Journal of Medicinal Chemistry
BRIEF ARTICLE
5-(3-Bromo-4-(2-cyclohexylethoxy)benzylidene)thiazoli-
dine-2,4-dione (4). 4 was obtained by recrystallization from hexane/
ethyl acetate as a yellow solid (1.08 g, 82% yield). 1H NMR (300 MHz,
DMSO-d6) δ 12.57 (s, 1H), 7.84 (s, 1H), 7.83 (s, 1H), 7.57 (d, J = 10.8
Hz, 1H), 7.28 (d, J = 10.8 Hz, 1H), 4.17 (t, J = 12.6 Hz, 2H), 1.61ꢀ1.75
(m, 7H), 1.46ꢀ1.52 (m, 1H), 1.06ꢀ1.26 (m, 3H), 0.89ꢀ0.96 (m, 2H).
MS (ESI): m/z 410 [M ꢀ H]ꢀ.
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5-(3-Chloro-4-(cyclohexyloxy)benzylidene)thiazolidine-2,
4-dione (5). 5 was obtained by recrystallization from hexane/ethyl
1
acetate as a yellow solid (1.30 g, 88% yield). H NMR (300 MHz,
DMSO-d6) δ 12.58 (s, 1H), 7.72 (s, 1H), 7.69 (s, 1H), 7.51 (d, J = 13.2
Hz, 1H), 7.37 (d, J = 13.2 Hz, 1H), 4.56ꢀ4.61 (m, 1H), 2.02ꢀ2.49
(m, 2H), 1.69ꢀ1.86 (m, 2H), 1.50ꢀ1.53 (m, 2H), 1.35ꢀ1.45 (m, 4H).
MS (ESI): m/z 336 [M ꢀ H]ꢀ.
5-(3-Chloro-4-(cyclohexylmethoxy)benzylidene)thiazoli-
dine-2,4-dione (6). 6 was obtained by recrystallization from hexane/
ethyl acetate as a yellow solid (1.30 g, 88% yield). 1H NMR (300 MHz,
DMSO-d6) δ 12.58 (s, 1H), 7.72 (s, 1H), 7.69 (s, 1H), 7.52 (d, J = 8.7
Hz, 1H), 7.30 (d, J = 8.7 Hz, 1H), 3.94 (d, J = 6.0 Hz, 2H), 1.62ꢀ1.82
(m, 6H), 1.03ꢀ1.26 (m, 5H). MS (ESI): m/z 350 [M ꢀ H]ꢀ.
5-(3-Chloro-4-(cyclohexylpropoxy)benzylidene)thiazoli-
dine-2,4-dione (7). 7 was obtained by recrystallization from hexane/
ethyl acetate as a yellow solid (1.29 g, 88% yield). 1H NMR (300 MHz,
DMSO-d6) δ 12.58 (s, 1H), 7.71 (s, 1H), 7.69 (s, 1H), 7.53 (d, J = 8.4 Hz,
1H), 7.30 (d, J = 8.4 Hz, 1H), 4.12 (t, J= 12.6 Hz, 2H), 1.62ꢀ1.77 (m, 7H),
1.07ꢀ1.34 (m, 6H), 0.83ꢀ0.91 (m, 2H). MS (ESI): m/z 378 [M ꢀ H]ꢀ.
5-(3-Chloro-4-(cyclohexylbutoxy)benzylidene)thiazoli-
dine-2,4-dione (8). 8 was obtained by recrystallization from hexane/
ethyl acetate as a yellow solid (1.28 g, 87% yield). 1H NMR (300 MHz,
DMSO-d6) δ 12.58 (s, 1H), 7.73 (s, 1H), 7.69 (s, 1H), 7.53 (d, J = 9.0
Hz, 1H), 7.30 (d, J = 9.0 Hz, 1H), 4.14 (t, J = 12.3 Hz, 2H), 1.65ꢀ1.76
(m, 7H), 1.22ꢀ1.61 (m, 2H), 1.06ꢀ1.20 (m, 6H), 0.81ꢀ0.88 (m, 2H).
MS (ESI): m/z 392 [M ꢀ H]ꢀ.
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’ AUTHOR INFORMATION
Corresponding Author
*Phone: +82-62-230-7635. Fax: +82-62-232-2474. E-mail: hcho@
chosun.ac.kr.
’ ACKNOWLEDGMENT
(16) Martin, P. Wound healing—aiming for perfect skin regenera-
tion. Science 1997, 276, 75–81.
This work was supported by National Research Foundation of
Korea (NRF), funded by the Ministry of Education, Science and
Technology (MEST) through the Research Center for Resistant
Cells (R13-2003-009), Chosun University, Gwangju 501-759,
Republic of Korea.
(17) Werner, S.; Grose, R. Regulation of wound healing by growth
factors and cytokines. Physiol. Rev. 2003, 83, 835–870.
(18) Kolodsick, J. E.; Peters-Golden, M.; Larios, J.; Toews, G. B.;
Thannickal, V. J.; Moore, B. B. Prostaglandin E2 inhibits fibroblast to
myofibroblast transition via E. prostanoid receptor 2 signaling and cyclic
adenosine monophosphate elevation. Am. J. Respir. Cell Mol. Biol. 2003,
29, 537–544.
’ ABBREVIATIONS USED
PG, prostaglandin; 15-PGDH, 15-hydroxyprostaglandin dehy-
drogenase; PPARγ, peroxisome proliferator-activated receptor
γ; NAD+, nicotinamide adenine dinucleotide (oxidized form);
NADH, nicotinamide adenine dinucleotide (reduced form);
DTT, dithiothreitol; SDS, sodium dodecyl sulfate; EDTA, ethy-
lenediamine-N,N,N0,N0-tetraacetic acid; GST, glutathione S-
transferase; TLC, thin layer chromatography; THF, tetrahydro-
furan; DMSO, dimethylsulfoxide; DMF, N,N-dimethylforma-
mide; CBF, cochlear blood flow
’ REFERENCES
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