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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 24
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Original Articles

Synthesis, X-ray crystallographic studies, DFT calculations and nanostructural features of annulated imidazo[4,5-b]pyridine derivatives

Pages 2426-2448 | Received 16 Jul 2017, Published online: 30 Nov 2017

References

  • (a) Macdonald, J.; Oldfield, V.; Bavetsias, V.; Blagg, J. Org. Biomol. Chem. 2013, 11, 2335–2347; (b) Lach, F.; Kaza, P. ACS Comb. Sci. 2012, 14, 491–495; (c) Lukasik, P. M.; Elabar, S.; Lam, F.; Shao, H.; Liu, X.; Abbas, A. Y.; Wang, S. Eur. J. Med. Chem. 2012, 57, 311–322; (d) Duchek, J.; Vasella, A. Helv. Chim. Acta 2011, 94, 977–986; (e) Burley, G. A.; Davies, D. L.; Griffith, G. A.; Lee, M.; Singh, K. J. Org. Chem. 2010, 75, 980–983; (f) Zaki, M. E. A.; Proenca, N. F. Tetrahedron 2007, 63, 3745–3753; (g) Crozet, M. D.; Suspene, C.; Kaafareu, M.; Crozet, M. P.; Vanelle, P. Heterocycles 2004, 63, 1629–1635.
  • (a) Cristalli, G.; Vittori, S.; Eleuteri, A.; Volpini, R.; Camaioni, E.; Lupidi, G.; Mohmoud, N.; Bevilacqua, F.; Palu, G. J. Med. Chem. 1995, 38, 4019–4025; (b) Cundy, D. J.; Holan, G.; Otaegui, M; Simpson, G. W. Bioorg. Med. Chem. Lett. 1997, 7, 669–674.
  • Temple, C. J. Med. Chem. 1990, 33, 656–661.
  • Bukowski, L.; Janowiec, M. Pharmazie 1989, 44, 267–269.
  • (a) Temple, C.; Rose, J. D.; Comber, R. N.; Rener, G. A. J. Med. Chem. 1987, 30, 1746–1751; (b) Cristalli, G.; Vittori, S.; Eleuteri, A.; Grifantini, M.; Volpini, R.; Lupidi, G.; Capolongo, L.; Pesenti, E. J. Med. Chem. 1991, 34, 2226–2230.
  • (a) Alamgir, M.; Black, D. S. C.; Kumar, N. Bioact. Heterocycl. III 2007, 9, 87–118; (b) Carvalho, L. C. R.; Fernandes, E.; Marques, M. M. B. Chem. Eur. J. 2011, 17, 12544–12555.
  • (a) (i). Eisenbrand, G.; Tang, W. Toxicology 1993, 84, 1–82; (ii) Hatch, F. T.; Knize, M. G.; Felton, J. S.; Morgan, R. W. Environ. Mol. Mutagen 1991, 17, 4–19; (b) Yi, P.; Yung, J.; Huang, D.-S.; Lu, W.; Wu, N.; Feng, S.-P.; Pan, Q.-S.; Wang, Z.-F.; Min, Y. Adv. Mat. Res. 2013, 634, 930–933; (c) Ménad, D.; Naulescu-Duvez, I.; Dijkstra, H. P.; Naulescu-Duvez, D.; Suijkerbuijk, B. M. J. M.; Zambon, A.; Nourry, A.; Roman, E.; Davies, L.; Manne, H. A.; et al. J. Med. Chem. 2009, 52, 3881–3891; (d) Bavetsias, V.; Large, J. M.; Sun, C.; Bouloc, N.; Kosmopoulou, M.; Matteucii, M.; Wilsher, N. E.; Martins, V.; Reynisson, J.; Atrash, B.; et al. J. Med. Chem. 2010, 53, 5213–5228; (e) Learn, K. S.; Wagner, J. C.; Alborn, M. S.; Angelis, T. S.; Thelma, S.; Huang, Z.; Ghosh, A. K.; Wah, W.; Cheng, M.; Dorsey, B. D.; et al. Med. Chem. Commun. 2012, 3, 1138–1142; (f) Casimira-Garcia, A.; Filzen, G. F.; Flynn, D.; Bigge, C. F.; Chen, J.; Davis, J. A.; Dudhley, D. A.; Edmunds, J. J.; Esmaeil, N.; Geyer, A.; et al. J. Med. Chem. 2011, 54, 4219–4233; (g) Komoto, M.; Yamashige, R.; Matsuanga, K.; Yokoyama, S.; Hirao, I. Nat. Biotect. 2013, 31, 453–457; (h) Yamashige, R.; Kimoto, M.; Takezawa, Y.; Sato, A.; Mitsui, T.; Yokoyama, S.; Hirao, I. Nucleic Acid Res. 2012, 40, 2793–2806; (i) Hirao, I.; Mitsui, T.; Kimoto, M.; Yomoyama, S. J. Am. Chem. Soc. 2007, 129, 15549–15555.
  • (a) Kem, W. R. Invert. Neurosci. 1997, 3, 251–259; (b) Amzel, L. M. Curr. Opin. Biotechnol. 1998, 9, 366–369; (c) Kubinyi, H.; Recept, J. Signal Transduct. Res. 1999, 19, 15–39.
  • (a) Marco, J. L.; Rios, C.; de los Carreiras, M. C.; Banos, J. E.; Badia, A.; Vivas, N. M. Arch. Pharm. 2002, 335, 347–353; (b) Rios, C.de los; Marco, J. L.; Carreiras, M. C.; Chincho, P. M.; Garcia, A. G.; Villarroya, M. Bioorg. Med. Chem. 2002, 10, 2077–2090; (c) Marco, J. L.; Rios, C.; de los Carreiras, M. C.; Banos, J. E.; Badia, A.; Vivas, N. M. Bioorg. Med. Chem. 2001, 9, 727–737; (d) Marco, J. L.; Martinez-Grau, A. Bioorg. Med. Chem. Lett. 1997, 7, 3165–3170.
  • da Silva, C. H. T. P.; Campo, V. L.; Carvalho, I.; Taft, C. A. J. Mol. Graph. Modell. 2005, 25, 169–175.
  • Hartman, S. C.; Buchanan, J. M. Annu. Rev. Biochem. 1959, 28, 365–410.
  • Orgel, L. E. Crit. Rev. Biochem. Mol. Biol. 2004, 39, 99–123.
  • Das, A. J. Mol. Str. 2017, 1147, 520–540.
  • Obolensky, O. I.; Semenikhina, V. V.; Solov’yov, A. V.; Greiner, W. Int. J. Quantum Chem. 2007, 107, 1335–1343.
  • Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A. 2003, 107, 8377–8379.
  • Gung, B. N.; Amicangelo, J. C. J. Org. Chem. 2006, 71, 9261–9270.
  • Ninkovic, D. B.; Ganjic, G. V.; Zarić, S. D. Crys. Growth. Des. 2012, 12, 1060–1063.
  • (a) Wheeler, S. E. J. Amer. Chem. Soc. 2011, 133, 10262–10274; (b) Salonen, L. M.; Ellermann, M.; Diederich, F. Angew. Chem. Int. Ed. (Eng.) 2011, 50, 4804–4806; (c) Barattini, S.; Greenland, B. W.; Merino, D. H.; Weng, W.; Seppala, J.; Colquhoun, H. M.; Hayes, W.; Mackey, M. E.; Hamley, L. W.; Rowan, S. J. J. Am. Chem. Soc., 2010, 132, 12051–12058; (d) Watt, M.; Hardbeck, L. K. E.; KirkPatric, C. C.; Lewis, M. J. Am. Chem. Soc. 2011, 133, 3854–3862.
  • (a) Desiraju, G. R.; Gavezzotti, A. J. J. Chem. Soc., Chem. Commun. 1989, 621–623; (b) Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342–8356; (c) Dahl, T. Acta Chem. Scand. 1994. 48, 95–106; (d) Claessens, C. G.; Stoddart, J. F. J. Phys. Org. Chem. 1997, 10, 254–272; (e) Meyer, E. A.; Castellano, R. K.; Deiderich, F. Angew. Chem. Int. Ed. 2003, 42, 1210–1250; (f) Mooibroek, T. J.; Gamez, P. Inorg. Chim. Acta 2007, 360, 381–404.
  • (a) Burley, S. K.; Petsko, G. A. Science 1985, 229, 23–29; (b) Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125–189; (c) Bhattacharya, R.; Samanta, U.; Chakrabarti, P. Protein Eng. 2002, 15, 91–100; (d) Gazit, E. FASEB J. 2002, 16, 77–83.
  • Mishra, B. K.; Sathyamurthy, N. J. Phys. Chem. A 2005, 109, 6–8.
  • Mishra, B. K.; Sathyamurthy, N. J. Theor. Comput. Chem. 2006, 5, 609–619.
  • Sponer, J.; Hobza, P. Chem. Phys. Lett. 1997, 267, 263–270.
  • Kim, D.; Tarakeshwar, P.; Kim, K. S. J. Phys. Chem. A 2004, 108, 1250–1258.
  • Mignon, P.; Loverix, S.; Proft, F. D.; Geerlings, P. J. Phys. Chem. A 2004, 108, 6038–6044.
  • Mignon, P.; Loverix, S.; Geerlings, P. Chem. Phys. Lett. 2005, 401, 40–46.
  • Piacenza, M.; Grimme, S. Chem. Phys. Chem. 2005, 6, 1554–1558.
  • Tsuzuki, S.; Mikami, M.; Yamada, S. J. Am. Chem. Soc. 2007, 129, 8656–8662.
  • Kim, D. Y.; Singh, N. J.; Kim, K. S. J. Chem. Theory Comput. 2008, 4, 1401–1407.
  • Wang, W.; Hobza, P. Chem. Phys. Chem. 2008, 9, 1003–1009.
  • Hohenstein, E. G.; Sherrill, C. D. J. Phys. Chem. A 2009, 113, 878–886.
  • Geronimo, I.; Lee, E. C.; Singh, N. J.; Kim, K. S. J. Chem. Theory Comput. 2010, 6, 1931–1934.
  • Geng, Y.; Takatani, T.; Hohenstein, E. G.; Sherrill, C. D. J. Phys. Chem. A 2010, 114, 3576–3582.
  • Ray, S.; Das, A. J. Mol. Str. 2015, 1089, 146–152.
  • Xia, Y.; Yang, P.; Sun, Y.; Wu, Y.; Mayers, B.; Gates, B.; Yin, Y.; Kim, F.; Yan, H. Adv. Mater. 2003, 15, 353–389.
  • Liu, H. B.; Li, Y. L.; Xiao, S. Q.; Gan, H. Y.; Jiu, T. G.; Li, H. M.; Jiang, L.; Zhu, D. B.; Yu, D. P.; Xiang, B.; J. Amer. Chem. Soc. 2003, 125, 10794–10795.
  • Kaiser, T. E.; Wang, H.; Stepanenko, V.; Wurthner, F. Angew. Chem., Int. Ed. 2007, 46, 5541–5544.
  • Wu, D. Q.; Zhi, L. J.; Bodwell, G. J.; Cui, G. L.; Tsao, N.; Mullen, K. Angew. Chem., Int. Ed. 2007, 46, 5417–5420.
  • (a) Martĭnez-Grau, A.; Marco, J. L. Bioorg. Med. Chem. Lett. 1997, 7, 3165–3170; (b) Carreiras, M. C.; Eleuterio, A.; Dias, C.; Brito, M. A.; Brites, D.; Marco-Contelles J.; Gómez-Sanchez, E. Heterocycles 2007, 71, 2249–2262,
  • Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Amer. Chem. Soc. 2002, 124, 104–112.
  • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 09, Revision A.02-SMP; Gaussian, Inc.: Wallingford, CT, 2009.
  • (a) Barquera-Lozada, J. E.; Cuevas, G. J. Org. Chem. 2009, 74, 874–883; (b) Quijano-Quinones, R. F.; Quesadas-Rojas, M.; Cuevas, G.; Mena-Rejon, G. J. Molecules 2012, 17, 4661–4671; (c) Adhikary, A.; Kumar, A.; Khanduri, D.; Sevilla, M. D. J. Am. Chem. Soc. 2008, 130, 10282–10292.

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