Chinese Journal of Organic Chemistry >
Synthesis and Application of Acridine Derivatives
Received date: 2017-10-09
Revised date: 2017-10-19
Online published: 2017-11-03
Supported by
Project supported by the National Natural Science Foundation of China (No. 21462043).
Due to the special functional structural units and important applications in many fields, the study of acridine derivatives has become a hot topic worldwide. The large conjugated ring enables these dyes to be markers for fluorescence and imaging. Thanks to the ability of embedding into DNA chain, they have a wide range of applications in medicine and other fields. These dyes have the very similar color index value to that of the natural compounds. As an alternative to metal semiconductor material, acridines have presented potential value in the field of organic semiconductor materials. In recent years, emerging of the new and simple preparation technique, such as microwave assisted synthesis, metal free catalysis, one pot synthesis, and so on, has brought more attention to the synthesis and application of acridines. In this paper, various synthetic methods of acridine derivatives since 2010 and their applications in medicine, fluorescent materials, industrial dyeing materials and electroluminescence are introduced. The work about acridines accomplished in our group is also introduced. In the end, the future prospective of synthesis and application of acridine derivatives is proposed.
Songbuer, Li Minghui, Imerhasan Mukhtar . Synthesis and Application of Acridine Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(3) : 594 -611 . DOI: 10.6023/cjoc201710007
[1] Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Buriol, L.; Machado, P. Chem. Rev. 2009, 109, 4140.
[2] Kalirajan, R.; Muralidharan, V.; Jubie, S.; Gowramma, B.; Gomathy, S.; Sankar, S.; Elango, K. J. Heterocycl. Chem. 2012, 49, 748.
[3] Bonse, S.; Santelli, R. C.; Barbe, J.; Krauth-Siegel, R. L. J. Med. Chem. 1999, 42, 5448.
[4] Nadaraj, V.; Selvi, S. T.; Mohan, S. Eur. J. Med. Chem. 2009, 44, 976.
[5] Wilson, W. R.; Thompson, L. H.; Anderson, R. F.; Denny, W. A. J. Med. Chem. 1989, 32, 31.
[6] Bastianelli, C.; Caia, V.; Cum, G.; Gallo, R.; Mancini, V. J. Chem. Soc., Perkin Trans. 21991, 679.
[7] Jaycox, D.; Gribble, G. W.; Hacker, J. Heterocycl. Chem. 1987, 24, 1405.
[8] Zhang, X.-P.; Shi, H.-L.; Yan, M. Med. Ind. 1984, 3, 8(in Chinese). (张秀平, 时惠麟, 颜闵, 医药工业, 1984, 3, 8.)
[9] Velingkar, V. S.; Dandekar, V. D. Chin. J. Chem. 2011, 29, 504.
[10] Ferreira, R.; Avinó, A.; Mazzini, S.; Eritja, R. Molecules 2012, 17, 7067.
[11] Geddes, C. D. Dyes Pigm. 2000, 45, 243.
[12] Goel, A.; Kumar, V.; Singh, S. P.; Sharma, A.; Prakash, S.; Singh, C.; Anand, R. S. J. Mater. Chem. 2012, 22, 14880.
[13] Chen, P.; Wang, Y.-Y.; Zhang, Y. M.; Zhang, X. A. Acta Chim. Sinica 2016, 74, 669(in Chinese). (陈鹏, 王宇洋, 张宇模, 张晓安, 化学学报, 2016, 74, 669.)
[14] Bernthsen, A. Ann. 1878, 192, 1.
[15] Bernthsen, A. Ann. 1884, 224, 1.
[16] Popp, F. D. J. Org. Chem. 1962, 27, 2658.
[17] Roopan, S. M.; Nawaz Khan, F. R. Med. Chem. Res. 2011, 20, 732.
[18] Das, S.; Thakur, A. J. Green Chem. Lett. Rev. 2011, 4, 131.
[19] Avila, J. M.; Vargas, F. D.; Camacho, S. P. D.; Rivero, I. A. RSC Adv. 2012, 2, 1827.
[20] Kaur, B.; Kumar, H. J. Chem. Sci. 2013, 125, 989.
[21] Kaur, B.; Parmar, A.; Kumar, H. Heterocycl. Lett. 2011, 1, 59.
[22] Kaur, B.; Parmar, A.; Kumar, H. Synth. Commun. 2012, 42, 453.
[23] Puri, S.; Kaur, B.; Parmar, A.; Kumar, H. Heterocycl. Commun. 2009, 15, 57.
[24] Gómez, A. H.; Herd, E.; Uzelac, M.; Cadenbach, T.; Kennedy, A. R.; Borilovic, I.; Aromí, G.; Hevia, E. Organometallics 2015, 34, 2614.
[25] Kozlov, N. G.; Bondarev, S. L.; Kadutskii, A. P.; Basalaeva, L. I. Zh. Org. Khim. 2010, 46, 209.
[26] Kozlov, N. G.; Bondarev, S. L.; Knyukshto, V. N.; Odnoburtsev, B. A.; Basalaeva, L. I. Zh. Org. Khim. 2010, 46, 1639.
[27] Kozlov, N. G. Zh. Org. Khim. 2011, 47, 1675.
[28] Kozlov, N. G.; Gusak, K. N. Zh. Org. Khim. 2006, 42, 1680.
[29] Kozlov, N. G.; Tereshko, A. B.; Gusak, K. N. Zh. Org. Khim. 2006, 42, 281.
[30] Kozlov, N. G.; Gusak, K. N. Zh. Obshch. Khim. 2006, 76, 294.
[31] Silaichev, P. S.; Dmitriev, M. V.; Aliev, Z. G.; Maslivets, A. N. Zh. Org. Khim. 2010, 46, 1173.
[32] Romain, M.; Tondelier, D.; Geffroy, B.; Shirinskaya, A.; Jeannin, O.; Berthelot, J. R.; Poriel, C. Chem. Commun. 2015, 51, 1313.
[33] Ghadari, R.; Hajishaabanha, F.; Mahyari, M.; Shaabani, A.; Khavasi, H. R. Tetrahedron Lett. 2012, 53, 4018.
[34] Ghorbani-Vaghei, R.; Malaekehpoor, S. M. J. Iran. Chem. Soc. 2010, 7, 957.
[35] Yesildag, I.; Ulus, R.; Basar, E.; Aslan, M.; Kaya, M.; Buülbül, M. Monatsh Chem. 2014, 145, 1027.
[36] Mahajan, S.; Khullar, S.; Mandal, S. K.; Singh, I. P. Chem. Commun. 2014, 50, 10078.
[37] Yang, X. J.; Zhang, C.; Wu, L. Q. RSC Adv. 2015, 5, 18945.
[38] Yang, X. J.; Zhang, C.; Wu, L. Q. RSC Adv. 2015, 5, 25115.
[39] Jagadishbabu, N.; Shivashankar, K. RSC Adv. 2015, 5, 95240.
[40] Liang, T.; Xiao, J.; Xiong, Z. Y.; Li, X. W. J. Org. Chem. 2012, 77, 3583.
[41] Caballero, A. B.; Guillena, G. G.; Nájera, C. J. Org. Chem. 2013, 78, 5349.
[42] Wang, H. Y.; Li, L. L.; Lin, W.; Xu, P.; Huang, Z. B.; Shi, D. Q. Org. Lett. 2012, 14, 4598.
[43] Li, C. M.; Zhang, F. R. RSC Adv. 2016, 6, 75359.
[44] Hao, W. J.; Wang, J. Q.; Xu, X. P.; Zhang, S. L.; Wang, S. Y.; Ji, S. J. J. Org. Chem. 2013, 78, 12362.
[45] Rogness, D. C.; Larock, R. C. J. Org. Chem. 2010, 75, 2289.
[46] Han, X. D.; Zhao, Y. L.; Meng, J.; Ren, C. Q.; Liu, Q. J. Org. Chem. 2012, 77, 5173.
[47] Verma, A. K.; Reddy Kotla, S. K.; Aggarwal, T.; Kumar, S.; Nimesh, H.; Tiwari, R. K. J. Org. Chem. 2013, 78, 5372.
[48] Gimenez-Arnau, E.; Missailidis, S.; Stevens, M. F. G. An-ti-Cancer Drug Des. 1998, 13, 431.
[49] McCarthy, P. J.; Pitts, T. P.; Gunawardana, G. P.; Kelly-Borges, M.; Pomponi, S. A. J. Nat. Prod. 1992, 55, 1664.
[50] Sarkar, P.; Mukhopadhyay, C. Green Chem. 2015, 17, 3452.
[51] Khalil, I. M.; Barker, D.; Copp, B. R. J. Org. Chem. 2016, 81, 282.
[52] Marshall, K. M.; Barrows, L. R. Nat. Prod. Rep. 2004, 21, 731.
[53] Gu, Z. Y.; Liu, C. G.; Wang, S. Y.; Ji, S. J. Org. Lett. 2016, 18, 2379.
[54] Ma, Y. G.; Qiang, W. W.; Li, C.; Zhang, M. M.; Wang, X. S. Monatsh. Chem. 2016, 147, 1233.
[55] Tsvelikhovsky, D.; Buchwald, S. L. J. Am. Chem Soc. 2010, 132, 14048.
[56] Dubrovskiy, A. V.; Larock, R. C. J. Org. Chem. 2012, 77, 11232.
[57] Lian, Y. J.; Hummel, J. R.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 12548.
[58] Guo, H. M.; Mao, R. Z.; Wang, Q. T.; Niu, H. Y.; Xie, M. S.; Qu, G. R. Org. Lett. 2013, 15, 5460.
[59] Su, Q.; Li, P.; He, M. N.; Wu, Q. L.; Ye, L.; Mu, Y. Org. Lett. 2014, 16, 18.
[60] Zheng, Z. S.; Dian, L. Y.; Yuan, Y. C.; Negrerie, D. Z.; Du, Y. F.; Zhao, K. J. Org. Chem. 2014, 79, 7451.
[61] Pang, X. L.; Chen, C.; Su, X.; Li, M.; Wen, L. R. Org. Lett. 2014, 16, 6228.
[62] Wang, T. J.; Chen, W. W.; Li, Y. Xu, M. H. Org. Biomol. Chem. 2015, 13, 6580.
[63] Sarkar, R.; Mukhopadhyay, C. Org. Biomol. Chem. 2016, 14, 2706.
[64] Zhikharko, Y. D.; Kozlov, N. G.; Basalaeva, L. I. Zh. Org. Khim. 2016, 52, 383.
[65] Natrajan, A.; Wen, D. Green Chem. 2011, 13, 913.
[66] Hyodo, I.; Tobisu, M.; Chatani, N. Chem. Commun. 2012, 48, 308.
[67] Zhang, Z. G.; Gao, Y.; Liu, Y.; Li, J. J.; Xie, H. X.; Li, H.; Wang, W. Org. Lett. 2015, 17, 5492.
[68] Chate, A. V.; Rathod, U. B.; Kshirsagar, J. S.; Gaikwad, P. A.; Mane, K. D.; Mahajan, P. S.; Nikam, M. D.; Gill, C. H. Chin. J. Catal. 2016, 37, 146.
[69] Imerhasan, M.; Wang, T.; Helil, S.; Osman, K.; Muhammad, T. Chin. J. Org. Chem. 2010, 30, 1884(in Chinese). (穆赫塔尔·伊米尔艾山, 王婷, 萨提瓦力迪·海力力, 库尔班·吾斯曼, 吐尔洪·买买提, 有机化学, 2010, 30, 1884.)
[70] Sondhi, S. M.; Singh, J.; Rani, R.; Gupta, P. P.; Agrawal, S. K.; Saxena, A. K. Eur. J. Med. Chem. 2010, 45, 555.
[71] Patel, M. M.; Mali, M. D.; Patel, S. K. Bioorg. Med. Chem. Lett. 2010, 20, 6324.
[72] Graham, L. A.; Wilson, G. M.; West, T. K.; Day, C. S.; Kucera, G. L.; Bierbach, U. ACS Med. Chem. Lett. 2011, 2, 687.
[73] Kumar, P.; Kumar, R.; Prasad, D. N. P. Arabian J. Chem. 2013, 6, 79.
[74] Mahsud, L.; Imerhasan, M.; Mahmud, M. A.; Helil, S.; Liu, H. J. Chin. J. Org. Chem. 2014, 34, 1235(in Chinese). (力瓦依丁·买合苏提, 穆赫塔尔·伊米尔艾山, 麦麦提依明·马合木提, 萨特瓦尔迪·赫力力, 刘华君, 有机化学, 2014, 34, 1235.)
[75] Haydar, G.; Imerhasan, M.; Eshbakova, K. A.; Kurbanbaeva, A. E. J. Pharm. Biol. Sci. 2016, 4, 41.
[76] Tian, X. Y.; Yang, D.; Pan, Y. M.; Tong, B. H.; Su, G. F.; Wang, H. S. Chin. J. Org. Chem. 2011, 31, 346(in Chinese). (田小艳, 杨达, 潘英明, 童碧海, 苏桂发, 王恒山, 有机化学, 2011, 31, 346.)
[77] Percivalle, C.; Mahmood, T.; Ladame, S. Med. Chem. Commun. 2013, 4, 211.
[78] Centelles, V. M.; Burguete, M. I.; Galindo, F.; Izquierdo, M. A.; Kumar, D. K.; White, A. J. P.; Luis, S. V.; Vilar, R. J. Org. Chem. 2012, 77, 490.
[79] Jana, A.; Saha, B.; Karthik, S.; Barman, S.; Ikbal, M.; Ghosh, S. K.; Singh, N. D. P. Photochem. Photobiol. Sci. 2013, 12, 1041.
[80] Fusco, M. D.; Quintavalla, A.; Trombini, C.; Lombardo, M.; Roda, A.; Guardigli, M.; Mirasoli, M. J. Org. Chem. 2013, 78, 11238.
[81] Chen, D.; Zhang, X. Q.; Zhang, J. Y.; Wang, Y. Chem. J. Chin. Univ. 2015, 36, 484(in Chinese). (陈栋, 张学强, 张晶莹, 王悦, 高等学校化学学报, 2015, 36, 484.)
[82] Seo, J. A.; Jeon, S. K.; Gong, M. S.; Lee, J. Y.; Noh, C. H.; Kim, S. H. J. Mater. Chem. C 2015, 3, 4640.
[83] Zhao, Y.-P. M.S. Thesis, Fujian Medical University, Fuzhou, 2015(in Chinese). (赵燕苹, 硕士论文, 福建医科大学, 福州, 2015.)
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