SYNTHESIS AND ANTI-PROLIFERATIVE ACTIVITY OF NOVEL TRICYCLIC COMPOUNDS
693
and recrystallized from ethanol to give the corresponding
pure compounds 8a–8d.
133.80, 135.12, 136.15, 148.44, 153.00, 155.12, 159.16,
191.74. MS: m/z: 367 [M]+. Found, %: C 62.12; H 4.68;
N 11.45; S, 874. C19H17N3O3S (367.42). Calculated, %:
C 62.11; H 4.66; N 11.44; S, 873.
3-(2,5-Dimethoxyphenyl)-4-oxoindeno[1,2-c]-
pyrazole-2(1H,3H,4H)carboxamide (8a). Yield 85%,
mp 265–268°C. IR spectrum, ν, cm–1: 3448 (NH), 3256
Synthesis of compounds 9a–9c. A mixture of
a compound 3a–3c (1 mmol) with hydroxylamine
hydrochloride (1 mmol) in absolute ethanol (30 mL)
and TEA (10 mL) was refluxed for 5 h, then poured into
acidified ice water. The solid formed was filtered off,
washed with water, dried, and recrystallized from ethanol
to give the corresponding pure products 9a–9c.
1
(NH2), 1718 (C=O), 1679 (C=O). H NMR spectrum,
δ, ppm: 3.35 s, 3.40 s (6H, 2OCH3), 4.45 s (1H, CH),
6.64 s (2H, NH2, D2O exchangeable), 7.55–8.15 m (7H,
13
Ar-H), 9.67 s (1H, NH, D2O exchangeable). C NMR
spectrum, δ, ppm: 55.45, 56.08, 60.24, 106.36, 111.28,
112.52, 113.08, 122.15, 123.16, 126.34, 128.18, 133.85,
135.18, 136.10, 148.50, 152.80, 155.10, 159.13, 191.86.
MS: m/z: 351 [M]+. Found, %: C 64.97; H 4.89; N 11.97.
C19H17N3O4 (351.36). Calculated, %: C 64.95; H 4.88;
N 11.96.
3-(2,5-Dimethoxyphenyl)-1,3-dihydro-4H-indeno-
[1,2-c]isoxazol-4-one (9a). Yield 77%, mp 244–246°C.
IR spectrum, ν, cm–1: 3425 (NH), 1715 (C=O). 1H NMR
spectrum, δ, ppm: 3.78 s, 3.90 s (6H, 2OCH3), 6.75 s
(1H, CH), 6.80–8.40 m (7H,Ar-H), 9.01 s (1H, NH, D2O
exchangeable). 13C NMR spectrum, δ, ppm: 55.48, 56.00,
78.68, 109.14, 112.00, 112.34, 114.14, 123.13, 126.42,
128.32, 129.00, 133.93, 135.13, 136.10, 148.86, 153.54,
154.80, 192.22. MS: m/z: 309 [M]+. Found, %: C 69.91;
H 4.90; N 4.52. C18H15NO4 (309.32). Calculated, %: C
69.89; H 4.89; N 4.53.
3-(3-Methoxyphenyl)-4-oxoindeno[1,2-c]pyrazole-
2(1H,3H,4H)-carboxamide (8b). Yield 88%, mp 280–
283°C. IR spectrum, ν, cm–1: 3392 (NH), 3181 (NH2),
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1710 (C=O), 1643 (C=O). H NMR spectrum, δ, ppm:
3.36 s (3H, OCH3), 3.82 s (1H, CH), 6.62 s (2H, NH2, D2O
exchangeable), 7.55–8.13 m (8H,Ar-H), 9.67 s (1H, NH,
D2O exchangeable). 13C NMR spectrum, δ, ppm: 55.30,
65.62, 106.30, 111.56, 112.32, 119.25, 123.02, 126.40,
128.16, 129.80, 133.90, 135.12, 136.18, 144.10, 155.12,
159.00, 160.18, 191.80. MS: m/z: 321 [M]+. Found,
%: C 67.29; H 71.01; N 13.10. C18H15N3O3 (321.33).
Calculated, %: C 67.28; H 71.00; N 13.08.
3-(3-Methoxyphenyl)-1,3-dihydro-4H-indeno-
[1,2-c]isoxazol-4-one (9b). Yield 78%, mp 263–264°C.
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IR spectrum, ν, cm–1: 3407 (NH), 1720 (C=O). H
NMR spectrum, δ, ppm: 3.78 s (3H, OCH3), 6.99 s (1H,
CH), 7.01–8.69 m (8H, Ar-H), 12.77 s (1H, NH, D2O
exchangeable). 13C NMR spectrum, δ, ppm: 55.45, 84.68,
109.14, 111.00, 113.14, 119.42, 123.10, 126.40, 128.30,
129.54, 133.90, 135.10, 136.16, 142.25, 154.86, 160.34,
192.24. MS: m/z: 279 [M]+. Found, %: C 73.13; H 4.70;
N 5.03. C17H13NO3 (279.29). Calculated, %: C 73.11; H
4.69; N 5.02.
3-(4-Chloro-3-nitrophenyl)-4-oxoindeno[1,2-c]-
pyrazole-2(1H,3H,4H)carboxamide (8c). Yield 94%,
mp 184–186°C. IR spectrum, ν, cm–1: 3461 (NH), 3168
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(NH2), 1710 (C=O), 1681 (C=O). H NMR spectrum,
δ, ppm: 4.36 s (1H, CH), 6.67 s (2H, NH2, D2O
exchangeable), 7.58–8.52 m (7H, Ar-H), 10.52 s (1H,
NH, D2O exchangeable). 13C NMR spectrum, δ, ppm:
65.10, 106.32, 123.08, 124.56, 125.32, 126.40, 128.16,
132.12, 132.80, 133.90, 135.14, 136.10, 142.10, 147.18,
155.15, 159.00, 191.84. MS: m/z: 370 [M]+. Found, %: C
55.06; H 3.00; Cl 9.58; N 15.13. C17H11ClN4O4 (370.75).
Calculated, %: C 55.07; H 2.99; Cl 9.56; N 15.11.
3-(5-Methylfuran-2-yl)-1,3-dihydro-4H-indeno-
[1,2-c]isoxazol-4-one (9c). Yield 81%, mp 112–114°C.
1
IR spectrum, ν, cm–1: 3259 (NH), 1685 (C=O). H
NMR spectrum, δ, ppm: 2.36 s (3H, CH3), 6.50 s (1H,
CH), 7.37–8.61 m (6H, Ar-H), 12.49 s (1H, NH, D2O
exchangeable). 13C NMR spectrum, δ, ppm: 13.60, 83.98,
106.22, 109.33, 109.52, 123.17, 126.45, 128.42, 133.96,
135.18, 136.18, 152.24, 152.34, 154.80, 192.15. MS: m/z:
253 [M]+. Found, %: C 71.13; H 4.40; N 5.54. C15H11NO3
(253.25). Calculated, %: C 71.14; H 4.38; N 5.53.
3-(2,5-Dimethoxyphenyl)-4-oxoindeno[1,2-c]-
pyrazole-2(1H,3H,4H)-carbothioamide (8d). Yield
77%, mp 181–183°C. IR spectrum, ν, cm–1: 3433 (NH),
3316 (NH2), 1716 (C=O), 1684 (C=O). 1H NMR spectrum,
δ, ppm: 3.51 s (1H, CH), 3.78 s, 3.76 s (6H, 2OCH3),
6.94 s (2H, NH2, D2O exchangeable), 7.01–8.34 m
Synthesis of compounds 10a, 10b. A mixture of a
compound 3a or 3b (1 mmol) with ethyl cyanoacetate
(1 mmol) and anhydrous ammonium acetate (2 g)
in absolute ethanol (40 mL) was refluxed for 2 h.
Thus formed precipitate was filtered off, dried and
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(7H, Ar-H), 11.41 s (1H, NH, D2O exchangeable). C
NMR spectrum, δ, ppm: 55.46, 56.08, 65.24, 106.32,
111.34, 112.50, 113.08, 122.16, 123.10, 126.30, 128.22,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 4 2020