A. Keivanloo et al.
δ = 34.6, 36.8, 75.0, 117.2, 117.5, 122.1, 122.4, 124.9,
125.0, 125.1, 125.2, 129.0, 129.1, 129.2, 133.6, 133.7,
135.9, 136.1, 136.6, 143.8, 148.4, 148.5, 155.3, 173.0 ppm;
IR (KBr): ꢀ = 1769, 1712, 1600, 1536, 1491, 1449, 1350,
1235, 1132, 1040, 998, 876, 825, 771, 720, 697 cm−1; MS:
m/z=724 (M+).
yield 90%; m.p.: 207 °C; 1H NMR (300 MHz, DMSO-d6):
δ=4.72 (s, 2H, CH2), 5.59 (s, 2H, CH2), 7.28–7.44 (m, 15H,
ArH), 8.08 (s, 1H, CH triazole), 9.71 (s, 1H, NH) ppm; 13
C
NMR (75 MHz, DMSO-d6): δ = 34.0, 53.2, 69.7, 123.8,
127.2, 128.4, 128.6, 128.7, 129.0, 129.2, 136.5, 140.0,
142.7, 155.3, 173.3 ppm; IR (KBr): ꢀ =3310, 1771, 1712,
1596, 1490, 1445, 1330, 1252, 1209, 1120, 1046, 940, 707,
700 cm−1; MS: m/z=423 (M+).
1,3‑Bis[[1‑(4‑nitrophenyl)‑1H‑1,2,3‑triazol‑4‑yl]‑
methyl]‑5,5‑diphenylimidazolidine‑2,4‑dione (7b,
C33H24N110O6) Orange powder solid; yield 79%; m.p.: 258–
259 °C; H NMR (300 MHz, DMSO-d6): δ = 4.76 (s, 2H,
CH2), 4.99 (s, 2H, CH2), 7.35–7.37 (m, 10H, ArH), 7.96 (d,
J=8.7 Hz, 2H, ArH), 8.01 (s, 1H, CH of triazole), 8.23 (d,
J=8.7 Hz, 2H, ArH), 8.43–8.48 (m, 4H, ArH), 9.01 (s, 1H,
CH triazole) ppm; 13C NMR (75 MHz, DMSO-d6): δ=34.6,
36.8, 74.9, 120.8, 121.1, 122.0, 122.4, 126.0, 126.1, 129.0,
129.1, 129.3, 136.7, 140.9, 141.1, 144.0, 147.1, 147.2,
155.3, 173.0 ppm; IR (KBr): ꢀ = 1769, 1718, 1596, 1520,
1440, 1340, 1107, 1043, 985, 937, 851, 774, 745 cm−1; MS:
m/z=656 (M+).
3‑[[1‑(2‑Chlorobenzyl)‑1H‑1,2,3‑triazol‑4‑yl]methyl]‑5,5‑di‑
phenylimidazolidine‑2,4‑dione (10b, C25H20ClN5O2) White
1
powder solid; yield 87%; m.p.: 160–161 °C; H NMR
(300 MHz, DMSO-d6): δ=4.74 (s, 2H, CH2), 5.71 (s, 2H,
CH2), 7.19 (dd, J = 7.2, 1.6 Hz, 1H, ArH), 7.34–7.44 (m,
12H, ArH), 7.53 (dd, J=7.8, 1.2 Hz, 1H, ArH), 8.04 (s, 1H,
CH of triazole), 9.72 (s, 1H, NH) ppm; 13C NMR (75 MHz,
DMSO-d6): δ=34.0, 51.1, 69.7, 124.2, 127.2, 128.2, 128.7,
129.0, 130.1, 130.7, 130.9, 133.1, 133.7, 140.0, 142.5,
155.3, 173.3 ppm; IR (KBr): ꢀ = 3312, 1766, 1702, 1600,
1446, 1411, 1337, 1216, 1110, 1052, 940, 915, 828, 758,
732, 694, 668 cm−1; MS: m/z=457 (M+).
1,3‑Bis[[1‑(2‑chloro‑4‑nitrophenyl)‑1H‑1,2,3‑triazol‑4‑yl]‑
methyl]‑5,5‑diphenylimidazolidine‑2,4‑dione (7c,
C33H22Cl2N10O6) Dark orange powder solid; yield 83%; m.p.:
202–204 °C; 1H NMR (300 MHz, DMSO-d6): δ=4.78 (s,
2H, CH2), 4.98 (s, 2H, CH2), 7.33–7.40 (m, 10H, ArH),
7.75 (d, J=9 Hz, 1H, ArH), 7.80 (s, 1H, CH triazole), 8.03
(d, J=8.7 Hz, 1H, ArH), 8.37–8.43 (m, 4H, ArH), 8.58 (d,
J=2.4 Hz, 1H, ArH), 8.62 (d, J=2.4 Hz, 1H, ArH), 8.64 (s,
1H, CH of triazole) ppm; 13C NMR (75 MHz, DMSO-d6):
δ=34.6, 36.8, 75.0, 124.0, 124.1, 125.2, 125.6, 126.3, 126.4,
128.9, 129.0, 129.1, 129.2, 129.3, 129.6, 129.7, 136.7,
139.3, 139.5, 142.8, 143.9, 148.6, 148.7, 155.3, 173.1 ppm;
IR (KBr): ꢀ = 1770, 1715, 1600, 1533, 1443, 1340, 1235,
1107, 1045, 980, 851, 770 cm−1; MS: m/z=724 (M+).
3‑[[1‑(4‑Methylbenzyl)‑1H‑1,2,3‑triazol‑4‑yl]methyl]‑5,5‑di‑
phenylimidazolidine‑2,4‑dione (10c, C25H20ClN5O2) White
1
powder solid; yield 88%; m.p.: 169–170 °C; H NMR
(300 MHz, DMSO-d6): δ=2.30 (s, 3H, CH3), 4.70 (s, 2H,
CH2), 5.52 (s, 2H, CH2), 7.16–7.22 (m, 4H, ArH), 7.33–7.43
(m, 10H, ArH), 8.02 (s, 1H, CH of triazole), 9.70 (s, 1H,
NH) ppm; 13C NMR (75 MHz, DMSO-d6): δ=21.2, 34.0,
53.0, 69.7, 123.6, 127.2, 128.4, 128.7, 129.0, 129.7, 133.5,
137.9, 140.0, 142.6, 155.3, 173.3 ppm; IR (KBr): ꢀ =3312,
1769, 1712, 1600, 1488, 1446, 1331, 1254, 1209, 1120,
1046, 940 cm−1; MS: m/z=437 (M+).
Antibacterial assay
General procedure for synthesis of 3‑[(1‑benzyl‑
1H‑1,2,3‑triazol‑4‑yl)methyl]‑5,5‑diphenyl‑
imidazolidine‑2,4‑diones 10a‑10c
The evaluation of antibacterial activities of new 1,2,3-tri-
azole-linked 1,2,4-triazino[5,6-b]indole was performed by
using a well-difusion method against Micrococcus luteus
(M. luteus) and Pseudomonas aeruginosa (P. aeruginosa).
The nutrient agar and broth cultures were prepared and incu-
bated at 37 °C. To the nutrient agar plates, a suspension
of 40 mm3 of each bacterium was added. Cups (5 mm in
diameter) were cut at the end to each well. Besides, 30 mm3
of the test compounds at a concentration of 1000 µg cm−3
was added in DMSO. The plates were incubated at 37 °C
for 24 h, and the inhibition zone was measured in mm.
Results were reported as the inhibition zone in mm. The
anti-bacterial activities were compared with tetracycline as
the standard drug. DMSO was applied as a negative control.
To a mixture of benzyl chloride (8, 1.2 mmol) and sodium
azide (9, 1.2 mmol) in 3 cm3 H2O were added 5,5-diphenyl-
3-(prop-2-yn-1-yl)imidazolidine-2,4-dione (3, 1 mmol),
L3 (2 mol%), CuSO4 (2 mol%), and NaAsc (4 mol%). The
resulting mixture was stirred at 70 °C until the disappear-
ance of compound 3 (monitored by TLC). After completion
of the reaction, the solvent was evaporated to dryness. The
solid obtained was washed with ammonia (1/1) and then
H2O and dried. The crude product was purifed by recrystal-
lization from ethanol.
3‑[(1‑Benzyl‑1H‑1,2,3‑triazol‑4‑yl)methyl]‑5,5‑diphenylimi‑
dazolidine‑2,4‑dione (10a, C25H21N5O2) White powder solid;
1 3