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2020 , Vol. 40 >Issue 4: 988 - 996

DOI: https://doi.org/10.6023/cjoc201908029

研究论文

朝格尔碱衍生物的制备及其催化的4H-色烯并[2,3-b]吡啶-3-腈的合成

  • 陈雯 ,
  • 苑睿 ,
  • 房越 ,
  • 董宏瑞 ,
  • 布麦热叶木·亚生 ,
  • 苏柳娟 ,
  • 任璇璇 ,
  • 周杭 ,
  • 宛瑜 ,
  • 张鹏 ,
  • 周生亮 ,
  • 吴翚
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  • a 江苏师范大学化学与材料科学学院 江苏徐州 221116;
    b 江苏师范大学江苏省药用植物生物技术重点实验室 江苏徐州 221116;
    c 江苏师范大学生命科学学院 江苏徐州 221116

收稿日期: 2019-08-21

  修回日期: 2019-11-16

  网络出版日期: 2020-05-06

基金资助

江苏省高校优势学科建设工程、江苏省高等学校自然科学研究（No.19KJB430019）、徐州市科技计划项目（No.KC19242）、江苏师范大学博士学位教师科研支持（No.17XLR023）和江苏省研究生科研创新计划（Nos.KYCX18_2111，KYCX18_2116）资助项目.

收起

Preparation and Application in the Synthesis of 4H-Chromeno-[2,3-b]pyridine-3-carbonitriles of Tröger's Base Derivatives

  • Chen Wen ,
  • Yuan Rui ,
  • Fang Yue ,
  • Dong Hongrui ,
  • Yasen Bumaryam ,
  • Su Liujuan ,
  • Ren Xuanxuan ,
  • Zhou Hang ,
  • Wan Yu ,
  • Zhang Peng ,
  • Zhou Shengliang ,
  • Hui Wu
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  • a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116;
    b Key Laboratory of Biotechnology for Medicinal Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou, Jiangsu 221116;
    c School of Life Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received date: 2019-08-21

  Revised date: 2019-11-16

  Online published: 2020-05-06

Supported by

Project supported by the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Natural Science Research Projects in Universities of Jiangsu Province (No.19KJB430019), the Science and Technology Foundation of Xuzhou City (No. KC19242), the Aid Project for Ph.D. Faculties in Jiangsu Normal University (No. 17XLR023) and the Graduate Student Scientific Research Innovation Projects in Jiangsu Province (Nos. KYCX18_2111, KYCX18_2116).

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摘要

由朝格尔碱-氨基合成了一系列席夫碱（4），将其作为高效催化剂催化了取代水杨醛、丙二腈和取代2-巯基咪唑的多组分反应，得到一系列5-（1H-咪唑-2-硫代）-2，4-二氨基-5H-色烯并[2，3-b]吡啶-3-腈衍生物（8）.通过1H NMR初步探讨了催化机理.生物活性结果表明：大多数产品对人乳腺癌细胞（MCF-7）和腺癌人肺泡基底上皮细胞（A549）表现出高度抑制作用.5-（1H-咪唑-2-基硫基）-2，4-二氨基-7-氟-5H-苯并[2，3-b]吡啶-3-腈（8s）对金黄色葡萄球菌（野生型）和大肠杆菌（野生型）具有抗菌活性.这些结果扩展了朝格尔碱衍生物在有机催化中的应用，显示产品在新药开发领域具有潜力.

关键词： 朝格尔碱; 有机催化; 色烯[2,3-b]吡啶; 生物活性

本文引用格式

陈雯 , 苑睿 , 房越 , 董宏瑞 , 布麦热叶木·亚生 , 苏柳娟 , 任璇璇 , 周杭 , 宛瑜 , 张鹏 , 周生亮 , 吴翚 . 朝格尔碱衍生物的制备及其催化的4H-色烯并[2,3-b]吡啶-3-腈的合成[J]. 有机化学, 2020 , 40(4) : 988 -996 . DOI: 10.6023/cjoc201908029

Abstract

A series of Schiff base catalysts (4) derived from Tröger's base-NH2 were synthesized and used to promote the multi-component reactions of substituted salicylaldehydes, malononitrile and substituted 2-mercaptoimidazole to afford 5-(1H-imidazol-2-ylthio)-2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile derivatives (8) efficiently. The reaction mechanism was discussed based on the 1H NMR analysis preliminarily. Most of products showed high inhibitory on the human breast adenocarcinoma cell (MCF-7) and adenocarcinomic human alveolarbasal epithelial cell (A549). 5-(1H-Imidazol-2-ylthio)-2,4-diamino-7-fluoro-5H-chromeno[2,3-b]pyridine-3-carbonitrile has antibacterial activity against Staphylococcus aureus (wild type) and Escherichia coli (wild type). The results expanded the application of Tröger's bases in organocatalysis and showed the potential of products in new drug development.

Key words： Tröger's base; organoatalysis; chromeno[2,3-b]pyridine; biological activity

参考文献

[1] Weinstein, D. S.; Gong, H.; Doweyko, A. M. J. Med. Chem. 2011, 54, 7318.
[2] Kolokythas, G.; Pouli, N.; Marakos, P.; Pratsinis, H.; Kletsas, D. Eur. J. Med. Chem. 2006, 41, 71.
[3] Azuine, M. A.; Tokuda, H.; Takayasu, J. J. Pharm. Pharmacol. 2004, 49, 161.
[4] Srivastava, S.; Tripathi, K. R. P.; Ramachandran, R. J. Biol. Chem. 2005, 280, 30273.
[5] Evdokimov, N. M.; Kireev, A. S.; Yakovenko, A. A. J. Org. Chem. 2007, 72, 3443.
[6] Anderson, D. R.; Hegde, S.; Reinhard, E.; Bioorg. Med. Chem. Lett. 2005, 15, 1587.
[7] Bristol, J. A.; Gold, E. H.; Gross, I.; Lovey, R. G.; Long, J. J. Med. Chem. 1981, 24, 1010.
[8] Venkati, M.; Krupadananm, G. L. D. Synth. Commun. 2001, 31, 2589.
[9] Nohara, A.; Ishiguro, T.; Ukawa, K.; Sugihara, H.; Maki, Y.; Sanno, Y. J. Med. Chem. 1985, 28, 559.
[10] Martin, M. J.; La-casa, C.; Alarcon-de-la-Lastra, C.; Cabeza, J.; Villegas, I.; Motilva, V. J. Med. Chem. 1998, 53, 82.
[11] Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.; Labreque, D.; Bubenick, M.; Denis, R.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Kasibhatla, S.; Cai, S. X. J. Med. Chem. 2008, 51, 417.
[12] Raju, R. R.; Mohan, S. K.; Reddy, S. J. J. Sci. Ind. Res. 2003, 62, 334.
[13] Panda, D.; Singh, J. P.; Wilson, L. J. Biol. Chem. 1997, 272, 7681.
[14] Haveliwala, D. D.; Kamdar, N. R.; Mistry, P. T.; Patel, S. K. Helv. Chim. Acta 2013, 96, 897.
[15] Kamdar, N. R.; Haveliwala, D. D.; Mistry, P. T.; Patel, S. K. Eur. J. Med. Chem. 2010, 45, 5056.
[16] Lee, X. P.; Kumazawa, T.; Hasegawa, C.; Arinobi, T.; Kato, A.; Seno, H.; Sato, K. Forensic Toxicol. 2010, 28, 96.
[17] Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.; Zhao, J.; Crogan-Grundy, C.; Xu, L.; Lamothe, S.; Gourdeau, H.; Denis, R.; Tseng, B.; Kasibhatla, S.; Cai, S. X. J. Med. Chem. 2007, 50, 2858.
[18] Akyol-Salman, I.; Lece-Sertoz, D.; Baykal, O. J. Ocul. Pharmacol. Ther. 2007, 23, 280.
[19] Mishra, S.; Ghosh, R. Synth. Commun. 2012, 42, 2229.
[20] Evdokimov, N. M.; Kireev, A. S.; Yakovenko, A. A.; Antipin, M. Y.; Magedov, I. V.; Kornienko, A. Tetrahedron Lett. 2006, 47, 9309.
[21] Siddiqui, Z. N.; Khan, K. New J. Chem. 2013, 37, 1595.
[22] Tröger, J. J. Prak. Chem. 1887, 36, 225.
[23] Satishkumar, S.; Periasamy, M.; Tetrahedron:Asymmetry 2009, 20, 2257.
[24] Kejík, Z.; Bříza, T.; Havlík, M.; Dolenský, B.; Kaplánek, R.; Králová, J.; Mikula, I.; Martásek, P. Dyes Pigm. 2016, 134, 212.
[25] Veale, E. B.; Frimannsson, D. O.; Lawler, M.; Gunnlaugsson, T. Org. Lett. 2009, 11, 4040.
[26] Paul, A.; Maji, B.; Misra, S. K.; A. Jain, K.; Muniyappa, K.; Bhattacharya, S. J. Med. Chem. 2012, 55, 7460.
[27] Yuan, R.; Li, M. Q.; Xu, J. B.; Huang, S. Y.; Zhou, S. L.; Zhang, P.; Liu, J. J.; Wu, H. Tetrahedron 2016, 72, 4081.
[28] Xiao, Y. C.; Zhang, L. L.; Xu, L.; Chung, T. S. J. Membr. Sci. 2017, 521, 65.
[29] Ishiwari, F.; Takeuchi, N.; Sato, T.; Yamazaki, H.; Osuga, R.; Kondo, J. N.; Fukushima, T. ACS Macro Lett. 2017, 6, 775.
[30] Yuan, R.; Wang, Y. J.; Fang, Y.; Ge, W. H.; Lin, W.; Li, M. Q.; Xu, J. B.; Wan, Y.; Liu, Y.; Wu, H. Chem. Eng. J. 2017, 316, 1026.
[31] Brown, H. C.; McDaniel, D. H.; Hafliger, O. In Determination of Organic Structures
(b)y Physical Methods, Eds.:Braude, E. A.; Nachod, F. C., Academic Press, New York, 1955, 9, p. 22.
[32] Parsons, R. Handbook of Electrochemical Constants, Butterworths Scientific Publications, London, 1959, p. 35.
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