Mechanochemical click reaction as a tool for making carbohydrate-based triazole-linked self-assembling materials (CTSAMs)

Huisgen, 1963, Angew Chem Int Ed, 2, 565, 10.1002/anie.196305651 Rostovtsev, 2002, Angew Chem, 114, 2708, 10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0 Rostovtsev, 2002, Angew Chem Int Ed, 41, 2596, 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 Tornøe, 2002, J Org Chem, 67, 3057, 10.1021/jo011148j Xu, 2014, Asian J Org Chem, 3, 582, 10.1002/ajoc.201300245 Sessler, 2010, J Am Chem Soc, 132, 14058, 10.1021/ja107098r Muthana, 2009, J Org Chem, 74, 2928, 10.1021/jo8027856 Billing, 2005 Bodine, 2004, J Am Chem Soc, 126, 1638, 10.1021/ja039374t Diaz, 2004, J Polym Sci Part A Polym Chem, 42, 4392, 10.1002/pola.20330 Binder, 2007, Macromol Rapid Commun, 28, 15, 10.1002/marc.200600625 Kantheti, 2013, J Coat Technol Res, 10, 609, 10.1007/s11998-013-9494-2 Reck, 2005, J Med Chem, 48, 499, 10.1021/jm0400810 Horne, 2009, Angew Chem Int Ed, 48, 4718, 10.1002/anie.200805900 Naito, 1996, J Med Chem, 39, 3019, 10.1021/jm9507993 Genin, 2000, J Med Chem, 43, 953, 10.1021/jm990373e Alvarez, 1994, J Med Chem, 37, 4185, 10.1021/jm00050a015 Buckle, 1986, J Med Chem, 29, 2262, 10.1021/jm00161a022 Marsault, 2011, J Med Chem, 54, 1961, 10.1021/jm1012374 Zhao, 2008, Bioorg Med Chem, 16, 6333, 10.1016/j.bmc.2008.05.012 Johnson, 2008, Macromol Rapid Commun, 29, 1052, 10.1002/marc.200800208 Aprahamian, 2007, Bull Chem Soc Jpn, 80, 1856, 10.1246/bcsj.80.1856 Hänni, 2010, Chem Soc Rev, 39, 1240, 10.1039/B901974J Kushwaha, 2013, J Org Chem, 78, 8184, 10.1021/jo4012392 Roy, 2013, Braz J Pharm Sci, 49, 85, 10.1590/S1984-82502013000100010 Chabre, 2008, J Org Chem, 73, 5602, 10.1021/jo8008935 Deguise, 2007, New J Chem, 31, 1321, 10.1039/b701237c Wu, 2005, Chem Commun, 5775, 10.1039/b512021g Wang, 2008, Proc Natl Acad Sci U S A, 105, 3690, 10.1073/pnas.0712326105 Touaibia, 2007, ChemMedChem, 2, 1190, 10.1002/cmdc.200700063 Mackeviča, 2014, ARKIVOC, 90, 10.3998/ark.5550190.p008.402 Tejler, 2007, Carbohydr Res, 342, 1869, 10.1016/j.carres.2007.03.012 Turnbull, 2013, Chem Soc Rev, 42, 4613, 10.1039/C2CS35430F Leaver, 2011, Org Biomol Chem, 9, 8465, 10.1039/c1ob06317k Dedol, 2010, Carbohydr Res, 345, 1123, 10.1016/j.carres.2010.03.041 Carvalho, 2010, Bioorg Med Chem, 18, 2412, 10.1016/j.bmc.2010.02.053 Branderhorst, 2007, Chem Commun, 5043, 10.1039/b711070g Touaibia, 2007, Chem Commun, 380, 10.1039/B612471B Pasini, 2013, Molecules, 18, 9512, 10.3390/molecules18089512 Campo, 2010, Chem Sci, 1, 507, 10.1039/c0sc00301h Pietrzik, 2008, Beilstein J Org Chem, 4 Tyagi, 2012, RSC Adv, 2, 11366, 10.1039/c2ra21341a Ghorai, 2011, Org Lett, 13, 5512, 10.1021/ol2022356 Driggers, 2008, Nat Rev Drug Discov, 7, 608, 10.1038/nrd2590 Yanai, 2008, Org Biomol Chem, 6, 2679, 10.1039/b803924k Vasella, 2001, Chimia, 55, 839, 10.2533/chimia.2001.839 Davis, 1999, Tetrahedron, 55, 4501, 10.1016/S0040-4020(99)00138-6 Ghadban, 2013, Polymers, 5, 431, 10.3390/polym5020431 Slavin, 2011, Eur Polym J, 47, 435, 10.1016/j.eurpolymj.2010.09.019 Poláková, 2011, Bioconjug Chem, 22, 289, 10.1021/bc100421g Lo Conte, 2010, J Org Chem, 75, 6326, 10.1021/jo100928g Kramer, 2007, Protoc Exch Zhang, 2013, Molecules, 18, 7145, 10.3390/molecules18067145 El-Sagheer, 2010, Chem Soc Rev, 39, 1388, 10.1039/b901971p Kayet, 2013, J Org Chem, 78, 9865, 10.1021/jo401576n Dey, 2011, Synlett, 17, 2521 Zhang, 2005, J Am Chem Soc, 127, 15998, 10.1021/ja054114s Krasiński, 2004, Org Lett, 6, 1237, 10.1021/ol0499203 Tyagi, 2013, Carbohydr Res, 379, 55, 10.1016/j.carres.2013.06.018 Kumar, 2014, J Org Chem, 79, 3427, 10.1021/jo5001753 Chabre, 2013, Chem Soc Rev, 42, 4657, 10.1039/c3cs35483k Bernardi, 2013, Chem Soc Rev, 42, 4709, 10.1039/C2CS35408J Ryu, 2010, J Mater Chem, 20, 1806, 10.1039/b921685e García, 2011, Chem Commun, 47, 5016, 10.1039/c0cc05685e Bhalla, 2011, Langmuir, 27, 15275, 10.1021/la203774p Yuan, 2012, J Mater Chem, 22, 10472, 10.1039/c2jm30620d Mummidivarapu, 2013, J Org Chem, 78, 3570, 10.1021/jo400038x Ramírez-López, 2011, Chem Commun, 47, 10281, 10.1039/c1cc13251b Hemamalini, 2013, New J Chem, 37, 2419, 10.1039/c3nj00072a Godeau, 2009, Chem Commun, 5127, 10.1039/b906212b Perez-Balderas, 2009, Eur J Org Chem, 2441, 10.1002/ejoc.200801170 Sarmiento-Sánchez, 2011, ARKIVOC, 177, 10.3998/ark.5550190.0012.913 Gilbert, 1989, Propellants Explos Pyrotech, 14, 19, 10.1002/prep.19890140105 Hayes, 2003, Tetrahedron, 59, 7983, 10.1016/j.tet.2003.08.011 Klapötke, 2007, J Am Chem Soc, 129, 6908, 10.1021/ja071299p Ju, 2006, J Org Chem, 71, 6697, 10.1021/jo061114h Scriven, 1988, Chem Rev, 88, 297, 10.1021/cr00084a001 Lieber, 1957, J Org Chem, 22, 238, 10.1021/jo01354a003 Khurana, 2008 Habibi, 2014, Chem Soc Rev, 43, 1519, 10.1039/C3CS60204D Raghavan, 2012, Soft Matter, 8, 8539, 10.1039/c2sm25107h http://www.stenutz.eu/chem/solv24.php?sort=3. Zhang, 2014, Med Chem Res Mohebbi, 2014, Med Chem Res, 23, 4531, 10.1007/s00044-014-1014-0 Mady, 2014, Eur J Med Chem, 84, 433, 10.1016/j.ejmech.2014.07.042 Shin, 2013, Bioorg Med Chem Lett, 23, 1193, 10.1016/j.bmcl.2013.01.033 Aher, 2009, Bhat M K Bioorg Med Chem Lett, 19, 759, 10.1016/j.bmcl.2008.12.026 Adejoro, 2012, J Comput Met Mol Des, 2, 142 Kim, 2013, Bull Korean Chem Soc, 34, 1043, 10.5012/bkcs.2013.34.4.1043 Renganayaki, 2012, Int J Chem Tech Res, 4, 983 Foster, 2010, Phys Chem Chem Phys, 12, 307, 10.1039/B912859J 2011, Semi-empirical calculations, 391 Stewart, 1989, J Comput Chem, 10, 209, 10.1002/jcc.540100208 Stewart, 1989, J Comput Chem, 10, 221, 10.1002/jcc.540100209 Stewart, 1991, J Comput Chem, 12, 320, 10.1002/jcc.540120306 Stewart, 2004, J Mol Model, 10, 155, 10.1007/s00894-004-0183-z Roy, 2013, Fitoterapia, 90, 140, 10.1016/j.fitote.2013.07.015