SYNTHESIS AND ANTICANCER ACTIVITY OF A NOVEL SERIES
317
8
(
.25–8.30 m (2H, Ar-H), 8.37–8.41 m (1H, Ar-H), 8.54 s
1H, Ar-H), 8.82 s (1H, Ar-H). MS: 519 [M + H]+.
E)-1-(2-{[1-(2-Nitrophenyl)-1H-1,2,3-triazol-4-yl]-
methoxy}phenyl)-3-(tetrazolo[1,5-a]quinolin-4-yl)-
8.75–8.79 d (1H, Ar-H), 8.84 s (1H, Ar-H), 8.91 s (1H,
Ar-H). MS: 519 [M + H]+.
(
(E)-1-{3-[(1-Phenyl-1H-1,2,3-triazol-4-yl)methoxy]-
phenyl}-3-(tetrazolo[1,5-a]quinolin-4-yl)prop-2-en-1-
–
1
–1
prop-2-en-1-one (7d). Yield 80%. IR spectrum, ν, cm :
one (7i). Yield 84%. IR spectrum, ν, cm : 1649 (C=O),
1
1590 (C=N). 1H NMR spectrum, δ, ppm: 5.42 s (2H,
1
651 (C=O), 1593 (C=N). H NMR spectrum, δ, ppm:
CH ), 7.33–7.36 d (2H, Ar-H), 7.69–7.71 m (4H, Ar-H),
5
.43 s (2H, CH ), 7.28–7.34 m (4H, Ar-H), 7.47–7.62 m
2
2
7
8
.88–7.92 d (1H, Ar-H), 7.92–8.06 m (8H, Ar-H), 8.16–
.18 d (2H, Ar-H), 8.24–8.26 d (1H, Ar-H), 8.67–8.69 d
(
3H, Ar-H), 7.65–7.81 m (2H, Ar-H), 7.88–7.92 d (1H,
Ar-H), 8.00–8.11 m (2H,Ar-H), 8.32–8.36 m (2H,Ar-H),
8
.56 s (1H, Ar-H), 8.82 s (1H, Ar-H). MS: 519 [M + H]+.
(1H, Ar-H), 8.82 s (1H, Ar-H), 9.06 s (1H, Ar-H). MS:
74 [M + H]+.
E)-1-(4-{[1-(4-Chlorophenyl)-1H-1,2,3-triazol-4-
yl]methoxy}phenyl)-3-(tetrazolo[1,5-a]quinolin-4-yl)-
4
(E)-1-{3-[(1-Phenyl-1H-1,2,3-triazol-4-yl)methoxy]-
(
phenyl}-3-(tetrazolo[1,5-a]quinolin-4-yl)prop-2-en-1-
one (7e). Yield 82%. IR spectrum, ν, cm : 1650 (C=O),
1
CH ), 7.21–7.25 t (1H, Ar-H), 7.32–7.44 m (3H, Ar-H),
7
7
–
1
–1
1
prop-2-en-1-one (7j). Yield 82%. IR spectrum, ν, cm :
1
5
590 (C=N). H NMR spectrum, δ, ppm: 5.41 s (2H,
1
644 (C=O), 1586 (C=N). H NMR spectrum, δ, ppm:
2
.42 s (2H, CH ), 7.34–7.38 m (3H, Ar-H), 7.55–7.63 m
.47–7.51 m (2H, Ar-H), 7.55–7.60 m (3H, Ar-H), 7.64–
.79 m (2H, Ar-H), 7.80–7.84 t (1H, Ar-H), 7.89–8.00 m
2
(2H, Ar-H), 7.78–7.85 m (1H, Ar-H), 7.94–7.80 m (2H,
Ar-H), 8.19–8.25 m (2H,Ar-H), 8.64–8.66 d (1H,Ar-H),
(2H, Ar-H), 8.09–8.15 m (3H, Ar-H), 8.22–8.26 m (3H,
8
.82 s (1H, Ar-H), 9.04 s (1H, Ar-H). MS: 508 [M + H]+.
(E)-1-(4-{[1-(4-Nitrophenyl)-1H-1,2,3-triazol-4-yl]-
Ar-H), 8.64–8.66 d (1H, Ar-H), 8.70–8.74 d (1H, Ar-H),
8
.84s (1H, Ar-H), 9.12 s (1H, Ar-H). MS: 474 [M + H]+.
methoxy}phenyl)-3-(tetrazolo[1,5-a]quinolin-4-yl)-
prop-2-en-1-one (7k). Yield 86%. IR spectrum, ν, cm :
1
5
(
E)-1-(3-{[1-(4-Chlorophenyl)-1H-1,2,3-triazol-4-
–1
yl]methoxy}phenyl)-3-(tetrazolo[1,5-a]quinolin-4-yl)-
prop-2-en-1-one (7f). Yield 83%. IR spectrum, ν, cm :
1
5
1
652 (C=O), 1593 (C=N). H NMR spectrum, δ, ppm:
–
1
.42 s (2H, CH ), 7.20–7.24 m (2H, Ar-H), 7.33–7.36 m
1
2
648 (C=O), 1587 (C=N). H NMR spectrum, δ, ppm:
(1H, Ar-H), 7.54–7.58 t (1H, Ar-H), 7.96–8.06 m (8H,
.41 s (2H, CH ), 7.47–7.49 d (1H, Ar-H), 7.57–7.65 m
2
Ar-H), 8.22–8.26 m (4H,Ar-H), 8.44–8.48 m (2H,Ar-H),
(
3H, Ar-H), 7.74–7.78 t (2H, Ar-H), 7.89–7.90 t (1H,
8
.65–8.69 m (2H, Ar-H), 8.82 s (1H, Ar-H), 9.21 s (1H,
ArH), 7.94–7.96 d (1H, Ar-H), 8.04–8.09 m (3H, Ar-H),
8
8
MS: 508 [M + H]+.
E)-1-(3-{[1-(4-Nitrophenyl)-1H-1,2,3-triazol-4-yl]-
methoxy}phenyl)-3-(tetrazolo[1,5-a]quinolin-4-yl)-
prop-2-en-1-one (7g). Yield 85%. IR spectrum, ν, cm :
1
5
(
+
Ar-H), 12.09 s (1H, Ar-H). MS: 519 [M + H] .
.24–8.26 d (1H, Ar-H), 8.67–8.69 d (1H, Ar-H), 8.76–
.80 d (1H, Ar-H), 8.85 s (1H, Ar-H), 9.09 s (1H, Ar-H).
(E)-1-(4-{[1-(2-Nitrophenyl)-1H-1,2,3-triazol-4-yl]-
methoxy}phenyl)-3-(tetrazolo[1,5-a]quinolin-4-yl)-
prop-2-en-1-one (7l). Yield 82%. IR spectrum, ν, cm :
1
5
–1
(
1
645 (C=O), 1591 (C=N). H NMR spectrum, δ, ppm:
.42 s (2H, CH ), 7.25–7.32 m (3H, Ar-H), 7.41–7.52 m
2
–
1
(
1H, Ar-H), 7.59–7.62 t (1H, Ar-H), 7.83–7.87 d (1H,
Ar-H), 7.79–8.00 m (5H,Ar-H), 8.22–8.31 d (2H,Ar-H),
.38–8.43 m (2H,Ar-H), 8.65–8.367 d (1H,Ar-H), 8.80 s
1H, Ar-H), 9.12 s (1H, Ar-H), 12.10 s (1H, Ar-H). MS:
19 [M + H]+.
1
592 (C=N), 1653 (C=O). H NMR spectrum, δ, ppm:
.43 s (2H, CH ), 7.22–7.27 t (1H, Ar-H), 7.34–7.38 m
2
8
(
5
2H, Ar-H), 7.47–7.52 m (2H, Ar-H), 7.60–7.66 m (2H,
Ar-H), 7.74–7.80 m (2H, Ar-H), 7.86–7.92 t (1H, Ar-H),
8
8
.04–8.11 m (2H, Ar-H), 8.23–8.31 m (3H, Ar-H), 8.42–
.52 m (3H, Ar-H), 8.66–8.70 m (2H, Ar-H), 8.85 s (1H,
ACKNOWLEDGMENTS
Ar-H), 9.23 s (1H, Ar-H). MS: 519 [M + H]+.
E)-1-(3-{[1-(2-Nitrophenyl)-1H-1,2,3-triazol-4-yl]-
methoxy}phenyl)-3-(tetrazolo[1,5-a]quinolin-4-yl)-
The authors are thankful to The Head, Department of Chem-
istry, Osmania University, Hyderabad for providing Laboratory
facilities and one of the authors M. Nagraj thankful to UGC,
New Delhi, India for financial support. We also thankful to The
Director, CFRD, Osmania University, Hyderabad for providing
spectral analysis facilities.
(
–
1
prop-2-en-1-one (7h). Yield 79%. IR spectrum, ν, cm :
1
1
645 (C=O), 1592 (C=N). H NMR spectrum, δ, ppm:
5
.41 s (2H, CH ), 7.47–7.50 d.d (1H, Ar-H), 7.61–7.65 t
2
CONFLICT OF INTEREST
(1H, Ar-H), 7.68–7.70 m (2H, Ar-H), 7.84–8.09 m (6H,
Ar-H), 8.23–8.25 d.d (2H,Ar-H), 8.65–8.67 d (1H,Ar-H),
No conflict of interest was declared by the authors.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 2 2020