C.B. Vagish, K. Kumara, H.K. Vivek et al.
Journal of Molecular Structure 1230 (2021) 129899
1
27.36 (1C, 6”-C), 129.22 (2C, 3”,5”-C), 129.53 (1C, 4”-C), 130.03
1C, 1”-C), 131.44 (1C, 4a-C), 134.53 (1C, 5’-C), 139.68 (1C, 4-C),
42.79 (1C, Cou-C=C-CO), 143.54 (1C, 8a-C), 159.12 (1C, lactone-
C=O, 2-C), 189.78 (1C, C=O); MS (m/z): 425.03 (M+, 100), 427.03
M+2, 63), 429.02 (M+4, 10); Anal. Calcd. for C Cl N O (%):
with the space group Pbca. The Hirshfeld surface analysis reveals
that the major contribution for crystal stabilization is due to H…H
(53.3%) interaction. The structural coordinates were optimized us-
ing DFT calculation are in good agreement with the experimental
results. The energy gap (5.5963 eV) value of 6e molecule reveals
that the molecule is chemically hard and less reactive. Amongst the
series, the compound, 7c found more anticancer potential against
PC-3 and DU-145 cell lines with an IC50 value of 10.538 ± 0.3, and
9.845 ± 0.6 μM, respectively, with very low toxicity at 10 μM, and
was supported by molecular docking and satisfactory ADME/Tox
studies.
(
1
(
H
13
21
2
3
3
C, 59.17; H, 3.07; N, 9.86; Found: C, 59.12; H, 3.04; N, 9.79
.8.4 3-(3-(1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazol-
-yl)-3-oxoprop-1-en-1-yl)-4-chloro-2H-chromen-2-one, 7c:
Obtained as yellowish solid, m.p. 238-240°C; IR (Ѵmax, cm 1):
98 (C-Br), 949 (N-N=N), 1291 (C-N), 1516 (N=N), 1606 (C=C),
3
4
−
5
1
1
723 (C=O) 1741 (lactone-C=O); H NMR (DMSO, δ ppm): 2.398
(
s, 3H, triazole-CH ), 7.112-7.150 (m, 1H, Ar-H), 7.251-7.271 (d,
3
2
H, Ar-H), 7.322-7.361 (d, 1H, J=9.7 Hz, CH=), 7.504-7.527 (d,
H, Ar-H), 7.780-7.818 (d, 1H, J=9.5 Hz, =CH), 7.920-7.940 (d, 2H,
Credit authors information
2
Ar-H); 13C NMR (DMSO, δ ppm): 13.95 (1C, 5’-CH ), 112.82 (1C,
3
Vagish ChannaBasappa: Conceptualization, Methodology, Writ-
ing - Original Draft, Investigation, Formal analysis, Validation.
Karthik Kumara: Validation, Software, Investigation and Visual-
ization
8
-C), 114.20 (1C, 3-C), 114.97 (1C, 6-C), 119.16 (1C, 5-C), 119.83
1C, 7-C), 120.92 (1C, Cou-C=C-CO), 123.48 (1C, 4’-C), 124.32 (1C,
”-C), 126.27 (1C, 6”-C), 127.44 (1C, 3”-C), 128.91 (1C, 5”-C), 129.57
1C, 4”-C), 130.32 (1C, 4a-C), 131.49 (1C, 5’-C), 132.57 (1C, 4-C),
33.92 (1C, Cou-C=C-CO), 135.66 (1C, 1”-C), 139.72 (1C, 8a-C),
59.72 (lactone-C=O, 2-C), 188.00 (1C, C=O); MS (m/z): 483.00
(
2
(
Vivek Hamse Kameshwar: Software, Formal analysis, Validation
and Visualization
1
1
Srinivasan Bharath: Software, Formal analysis, Validation and
Visualization
(
M+, 82), 485.06 (M+2, 100), 487.06 (M+4, 36); Anal. Calcd. for
C
3
H
BrClN O (%): C, 54.51; H, 3.12; N, 8.67; Found: C, 54.46; H,
Lokanath N Krishnappagowda: Conceptualization, Supervision
Ajay Kumar Kariyappa: Conceptualization, Methodology, Writ-
ing - Review & Editing, Supervision.
2
2
15
3
3
.04; N, 8.61
.8.5 4-Chloro-3-(3-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-
triazol-4-yl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one, 7d: Ob-
3
−1
tained as oily mass; IR (Ѵmax, cm ): 940 (N-N=N), 1273 (C-N),
507 (N=N), 1615 (C=C), 1732 (C=O) 1750 (lactone-C=O); 1282 (C-
Declaration of Competing Interest
1
1
F); H NMR (DMSO, δ ppm): 2.389 (s, 3H, triazole-CH ), 7.118-7.132
3
The authors declare that they have no known competing finan-
cial interests or personal relationships that could have appeared to
influence the work reported in this paper.
(
m, 2H, Ar-H), 7.262-7.287 (m, 2H, Ar-H), 7.326-7.354 (d, 1H, J=6.5
Hz, CH=), 7.516-7.533 (m, 2H, Ar-H), 7.770-7.813 (d, 1H, J=10.7 Hz,
CH), 7.912-7.934 (m, 2H, Ar-H); 13C NMR (DMSO, δ ppm): 13.82
1C, 5’-CH ), 110.72 (1C, 8-C), 113.29 (1C, 3-C), 119.05 (1C, 6-C),
=
(
3
Acknowledgments
1
25.74 (1C, 5-C), 127.37 (1C, 7-C), 128.00 (1C, Cou-C=C-CO), 128.17
1C, 4’-C), 129.18 (C, 2”,6”-C), 129.35 (1C, 1”-C), 130.03 (1C, 3”-C),
32.42 (1C, 5”-C), 134.07 (1C, 4”-C), 134.97 (1C, 4a-C), 137.33 (1C,
’-C), 139.42 (1C, 4-C), 145.24 (1C, Cou-C=C-CO), 148.31 (1C, 8a-C),
66.07 (lactone-C=O, 2-C), 184.24 (1C, C=O); MS (m/z): 423.82
M+, 100), 425.07 (M+2, 32); Anal. Calcd. for C ClFN O (%):
(
The authors are grateful to the IOE Instrumentation Facility, Vi-
jnana Bhavana, University of Mysore, for recording spectra and X-
ray diffraction studies.
1
5
1
(
H
15
2
2
3
3
Supplementary materials
C, 62.35; H, 3.57; N, 9.91; Found: C, 62.29; H, 3.51; N, 9.82
.8.6 4-Chloro-3-(3-(1-(2,4-dimethylphenyl)-5-methyl-1H-
,2,3-triazol-4-yl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one, 7e:
3
1
Obtained as light brown solid, m.p. 226-228°C; IR (Ѵmax, cm 1):
−
9
31 (N-N=N), 1282 (C-N), 1516 (N=N), 1606 (C=C), 1714 (C=O),
References
1
1
750 (lactone-C=O); H NMR (DMSO, δ ppm): 2.204 (s, 3H, CH ),
3
2
1
.356 (s, 3H, Ar-CH ), 2.606 (s, 3H, triazole-CH ), 7.176-7.213 (d,
3 3
H, J=9.2 Hz, CH=), 7.276 (s, 2H, Ar-H), 7.418-7.436 (d, 2H, Ar-H),
[
7
.911-7.929 (d, 3H, Ar-H), 7.996-8.034 (d, 1H, J=9.5 Hz, =CH);
1
3
C NMR (DMSO, δ ppm): 13.35 (1C, 5’-CH ), 13.64 (1C, 2”-CH ),
3
3
1
8.60 (1C, 4”-CH ), 101.22 (1C, 8-C), 107.24 (1C, 3-C), 107.67 (1C,
3
6
-C), 118.78 (1C, 5-C), 123.64 (1C, 7-C), 123.83 (1C, 6”-C), 126.47
(
(
1C, Cou-C=C-CO), 130.79 (2C, 2”,3”-C), 132.40 (1C, 1”-C), 133.34
1C, 4’-C), 133.97 (1C, 5”-C), 134.41 (2C, 5’,4a-C), 136.21 (1C, 4-C),
1
41.90 (1C, 4’-C), 147.61 (1C, 8a-C), 150.97 (1C, Cou-C=C-CO),
68.37 (1C, lactone-C=O), 186.90 (1C, C=O, 2-C); MS (m/z): 419.13
ClN O (%): C,
1
(
M+, 100), 421.30 (M+2, 32). Anal. Calcd. for C
H
23 18
3
3
6
5.80; H, 4.32; N, 10.01; Found: C, 65.72; H, 4.25; N, 9.94.
. Conclusion
Microwave induced synthesis often reduces the reaction tem-
4
[
perature, and time. The target compounds, 7(a-e) were synthesized
by conventional reflux and MW irradiation methods. The reaction
optimization conditions reveal that, microwave assisted synthesis
requires lesser reaction time comparable to conventional heating.
The compound 6e is crystallized in orthorhombic crystal system
9