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R. Kant et al. / European Journal of Medicinal Chemistry 124 (2016) 218e228
4.4.10. [1-(4-Nitrophenyl)-1H-1,2,3-triazol-4-yl]methyl 1-
cyclopropyl-6-fluoro-7-(4-{[1-(4-nitrophenyl)-1H-1,2,3-triazol-4-
yl]methyl}piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-
carboxylate (4j)
34.6, 31.9 (eCH3), 31.4 (eCH3), 8.2; Elemental analysis for
39H36FN9O5: Calculated: C 64.19, H 4.97, N 17.27; Found: C 64.21, H
4.96, N 17.25.
C
Yellow solid, Yield: 61%, M.P: 261e263 ꢁC; 1H NMR (CDCl3)
d
:
4.4.14. [1-(4-Ethylphenyl)-1H-1,2,3-triazol-4-yl]methyl 1-
cyclopropyl-7-(4-{[1-(4-ethylphenyl)-1H-1,2,3-triazol-4-yl]methyl}
piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
(4n)
8.58 (s, 1H, Ar-H), 8.49 (s, 1H, eC]CH of triazole), 8.45e8.40 (m,
4H, Ar-H and eC]CH of triazole), 8.09e7.99 (m, 6H, Ar-H),
7.26e7.25 (m, 1H, Ar-H), 5.55 (s, 2H, eOCH2), 3.89 (s, 2H, eNCH2),
3.44e3.42 (m, 1H, eNCH), 3.32 (bs, 4H, 2 ꢂ eNCH2), 2.82 (bs, 4H,
Brownish semi solid, Yield: 78%, 1H NMR (CDCl3)
d: 8.44 (s, 1H,
2 ꢂ eNCH2), 1.33e1.31 (m, 2H, eCH2), 1.14e1.12 (m, 2H, eCH2); 13
C
Ar-H), 8.21 (s, 1H, eC]CH of triazole), 7.95e7.90 (m, 2H, Ar-H and
eC]CH of triazole), 7.59e7.52 (m, 4H, Ar-H), 7.27e7.20 (m, 5H, Ar-
H), 5.44 (s, 2H, eOCH2), 3.82 (s, 2H, eNCH2), 3.33 (bs, 1H, eNCH),
3.25 (bs, 4H, 2 ꢂ eNCH2), 2.83 (bs, 4H, 2 ꢂ eNCH2), 2.64e2.60 (m,
4H, 2 ꢂ AreCH2), 1.21e1.19 (m, 8H, eCH2 and 2 ꢂ eCH3), 1.04 (bs,
NMR (CDCl3) d: 173.43 (eCO),164.7 (eCO),162.8,159.9,159.3,156.6,
153.7, 148.5, 145.3, 144.5, 140.7, 138.0, 133.5, 123.0, 122.8, 122.7,
120.9, 120.4, 120.3, 120.2, 120.0, 117.8, 117.7, 117.6, 117.4, 113.5, 113.1,
109.3, 104.7, 57.9, 53.1, 52.6, 49.7, 34.7, 8.3; Elemental analysis for
C
35H30FN11O7: Calculated: C 57.14, H 4.11, N 20.94; Found: C 57.16, H
2H, eCH2); 13C NMR (CDCl3)
d: 173.4 (eCO), 163.2 (eCO), 158.9,
4.10, N 20.96.
154.6, 151.7, 148.3, 145.2, 138.0, 135.0, 134.9, 134.1, 131.1, 129.2, 129.1,
120.6, 120.2, 113.1, 110.0, 107.9, 104.5, 57.1, 52.0, 51.4, 49.7, 34.5, 29.6,
28.4,15.3,14.0, 8.1; Elemental analysis for C39H40FN9O3: Calculated:
C 66.75, H 5.74, N 17.96; Found: C 66.71, H 5.77, N 17.93.
4.4.11. [1-(2-Chlorophenyl)-1H-1,2,3-triazol-4-yl]methyl 7-(4-{[1-
(2-chlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}piperazin-1-yl)-1-
cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
(4k)
4.4.15. [1-(4-Pentylphenyl)-1H-1,2,3-triazol-4-yl]methyl 1-
cyclopropyl-6-fluoro-4-oxo-7-(4-{[1-(4-pentylphenyl)-1H-1,2,3-
triazol-4-yl]methyl}piperazin-1-yl)-1,4-dihydroquinoline-3-
carboxylate (4o)
Brown solid, Yield: 80%, M.P: 99e101 ꢁC; 1H NMR (CDCl3)
d: 8.55
(s, 1H, Ar-H), 8.27 (s, 1H, eC]CH of triazole), 8.01 (s, 1H, eC]CH of
triazole), 7.98e7.95 (m, 1H, Ar-H), 7.65e7.56 (m, 4H, Ar-H),
7.49e7.43 (m, 4H, Ar-H), 7.27e7.25 (d, J ¼ 6.88 Hz, 1H, Ar-H), 5.55
(s, 2H, eOCH2), 3.90 (s, 2H, eNCH2), 3.47e3.44 (m, 1H, eNCH), 3.33
(bs, 4H, 2 ꢂ eNCH2), 2.83 (m, 4H, 2 ꢂ eNCH2), 1.33e1.31 (d,
Brownish semi solid, Yield: 84%, 1H NMR (CDCl3)
d: 8.48 (s, 1H,
Ar-H), 8.26 (s, 1H, eC]CH of triazole), 7.98e7.91 (m, 2H, Ar-H and
eC]CH of triazole), 7.72 (bs, 2H, Ar-H), 7.62e7.60 (m, 2H, Ar-H),
7.30e7.24 (m, 5H, Ar-H), 5.46 (s, 2H, eOCH2), 3.83 (s, 2H, eNCH2),
3.39 (bs, 1H, eNCH), 3.29 (bs, 4H, 2 ꢂ eNCH2), 2.81 (bs, 4H,
2 ꢂ eNCH2), 2.65e2.59 (m, 8H, 2 ꢂ AreCH2eCH2), 1.30e1.25 (m,
10H, eCH2 and 2 ꢂ eCH2eCH2), 1.08 (bs, 2H, eCH2), 0.89e0.85 (m,
J ¼ 6.88 Hz, 2H, eCH2), 1.13 (bs, 2H, eCH2); 13C NMR (CDCl3)
d: 173.2
(eCO), 164.6 (eCO), 154.5, 152.1, 148.3, 144.5, 144.4, 143.2, 137.9,
134.7,130.8,130.7, 130.6,128.7, 128.4,127.9, 127.8, 127.7,126.3,113.2,
112.9, 109.2, 104.9, 57.7, 52.9, 52.4, 49.6, 34.6, 8.1; Elemental anal-
ysis for C35H30Cl2FN9O3: Calculated: C 58.83, H 4.23, N 17.64;
Found: C 58.80, H 4.24, N 17.63.
6H, 2 ꢂ eCH3); 13C NMR (CDCl3)
d: 172.9 (eCO), 166.2 (eCO), 154.5,
148.3, 147.4, 144.6, 143.9, 140.3, 138.4, 138.0, 135.3, 134.1, 129.7,
129.6, 120.5, 120.4, 113.2, 109.9, 104.9, 57.6, 52.7, 51.9, 49.6, 35.4,
31.3, 30.9, 30.8, 29.6, 22.6, 22.4, 14.0, 13.9, 8.1; Elemental analysis
for C45H52FN9O3: Calculated: C 68.77, H 6.67, N 16.04; Found: C
68.81, H 6.64, N 16.02.
4.4.12. [1-(3-Chlorophenyl)-1H-1,2,3-triazol-4-yl]methyl 7-(4-{[1-
(3-chlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}piperazin-1-yl)-1-
cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
(4l)
Brown solid, Yield: 74%, M.P: 109e111 ꢁC; 1H NMR (CDCl3)
d:
4.4.16. [1-(3,5-Dimethylphenyl)-1H-1,2,3-triazol-4-yl]methyl 1-
cyclopropyl-7-(4-{[1-(3,5-dimethylphenyl)-1H-1,2,3-triazol-4-yl]
methyl}piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-
carboxylate (4p)
8.53 (s, 1H, Ar-H), 8.33 (s, 1H, eC]CH of triazole), 8.04 (s, 1H, eC]
CH of triazole), 7.97e7.94 (m, 1H, Ar-H), 7.82e7.81 (d, J ¼ 7.64 Hz,
2H, Ar-H), 7.66e7.65 (m, 2H, Ar-H), 7.49e7.39 (m, 4H, Ar-H),
7.26e7.24 (d, J ¼ 6.12 Hz, 1H, Ar-H), 5.52 (s, 2H, eOCH2), 3.87 (s,
2H, eNCH2), 3.43e3.40 (m, 1H, eNCH), 3.32 (bs, 4H, 2 ꢂ eNCH2),
2.81 (m, 4H, 2 ꢂ eNCH2), 1.34e1.29 (m, 2H, eCH2), 1.12 (bs, 2H,
Brownish semi solid, Yield: 75%, 1H NMR (CDCl3)
d: 8.52 (s, 1H,
Ar-H), 8.20 (s, 1H, eC]CH of triazole), 8.01e7.98 (m, 2H, Ar-H and
eC]CH of triazole), 7.45e7.20 (m, 5H, Ar-H), 7.11e7.02 (m, 2H, Ar-
H), 5.50 (s, 2H, eOCH2), 3.99 (s, 2H, eNCH2), 3.47 (bs, 1H, eNCH),
3.40 (bs, 4H, 2 ꢂ eNCH2), 2.77 (bs, 4H, 2 ꢂ eNCH2), 2.38, 2.37 (s,
each 6H, 4 ꢂ eCH3), 1.26e1.25 (m, 2H, eCH2), 1.09 (bs, 2H, eCH2);
eCH2); 13C NMR (CDCl3)
d: 173.2 (eCO), 164.6 (eCO), 154.6, 152.1,
148.3, 144.5, 144.4, 137.9, 137.7, 135.5, 135.4, 130.8, 130.7, 128.8,
122.6, 120.7, 120.6, 118.4, 118.3, 113.2, 112.9, 109.1, 104.9, 57.7, 52.9,
52.5, 49.6, 34.6, 8.1; Elemental analysis for
C
35H30Cl2FN9O3:
13C NMR (CDCl3)
d: 172.9 (eCO), 164.6 (eCO), 152.1, 148.5, 148.3,
Calculated: C 58.83, H 4.23, N 17.64; Found: C 58.81, H 4.24, N 17.65.
144.4, 143.1, 141.5, 137.9, 130.9, 128.4, 127.4, 126.4, 122.9, 113.4, 113.1,
104.8, 57.9, 52.6, 52.0, 49.5, 34.7, 22.7, 21.0, 8.3; Elemental analysis
for C39H40FN9O3: Calculated: C 66.75, H 5.74, N 17.96; Found: C
66.78, H 5.75, N 17.91.
4.4.13. [1-(4-Acetylphenyl)-1H-1,2,3-triazol-4-yl]methyl 7-(4-{[1-
(4-acetylphenyl)-1H-1,2,3-triazol-4-yl]methyl}piperazin-1-yl)-1-
cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
(4m)
4.4.17. [1-(2-Methoxyphenyl)-1H-1,2,3-triazol-4-yl]methyl 1-
cyclopropyl-6-fluoro-7-(4-{[1-(2-methoxyphenyl)-1H-1,2,3-triazol-
4-yl]methyl}piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-
carboxylate (4q)
Orange solid, Yield: 56%, M.P: 224e226 ꢁC; 1H NMR (CDCl3)
d:
8.57 (s, 1H, Ar-H), 8.42 (s, 1H, eC]CH of triazole), 8.15e8.08 (m, 5H,
Ar-H and eC]CH of triazole), 8.04e8.00 (m, 1H, Ar-H), 7.91e7.88
(dd, J ¼ 3.04 and 8.40 Hz, 4H, Ar-H), 7.27e7.26 (m, 1H, Ar-H), 5.54 (s,
2H, eOCH2), 3.89 (s, 2H, eNCH2), 3.43e3.41 (m, 1H, eNCH), 3.33
(bs, 4H, 2 ꢂ eNCH2), 2.83 (bs, 4H, 2 ꢂ eNCH2), 2.67, 2.65 (s, each 3H,
2 ꢂ eCH3), 1.33e1.30 (m, 2H, eCH2), 1.12e1.10 (m, 2H, eCH2); 13C
White solid, Yield: 76%, M.P: 92e94 ꢁC; 1H NMR (CDCl3)
d: 8.48
(s, 1H, Ar-H), 8.20 (s, 1H, eC]CH of triazole), 7.98e7.93 (m, 2H, Ar-
H and eC]CH of triazole), 7.62e7.59 (m, 4H, Ar-H), 7.48e7.43 (m,
4H, Ar-H), 7.21e7.20 (m,1H, Ar-H), 5.48 (s, 2H, eOCH2), 4.03, 3.99 (s,
each 3H, 2 ꢂeOCH3), 3.84 (s, 2H, eNCH2), 3.40e3.35 (m,1H, eNCH),
3.27e3.24 (m, 4H, 2 ꢂ eNCH2), 2.75e2.72 (m, 4H, 2 ꢂ eNCH2),
1.26e1.23 (m, 2H, eCH2),1.08e1.07 (m, 2H, eCH2); 13C NMR (CDCl3)
NMR (CDCl3) d: 196.6 (eCO), 173.2 (eCO), 162.3 (eCO), 161.8, 157.4,
155.6, 150.7, 148.6, 148.4, 144.6, 140.0, 136.8, 133.5, 130.1, 130.0,
122.5, 121.0, 120.1, 119.9, 117.5, 109.3, 104.8, 57.8, 52.9, 52.6, 49.7,