Synthesis and Application of Acridine Derivatives
- Corresponding author: Imerhasan Mukhtar, imerhasan@yahoo.com
Citation:
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
Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Buriol, L.; Machado, P. Chem. Rev. 2009, 109, 4140.
doi: 10.1021/cr9001098
Kalirajan, R.; Muralidharan, V.; Jubie, S.; Gowramma, B.; Gomathy, S.; Sankar, S.; Elango, K. J. Heterocycl. Chem. 2012, 49, 748.
doi: 10.1002/jhet.848
Bonse, S.; Santelli, R. C.; Barbe, J.; Krauth-Siegel, R. L. J. Med. Chem. 1999, 42, 5448.
doi: 10.1021/jm990386s
Nadaraj, V.; Selvi, S. T.; Mohan, S. Eur. J. Med. Chem. 2009, 44, 976.
doi: 10.1016/j.ejmech.2008.07.004
Wilson, W. R.; Thompson, L. H.; Anderson, R. F.; Denny, W. A. J. Med. Chem. 1989, 32, 31.
doi: 10.1021/jm00121a007
Bastianelli, C.; Caia, V.; Cum, G.; Gallo, R.; Mancini, V. J. Chem. Soc., Perkin Trans. 21991, 679.
Jaycox, D.; Gribble, G. W.; Hacker, J. Heterocycl. Chem. 1987, 24, 1405.
doi: 10.1002/jhet.v24:5
Zhang, X.-P.; Shi, H.-L.; Yan, M. Med. Ind. 1984, 3, 8(in Chinese).
Velingkar, V. S.; Dandekar, V. D. Chin. J. Chem. 2011, 29, 504.
doi: 10.1002/cjoc.201190113
Ferreira, R.; Avinó, A.; Mazzini, S.; Eritja, R. Molecules 2012, 17, 7067.
doi: 10.3390/molecules17067067
Geddes, C. D. Dyes Pigm. 2000, 45, 243.
doi: 10.1016/S0143-7208(00)00025-5
Goel, A.; Kumar, V.; Singh, S. P.; Sharma, A.; Prakash, S.; Singh, C.; Anand, R. S. J. Mater. Chem. 2012, 22, 14880.
doi: 10.1039/c2jm31052j
Chen, P.; Wang, Y.-Y.; Zhang, Y. M.; Zhang, X. A. Acta Chim. Sinica 2016, 74, 669(in Chinese).
doi: 10.11862/CJIC.2016.069
Popp, F. D. J. Org. Chem. 1962, 27, 2658.
doi: 10.1021/jo01054a518
Roopan, S. M.; Nawaz Khan, F. R. Med. Chem. Res. 2011, 20, 732.
doi: 10.1007/s00044-010-9381-7
Das, S.; Thakur, A. J. Green Chem. Lett. Rev. 2011, 4, 131.
doi: 10.1080/17518253.2010.521775
Avila, J. M.; Vargas, F. D.; Camacho, S. P. D.; Rivero, I. A. RSC Adv. 2012, 2, 1827.
doi: 10.1039/c1ra01135a
Kaur, B.; Kumar, H. J. Chem. Sci. 2013, 125, 989.
doi: 10.1007/s12039-013-0431-9
Kaur, B.; Parmar, A.; Kumar, H. Heterocycl. Lett. 2011, 1, 59.
Kaur, B.; Parmar, A.; Kumar, H. Synth. Commun. 2012, 42, 453.
Puri, S.; Kaur, B.; Parmar, A.; Kumar, H. Heterocycl. Commun. 2009, 15, 57.
Gómez, A. H.; Herd, E.; Uzelac, M.; Cadenbach, T.; Kennedy, A. R.; Borilovic, I.; Aromí, G.; Hevia, E. Organometallics 2015, 34, 2614.
doi: 10.1021/om501251q
Kozlov, N. G.; Bondarev, S. L.; Kadutskii, A. P.; Basalaeva, L. I. Zh. Org. Khim. 2010, 46, 209.
Kozlov, N. G.; Bondarev, S. L.; Knyukshto, V. N.; Odnoburtsev, B. A.; Basalaeva, L. I. Zh. Org. Khim. 2010, 46, 1639.
Kozlov, N. G. Zh. Org. Khim. 2011, 47, 1675.
Kozlov, N. G.; Tereshko, A. B.; Gusak, K. N. Zh. Org. Khim. 2006, 42, 281.
Kozlov, N. G.; Gusak, K. N. Zh. Obshch. Khim. 2006, 76, 294.
Silaichev, P. S.; Dmitriev, M. V.; Aliev, Z. G.; Maslivets, A. N. Zh. Org. Khim. 2010, 46, 1173.
Romain, M.; Tondelier, D.; Geffroy, B.; Shirinskaya, A.; Jeannin, O.; Berthelot, J. R.; Poriel, C. Chem. Commun. 2015, 51, 1313.
doi: 10.1039/C4CC08028A
Ghadari, R.; Hajishaabanha, F.; Mahyari, M.; Shaabani, A.; Khavasi, H. R. Tetrahedron Lett. 2012, 53, 4018.
doi: 10.1016/j.tetlet.2012.05.107
Yeşildağ, I.; Ulus, R.; Başar, E.; Aslan, M.; Kaya, M.; Buülbül, M. Monatsh Chem. 2014, 145, 1027.
doi: 10.1007/BF03246091
Ghorbani-Vaghei, R.; Malaekehpoor, S. M. J. Iran. Chem. Soc. 2010, 7, 957.
doi: 10.1007/s00706-013-1145-x
Mahajan, S.; Khullar, S.; Mandal, S. K.; Singh, I. P. Chem. Commun. 2014, 50, 10078.
doi: 10.1039/C4CC03079F
Yang, X. J.; Zhang, C.; Wu, L. Q. RSC Adv. 2015, 5, 18945.
doi: 10.1039/C4RA16372A
Yang, X. J.; Zhang, C.; Wu, L. Q. RSC Adv. 2015, 5, 25115.
doi: 10.1039/C5RA00887E
Jagadishbabu, N.; Shivashankar, K. RSC Adv. 2015, 5, 95240.
doi: 10.1039/C5RA19595K
Caballero, A. B.; Guillena, G. G.; Nájera, C. J. Org. Chem. 2013, 78, 5349.
doi: 10.1021/jo2025114
Liang, T.; Xiao, J.; Xiong, Z. Y.; Li, X. W. J. Org. Chem. 2012, 77, 3583.
doi: 10.1021/jo400522m
Wang, H. Y.; Li, L. L.; Lin, W.; Xu, P.; Huang, Z. B.; Shi, D. Q. Org. Lett. 2012, 14, 4598.
doi: 10.1021/ol302058g
Li, C. M.; Zhang, F. R. RSC Adv. 2016, 6, 75359.
doi: 10.1039/C6RA18048E
Hao, W. J.; Wang, J. Q.; Xu, X. P.; Zhang, S. L.; Wang, S. Y.; Ji, S. J. J. Org. Chem. 2013, 78, 12362.
doi: 10.1021/jo401773j
Rogness, D. C.; Larock, R. C. J. Org. Chem. 2010, 75, 2289.
doi: 10.1021/jo1000687
Han, X. D.; Zhao, Y. L.; Meng, J.; Ren, C. Q.; Liu, Q. J. Org. Chem. 2012, 77, 5173.
doi: 10.1021/jo300615t
Verma, A. K.; Reddy Kotla, S. K.; Aggarwal, T.; Kumar, S.; Nimesh, H.; Tiwari, R. K. J. Org. Chem. 2013, 78, 5372.
doi: 10.1021/jo400539x
Gimenez-Arnau, E.; Missailidis, S.; Stevens, M. F. G. Anti-Cancer Drug Des. 1998, 13, 431.
McCarthy, P. J.; Pitts, T. P.; Gunawardana, G. P.; Kelly-Borges, M.; Pomponi, S. A. J. Nat. Prod. 1992, 55, 1664.
doi: 10.1021/np50089a016
Sarkar, P.; Mukhopadhyay, C. Green Chem. 2015, 17, 3452.
doi: 10.1039/C5GC00156K
Khalil, I. M.; Barker, D.; Copp, B. R. J. Org. Chem. 2016, 81, 282.
doi: 10.1021/acs.joc.5b02312
Marshall, K. M.; Barrows, L. R. Nat. Prod. Rep. 2004, 21, 731.
doi: 10.1039/b401662a
Gu, Z. Y.; Liu, C. G.; Wang, S. Y.; Ji, S. J. Org. Lett. 2016, 18, 2379.
doi: 10.1021/acs.orglett.6b00843
Ma, Y. G.; Qiang, W. W.; Li, C.; Zhang, M. M.; Wang, X. S. Monatsh. Chem. 2016, 147, 1233.
doi: 10.1007/s00706-015-1625-2
Tsvelikhovsky, D.; Buchwald, S. L. J. Am. Chem Soc. 2010, 132, 14048.
doi: 10.1021/ja107511g
Dubrovskiy, A. V.; Larock, R. C. J. Org. Chem. 2012, 77, 11232.
doi: 10.1021/jo302378w
Lian, Y. J.; Hummel, J. R.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 12548.
doi: 10.1021/ja406131a
Guo, H. M.; Mao, R. Z.; Wang, Q. T.; Niu, H. Y.; Xie, M. S.; Qu, G. R. Org. Lett. 2013, 15, 5460.
doi: 10.1021/ol402596g
Su, Q.; Li, P.; He, M. N.; Wu, Q. L.; Ye, L.; Mu, Y. Org. Lett. 2014, 16, 18.
doi: 10.1021/ol402732n
Zheng, Z. S.; Dian, L. Y.; Yuan, Y. C.; Negrerie, D. Z.; Du, Y. F.; Zhao, K. J. Org. Chem. 2014, 79, 7451.
doi: 10.1021/jo5011697
Pang, X. L.; Chen, C.; Su, X.; Li, M.; Wen, L. R. Org. Lett. 2014, 16, 6228.
doi: 10.1021/ol503156g
Wang, T. J.; Chen, W. W.; Li, Y. Xu, M. H. Org. Biomol. Chem. 2015, 13, 6580.
doi: 10.1039/C5OB00755K
Sarkar, R.; Mukhopadhyay, C. Org. Biomol. Chem. 2016, 14, 2706.
doi: 10.1039/C5OB02655E
Zhikharko, Y. D.; Kozlov, N. G.; Basalaeva, L. I. Zh. Org. Khim. 2016, 52, 383.
Natrajan, A.; Wen, D. Green Chem. 2011, 13, 913.
doi: 10.1039/c0gc00758g
Hyodo, I.; Tobisu, M.; Chatani, N. Chem. Commun. 2012, 48, 308.
doi: 10.1039/C1CC16582H
Zhang, Z. G.; Gao, Y.; Liu, Y.; Li, J. J.; Xie, H. X.; Li, H.; Wang, W. Org. Lett. 2015, 17, 5492.
doi: 10.1021/acs.orglett.5b02877
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.
doi: 10.1016/S1872-2067(15)61005-1
Imerhasan, M.; Wang, T.; Helil, S.; Osman, K.; Muhammad, T. Chin. J. Org. Chem. 2010, 30, 1884(in Chinese).
Sondhi, S. M.; Singh, J.; Rani, R.; Gupta, P. P.; Agrawal, S. K.; Saxena, A. K. Eur. J. Med. Chem. 2010, 45, 555.
doi: 10.1016/j.ejmech.2009.10.042
Patel, M. M.; Mali, M. D.; Patel, S. K. Bioorg. Med. Chem. Lett. 2010, 20, 6324.
doi: 10.1016/j.bmcl.2010.06.001
Graham, L. A.; Wilson, G. M.; West, T. K.; Day, C. S.; Kucera, G. L.; Bierbach, U. ACS Med. Chem. Lett. 2011, 2, 687.
doi: 10.1021/ml200104h
Kumar, P.; Kumar, R.; Prasad, D. N. P. Arabian J. Chem. 2013, 6, 79.
doi: 10.1016/j.arabjc.2012.04.039
Mahsud, L.; Imerhasan, M.; Mahmud, M. A.; Helil, S.; Liu, H. J. Chin. J. Org. Chem. 2014, 34, 1235(in Chinese).
Haydar, G.; Imerhasan, M.; Eshbakova, K. A.; Kurbanbaeva, A. E. J. Pharm. Biol. Sci. 2016, 4, 41.
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).
Percivalle, C.; Mahmood, T.; Ladame, S. Med. Chem. Commun. 2013, 4, 211.
doi: 10.1039/C2MD20173A
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.
doi: 10.1021/jo202077v
Jana, A.; Saha, B.; Karthik, S.; Barman, S.; Ikbal, M.; Ghosh, S. K.; Singh, N. D. P. Photochem. Photobiol. Sci. 2013, 12, 1041.
doi: 10.1039/c3pp25362g
Fusco, M. D.; Quintavalla, A.; Trombini, C.; Lombardo, M.; Roda, A.; Guardigli, M.; Mirasoli, M. J. Org. Chem. 2013, 78, 11238.
doi: 10.1021/jo401683r
Chen, D.; Zhang, X. Q.; Zhang, J. Y.; Wang, Y. Chem. J. Chin. Univ. 2015, 36, 484(in Chinese).
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.
doi: 10.1039/C5TC00640F
Zhao, Y. -P. M. S. Thesis, Fujian Medical University, Fuzhou, 2015(in Chinese).
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