lett. 2008, 18, 3278.
[28] Baer, J. E.; Lockwood, R. G. J. Org. Chem. 1954, 76, 1162.
[29] Boyd, R. N.; Meadow, M. Anal. Chem. 1960, 32, 551.
[30] Luzzio, F. A. Synth. Commun. 1984, 14, 209.
[31] Finnegan, W. G.; Henry, R. A.; Lieber, E. J. Org. Chem. 1953, 75, 779.
[32] Herbst, R. M.; Roberts, C. W.; Harvill, E. J. J. Org. Chem. 1951, 16, 139.
[33] Rule, N. G.; Detty, M. R.; Kaeding, J. E.; Sinicropi, J. A. J. Org. Chem. 1995, 60, 1665.
[34] Wei, X. C.; Du, Z. Y.; Zheng, X.; Cui, X. X.; Conney, A. H.; Zhang, K. Eur. J. Med. Chem. 2012, 53, 235.
[35] Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
[36] Zakharychev, V. V.; Kuzenkov, A. V. Chem. Heterocycl. Compd. 2007, 43, 989.
[37] Wallace, R. J. Jr.; Nash, D. R.; Steele, L. C.; Steingrube, V. J. Clin. Microbiol. 1986, 24, 976.
[38] Liang, G.; Zhou, H.; Wang, Y.; Gurley, E. C.; Feng, B.; Chen, L.; Xiao, J.; Yang, S.; Li, X. J. Cell. Mol. Med. 2009, 13, 3370.
[39] Weber, W. M.; Hunsaker, L. A.; Abcouwer, S. F.; Deck, L. M.; Vanderjagt, L. D. L. Bioorg. Med. Chem. 2005, 13, 3811.
[40] Sato, T.; Ino, H.; Fujitsuka, M.; Tanaka, K. Tetrahedron Lett. 1997, 38, 6039.
[41] Hazarkhani, H. Kumar, P.; Kondiram, K. S.; Shafi, G.; Ikhlas, M. S. G. Synthetic Communications 2010, 40, 2887.
[42] Musumarra, G.; Ballistreri, F. P. Org. Magn. Res. 1980, 14, 384.

杂环酮腙与类似物的合成及其对结核杆菌的抑制活性

Synthesis and Anti-mycobacterial Activities of Heterocyclic Hydrazones and Their Bioisosteric Compounds

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[14]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[15]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.