Synthesis and biological evaluation of quinoline-triazole and quinolone-triazole conjugates
One-pot synthesis of novel quinoline- and quinolone-substituted
1,2,3-triazoles has been performed from the key intermediates, quinoline-
and quinolone-substituted propargyl derivatives 1-3
(48%-88% yields). The antioxidant properties of the newly synthesized
compounds, 1a-1c, 2a-2c, and 3a-3c, were evaluated by monitoring DPPH
(2,2-diphenyl-1-picrylhydrazyl) radical scavenging abilities, metal
chelating effects, and reducing power. The scavenging effects of compounds
on the free radical decreased in the order of 3b>>> 3a>>>
1b} and were found to be 36.3%, 34.9%, and 27.6% at the
concentration of 500 μμ\mu g/mL, respectively. All of the compounds showed
low chelating capacity. Furthermore, the antibacterial activity was studied
against gram-positive and gram-negative bacteria and the DNA binding ability
of the compounds was evaluated with calf thymus DNA using agarose gel
electrophoresis.
___
- Esvaran, S.; Adhikari, A. V.; Shetty, N. S.
Eur. J. Med. Chem
.
2009
,
44
, 4637-4647.
- Clemons, M.; Coleman, R. E.; Verma, S.
Cancer Treat Rev
.
2004
,
30
, 325-332.
- Radhika, C.; Venkatesham, A.; Sarangapani, M.
Med. Chem. Res
.
2012
,
21
, 3509-3513.
- Kumar, S. S.; Kavitha, H. P.
Mini-Rev. Org. Chem
.
2013
,
10
, 40-65.
- Plech, T.; Luszczki, J. J.; Wujec, M.; Flieger, J.; Pizon, M.
Eur. J. Med. Chem
.
2013
,
60
, 208-215.
- Patel, N. B.; Khan, I. H.; Pannecouque, C., Clercq, E. D.
Med. Chem. Res
.
2013
,
22
, 1320-1329.
- Chaudhary, P. M.; Chavan, S. R.; Shirazi, F.; Razdan, M.; Nimkar, P.; Maybhate, S. P.; Likhite, A. P.; Gonnade,
R.; Hazara, B. G.; Deshpande, S. R.
Bioorg. Med. Chem. Lett
.
2009
,
17
, 2433-2440.
- Huisgen, R. In
1,3-Dipolar Cycloaddition Chemistry
; Padwa, A.; Ed. Wiley: New York, NY, USA, 1984.
- Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; der Eycken, E. V.
Org. Lett.
2004
,
6
, 4223-4225.
- Gümüş, A.; Uçur, S.
Heterocycl. Commun
.
2014
,
20
, 361-364.
- Kumar, S.; Bawa, S.; Gupta, H.
Mini-Rev. Med. Chem.
2009
,
9
, 1648-1654.
- Chen, Y. L.; Huang, C. J.; Huang, Z. Y.; Tseng, C. H.; Chang, F. S.; Yang, S. H.; Lin, S. R.; Tzeng, C. C.
Bioorg.
Med. Chem.
2006
,
14
, 3098-3105.
- Chen, Y. L.; Zhao, Y. L.; Lu, C. M.; Tzeng, C. C.; Wang, J. P.
Bioorg. Med. Chem.
2006
,
14
, 4373-4378.
- Feng, Y.; Lau, E.; Scortegagna, M.; Ruller, C.; De, S. K.; Barile, E.; Krajewski, S.; Aza-Blanc, P.; Williams, R.;
Pinkerton, A. B. et al.
Pigm. Cell Melanoma Res.
2013
,
26
, 136-142.
- Gholap, A. R.; Toti, K. S.; Shirazi, F.; Kumari, R.; Bhat, M. K.; Deshpande, M. V.; Srinivasan, K. V.
Bioorg.
Med. Chem.
2007
,
15
, 6705-6715.
- Krafts, K.; Hempelmann, E.; Skorska-Stania, A.
Parasitol. Res.
2012
,
111
, 1-6.
- Sanchez, J. P.; Domagala, J. M.; Hagen, S. E.; Heifetz, C. L.; Hutt, M. P.; Nichols, J. B.; Trehan, A. K.
J. Med.
Chem.
1988
,
31
, 983-991.
- Sabatini, S.; Gosetto, F.; Manfroni, G.; Tabarrini, O.; Kaatz, G. W.; Patel, D.; Cecchetti, V.
J. Med. Chem
.
2011
,
54
, 5722-5736.
- Srinivasan, S.; Shafreen, R. M. B.; Nithyanand, P.; Manisankar, P.; Pandian, S. K.
Eur. J. Med. Chem.
2010
,
45
,
6101-6105.
- Wang, Y.; Damu, G. L. V.; Lv, J. S.; Geng, R. X.; Yang, D. C.; Zhou, C. H.
Bioorg. Med. Chem. Lett.
2012
,
22
,
5363-5366.
- Truong, V. V.; Nam, T. D.; Hung, T. N.; Nga, N. T.; Quan, P. M.; Chinh, L. V.; Jung, S. H.
Bioorg. Med. Chem.
Lett.
2015
,
25
, 5182-5185.
- Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B.
Angew. Chem. Int. Ed.
2002
,
41
, 2596-2599.
- Feldman, A. K.; Colasson, B.; Fokin, V. V.
Org. Lett
.
2004
,
6
, 3897-3899.
- Jiang, Y.; Li, X.; Zhao, Y.; Jia, S.; Li, M.; Zhao, Z.; Zhang, R.; Li, W.; Zhang, W.
RSC Adv.
2016
,
6
, 110102-110107.
- Hajipour, A. R.; Karimzadeh, M.; Ghorbani, S.
Synlett
2014
,
25
, 2903-2907.
- Ilhan, S.; Baykara, H.; Oztomsuk, A.; Okumus, V.; Levent, A.; Seyitoglu, M. S.; Ozdemir, S.
Spect. Acta A
2014
,
118
, 632-642.
- Ağırtaş, M. S.; Dede, E.; Gümüş, S.; Dündar, A.; Okumus, V.
Zeit. Anorg. Allg. Chem.
2014
,
640
, 1953-1959.
- Dundar, A.; Okumus, V.; Ozdemir, S.; Yildiz, A.
Int. J. Food Prop.
2013
,
16
, 1105-1116.
- Raju, D.; Vishwakarma, R. K.; Khan, B. M.; Mehta, U. J.; Absar, A.
Mater. Lett.
2014
,
129
, 159-161.
- Blois, M. S.
Nature
1958
,
181
, 1199-1200.
- Oyaizu, M.
Japan. J. Nutr.
1986
,
44
, 307-315.
- Kalemba, D.; Kunicka, A.
Curr. Med. Chem.
2003
,
10
, 813-829.
- Keypour, H.; Shooshtari, A.; Rezaeivala, M.; Kup, F. O.; Rudbari, H. A.
Polyhedron
2015
,
97
, 75-82.