D. V. Jawale et al. / Bioorg. Med. Chem. Lett. 22 (2012) 436–439
439
3.13 (d, J = 8.10 Hz, 2H, CH2). DART-MS (ESI+, m/z): 364 (M+), 366
Acknowledgments
(M++2). 13C NMR (100 MHz, DMSO-d6, d ppm): 169.10, 168.79,
162.83, 138.13, 137.43, 130.09(2C), 129.01 (2C), 54.90, 39.47.
1-((2,4-dioxothiazolidin-5-yl)methyl)-3-(4’-fluoro benzene sulf-
ony)urea: (8d) Yield 76%, mp 169–170 °C, 1H NMR (300 MHz,
DMSO-d6, d ppm): 12.27 (br s, 1H, NH, D2O exchangeable, 2,4-
TZD’s), 10.33 (br s, 1H, NH, D2O exchangeable, sulfonylurea), 9.77
(br s, 1H, NH, D2O exchangeable, sulfonylurea), 7.60–7.9.77 (m,
4H, ArH), 3.42 (t, J = 6.60 Hz, J = 4.20 Hz,1H, methine proton, TZD-
5-H), 3.05 (d, J = 8.10 Hz, 2H, CH2). DART-MS (ESI+, m/z): 348
(M+). 13C NMR (100 MHz, DMSO-d6, d ppm): 169.17, 168.11,
167.61, 164.10, 135.39, 131.24, 130.75, 51.76, 39.29.
1-((2,4-dioxothiazolidin-5-yl) methyl)-3-(2’,4’-dichloro benzene
sulfonyl) urea (8e): Yield 75%, mp 158–159 °C, 1H NMR (300 MHz,
DMSO-d6, d ppm): 12.15 (br s, 1H, NH, D2O exchangeable, 2,4-
TZD’s), 10.19 (br s, 1H, NH, D2O exchangeable, sulfonylurea), 9.18
(br s, 1H, NH, D2O exchangeable, sulfonylurea), 7.23–7.8.15 (m,
3H, ArH), 3.47 (t, J = 6.60 Hz, J = 4.20 Hz, 1H, methine proton,
TZD-5-H), 2.95 (d, J = 8.10 Hz, 2H, CH2). DART-MS (ESI+, m/z): 398
(M+), 400(M++2), 402(M++4). 13C NMR (100 MHz, DMSO-d6, d
ppm): 169.07, 168.47, 162.73, 139.61, 138.57, 133.10, 131.05,
130.81, ‘128.13, 51.47, 39. 30.
1-((2,4-dioxothiazolidin-5-yl) methyl)-3-(2’,5’-dichloro benzene
sulfonyl) urea (8f): Yield 73%, mp 105–106 °C, 1H NMR (300 MHz,
DMSO-d6, d ppm): 12.07 (br s, 1H, NH, D2O exchangeable, 2,4-
TZD’s), 10.41 (br s, 1H, NH, D2O exchangeable, sulfonylurea), 9.27
(br s, 1H, NH, D2O exchangeable, sulfonylurea), 7.83–8.17 (m, 3H,
ArH), 3.45 (t, J = 6.60 Hz, J = 4.20 Hz, 1H, methine proton, TZD-5-
H), 2.98 (d, J = 8.10 Hz, 2H, CH2). DART MS (ESI+, m/z): 398 (M+),
400(M++2), 402(M++4). 13C NMR (100 MHz, DMSO-d6, d ppm):
169.15, 168.83, 163.13, 143.13, 134.15, 133.01, 129.14, 134.63,
134.15, 54.37, 39. 63.
1-((2,4-dioxothiazolidin-5-yl)methyl)-3-(2’,4’-dibromo benzene-
sulfonyl) urea (8g): Yield 75%, mp 165–166 °C, 1H NMR (300 MHz,
DMSO-d6, d ppm): 12.18 (br s, 1H, NH, D2O exchangeable, 2,4-
TZD’s), 10.23 (br s, 1H, NH, D2O exchangeable, sulfonylurea), 8.67
(br s, 1H, NH, D2O exchangeable, sulfonylurea), 7.95–8.17 (m, 3H,
ArH), 3.54 (t, J = 6.60 Hz, J = 4.20 Hz, 1H, methine proton, TZD-
5H), 3.18 (d, J = 8.10 Hz, 2H, CH2). DART MS (ESI+, m/z): 486 (M+).
13C NMR (100 MHz, DMSO-d6, d ppm): 169.21, 168.90, 162.58,
145.23, 138.41, 135.13, 133.61, 133.13, 55.10, 39. 73.
Authors are thankful to Professor D. B. Ingle for his invaluable
discussions and guidance. Authors are also very much grateful to
CDRI Lucknow for providing scanning and screening of newly syn-
thesized compounds. One of the authors, D.V. Jawale is also grate-
ful to U.G.C., New Delhi, India for Research Fellowship in Sciences
for meritorious students.
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