Month 2019
Novel Furochromone Derivatives: Synthesis and Anticancer Activity Studies
1
(%): 64.1, mp: 340–341°C. Spectroscopic analysis: H-
NMR (DMSO-d6, 400 MHz, δ ppm): 4.1 (s, 3H, 8-OCH3),
4.3 (s, 3H, 5-OCH3), 5.0 (s, 2H, N–CH2), 6.5 (s, 1H, 3-H),
146.9 (C), 145.7 (C), 133.7 (C), 129.3 (C), 121.1 (C),
119.1 (C), 116.2 (C), 113.3 (C), 105.3 (CH), 61.7 (O–
CH3), 61.3 (O–CH3); MS (ESI+) m/z (rel. intensity):
389.40 (M + H, 100%); Anal. Calcd for C17H11NO6S2 C:
52.43, H: 2.85, N: 3.60, S: 16.47%; found: C: 52.04, H:
7.1 (d, 1H, j3 2 = 2.3 Hz, 30-H), 7.5 (s, 1H, ¼CH), 7.6 (d,
0
0
2H, ja,b = ja ,b = 8.7 Hz, a,a0-H), 7.7 (d, 1H, j2 3 = 2.3 Hz,
0
0
0 0
20-H), 8.3 (d, 2H, jb,a = jb ,a = 8.7 Hz, b,b -H) [21].
3-[2-(4-Chloro-phenyl)-2-oxo-ethyl]-5-(5,8-dimethoxy-40,50-
furo-6,7-chromone-2-ylmethylenyl)-thiazolidine-2,4-dione
(K5). Yield (%): 34.5, mp: 269–271°C. Spectroscopic
0
0
0
2.87, N: 3.73, S: 15.98%.
Ethyl 2-(5-((4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-7-
yl)methylene)-2,4-dioxothiazolidin-3-yl)acetate (K10). Yield
1
(%): 31.8, mp: 243°C. Spectroscopic analysis: H-NMR
analysis: 1H-NMR (DMSO-d6, 400 MHz, δ ppm): 4.0
(s, 3H, 8-OCH3), 4.2 (s, 3H, 5-OCH3), 5.1 (s, 2H, N–
(CDCl3, 400 MHz, δ ppm): 1.31 (t, 3H, CH3), 4.08 (s,
3H, OCH3), 4.26 (q, 2H, CH2O), 4.29 (s, 3H, OCH3),
4.50 (s, 2H, N–CH2), 6.45 (s, 1H, 3-H), 7.06 (d, 1H,
CH2), 6.4 (s, 1H, 3-H), 7.0 (d, 1H, j3 2 = 2.3 Hz, 30-
0
0
H), 7.4 (d, 2H, ja,b = ja ,b = 8.5 Hz, a,a0-H), 7.5 (s,
j3 2 = 2.4 Hz, 30-H), 7.52 (s, 1H, ¼CH), 7.69 (d, 1H,
0
0
0 0
j2 3 = 2.4 Hz, 20-H); 13C-NMR (CDCl3, 100 MHz, δ
ppm): 177.7 (CO), 168.3 (CO), 166.1 (CO), 164.8 (CO),
156.4 (C), 149.4 (C), 147.6 (C), 146.2 (C), 146.1 (C),
130.5 (C), 129.9 (C), 124.4 (C), 120.4 (C), 116.6 (C),
114.2 (C), 105.5 (CH), 62.6 (O–CH3), 62.5 (O–CH3),
61.7 (O–CH2), 42.4 (N–CH2), 14.3 (CH3); MS (ESI+) m/
z (rel. intensity): 460.1 (M + H, 100%); Anal. Calcd for
C21H17NO9S C: 54.90, H: 3.73, N: 3.05, S: 6.98%;
1H, ¼CH), 7.6 (d, 1H, j2 3 = 2.3 Hz, 20-H), 7.9 (d,
0
0
0
0
2H, jb,a = jb ,a = 8.5 Hz, b,b0-H) [21].
0
0
3-[2-(4-Nitro-phenyl)-2-oxo-ethyl]-5-(5,8-dimethoxy-40,50-
furo-6,7-chromone-2-ylmethylenyl)thiazolidine-2,4-dione
(K6).
Yield (%): 71.7, mp: 344–345°C. Spectroscopic
1
analysis: H-NMR (DMSO-d6, 400 MHz, δ ppm): 4.0 (s,
3H, 8-OCH3), 4.2 (s, 3H, 5-OCH3), 5.2 (s, 2H, N–CH2),
6.4 (s, 1H, 3-H), 7.0 (d, 1H, j3 2 = 2.2 Hz, 30-H), 7.5 (s,
0
0
1H, ¼CH), 7.6 (d, 1H, j2 3 = 2.3 Hz, 20-H), 8.1 (d, 2H, ja,
0
0
found: C: 55.15, H: 3.88, N: 3.17, S: 6.95%.
b = jb ,a = 8.8 Hz, a,a0-H), 8.3 (d, 2H, jb,a = jb ,a = 8.8 Hz,
0
0
0
0
Ethyl 2-(5-((4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-7-
yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetate (K11).
b,b0-H) [21].
1
3-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-5-(5,8-dimethoxy-
40,50-furo-6,7-chromone-2-ylmethylenyl)-thiazolidine-2,4-dione
(K7). Yield (%): 47.0, mp: 242–243°C. Spectroscopic
Yield (%): 60.6, mp: 235°C. Spectroscopic analysis: H-
NMR (CDCl3, 400 MHz, δ ppm): 1.30 (t, 3H, CH3), 4.08
(s, 3H, OCH3), 4.25 (q, 2H, CH2O), 4.33 (s, 3H, OCH3),
4.87 (s, 2H, N–CH2), 6.48 (s, 1H, 3-H), 7.06 (d, 1H,
analysis: 1H-NMR (DMSO-d6, 400 MHz, δ ppm): 3.9
(s, 3H, Ph-OCH3), 4.1 (s, 3H, 8-OCH3), 4.3 (s, 3H,
5-OCH3), 5.2 (s, 2H, N–CH2), 6.5 (s, 1H, 3-H), 7.0 (d,
j3 2 = 2.0 Hz, 30-H), 7.35 (s, 1H, ¼CH), 7.69 (d, 1H,
0
0
j2 3 = 2.0 Hz, 20-H); 13C-NMR (CDCl3, 100 MHz, δ
ppm): 194.5 (CS), 177.8 (CO), 166.6 (CO), 165.8 (CO),
156.5 (C), 149.5 (C), 147.6 (C), 146.3 (C), 146.2 (C),
131.8 (C), 130.5 (C), 122.7 (C), 120.4 (C), 116.8 (C),
114.2 (C), 105.5 (CH), 62.7 (O–CH3), 62.4 (O–CH3),
61.7 (O–CH2), 45.0 (N–CH2), 14.3 (CH3); MS (ESI+) m/
z (rel. intensity): 476.1 (M + H, 100%); Anal. Calcd for
C21H17NO8S2 C: 53.04, H: 3.61, N: 2.95, S: 13.46%;
0
0
2H, jb,a = jb ,a = 8.9 Hz, b,b0-H), 7.1 (d, 1H, j3 2 = 2.3 Hz,
0
0
0 0
30-H), 7.6 (s, 1H, ¼CH), 7.7 (d, 1H, j2 3 = 2.3 Hz, 20-H),
0
0
8.0 (d, 2H, ja,b = ja ,b = 8.9 Hz, a,a0-H) [21].
0
0
5-((4,9-Dimethoxy-5-oxo-5H-furo[3,2-g]chromen-7-yl)
methylene)thiazolidine-2,4-dione (K8).
Yield (%): 46.5,
1
mp: 297°C. Spectroscopic analysis: H-NMR (DMSO-d6,
400 MHz, δ ppm): 3.96 (s, 3H, 8-OCH3), 4.15 (s, 3H,
5-OCH3), 6.75 (s, 1H, 3-H), 7.29 (d, 1H, 30-H), 7.59 (s,
1H, ¼CH), 8.17 (d, 1H, 20-H), 12.81 (s, 1H, NH);
13C-NMR (DMSO-d6, 100 MHz, δ ppm): 176.5 (CO),
169.1 (CO), 166.8 (CO), 156.5 (C), 148.9 (C), 147.3 (C),
146.9 (C), 145.8 (C), 131.9 (C), 129.4 (C), 122.1 (C),
119.2 (C), 115.7 (C), 113.4 (C) 105.3 (CH), 61.8
(O–CH3), 61.4 (O–CH3); MS (ESI+) m/z (rel. intensity):
374.0 (M + H, 100%); Anal. Calcd for C17H11NO7S C:
54.69, H: 2.97, N: 3.75, S: 8.59%; found: C: 54.58, H:
found: C: 52.62, H: 3.52, N: 3.17, S: 13.43%.
2-(5-((4,9-Dimethoxy-5-oxo-5H-furo[3,2-g]chromen-7-yl)
methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (K12).
Yield (%): 50.3, decomp.p.: 320°C. Spectroscopic analysis:
1H-NMR (DMSO-d6, 400 MHz, δ ppm): 3.94 (s, 3H,
OCH3), 4.15 (s, 3H, OCH3), 4.56 (s, 2H, N–CH2), 6.81
(s, 1H, 3-H), 7.26 (d, 1H, j3 2 = 2.0 Hz, 30-H), 7.65 (s,
0
0
1H, ¼CH), 8.14 (d, 1H, j2 3 = 2.4 Hz, 20-H); 13C-NMR
(DMSO-d6, 100 MHz, δ ppm): 194.9 (CS), 176.5 (CO),
166.9 (CO), 165.9 (CO), 156.1 (C), 148.8 (C), 147.3 (C),
146.9 (C), 145.7 (C), 130.0 (C), 129.3 (C), 123.0 (C),
119.1 (C), 116.6 (C), 113.3 (C), 105.3 (CH), 61.7
(O–CH3), 61.4 (O–CH3), 45.9 (N–CH2); MS (ESI+) m/z
(rel. intensity): 448.0 (M + H, 100%); Anal. Calcd for
C19H13NO8S2-2H2O C: 47.20, H: 3.54, N: 2.90, S:
0
0
3.06, N: 3.85, S: 8.32%.
5-((4,9-Dimethoxy-5-oxo-5H-furo[3,2-g]chromen-7-yl)
methylene)-2-thioxothiazolidin-4-one (K9). Yield (%): 52.8,
mp: 323°C. Spectroscopic analysis: H-NMR (DMSO-d6,
1
400 MHz, δ ppm): 3.96 (s, 3H, OCH3), 4.17 (s, 3H,
OCH3), 6.79 (s, 1H, 3-H), 7.30 (d, 1H, j3 2 = 2.4 Hz, 30-
0
0
H), 7.45 (s, 1H, ¼CH), 8.17 (d, 1H, j2 3 = 2.4 Hz, 20-H);
13C-NMR (DMSO-d6, 100 MHz, δ ppm): 197.6 (CS),
176.4 (CO), 168.9 (CO), 156.2 (C), 148.8 (C), 147.3 (C),
0
0
13.23%; found: C: 47.19, H: 3.34, N: 3.19, S: 12.84%.
2-(5-((4,9-Dimethoxy-5-oxo-5H-furo[3,2-g]chromen-7-yl)
methylene)-2,4-dioxothiazolidin-3-yl)acetic acid (K13).
A
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet