6
Tetrahedron
ACCEPTED MANUSCRIPT
7. Morones, J. R.; Elechiguerra, J. L.; Camacho, A.; Holt, K.; Kouri,
reaction was stirred at room temperature over 4 days. Once the
J. B.; Ramırez, J. T.; Yacaman, M.J., Nanotechnology, 2005, 16,
2346-2353.
reaction was over, it was poured into water an extractions with
dichloromethane were done. After evaporation, 1.12 g (70%
yield) of an orange solid was obtained, identified as 11; m.p.:
8. Simoncic B.; Tomsic, B. Textile Research Journal, 2010, 80,
1720-1737; Monge, M. An. Quim. 2009, 105, 33-41.
195-197 C; nmax ATR (υ, cm-1): 2885, 1722, 1612, 1466, 1239,
o
9. Devi, L. S.; Joshi, S. R. Microbiology, 2012, 40, 27-34.
10. (a) Niembro, S.; Vallribera, A.; Moreno-Mañas, M. New J. Chem.
2008, 32, 94-98; (b) Niembro, S.; Shafir, A.; Vallribera, A.;
Alibés, R. Org. Lett. 2008, 10, 3215-3218; Synfacts, 2008, 1228;
(c) Berini, R.; Cacchi, S.; Fabrizi, G.; Niembro, S.; Prastaro, A.;
Shafir, A.; Vallribera, A. ChemSusChem 2009, 2, 1031-1040; (d)
Berini, R.; Cacchi, S.; Fabrizi, G.; Forte, G.; Petrucci, F.; Prastaro,
A.; Niembro, S.; Shafir, A; Vallribera, A. Org. Biomol. Chem.
2009, 7, 2270-2273; (e) Berini, R.; Cacchi, S.; Fabrizi, G.; Forte,
G.; Petrucci, F.; Prastaro, A.; Niembro, S.; Shafir, A.; Vallribera,
A. Green Chem. 2010, 12, 150-158; (f) Niembro, S.; Shafir, A.
Vallribera, A. Arkivoc 2010, (iii), 181-190; (g) Boffi, A.; Cacchi,
S.; Pierpaolo, C.; Cirilli, R.; Fabrizi, G., Prastaro, A.; Niembro, S.
; Shafir, A., Vallribera, A. ChemCatChem 2011, 3, 347-353; (h)
Niembro, S.; Donnici, S.; Shafir, A.; Vallribera, A. Buil, L. B.;
Esteruelas, M. A.; Larramona, C. New J. Chem. 2013, 37, 278-
282; (f) Martín, L.; Molins, A.; Vallribera, A. New J. Chem. 2016,
40, 10208-10212; (i) Santacruz, L.; Niembro, N.; Santillana, A.;
Shafir, A.; Vallribera, A. New J. Chem. 2014, 38, 636-640.
11. Toh, H. S.; Batchelor-Mcauley, C.; Tschulik, K.; Compton R. G.
Science China Chemistry, 2014, 57, 1199-1210.
12. Lenardao, E. J.; Jacob, R. G.; Mesquita, K. D.; Lara, R. G.;
Webber, R.; Martínez, D. M.; Savegnago, L.; Mendes, S. R.;
Alves, D. G.; Perin, G. Green Chem. Lett. Rev. 2013, 6, 269-276.
13. Kalemba, D.; Kunicka, A. Curr. Med. Chem. 2003, 10, 813-829.
14. Srivastava, S.; Sinha, R.; Ro, D. Aquatic Toxicology, 2004, 66,
319–329.
15. Molander, G. A.; Brown, A. R. J. Org. Chem. 2006, 71, 9681-
9686.
16. Hou, J.-T.; Gao, J.-W.; Zhang, Z.-H. Monatsh. Chem. 2011, 142,
495-499.
1100; dH (250 MHz CDC13) 8.71 (s, 1H, Ar), 8.21 (d, J = 10.8
Hz, ArH, 1H), 7.98 (s, 1H, C=CH-N, 1H), 7.95 (d, J = 7.2 Hz,
ArH, 1H), 5.49 (bs, NCH2C=C, 2H), 4.52 (t, J = 5.0 Hz,
NCH2CH2, 2H), 4.37 (q, J = 7.2 Hz, OCH2CH3, 2H), 3.56 (bs,
(CH2)n, 232H), 3.38 (s, OCH3, 3H), 1.42 (t, J =7.2 Hz, OCH2CH3,
3H); MALDI-TOF: 2264.64 (naverage = 43).
1.7. 7-Chloro-6-fluoro-1-((1-(2-methoxy-PEG)-1H-1,2,3-triazol-
4-yl)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 12
In a 100 mL round bottom flask, 25 mL of a 2 M HCl solution
was added over 0.21 g (0.1 mmol) of fluoroquinolone 11. The
mixture was warmed up to reflux and let stirring overnight. Then,
the mixture was cooled down to r.t. and extractions with
chloroform were done. The combined organic phases were dried
and evaporated affording 0.19 g (100% yield) of a solid
o
identified as the carboxylic acid 12; m.p.: 201-203 C; nmax
ATR (υ, cm-1): 3437 (OH), 2923, 2851, 1613, 1518, 1348; dH
(250 MHz CDC13) 14.56 (s, OH, 1H), 9.12 (s, ArH, 1H), 8.40
(d, J = 5.8 Hz, ArH, 1H), 8.21 (m, ArH, 2H), 5.68 (bs,
NCH2C=C, 2H), 4.54 (t, J = 5.0 Hz, NCH2CH2, 2H), 3.56 (bs,
(CH2)n, 268H), 3.37 3.38 (s, OCH3, 3H); MALDI-TOF: 2264.64
(naverage = 43).
1.8. General procedure for the preparation of the silver
nanoparticles
17. Leyva, S. Leyva, E. Bol. Soc. Quim. Mex. 2008, 2, 1-13.
18. Koga, H.; Itoh, A.; Murayame, S.; Suzue, S.; Irikura, T. J. Med.
Chem. 1980, 23, 1358-1363.
19. Brust, M., Walker, M., Bethell, D., Schiffrin, D. J., Whyman, R. J.
Chem. Soc., Chem. Commun., 1994, 801-802.
20. C.-H.Xue, J. Chen, W. Yin, S.-T. Jia, J.-Z. Ma, Appl. Surf. Sc.
2012, 258, 2468-2472.
21. Liang, M.; Su, R.; Huang, R.; Qi, W.; Yu, Y.; Wang, L.; He, Z.
ACS Appl. Mater. Interfaces, 2014, 6, 4638-4649.
22. (a) Liu, G.; Li, Kaijun; Luo, Quanquing, Wang, H.; Zhang, Z. J.
Colloid Interf. Sci., 2017, 490, 642-651; (b) Ganji, N.; Khan, I. A.;
Bothum, G. D. Langmuir, 2018, 34, 2039-2945.
23. (a) Pd NP: Mejías, N.; Pleixats, R.; Shafir, A.; Medio-Simón, M.;
Asensio, G. Eur. J. Org. Chem. 2010, 5090-5099; (b) Rh NP:
Guo, W.; Pleixats, R.; Shafir, A.; Parella, T. Adv. Synth. Catal.
2015, 357, 89-99; (c) .Au NP: Guo, W.; Pleixats, R.; Shafir, A.
Chem. Asian J. 2015, 10, 2437-2443.
In a 250 mL erlenmeyer, 0.3 mmol (1 equiv.) of the
corresponding stabilizer in 50 mL of THF and a solution of
AgNO3 (0.049 g, 0.3 mmol, 1 eq.) in 6 mL of water were added.
Over this mixture, a previous prepared solution of NaBH4 (0.036
g, 0.9 mmol, 3.2 mol-equiv.) was added dropwise. The mixture
was let stirring during 3h at room temperature. After this period,
part of the THF was evaporated. Then, chloroform was added,
the phases were separated, and the organic fraction washed with
water. Finally, the organics were dried with Na2SO4 and
evaporated. The resulting dark red solid was washed with cold
diethyl ether, obtaining silver NPs.
Bibliography
24. Kumar, R.; Sathaiah, G.; Shekhar, A. C.;. Raju, K.; Rao, P. S.;
Shanthan, P.; Narsaiah, B.; Raju, Y. K.; Murthy, U. S. N. J.
Heterocyclic Chem., 2015, 52, 235-242.
25. (a) Gottenbos, Grijpma, D. W.; van der Mai, H. C.; Feijen, J.
Busscher, H. J. J. Antimicrob Chemother 2001, 48, 7-13; (b)
Abbaszadegan, A.; Ghahramani, Y; Gholami, A.; Hemmateenejad,
B.; Dorostkar, S.; Nabavizadeh, M.; Sharghi, H. J. Nanomater.
2015, 1-8.
1. (a) Zhou, H.; Wang, H.; Niu, H.; Gestos, A.; Lin, T. Adv. Func.
Mater. 2013, 23, 1664-1670; (b) Liu, Y.; Liu, Z.; Liu Y.; Hu. H.;
Li, Y.; Yan, P.; Yu, B.; Zhou, F. Small 2015, 11, 426-431; (c)
Wang, H.; Xue, Y.; Ding, J.; Feng, L.; Wang, X.; Lin, T. Angew.
Chem. Int. Ed. 2011, 50, 11433-11436.
2. (a) Wang, L.; Zang, X.; Li, B.; Sun, P.; Yang, J.; Xu, H.; Liu, Y.
ACS Appl. Mater. Interfaces 2011, 3, 1277-1281.
3. (a) Chen, S; Li, X.; Li, Y.; Sun, J. ACS Nano 2015, 9, 4070-4076;
Li, Y.-C.; Mannen, S.; Morgan, A. B.; Chang, S.; Yang, Y.-H.;
Condon, B.; Grulan J. C. Adv. Mater. 2011, 23, 3926-3931.
4. A Search for Antibacterial Agents, Chapter 4: Antibacterial
Modification of Textiles using Nanotechnology, V. Bobbarala Ed.,
IntechOpen, Rijeka, Croatia, 2012.
5. For reviews on silver as antibacterial agent see: (a) Zheng, K.;
Setyawati, M. I.; Leong, D. T.; Xie, J. Coord. Chem. Rev. 2018,
357, 1-17; (b) Chernousova, S.; Epple, M. Angew. Chem. Int. Ed.
2013, 52, 1636-1653; (c) Morones, J. R.; Elechiguerra, J. L.;
Camacho, A.; Holt, K.; Kouri, J. B.; Ramírez, J. T.; Yacaman, M.
J. Nanotechnology, 2005, 16, 2346-2353.
26. Zhang, Y.; Peng, H.; Huang, W.; Zhou, Y; Yan, D. J. Colloid
Interface Sci 2008, 325, 371-376.
Acknowledgments
We are thankful for financial support from Spain’s MICINN (CTQ2014-
53662-P) and MEC (CTQ2016-81797-REDC) and DURSI-Generalitat de
Catalunya (2017 SGR 465 and 2017 SGR 1726).
6.
(a) Xue, C.-H.; Chen, J.; Yin, W.; Jia, S.-T., Ma, J.-Z. Applied
Surface Science, 2012, 258, 2468-2472; (b) Wu, M.; Ma, B.; Pan,
T.; Chen, S.; Sun, J. Adv. Func. Mater. 2016, 26, 569-576; (c)
Eremenko, A. M.; Petrik, I. S.; Smirnova, N. P.; Rudnko, A. V.;
Marikvas, Y. S. Nanoscale Res. Lett., 2016, 11, 1-9.
Supplementary Material
Supplementary material of this article is available including
NMR, IR spectra and ESI of new compounds 2, 6, 8, 9, 11 and