Beilstein J. Org. Chem. 2014, 10, 3111–3121.
10.Wang, H.; Yang, Z. Nanoscale 2012, 4, 5259–5267.
3.75 (s, 3H), 3.73–3.64 (m, 2 H), 3.61–3.52 (m, 1H), 3.52–3.40
(m, 2H), 3.30 (s, 3H), 3.04–2.90 (m, 2H), 1.40–1.31 (m, 2H),
1.30–1.15 (m, 6H), 0.86 (t, J = 6.6 Hz, 3H); 13C NMR (100
MHz, DMSO) δ 159.5, 157.9, 130.1, 127.7, 113.2, 100.8, 99.5,
81.9, 68.5, 68.0, 62.5, 55.0, 54.7, 54.6, 39.2, 31.0, 29.9, 26.0,
22.0, 13.8; HRMS: [M + H]+calcd for C22H35N2O7; 439.2444;
found, 459.2445.
11.Ryan, D. M.; Nilsson, B. L. Polym. Chem. 2012, 3, 18–33.
12.Svobodová, H.; Noponen, V.; Kolehmainen, E.; Sievänen, E. RSC Adv.
13.Mangunuru, H. P. R.; Yang, H.; Wang, G. Chem. Commun. 2013, 49,
14.Hu, J.; Wu, J.; Wang, Q.; Ju, Y. Beilstein J. Org. Chem. 2013, 9,
Compound 16: Heptylurea, isolated as a white solid in quanti-
tative yield, mp 204.2–205.0 °C; 1H NMR (400 MHz, DMSO)
δ 7.39–7.34 (m, 2H), 6.94–6.89 (m, 2H), 6.06 (t, J = 5.5 Hz,
1H), 5.76 (d, J = 8.4 Hz, 1H), 5.53 (s, 1H), 5.18 (d, J = 5.5 Hz,
1H), 4.61 (d, J = 3.7 Hz, 1H), 4.14 (dd, J = 4.8, 9.8 Hz, 1H),
3.74 (s, 3H), 3.72–3.64 (m, 2 H), 3.61–3.52 (m, 1H), 3.52–3.41
(m, 2H), 3.30 (s, 3H), 3.02–2.92 (m, 2H), 1.40–1.31 (m, 2H),
1.30–1.17 (m, 8H), 0.90–0.82 (m, 3H); 13C NMR (100 MHz,
DMSO) δ 159.5, 157.9, 130.0, 127.7, 113.2, 100.8, 99.5, 81.9,
68.5, 68.0, 62.5, 55.0, 54.7, 54.6, 39.2, 31.0, 30.0, 29.9, 26.3,
22.0, 13.9; HRMS: [M + H]+ calcd for C23H37N2O7, 453.2601;
found, 453.2594.
15.Friggeri, A.; Gronwald, O.; van Bommel, K. J. C.; Shinkai, S.;
Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 10754–10758.
16.Komatsu, H.; Matsumoto, S.; Tamaru, S.; Kaneko, K.; Ikeda, M.;
Hamachi, I. J. Am. Chem. Soc. 2009, 131, 5580–5585.
17.Skilling, K. J.; Citossi, F.; Bradshaw, T. D.; Ashford, M.; Kellam, B.;
18.Vintiloiu, A.; Leroux, J.-C. J. Controlled Release 2008, 125, 179–192.
19.Bhuniya, S.; Seo, Y. J.; Kim, B. H. Tetrahedron Lett. 2006, 47,
20.Kiyonaka, S.; Sada, K.; Yoshimura, I.; Shinkai, S.; Kato, N.; Hamachi, I.
21.Hirst, A. R.; Escuder, B.; Miravet, J. F.; Smith, D. K.
Angew. Chem., Int. Ed. 2008, 47, 8002–8018.
Supporting Information
22.Zhao, F.; Ma, M. L.; Xu, B. Chem. Soc. Rev. 2009, 38, 883–891.
Supporting Information File 1
Additional experimental data.
23.Cao, S.; Fu, X.; Wang, N.; Wang, H.; Yang, Y. Int. J. Pharm. 2008, 357,
24.Vemula, P. K.; Li, J.; John, G. J. Am. Chem. Soc. 2006, 128,
25.Yang, Z.; Liang, G.; Guo, Z.; Guo, Z.; Xu, B. Angew. Chem., Int. Ed.
26.Roy, S.; Das, P. K. Biotechnol. Bioeng. 2008, 100, 756–764.
Acknowledgments
We are grateful for the financial support from the National
Science Foundation CHE1313633 and the Old Dominion
University.
27.Haines-Butterick, L.; Rajagopal, K.; Branco, M.; Salick, D.; Rughani, R.;
Pilarz, M.; Lamm, M. S.; Pochan, D. J.; Schneider, J. P.
Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 7791–7796.
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