Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Review Article

A Review on Synthetic Approaches of Phenanthridine

Author(s): Nilesh Kshirsagar, Ratnamala Sonawane*, Sultan Pathan*, Ganesh Kamble and Girdhar Pal Singh

Volume 19, Issue 6, 2022

Published on: 11 January, 2022

Page: [434 - 452] Pages: 19

DOI: 10.2174/1570178618666210218211424

Price: $65

Abstract

The phenanthridine family is widely found in medicinal chemistry and material science because of the biological activity and its presence in a variety of significant natural products and synthetic dye stuffs. The phenanthridine has many clinical applications, for e.g., being used as an anticancer agent, possessing antibacterial, antiprotozoal, pharmaceutical, and optoelectronic properties. Many methods have been reported for the synthesis of phenanthridine and phenanthridine alkaloids, such as Pd catalyzed C-C bond formation, a reaction involving C-H activation, radical, microwave-assisted, transition metal-catalyzed, one-pot cascade, benzyne mediated, photochemical, hypervalent iodine promoted methods, etc. Here, we have summarized the literature data from 2014 to the present concerning novel or improved synthetic approaches.

Keywords: Phenanthridine, palladium, visible light, fluorescent, cyclization, alkaloids.

Graphical Abstract

[1]
Balasubramanian, M. Comprehensive Heterocyclic Chemistry II; Pergamon Press: Oxford, UK, 1996, Vol. 5, pp. 245-300.
[http://dx.doi.org/10.1016/B978-008096518-5.00109-X]
[2]
Prajapati, S.M.; Patel, K.D.; Vekariya, R.H.; Panchal, S.N.; Patel, H.D. RSC Advances, 2014, 4, 24463.
[3]
Dubost, E.; Dumas, N.; Fossey, C.; Magnelli, R.; Butt-Gueulle, S.; Ballandonne, C.; Caignard, D.H.; Dulin, F.; Sopkova de-Oliveira Santos, J.; Millet, P.; Charnay, Y.; Rault, S.; Cailly, T.; Fabis, F. J. Med. Chem., 2012, 55(22), 9693-9707.
[http://dx.doi.org/10.1021/jm300943r] [PMID: 23102207]
[4]
Bhalla, V.; Vij, V.; Kumar, M.; Sharma, P.R.; Kaur, T. Org. Lett., 2012, 14(4), 1012-1015.
[http://dx.doi.org/10.1021/ol203339c] [PMID: 22280540]
[5]
Velusamy, M.; Chen, C.H.; Wen, Y.S.; Lin, J.T.; Lin, C.C.; Lai, C.H.; Chou, P.T. Organometallics, 2010, 29, 3912.
[http://dx.doi.org/10.1021/om100573r]
[6]
Tao, S.; Li, L.; Yu, J.; Jiang, Y.; Zhou, Y.; Lee, C.S.; Lee, S.T.; Zhang, X.; Kwon, O. Chem. Mater., 2009, 21, 1284.
[http://dx.doi.org/10.1021/cm803087c]
[7]
Kim, J.I.; Shin, I.S.; Kim, H.; Lee, J.K. J. Am. Chem. Soc., 2005, 127(6), 1614-1615.
[http://dx.doi.org/10.1021/ja043721x] [PMID: 15700976]
[8]
Abrunhosa, I.; Delain-Bioton, L.; Gaumont, A.C.; Gulea, M.; Masson, S. Tetrahedron, 2004, 60, 9263.
[http://dx.doi.org/10.1016/j.tet.2004.07.048]
[9]
Zhang, Y.; Sigman, M.S. J. Am. Chem. Soc., 2007, 129(11), 3076-3077.
[http://dx.doi.org/10.1021/ja070263u] [PMID: 17298071]
[10]
Biddle, M.M.; Lin, M.; Scheidt, K.A. J. Am. Chem. Soc., 2007, 129(13), 3830-3831.
[http://dx.doi.org/10.1021/ja070394v] [PMID: 17348659]
[11]
Tan, B.; Shi, Z.; Chua, P.J.; Zhong, G. Org. Lett., 2008, 10(16), 3425-3428.
[http://dx.doi.org/10.1021/ol801246m] [PMID: 18616339]
[12]
Viladomat, F.; Sellés, M.; Codina, C.; Bastida, J. Phytochemistry, 1986, 25, 2399-2401.
[13]
Budén, M.E.; Dorn, V.B.; Gamba, M.; Pierini, A.B.; Rossi, R.A. J. Org. Chem., 2010, 75(7), 2206-2218.
[http://dx.doi.org/10.1021/jo9025918] [PMID: 20210329]
[14]
Sarkar, S.N. Aquaculture, 2011, 318, 235-238.
[15]
Krane, B.D.; Fagbule, M.O.; Shamma, M. J. Nat. Prod., 1984, 47, 1-43.
[http://dx.doi.org/10.1021/np50031a001]
[16]
Merz, K.; Muller, T.; Vanderheiden, S.; Eisenbrand, G.; Mar-ko, D.; Bräse, S. Synlett, 2006, 3461-3463.
[17]
Slaninová, I.; Slanina, J.; Táborská, E. Cytometry A, 2007, 71(9), 700-708.
[http://dx.doi.org/10.1002/cyto.a.20423] [PMID: 17549765]
[18]
Nishiwaki, H.; Miura, M.; Imai, K.; Ono, R.; Kawashima, K. Cancer Res., 1974, 34(10), 2699-2703.
[PMID: 4413384]
[19]
Parenty, A.D.C.; Smith, L.V.; Guthrie, K.M.; Long, D-L.; Plumb, J.; Brown, R.; Cronin, L. J. Med. Chem., 2005, 48(14), 4504-4506.
[http://dx.doi.org/10.1021/jm050320z] [PMID: 15999988]
[20]
Kock, I.; Heber, D.; Weide, M.; Wolschendorf, U.; Clement, B. J. Med. Chem., 2005, 48(8), 2772-2777.
[http://dx.doi.org/10.1021/jm0490888] [PMID: 15828815]
[21]
Krasiński, A.; Radić Z.; Manetsch, R.; Raushel, J.; Taylor, P.; Sharpless, K.B.; Kolb, H.C. J. Am. Chem. Soc., 2005, 127(18), 6686-6692.
[http://dx.doi.org/10.1021/ja043031t] [PMID: 15869290]
[22]
Stevenson, P.; Sones, K.R.; Gicheru, M.M.; Mwangi, E.K. Acta Trop., 1995, 59(2), 77-84.
[http://dx.doi.org/10.1016/0001-706X(94)00080-K] [PMID: 7676909]
[23]
Duhamel, J.; Kanyo, J.; Dinter-Gottlieb, G.; Lu, P. Biochemistry, 1996, 35(51), 16687-16697.
[http://dx.doi.org/10.1021/bi9610919] [PMID: 8988005]
[24]
Luedtke, N.W.; Liu, Q.; Tor, Y. Chemistry, 2005, 11(2), 495-508.
[http://dx.doi.org/10.1002/chem.200400559] [PMID: 15549769]
[25]
Kshirsagar, N.; Sonawane, R.; Patil, P.; Nandre, J.; Sultan, P.; Sehlangia, S. Inorg. Chim. Acta, 2020, •••119805
[http://dx.doi.org/10.1016/j.ica.2020.119805]
[26]
Piantanida, I. Palm, B.S.; Čudić P.; Žinić M.; Schneider, H-J. Tetrahedron Lett., 2001, 42, 6779-6783.
[http://dx.doi.org/10.1016/S0040-4039(01)01386-7]
[27]
Piantanida, I. Palm, B.S.; Čudić P.; Žinić M.; Schneider, H-J. Tetrahedron, 2004, 60, 6225-6231.
[http://dx.doi.org/10.1016/j.tet.2004.05.009]
[28]
Dukši, M. Baretić D.; Čaplar, V.; Piantanida, I. Eur. J. Med. Chem., 2010, 45(6), 2671-2676.
[http://dx.doi.org/10.1016/j.ejmech.2010.02.017] [PMID: 20202724]
[29]
Goel, A.; Kumar, V.; Singh, S.P.; Sharma, A.; Prakash, S.; Singh, C.; Anand, R.S. J. Mater. Chem., 2012, 22, 14880.
[http://dx.doi.org/10.1039/c2jm31052j]
[30]
Bondarev, S.L.; Knyukshto, V.N.; Tikhomirov, S.A.; Pyrko, A.N. Opt. Spectrosc., 2006, 100, 386.
[http://dx.doi.org/10.1134/S0030400X06030131]
[31]
Zhang, J.; Lakowicz, J.R. J. Phys. Chem. B, 2005, 109(18), 8701-8706.
[http://dx.doi.org/10.1021/jp046016j] [PMID: 16852030]
[32]
Barday, M.; Janot, C.; Halcovitch, N.R.; Muir, J.; Aïssa, C. Angew. Chem. Int. Ed. Engl., 2017, 56(42), 13117-13121.
[http://dx.doi.org/10.1002/anie.201706804] [PMID: 28853234]
[33]
Barday, M.; Janot, C.; Halcovitch, N.R.; Muir, J.; Aïssa, C. Angew. Chem., 2017, 129, 13297.
[http://dx.doi.org/10.1002/ange.201706804]
[34]
Lian, Y.; Hummel, J.R.; Bergman, R.G.; Ellman, J.A. J. Am. Chem. Soc., 2013, 135(34), 12548-12551.
[http://dx.doi.org/10.1021/ja406131a] [PMID: 23957711]
[35]
Zhao, H-B.; Liu, Z-J.; Song, J.; Xu, H-C. Angew. Chem., 2017, 129, 12906.
[http://dx.doi.org/10.1002/ange.201707192]
[36]
Zhao, H-B.; Liu, Z-J.; Song, J.; Xu, H-C. Angew. Chem. Int. Ed. Engl., 2017, 56(41), 12732-12735.
[http://dx.doi.org/10.1002/anie.201707192] [PMID: 28815829]
[37]
Ramesh, D.; Kar, G.K.; Chatterjee, B.G.; Ray, J.K. J. Org. Chem., 1988, 53, 212.
[http://dx.doi.org/10.1021/jo00236a049]
[38]
Kuninobu, Y.; Tatsuzaki, T.; Matsuki, T.; Takai, K. J. Org. Chem., 2011, 76(17), 7005-7009.
[http://dx.doi.org/10.1021/jo200861s] [PMID: 21761938]
[39]
Ghosh, M.; Ahmed, A.; Dhara, S.; Ray, J.K. Tetrahedron Lett., 2013, 54, 4837.
[http://dx.doi.org/10.1016/j.tetlet.2013.06.089]
[40]
Guo, H-M.; Mao, R-Z.; Wang, Q-T.; Niu, H-Y.; Xie, M-S.; Qu, G-R. Org. Lett., 2013, 15(21), 5460-5463.
[http://dx.doi.org/10.1021/ol402596g] [PMID: 24152129]
[41]
Su, Q.; Li, P.; He, M.; Wu, Q.; Ye, L.; Mu, Y. Org. Lett., 2014, 16(1), 18-21.
[http://dx.doi.org/10.1021/ol402732n] [PMID: 24350595]
[42]
Shestakov, A.N.; Pankova, A.S.; Kuznetsov, M.A. Chem. Heterocycl. Compd., 2017, 53, 1103.
[http://dx.doi.org/10.1007/s10593-017-2179-5]
[43]
Liu, X.; Qing, Z.; Cheng, P.; Zheng, X.; Zeng, J.; Xie, H. Molecules, 2016, •••, 21.
[44]
Chen, Y-y.; Zhang, N-n.; Ye, L-m.; Chen, J-h.; Sun, X.; Zhang, X-j.; Yan, M.; Adv, R.S.C. RSC Advances, 2015, 5, 48046.
[45]
(a) Prajapati, S.M.; Patel, K.D.; Vekariya, R.H.; Panchal, S.N.; Patel, H.D.; Adv, R.S.C. RSC Advances, 2014.
(b) Lett. Org. Chem., 2020, 17, 743-748.
[http://dx.doi.org/10.2174/1570178617666200207110526]
[46]
Manske, R.H. Chem. Rev., 1942, 30, 113.
[http://dx.doi.org/10.1021/cr60095a006]
[47]
Theobald, R.S.; Schofield, K. Chem. Rev., 1950, 46, 170.
[http://dx.doi.org/10.1021/cr60143a004]
[48]
Marco-Contelles, J.; Pérez-Mayoral, E. Chem. Rev., 2009, 109, 2652-2671.
[http://dx.doi.org/10.1021/cr800482c] [PMID: 19361199]
[49]
Pictet, A.; Ankersmit, H.J. Justus Liebigs Ann. Chem., 1891, 266, 138-153.
[http://dx.doi.org/10.1002/jlac.18912660107]
[50]
Morgan, G.T.; Walls, L.P. J. Chem. Soc., 1931, 2447-2456.
[http://dx.doi.org/10.1039/JR9310002447]
[51]
Lysén, M.; Kristensen, J.L.; Vedsø, P.; Begtrup, M. Org. Lett., 2002, 4(2), 257-259.
[http://dx.doi.org/10.1021/ol0170051] [PMID: 11796064]
[52]
De Mayo, P.; Rigby, W. Nature, 1950, 166(4234), 1075.
[http://dx.doi.org/10.1038/1661075b0] [PMID: 14796696]
[53]
Narasimhan, N.S.; Chandrachood, P.S.; Shete, N.R. Tetrahedron, 1981, 37, 825-827.
[http://dx.doi.org/10.1016/S0040-4020(01)97703-8]
[54]
Catal. Sci. Technol., 2016, 6, 3302-3316.
[http://dx.doi.org/10.1039/C5CY02197A]
[55]
Jayakumar, Jayachandran; Vedarethinam, Guganchandar; Hsiao, Huan-Chang; Sun, Shang-You; Chuang, Shih-Ching International Edition, 2020, 59(2), 689-694.
[56]
Pramanik, S.; Jash, M.; Mondal, D.; Chowdhury, C. Adv. Synth. Catal., 2019, 361(22), 5223-5238.
[http://dx.doi.org/10.1002/adsc.201900833]
[57]
Gulbrandsen, H.S.; Serigstad, H.; Read, L. Eur. J. Org. Chem., 2019, 2019(35), 6044-6052.
[http://dx.doi.org/10.1002/ejoc.201901000]
[58]
Janke, S.; Boldt, S.; Ghazargan, K.; Ehlers, P.; Villinger, A.; Langer, P. Eur. J. Org. Chem., 2019, 2019(36), 6177-6197.
[http://dx.doi.org/10.1002/ejoc.201900913]
[59]
(a) Bao, Yinwei; Wang, Zhuo; Chen, Chen; Zhu, Bolin; Wang, Yuebo; Zhao, Jinghui; Gong, Jinyu; Han, Mengya; Liu,Chang. Tetrahedron, 2019, 75(10), 1450-1456.
(b) Synthetic Communications,, , 1-35.
[60]
Wang, Z.; Li, T.; Zhao, J.; Shi, X.; Jiao, D.; Zheng, H.; Chen, C.; Zhu, B. Org. Lett., 2018, 20(21), 6640-6645.
[http://dx.doi.org/10.1021/acs.orglett.8b02588] [PMID: 30350669]
[61]
Abe, Hitoshi; Kobayashi, Naoko; Kadoshima, Yutaka; Takeuchi, Yasuo; Harayama, Takashi; Horino. Yoshikazu Heterocycles, 2016, 93(2), 673-684.
[62]
Gupta, T.; Singh, J.B.; Singh, R.; Singh, R.M. Eur. J. Org. Chem., 2018, 2018(31), 4284-4295.
[http://dx.doi.org/10.1002/ejoc.201800725]
[63]
Jaiswal, Y.; Kumar, Y.; Pal, J.; Subramanian, R.; Kumar, A. Chem. Commun. (Camb.), 2018, 54(52), 7207-7210.
[http://dx.doi.org/10.1039/C8CC03556C] [PMID: 29897059]
[64]
Saini, G.; Kumar, P.; Kumar, G.S.; Mangadan, A.R.K.; Kapur, M. Org. Lett., 2018, 20(2), 441-444.
[http://dx.doi.org/10.1021/acs.orglett.7b03776] [PMID: 29313688]
[65]
Liu, X.; Mao, R.; Ma, C. Org. Lett., 2017, 19(24), 6704-6707.
[http://dx.doi.org/10.1021/acs.orglett.7b03427] [PMID: 29172546]
[66]
Raju, S.; Annamalai, P.; Chen, P-L.; Liu, Y-H.; Chuang, S-C. Org. Lett., 2017, 19(15), 4134-4137.
[http://dx.doi.org/10.1021/acs.orglett.7b01956] [PMID: 28718655]
[67]
Yang, S-Y.; Han, W-Y.; Zhang, D-L.; Zhou, X-J.; Bai, M.; Cui, B-D.; Wan, N-W.; Yuan, W-C.; Chen, Y-Z. Eur. J. Org. Chem., 2017, 2017(5), 996-1003.
[http://dx.doi.org/10.1002/ejoc.201601608]
[68]
Jen-Chieh Tetrahedron, 2016, 72(36), 5640-5645.
[http://dx.doi.org/10.1016/j.tet.2016.07.065]
[69]
Kuwata, Y.; Sonoda, M.; Tanimori, S. J. Heterocycl. Chem., 2017, 54(2), 1645-1651.
[http://dx.doi.org/10.1002/jhet.2725]
[70]
Raju, G.; Guguloth, V.; Satyanarayana, B. RSC Advances, 2016, 6(51), 45036-45040.
[http://dx.doi.org/10.1039/C6RA07423E]
[71]
Ge, J.; Wang, X.; Liu, T.; Shi, Z.; Xiao, Q.; Yin, D. RSC Advances, 2016, 6(23), 19571-19575.
[http://dx.doi.org/10.1039/C6RA00249H]
[72]
Han, W.; Zhou, X.; Yang, S.; Xiang, G.; Cui, B.; Chen, Y. J. Org. Chem., 2015, 80(22), 11580-11587.
[http://dx.doi.org/10.1021/acs.joc.5b02145] [PMID: 26513449]
[73]
Ding, S.; Zhao, Y.; Ma, Q.; Tian, S.; Ren, H.; Zhu, M.; Li, K. Miao. Z. Chem. Lett., 2018, 47(4), 562-565.
[http://dx.doi.org/10.1246/cl.180009]
[74]
Zhu, S-Q.; Xu, X-H.; Qing, F-L. Chem. Commun. (Camb.), 2017, 53(83), 11484-11487.
[http://dx.doi.org/10.1039/C7CC05411D] [PMID: 28990036]
[75]
Tang, J.; Sivaguru, P.; Ning, Y.; Zanoni, G.; Bi, X. Org. Lett., 2017, 19(15), 4026-4029.
[http://dx.doi.org/10.1021/acs.orglett.7b01771] [PMID: 28737404]
[76]
Wan, W.; Xu, X.; Chen, Y.; Jiang, H.; Wang, Y.; Deng, H.; Hao, J. Eur. J. Org. Chem., 2017, 2017(22), 3145-3151.
[http://dx.doi.org/10.1002/ejoc.201700470]
[77]
Guo, W-S.; Dou, Q.; Hou, J.; Wen, L-R.; Li, M. J. Org. Chem., 2017, 82(13), 7015-7022.
[http://dx.doi.org/10.1021/acs.joc.7b00907] [PMID: 28608685]
[78]
Zhang, T-Y.; Lin, J-B.; Li, Q-Z.; Kang, J-C.; Pan, J-L.; Hou, S-H.; Chen, C.; Zhang, S-Y. Org. Lett., 2017, 19(7), 1764-1767.
[http://dx.doi.org/10.1021/acs.orglett.7b00442] [PMID: 28291370]
[79]
Yang, Z.; Chen, F.; Zhang, S.; He, Y.; Yang, N.; Fan, Q-H. Org. Lett., 2017, 19(6), 1458-1461.
[http://dx.doi.org/10.1021/acs.orglett.7b00419] [PMID: 28263076]
[80]
Yao, Q.; Zhou, X.; Zhang, X.; Wang, C.; Wang, P.; Li, M. Org. Biomol. Chem., 2017, 15(4), 957-971.
[http://dx.doi.org/10.1039/C6OB02331B] [PMID: 28059413]
[81]
Nie, Z.; Ding, Q.; Peng, Y. Tetrahedron, 2016, 72(50), 8350-8357.
[http://dx.doi.org/10.1016/j.tet.2016.11.010]
[82]
Yang, J-C.; Zhang, J-J.; Guo, L-N. Org. Biomol. Chem., 2016, 14(41), 9806-9813.
[http://dx.doi.org/10.1039/C6OB02012G] [PMID: 27714246]
[83]
Li, Jialiang; Wan, Wen; Ma, Guobin; Jiang, Haizhen Hao, Jian Faming Zhuanli Shenqing CN 105348194 A 20160224, 2016.
[84]
Martin Synthesis, 2016, 48(7), 987-996.
[http://dx.doi.org/10.1055/s-0035-1561343]
[85]
Battula, S.; Kumar, A.; Gupta, A.P.; Ahmed, Q.N. Org. Lett., 2015, 17(22), 5562-5565.
[http://dx.doi.org/10.1021/acs.orglett.5b02699] [PMID: 26523429]
[86]
Wang, B.; Dai, Y.; Tong, W.; Gong, H. Org. Biomol. Chem., 2015, 13(47), 11418-11421.
[http://dx.doi.org/10.1039/C5OB01901J] [PMID: 26524544]
[87]
Liu, Y-R.; Tu, H-Y.; Zhang, X-G. Synthesis, 2015, 47(22), 3460-3466.
[http://dx.doi.org/10.1055/s-0034-1378810]
[88]
Fu, M-C.; Shang, R.; Zhao, B.; Wang, B.; Fu, Y. Science, 2019, 363(6434), 1429-1434.
[http://dx.doi.org/10.1126/science.aav3200] [PMID: 30923218]
[89]
Cheng, W-M.; Shang, R.; Fu, Y. Nat. Commun., 2018, 9(1), 5215-5217.
[http://dx.doi.org/10.1038/s41467-018-07694-w] [PMID: 30523253]
[90]
Cheng, W-M.; Shang, R.; Fu, M-C.; Fu, Y. Chemistry, 2017, 23(11), 2537-2541.
[http://dx.doi.org/10.1002/chem.201605640] [PMID: 28078753]
[91]
Wang, G-Z.; Shang, R.; Cheng, W-M.; Fu, Y. J. Am. Chem. Soc., 2017, 139(50), 18307-18312.
[http://dx.doi.org/10.1021/jacs.7b10009] [PMID: 29116777]
[92]
Cheng, W-M.; Shang, R.; Fu, Y. ACS Catal., 2017, 7, 907-911.
[http://dx.doi.org/10.1021/acscatal.6b03215]
[93]
Douglas, J.J.; Sevrin, M.J.; Stephenson, C.R.J. Org. Process Res. Dev., 2016, 20, 1134-1147.
[http://dx.doi.org/10.1021/acs.oprd.6b00125]
[94]
Xi, Y. Org. Biomol. Chem., 2013, 11, 2387-2403.
[http://dx.doi.org/10.1039/c3ob40137e] [PMID: 23426621]
[95]
Reckenthäler, M.; Griesbeck, A.G. Adv. Synth. Catal., 2013, 355, 2727-2744.
[http://dx.doi.org/10.1002/adsc.201300751]
[96]
Tucker, J.W.; Stephenson, C.R.J. J. Org. Chem., 2012, 77(4), 1617-1622.
[http://dx.doi.org/10.1021/jo202538x] [PMID: 22283525]
[97]
Marzo, L.; Pagire, S.K.; Reiser, O.; König, B. Angew. Chem. Int. Ed., 2018, 57, 10034.
[http://dx.doi.org/10.1002/anie.201709766]
[98]
Ravelli, D.; Dondi, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev., 2009, 38(7), 1999-2011.
[http://dx.doi.org/10.1039/b714786b] [PMID: 19551179]
[99]
Prier, C.K.; Rankic, D.A.; MacMillan, D.W.C. Chem. Rev., 2013, 113(7), 5322-5363.
[http://dx.doi.org/10.1021/cr300503r] [PMID: 23509883]
[100]
Romero, N.A.; Nicewicz, D.A. Chem. Rev., 2016, 116(17), 10075-10166.
[http://dx.doi.org/10.1021/acs.chemrev.6b00057] [PMID: 27285582]
[101]
Hari, D.P.; König, B. Chem. Commun. (Camb.), 2014, 50(51), 6688-6699.
[http://dx.doi.org/10.1039/C4CC00751D] [PMID: 24699920]
[102]
Fukuzumi and K. Ohkubo. Org. Biomol. Chem., 2014, 12, 6059-6071.
[http://dx.doi.org/10.1039/C4OB00843J] [PMID: 24984977]
[103]
Yang, J-C.; Zhang, J-Y.; Zhang, J-J.; Duan, X-H.; Guo, L-N. J. Org. Chem., 2018, 83(3), 1598-1605.
[http://dx.doi.org/10.1021/acs.joc.7b02861] [PMID: 29299918]
[104]
Yu, Y.; Yuan, W.; Huang, H.; Cai, Z.; Liu, P.; Sun, P. J. Org. Chem., 2018, 83(3), 1654-1660.
[http://dx.doi.org/10.1021/acs.joc.7b03080] [PMID: 29285936]
[105]
Mao, L-L.; Zheng, D-G.; Zhu, X-H.; Zhou, A-X.; Yang, S-D. Org. Chem. Front., 2018, 5(2), 232-236.
[http://dx.doi.org/10.1039/C7QO00790F]
[106]
Singh, M.; Yadav, A.K. Synlett, 2018, 29(2), 176-180.
[http://dx.doi.org/10.1055/s-0036-1590921]
[107]
Feng, S.; Li, T.; Du, C.; Chen, P.; Song, D.; Li, J.; Xie, X.; She, X. Chem. Commun. (Camb.), 2017, 53(33), 4585-4588.
[http://dx.doi.org/10.1039/C7CC01813D] [PMID: 28387777]
[108]
Zhou, S.; Li, J.; Schlangen, M.; Schwarz, H. Angew. Chem. Int. Ed. Engl., 2016, 55(38), 11678-11681.
[http://dx.doi.org/10.1002/anie.201606259] [PMID: 27510819]
[109]
Xu, Y.; Chen, Y.; Li, W.; Xie, Q.; Shao, L. J. Org. Chem., 2016, 81(18), 8426-8435.
[http://dx.doi.org/10.1021/acs.joc.6b01589] [PMID: 27529185]
[110]
Sun, X.; Yu, S. Chem. Commun. (Camb.), 2016, 52(72), 10898-10901.
[http://dx.doi.org/10.1039/C6CC05756J] [PMID: 27530901]
[111]
Wang, S.; Jia, W-L.; Wang, L.; Liu, Q. Eur. J. Org. Chem., 2015, 2015(31), 6817-6821.
[http://dx.doi.org/10.1002/ejoc.201500988]
[112]
Tetrahedron, 2015, 71(32), 5130-5136.
[http://dx.doi.org/10.1016/j.tet.2015.05.064]
[113]
An, X-D.; Yu, S. Org. Lett., 2015, 17(11), 2692-2695.
[http://dx.doi.org/10.1021/acs.orglett.5b01096] [PMID: 25964987]
[114]
Rohe, S.; McCallum, T.; Morris, A.O.; Barriault, L. J. Org. Chem., 2018, 83(17), 10015-10024.
[http://dx.doi.org/10.1021/acs.joc.8b01380] [PMID: 29979602]
[115]
Liu, X.; Wu, Z.; Zhang, Z.; Liu, P.; Sun, P. Org. Biomol. Chem., 2018, 16(3), 414-423.
[http://dx.doi.org/10.1039/C7OB02804K] [PMID: 29261209]
[116]
Yang, J-C.; Zhang, J-J. Org. Biomol. Chem., 2016, 14(41), 9806-9813.
[http://dx.doi.org/10.1039/C6OB02012G] [PMID: 27714246]
[117]
(a) Natarajan, P.; Kumar, N.; Sharma, M. Org. Chem. Front, 2016, 3(10), 1265-1270.
[http://dx.doi.org/10.1039/C6QO00275G]
(b) Zhang, R.; Shi, X.; Yan, Q.; Li, Z.; Wang, Z.; Yu, H.; Wang, X.; Qi, J.; Jiang, M. RSC Advances, 2017, 7(62), 38830-38833.
[http://dx.doi.org/10.1039/C7RA08484F]
[118]
Boudier, A.; Bromm, L.O.; Lotz, M.; Knochel, P. Angew. Chem. Int. Ed., 2000, 39, 4414.
[http://dx.doi.org/10.1002/1521-3773(20001215)39:24<4414:AID-ANIE4414>3.0.CO;2-C]
[119]
Eisenstadt, A.; Ager, D.J. Fine Chemicals through Heterogeneous Catalysis.Sheldon, R. A., van Bekkum, H., Eds.; Chemical Reviews Review BB Chem. Rev; Wiley-VCH: Weinheim, 2001.
[120]
Nicolaou, K.C.; Bulger, P.G.; Sarlah, D. Angew. Chem. Int. Ed., 2005, 44, 4442.
[http://dx.doi.org/10.1002/anie.200500368]
[121]
Corbet, J-P.; Mignani, G. Chem. Rev., 2006, 106(7), 2651-2710.
[http://dx.doi.org/10.1021/cr0505268] [PMID: 16836296]
[122]
Magano, J.; Dunetz, J.R. Chem. Rev., 2011, 111(3), 2177-2250.
[http://dx.doi.org/10.1021/cr100346g] [PMID: 21391570]
[123]
Gupta, T.; Singh, J.B.; Mishra, K.; Maiti, B.; Singh, R.M. Eur. J. Org. Chem., 2018, 2018(9), 1130-1135.
[http://dx.doi.org/10.1002/ejoc.201701574]
[124]
Gupta, T.; Singh, J.B.; Mishra, K.; Singh, R.M. RSC Advances, 2017, 7(86), 54581-54585.
[http://dx.doi.org/10.1039/C7RA09447G]
[125]
He, Y.; Wang, X.; Xiao, J-A.; Pang, J.; Gan, C.; Huang, Y.; Huang, C. RSC Advances, 2018, 8(6), 3036-3040.
[http://dx.doi.org/10.1039/C7RA12755C]
[126]
Lu, S-C.; Li, H-S.; Gong, Y-L.; Wang, X-L.; Li, F-R.; Li, F.; Duan, G-Y.; Xu, S. RSC Advances, 2017, 7(88), 55891-55896.
[http://dx.doi.org/10.1039/C7RA12318C]
[127]
Fang, J.; Shen, W-G.; Ao, G-Z.; Liu, F. Org. Chem. Front., 2017, 4(10), 2049-2053.
[http://dx.doi.org/10.1039/C7QO00473G]
[128]
Song, W.; Yan, P.; Shen, D.; Chen, Z.; Zeng, X.; Zhong, G. J. Org. Chem., 2017, 82(8), 4444-4448.
[http://dx.doi.org/10.1021/acs.joc.7b00343] [PMID: 28362091]
[129]
Yang, Z.; Song, X.; Wei, Z.; Cao, J.; Liang, D.; Duan, H.; Lin, Y. Tetrahedron Lett., 2016, 57(22), 2410-2413.
[http://dx.doi.org/10.1016/j.tetlet.2016.04.067]
[130]
Ramanathan, M.; Liu, S-T. J. Org. Chem., 2015, 80(10), 5329-5336.
[http://dx.doi.org/10.1021/acs.joc.5b00579] [PMID: 25923346]
[131]
Tang, C.; Yuan, Y.; Jiao, N. Org. Lett., 2015, 17(9), 2206-2209.
[http://dx.doi.org/10.1021/acs.orglett.5b00797] [PMID: 25875319]
[132]
Ding, Siyi; Zhao, Yuzhen; Tian, Shaopeng; Ma, Qiang; Ren, Huaping; Zhu, Min; Li, Peng; Fan, Tengfei Xu, Tingting Faming Zhuanli Shenqing. CN 108299297 A 20180720, 2018.
[133]
Liu, Xiang; Ma, Cheng Faming Zhuanli Shenqing. CN 107935925 A 20180420, 2018.
[134]
Liu, Yunkui; Shi, Dongdong; Xu, Zheng; Shenqing, Faming Zhuanli CN 107793358 A 20180313, 2018.
[135]
Liu, Yunkui; Xu, Zheng CN 107641100 A 20180130, 2018.
[136]
Liu, Yunkui; Ren, Shaobo; Wang, Heng; Shenqing, Faming Zhuanli CN 106316953 A 20170111, 2017.
[137]
Stevenson, P.; Sones, K.R.; Gicheru, M.M.; Mwangi, E.K. Acta Trop., 59(2), 257-258.
[http://dx.doi.org/10.1016/0001-706X(94)00080]
[138]
Borst, P. IUBMB Life, 2005, 57(11), 745-747.
[http://dx.doi.org/10.1080/15216540500380855] [PMID: 16511967]
[139]
Wang Qingminet al Faming Zhuanli Shenqing. 110074124, 2019.
[140]
Bouquet, J.; Rivaud, M.; Chevalley, S.; Deharo, E.; Jullian, V.; Valentin, A. Malar. J., 2012, 11, 67.
[http://dx.doi.org/10.1186/1475-2875-11-67] [PMID: 22404785]
[141]
John, P. Chemistry (Easton), 1974, 39(22), 3239-3241.
[http://dx.doi.org/10.1021/jo00936a013]
[142]
Chrzastek, L.; Mianowska, B.; Sliwa, W. Aust. J. Chem., 1994, 47, 2129.
[http://dx.doi.org/10.1071/CH9942129]
[143]
Park, G.Y.; Wilson, J.J.; Song, Y.; Lippard, S.J. Proc. Natl. Acad. Sci. USA, 2012, 109(30), 11987-11992.
[http://dx.doi.org/10.1073/pnas.1207670109] [PMID: 22773807]
[144]
Cappoen, D.; Jacobs, J.; Nguyen Van, T.; Claessens, S.; Diels, G.; Anthonissen, R.; Einarsdottir, T.; Fauville, M.; Ver-schaeve, L.; Huygen, K.; De Kimpe, N. Eur. J. Med. Chem., 2012, 48, 57-68.
[http://dx.doi.org/10.1016/j.ejmech.2011.11.033] [PMID: 22182928]
[145]
Cappoen, D.; Torfs, E.; Meiresonne, T.; Claes, P.; Semina, E.; Holvoet, F. Eur. J. Med. Chem., 2019. 181111549p
[http://dx.doi.org/10.1016/j.ejmech.2019.07.052] [PMID: 31376569]
[146]
Lasak, P.; Motyka, K.; Krystof, V.; Styskala, J. Molecules, 2018, 23(9), 2155.
[147]
(a) Ryohei, A.; Nobumichi, A.; Takanori, M. JP. Kokai Tokkyo Koho. JP. 2017132734 A 20170803, 2017.
(b) Clement, B.; Girreser, U.; Steinhauer, T.N.; Meier, C.; Marko, D.; Aichinger, G.; Kaltefleiter, I.; Stenzel, L.; Heber, D.; Weide, M.; Wolschendorf, U.; Zebothsen, I.; Nieden, D.Z. ChemMedChem, 2016, 11(19), 2155-2170.
[http://dx.doi.org/10.1002/cmdc.201600199] [PMID: 27546098]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy