1190
Vol. 62, No. 12
4.50 (t, 2H, J=4.8Hz, OCH2), 2.39 (m, 2H, OCH2CH2); ESI-
(E)-4-(3-(4-(3-(Hydroxyamino)-3-oxoprop-1-en-1-yl)-
HR-MS (m/z): [M+H]+ Calcd for C21H20N3O9S: 490.0920; benzamido)propoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole
Found: 490.0915; Anal. Calcd for C21H19N3O9S: C, 51.53; H, 2-Oxide (12g) The title compound was obtained starting
3.91; N, 8.59; Found: C, 51.38; H, 4.02; N, 8.46.
from 10 and 6g. Pale yellow waxy solid, yield: 58%. Analyti-
(E)-4-(4-((4-(3-(Hydroxyamino)-3-oxoprop-1-en-1-yl)- cal data for 12g: IR (KBr, cm−1): 3425, 2946, 1718, 1617, 1431,
benzoyl)oxy)butoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 1234, 1165; MS (ESI) m/z=489 [M+H]+; H-NMR (DMSO-d6,
1
2-Oxide (12c) The title compound was obtained start- 300MHz, δ ppm): 10.33 (br, 1H), 8.52 (br, 1H), 8.02 (d, 2H,
ing from 10 and 6c. Pale yellow waxy solid, yield: 56%. J=7.8Hz, Ar-H), 7.83 (d, J=7.8Hz, 2H, Ar-H), 7.73 (m, 1H,
Analytical data for 12c: IR (KBr, cm−1): 3452, 2965, 1716, Ar-H), 7.58–7.66 (m, 4H, Ar-H), 7.46 (d, J=16.2Hz, 1H, CH=),
1611, 1444, 1242, 1168, 1052; MS (ESI) m/z=504 [M+H]+; 6.52 (d, J=16.2Hz, 1H, CH=), 4.59 (t, 2H, J=4.8Hz, OCH2),
1H-NMR (DMSO-d6, 300MHz, δ ppm): 8.47 (br, 1H), 8.02 3.55 (t, 2H, J=4.8Hz, NCH2), 2.32 (m, 2H, OCH2CH2); ESI-
(d, 2H, J=7.8Hz, Ar-H), 7.79 (d, J=7.8Hz, 2H, Ar-H), 7.71 HR-MS (m/z): [M+H]+ Calcd for C21H21N4O8S: 489.1080;
(m, 1H, Ar-H), 7.53–7.66 (m, 4H, Ar-H), 7.44 (d, J=16.2Hz, Found: 489.1077; Anal. Calcd for C21H20N4O8S: C, 51.64; H,
1H, CH=), 6.51 (d, J=16.2Hz, 1H, CH=), 4.63 (t, 2H, 4.13; N, 11.47; Found: C, 51.83; H, 3.98; N, 11.23.
J=4.8Hz, OCH2), 4.53 (t, 2H, J=4.8Hz, OCH2), 2.26–2.33
(E)-4-(4-(4-(3-(Hydroxyamino)-3-oxoprop-1-en-1-yl)-
(m, 2H, OCH2CH2CH2); ESI-HR-MS (m/z): [M+H]+ Calcd benzamido)butoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole
for C22H22N3O9S: 504.1077; Found: 504.1084; Anal. Calcd for 2-Oxide (12h) The title compound was obtained starting
C22H21N3O9S: C, 52.48; H, 4.20; N, 8.35; Found: C, 52.33; H, from 10 and 6h. Pale yellow waxy solid, yield: 52%. Ana-
4.38; N, 8.17.
lytical data for 12h: IR (KBr, cm−1): 3429, 2944, 1724, 1620,
(E)-4-((4-((4-(3-(Hydroxyamino)-3-oxoprop-1-en-1-yl)- 1441, 1220, 1032; MS (ESI) m/z=503 [M+H]+; 1H-NMR
benzoyl)oxy)but-2-yn-1-yl)oxy)-3-(phenylsulfonyl)-1,2,5- (DMSO-d6, 300MHz, δ ppm): 10.26 (br, 1H), 8.48 (br,
oxadiazole 2-Oxide (12d) The title compound was obtained 1H), 8.06 (d, 2H, J=7.8Hz, Ar-H), 7.87 (d, J=7.8Hz, 2H,
starting from 10 and 6d. Pale yellow waxy solid, yield: 53%. Ar-H), 7.77 (m, 1H, Ar-H), 7.56–7.64 (m, 4H, Ar-H), 7.48
Analytical data for 12d: IR (KBr, cm−1): 3420, 2931, 1710, (d, J=16.2Hz, 1H, CH=), 6.56 (d, J=16.2Hz, 1H, CH=),
1
1615, 1450, 1170, 1020; MS (ESI) m/z=500 [M+H]+; H-NMR 4.60 (t, 2H, J=4.8Hz, OCH2), 3.57 (t, 2H, J=4.8Hz, NCH2),
(DMSO-d6, 300MHz, δ ppm): 8.55 (br, 1H), 8.08 (d, 2H, 2.06–2.11 (m, 2H, OCH2CH2CH2); ESI-HR-MS (m/z): [M+H]+
J=7.8Hz, Ar-H), 7.83 (d, J=7.8Hz, 2H, Ar-H), 7.75 (m, 1H, Calcd for C22H23N4O8S: 503.1237; Found: 503.1241; Anal.
Ar-H), 7.55–7.67 (m, 4H, Ar-H), 7.51 (d, J=16.2Hz, 1H, CH=), Calcd for C22H22N4O8S: C, 52.58; H, 4.41; N, 11.15; Found: C,
6.57 (d, J=16.2Hz, 1H, CH=), 5.11 (s, 2H, OCH2), 5.03 (s, 2H, 52.43; H, 6.59; N, 11.06.
OCH2); ESI-HR-MS (m/z): [M+H]+ Calcd for C22H18N3O9S:
(E)-4-((1-(4-(3-(Hydroxyamino)-3-oxoprop-1-en-1-yl)-
500.0764; Found: 500.0758; Anal. Calcd for C22H17N3O9S: C, benzamido)propan-2-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxa-
52.91; H, 3.43; N, 8.41; Found: C, 53.12; H, 3.37; N, 8.55. diazole 2-Oxide (12i) The title compound was obtained
(E)-4-((4-((4-(3-(Hydroxyamino)-3-oxoprop-1-en-1-yl)- starting from 10 and 6i. Pale yellow waxy solid, yield:
benzoyl)oxy)butan-2-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxa- 55%. Analytical data for 12i: IR (KBr, cm−1): 3414, 2928,
diazole 2-Oxide (12e) The title compound was obtained 1717, 1615, 1425, 1235, 1052; MS (ESI) m/z=489 [M+H]+;
starting from 10 and 6e. Pale yellow waxy solid, yield: 1H-NMR (DMSO-d6, 300MHz, δ ppm): 10.31 (br, 1H), 8.45
61%. Analytical data for 12e: IR (KBr, cm−1): 3432, 2939, (br, 1H), 8.03 (d, 2H, J=7.8Hz, Ar-H), 7.81 (d, J=7.8Hz, 2H,
1728, 1622, 1458, 1210, 1021; MS (ESI) m/z=504 [M+H]+; Ar-H), 7.75 (m, 1H, Ar-H), 7.54–7.63 (m, 4H, Ar-H), 7.48 (d,
1H-NMR (DMSO-d6, 300MHz, δ ppm): 10.28 (br, 1H), 8.49 J=16.2Hz, 1H, CH=), 6.54 (d, J=16.2Hz, 1H, CH=), 4.53
(br, 1H), 8.06 (d, 2H, J=7.8Hz, Ar-H), 7.88 (d, J=7.8Hz, 2H, (m, 1H, OCH), 3.88 (m, 2H, NCH2), 1.48 (d, 3H, J=6.3Hz,
Ar-H), 7.76 (m, 1H, Ar-H), 7.56–7.68 (m, 4H, Ar-H), 7.50 (d, CHCH3); ESI-HR-MS (m/z): [M+H]+ Calcd for C21H21N4O8S:
J=16.2Hz, 1H, CH=), 6.56 (d, J=16.2Hz, 1H, CH=), 4.56 489.1080; Found: 489.1086; Anal. Calcd for C21H20N4O8S: C,
(t, 2H, J=4.8Hz, OCH2), 4.35 (m, 2H, OCH), 2.25–2.30 (m, 51.64; H, 4.13; N, 11.47; Found: C, 51.39; H, 4.31; N, 11.62.
2H, OCHCH2), 1.45 (d, 3H, J=6.3Hz, CHCH3); Anal. Calcd
(E)-4-(2-(4-(3-(Hydroxyamino)-3-oxoprop-1-en-1-yl)-N-
for C22H22N3O9S: 504.1077; Found: 504.1072; Anal. Calcd for methylbenzamido)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadi-
C22H21N3O9S: C, 52.48; H, 4.20; N, 8.35; Found: C, 52.61; H, azole 2-Oxide (12j) The title compound was obtained
4.33; N, 8.27.
starting from 10 and 6j. Pale yellow waxy solid, yield:
(E)-4-(2-(4-(3-(Hydroxyamino)-3-oxoprop-1-en-1-yl)- 60%. Analytical data for 12j: IR (KBr, cm−1): 3426, 2935,
benzamido)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 1719, 1626, 1440, 1243, 1162; MS (ESI) m/z=489 [M+H]+;
2-Oxide (12f) The title compound was obtained starting 1H-NMR (DMSO-d6, 300MHz, δ ppm): 10.23 (br, 1H), 8.38
from 10 and 6f. Pale yellow waxy solid, yield: 61%. Analyti- (br, 1H), 8.07 (d, 2H, J=7.8Hz, Ar-H), 7.87 (d, J=7.8Hz,
cal data for 12f: IR (KBr, cm−1): 3436, 2945, 1621, 1453, 1211, 2H, Ar-H), 7.78 (m, 1H, Ar-H), 7.57–7.66 (m, 4H, Ar-H),
1
1166, 1018; MS (ESI) m/z=477 [M+H]+; H-NMR (DMSO- 7.50 (d, J=16.2Hz, 1H, CH=), 6.57 (d, J=16.2Hz, 1H, CH=),
d6, 300MHz, δ ppm): 10.21 (br, 1H), 8.65 (br, 1H), 8.04 (d, 4.68 (t, 2H, J=4.8Hz, OCH2), 3.53 (t, 2H, J=4.8Hz, NCH2),
2H, J=7.8Hz, Ar-H), 7.85 (d, J=7.8Hz, 2H, Ar-H), 7.70 (m, 3.04 (s, 3H, NCH3); ESI-HR-MS (m/z): [M+H]+ Calcd for
1H, Ar-H), 7.63 (d, J=7.8Hz, 2H, Ar-H), 7.55 (m, 2H, Ar-H), C21H21N4O8S: 489.1080; Found: 489.1075; Anal. Calcd for
7.49 (d, J=16.2Hz, 1H, CH=), 6.55 (d, J=16.2Hz, 1H, CH=), C21H20N4O8S: C, 51.64; H, 4.13; N, 11.47; Found: C, 51.77; H,
4.60 (t, 2H, J=4.8Hz, OCH2), 3.92 (t, 2H, J=4.8Hz, NCH2); 4.22; N, 11.58.
ESI-HR-MS (m/z): [M+H]+ Calcd for C20H19N4O8S: 475.0924;
Cell Culture SW620, HCT116, Lovo (human colon car-
Found: 475.0919; Anal. Calcd for C20H18N4O8S: C, 50.63; H, cinoma cells), MCF-7 (human breast adenocarcinoma cells),
3.82; N, 11.81; Found: C, 50.45; H, 4.01; N, 11.64. and Hela cells were maintained in 10% fetal bovine serum