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A Simple and Convenient Method for Synthesis of Artemisinin Dimer through Aliphatic Nitro Compounds
Corresponding Author(s) : Nitin Srivastava
Asian Journal of Chemistry,
Vol. 33 No. 1 (2021): Vol 33 Issue 1
Abstract
A simple way of synthesis of artemisinin dimer using nitro aliphatic compounds is reported. Herein, few artemisinin monomers and dimers have been synthesized with the help of linker nitroalkanes using iron catalyst supported on polymer (Fe/SBA-15). The synthesized artemisinin shows good anticancer and antimalarial activities.
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- A.Y. Sukhorukov, Front. Chem., 8, 595246 (2020); https://doi.org/10.3389/fchem.2020.595246
- G. Yan and M. Yang, Org. Biomol. Chem., 11, 2554 (2013); https://doi.org/10.1039/C3OB27354G
- R. Ballini and M. Petrini, Arkivoc, 195 (2009);https://doi.org/10.3998/ark.5550190.0010.912
- N. Nishiwaki, Molecules, 25, 3680 (2020); https://doi.org/10.3390/molecules25163680
- R. Ballini, S. Gabrielli, A. Palmieri and M. Petrini, Curr. Org. Chem., 15, 1482 (2011); https://doi.org/10.2174/138527211795378137
- R. Ballini and A. Palmieri, Curr. Org. Chem., 10, 2145 (2006); https://doi.org/10.2174/138527206778742632
- C. Czekelius and E.M. Carreira, Angew. Chem. Int. Ed., 44, 612 (2005); https://doi.org/10.1002/anie.200461879
- R. Ballini and A. Palmieri, Adv. Synth. Catal., 361, 5070 (2019); https://doi.org/10.1002/adsc.201900563
- A. Septembre-Malaterre, M.L. Rakoto, C. Marodon, Y. Bedoui, J. Nakab, E. Simon, L. Hoarau, S. Savriama, D. Strasberg, P. Guiraud, J. Selambarom and P. Gasque, Int. J. Mol. Sci., 21, 4986 (2020); https://doi.org/10.3390/ijms21144986
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- M. Jung, X. Li, D.A. Bustos, H.N. ElSohly, J.D. McChesney and W.K. Milhous, J. Med. Chem., 33, 1516 (1990); https://doi.org/10.1021/jm00167a036
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- D. Kalita, A.T. Khan, N.C. Barua and G. Bez, Tetrahedron, 55, 5177 (1999); https://doi.org/10.1016/S0040-4020(99)00164-7
- B. Kalita, N.C. Barua, M.S. Bezbarua and G. Bez, Synlett, 1411 (2001); https://doi.org/10.1055/s-2001-16776
- J.C. Borah, S. Gogoi, J. Boruwa, B. Kalita and N.C. Barua, Tetrahedron Lett., 45, 3689 (2004); https://doi.org/10.1016/j.tetlet.2004.02.150
- N. Gogoi, J. Boruwa and N.C. Barua, Tetrahedron Lett., 46, 7581 (2005); https://doi.org/10.1016/j.tetlet.2005.08.153
- J. Boruwa and N.C. Barua, Tetrahedron, 62, 1193 (2006); https://doi.org/10.1016/j.tet.2005.10.070
- N. Gogoi, J. Boruwa and N.C. Barua, Eur. J. Org. Chem., 1722 (2006); https://doi.org/10.1002/ejoc.200500833
- P.P. Saikia, G. Baishya, A. Goswami and N.C. Barua, Tetrahedron Lett., 49, 6508 (2008); https://doi.org/10.1016/j.tetlet.2008.08.113
- A. Goswami, P.P. Saikia, N.C. Barua, M.J. Bordoloi, A. Yadav, T.C. Bora, B.K. Gogoi, A.K. Saxena, N. Suri and M. Sharma, Bioorg. Med. Chem. Lett., 20, 359 (2010); https://doi.org/10.1016/j.bmcl.2009.10.097
- R. Ballini, L. Barboni and G. Giarlo, J. Org. Chem., 69, 6907 (2004); https://doi.org/10.1021/jo049048b
References
A.Y. Sukhorukov, Front. Chem., 8, 595246 (2020); https://doi.org/10.3389/fchem.2020.595246
G. Yan and M. Yang, Org. Biomol. Chem., 11, 2554 (2013); https://doi.org/10.1039/C3OB27354G
R. Ballini and M. Petrini, Arkivoc, 195 (2009);https://doi.org/10.3998/ark.5550190.0010.912
N. Nishiwaki, Molecules, 25, 3680 (2020); https://doi.org/10.3390/molecules25163680
R. Ballini, S. Gabrielli, A. Palmieri and M. Petrini, Curr. Org. Chem., 15, 1482 (2011); https://doi.org/10.2174/138527211795378137
R. Ballini and A. Palmieri, Curr. Org. Chem., 10, 2145 (2006); https://doi.org/10.2174/138527206778742632
C. Czekelius and E.M. Carreira, Angew. Chem. Int. Ed., 44, 612 (2005); https://doi.org/10.1002/anie.200461879
R. Ballini and A. Palmieri, Adv. Synth. Catal., 361, 5070 (2019); https://doi.org/10.1002/adsc.201900563
A. Septembre-Malaterre, M.L. Rakoto, C. Marodon, Y. Bedoui, J. Nakab, E. Simon, L. Hoarau, S. Savriama, D. Strasberg, P. Guiraud, J. Selambarom and P. Gasque, Int. J. Mol. Sci., 21, 4986 (2020); https://doi.org/10.3390/ijms21144986
D. Chaturvedi, A. Goswami, P.P. Saikia, N.C. Barua and P.G. Rao, Chem. Soc. Rev., 39, 435 (2010); https://doi.org/10.1039/B816679J
M. Jung, X. Li, D.A. Bustos, H.N. ElSohly, J.D. McChesney and W.K. Milhous, J. Med. Chem., 33, 1516 (1990); https://doi.org/10.1021/jm00167a036
G.H. Posner, P. Ploypradith, M.H. Parker, H. O’Dowd, S.H. Woo, J. Northrop, M. Krasavin, P. Dolan, T.W. Kensler, S. Xie and T.A. Shapiro, J. Med. Chem., 42, 4275 (1999); https://doi.org/10.1021/jm990363d
S. Ekthawatchai, S. Kamchonwongpaisan, P. Kongsaeree, B. Tarnchompoo, Y. Thebtaranonth and Y. Yuthavong, J. Med. Chem., 44, 4688 (2001); https://doi.org/10.1021/jm0103007
D. Kalita, A.T. Khan, N.C. Barua and G. Bez, Tetrahedron, 55, 5177 (1999); https://doi.org/10.1016/S0040-4020(99)00164-7
B. Kalita, N.C. Barua, M.S. Bezbarua and G. Bez, Synlett, 1411 (2001); https://doi.org/10.1055/s-2001-16776
J.C. Borah, S. Gogoi, J. Boruwa, B. Kalita and N.C. Barua, Tetrahedron Lett., 45, 3689 (2004); https://doi.org/10.1016/j.tetlet.2004.02.150
N. Gogoi, J. Boruwa and N.C. Barua, Tetrahedron Lett., 46, 7581 (2005); https://doi.org/10.1016/j.tetlet.2005.08.153
J. Boruwa and N.C. Barua, Tetrahedron, 62, 1193 (2006); https://doi.org/10.1016/j.tet.2005.10.070
N. Gogoi, J. Boruwa and N.C. Barua, Eur. J. Org. Chem., 1722 (2006); https://doi.org/10.1002/ejoc.200500833
P.P. Saikia, G. Baishya, A. Goswami and N.C. Barua, Tetrahedron Lett., 49, 6508 (2008); https://doi.org/10.1016/j.tetlet.2008.08.113
A. Goswami, P.P. Saikia, N.C. Barua, M.J. Bordoloi, A. Yadav, T.C. Bora, B.K. Gogoi, A.K. Saxena, N. Suri and M. Sharma, Bioorg. Med. Chem. Lett., 20, 359 (2010); https://doi.org/10.1016/j.bmcl.2009.10.097
R. Ballini, L. Barboni and G. Giarlo, J. Org. Chem., 69, 6907 (2004); https://doi.org/10.1021/jo049048b