S. Khelili et al. / European Journal of Medicinal Chemistry 54 (2012) 873e878
877
(125 MHz, d6-DMSO)
119.18, 121.48, 122.59, 124.38, 124.41, 129.61, 131.24, 134.26, 137.27,
146.41, 152.76, 159.00. Anal. (C20H20N3O4S) C, H, N, S.
d
: 23.89, 29.32, 37.11, 42.73, 75.77, 111.19,
of a 1 mg/mL oily solution of diethylstilboestrol dipropionate
(Sigma)]. The rats were anesthetized and then sacrified. The two
uterine horns were removed, cleared of adhering fat and connec-
tive tissue, and separated. Each horn was superfused with a Tyrode
solution (in mM: NaCl 137, KCl 2.7, CaCl2 1.8, MgCl2 1.1, NaH2PO4 0.4,
NaHCO3 11.9, glucose 5.6) bubbled continuously with a mixture of
O2 (95%) and CO2 (5%). The superfusate was maintained at 37 ꢁC.
4.1.5. N-(2,2-Dimethyl-6-nitro-3,4-dihydro-2H-1-benzopyran-4-
yl)-4H-1,2,4-benzothiadiazine-3-carboxamide 1,1-dioxide (7e)
White powder (90%); mp 272e273 ꢁC; 1H NMR (500 MHz, d6-
DMSO)
d
: 1.35 (3H, s, CH3), 1.47 (3H, s, CH3), 2.17 (2H, m, CH2), 5.30
Injections of 20 mU oxytocin (200 mL of a 0.1 U/mL solution of the
(1H, m, CH), 6.99 (d, 1H, 8-H), 7.54 (1H, t, 70-H), 7.74 (t, 1H, 60-H),
hormone in 0.9% NaCl) in the superfusion channel were repeated at
10-min intervals until the recorded contractions (AUC) were
constant. The mean of the three last injections gave the 100% of the
contractile response to oxytocin. For each drug concentration
added in the medium, injection of 20 mU oxytocin was repeated at
least three times. The contractile responses recorded (mean of
three AUC) were expressed as a percent of the reference value
(contractile response to oxytocin in the absence of drug) [22].
7.87 (2H, m, 50-H þ 80-H), 8.07 (2H, m, 7-H þ 5-H), 9.69 (1H, d,
CONH), 12.73 (1H, bs, NH); 13C NMR (125 MHz, d6-DMSO)
d: 24.16,
29.11, 36.76, 42.62, 77.78, 117.97, 119.28, 121.60, 122.92, 123.34,
123.70, 124.54, 127.33, 133.37, 134.70, 140.34, 146.65, 159.28. Anal.
(C19H18N4O6S) C, H, N, S.
4.1.6. 7-Chloro-N-(2,2-dimethyl-6-nitro-3,4-dihydro-2H-1-
benzopyran-4-yl)-4H-1,2,4-benzothiadiazine-3-carboxamide 1,1-
dioxide (7f)
Acknowledgements
White powder (95%); mp 284e287 ꢁC; 1H NMR (d6-DMSO)
d:
1.35 (3H, s, CH3),1.50 (3H, s, CH3), 2.20 (2H, m, CH), 5.30 (1H, m, CH),
7.35 (1H, m, CHarom), 7.75 (2H, m, CHarom), 7.80 (1H, s, CHarom), 8.10
(2H, m, CHarom), 9.65 (1H, s, CONH). Anal. (C19H17ClN4O6S) C, H, N, S.
This study was supported by grants from the National Fund for
Scientific Research (F.N.R.S., Belgium) from which P. Lebrun is
a Research Director. The authors gratefully acknowledge the tech-
nical assistance of Y. Abrassart, S. Counerotte, D. Dewalque, F.
Leleux, A.-M. Vanbellinghen and A. Van Praet.
4.1.7. N-(2,2-Dimethyl-6-nitro-3,4-dihydro-2H-1-benzopyran-4-yl)-
7-methyl-4H-1,2,4-benzothiadiazine-3-carboxamide 1,1-dioxide (7g)
White powder (90%); mp 310e312 ꢁC; 1H NMR (500 MHz, d6-
Appendix A. Supplementary data
DMSO)d: 1.35 (3H, s, CH3),1.47 (3H, s, CH3), 2.15 (2H, m, CH2), 5.12 (1H,
m, CH), 6.83 (1H, d, 8-H), 7.40 (1H, d, 50-H), 7.51 (1H, s, 80-H), 7.58 (1H,
Supplementary data related to this article can be found online at
d, 60-H), 7.90 (2H, m, 5-H þ 7-H), 9.49 (1H, d, CONH), 12.51 (1H, bs,
NH);13C NMR (125MHz,d6-DMSO)
d: 20.53, 24.16, 29.12, 36.74, 42.70,
77.79, 117.97, 119.17, 121.48, 122.61, 122.94, 123.69, 124.54, 132.29,
134.33, 137.39, 140.33, 146.28, 159.28. Anal. (C19H18N4O6S) C, H, N, S.
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