10
B. Romano et al. / Bioorg. Med. Chem. xxx (2015) xxx–xxx
544 (M+Å, 24), 470 (27), 272 (100), 198 (39), 172 (82), 57 (49).
Elemental Analysis for C22H28N2O4Se2ꢁHCl, Calcd/Found (%): C:
45.60/45.81; H: 5.00/4.68; N: 4.84/4.77.
mate in toluene as solvent and with DMAP as catalyst according
to the literature.44 Yellow solid; mp: 169–170 °C. Yield: 30%. IR
(KBr) cmꢀ1: 3344 (N–H), 2927 (C–H), 1717 (C@O), 817 (Se–Se).
1H NMR (400 MHz, CDCl3) d: 3.76 (s, 6H, 2OCH3); 6.96 (d, 4H,
B+B0, H3+H5, J3–2 = J5–6 = 7.3 Hz); 7.14 (d, 4H, B+B0, H2+H6, J2–3
=
4.1.2.4. Dihexyl (diselanediyldibenzene-4,1-diyl)biscarbamate
(2d). From hexyl chloroformate. Yellow solid; mp: 84 °C. Yield:
63%. IR (KBr) cmꢀ1: 3359 (N–H), 2954 (C–H), 1704 (C@O), 814
(Se–Se). 1H NMR (400 MHz, CDCl3) d: 0.86–0.87 (m, 6H, 2CH3);
J6–5 = 7.3 Hz); 7.47 (d, 4H, A+A0, H3+H5, J3–2 = J5–6 = 7.2 Hz); 7.56
(d, 4H, A+A0, H2+H6, J2–3 = J6–5 = 7.2 Hz); 10.34 (s, 2H, 2NH).
13C NMR (100 MHz, CDCl3) d: 56.3 (2C, 2CH3); 115.2 (4C, B+B0, C3,
C5); 119.9 (4C, A+A0, C3, C5); 123.7 (4C, B+B0, C2, C6); 124.2 (2C,
A+A0, C1); 134.3 (4C, A+A0, C2, C6); 140.1 (2C, A+A0, C4); 144.6 (2C,
B+B0, C1); 152.8 (2C, 2C@O); 157.6 (2C, B+B0, C4). MS (m/z% abun-
dance): 396 (53), 198 (98), 124 (99), 109 (100). Elemental
Analysis for C28H24N2O6Se2, Calcd/Found (%): C: 52.34/51.96; H:
3.74/3.95; N: 4.36/4.18.
1.25–1.28 (m, 8H, 2d+2
3.37 (m, 4H, 2bCH2); 4.05–4.07 (m, 4H, 2bCH2 + 2
4H, A+A0, H3+H5, J3–2 = J5–6 = 8.7 Hz); 7.50 (d, 4H, A+A0, H2+H6, J2–3
J6–5 = 8.7 Hz); 9.79 (s, 2H, 2NH). 13C NMR (100 MHz,CDCl3) d: 14.8
(2C, 2CH3); 22.9 (2C, 2 CH2); 25.9 (2C, 2dCH2); 31.8 (2C, 2 CH2);
33.6 (2C, 2bCH2); 61.6 (2C, 2
CH2); 119.7 (4C, A+A0, C3, C5);
e
CH2); 1.58–1.60 (m, 4H, 2
cCH2) 3.35–
a
CH2); 7.43 (d,
=
e
c
a
123.5 (2C, A+A0, C1); 134.3 (4C, A+A0, C2, C6); 140.6 (2C, A+A0, C4);
154.4 (2C, 2C@O). MS (m/z% abundance): 600 (M+Å, 16), 498 (36),
300 (78), 198 (66), 172 (78), 43 (100). Elemental Analysis for
4.1.2.9.
Bis(4-methylphenyl)
(diselanediyldibenzene-4,1-
diyl)biscarbamate hemihydrochloride (2i). From 4-methyl-
phenyl chloroformate. Yellow solid; mp: 174–175 °C. Yield: 12%.
IR (KBr) cmꢀ1: 3391 (N–H), 1726 (C@O), 819 (Se–Se). 1H NMR
(400 MHz, CDCl3) d: 2.31 (s, 6H, 2CH3); 7.10 (d, 4H, B+B0, H3+H5,
J3–2 = J5–6 = 8.4 Hz); 7.22 (d, 4H, B+B0, H2+H6, J2–3 = J6–5 = 8.4 Hz);
7.47 (d, 4H, A+A0, H3+H5, J3–2 = J5–6 = 8.4 Hz); 7.57 (d, 4H, A+A0,
H2+H6, J2–3 = J6–5 = 8.4 Hz); 10.35 (s, 2H, 2NH). 13C NMR
(100 MHz, CDCl3) d: 129.9 (4C, A+A0, C3, C5); 122.2 (4C, B+B0, C2,
C6); 124.3 (2C, A+A0, C1); 129.9 (4C, B+B0, C3, C5); 134.1 (4C, A+A0,
C2, C6); 135.2 (2C, B+B0, C4); 140.4 (2C, A+A0, C4); 147.9 (2C, B+B0,
C1); 154.2 (2C, 2C@O). MS (m/z% abundance): 396 (56), 198
(100), 107 (82). Elemental Analysis for C28H24N2O4Se2 (½) HCl,
Calcd/Found (%): C: 53.50/53.68; H: 4.14/4.45; N: 4.45/4.64.
C26H36N2O4Se2, Calcd/Found (%): C: 52.18/52.10; H: 6.06/5.85; N:
4.68/4.98.
4.1.2.5. Diisobutyl (diselanediyldibenzene-4,1-diyl)biscarba-
mate (2e). From isobutyl chloroformate. Yellow solid; mp:
110 °C. Yield: 32%. IR (KBr) cmꢀ1: 3360 (N–H), 2959 (C–H), 1705
(C@O), 816 (Se–Se). 1H NMR (400 MHz, CDCl3) d: 0.93 (d, 12H,
4CH3, JCH3–CH2 = 6.7 Hz); 1.90–1.93 (m, 2H, 2CH); 3.87 (d, 4H,
2CH2, JCH2–CH = 6.8 Hz); 7.43 (d, 4H, A+A0, H3+H5, J3–2 = J5–6
=
8.7 Hz); 7.51 (d, 4H, A+A0, H2+H6, J2–3 = J6–5 = 8.7 Hz); 9.80 (s, 2H,
2NH). 13C NMR (100 MHz,CDCl3) d: 19.8 (4C, 4CH3); 28.4 (2C,
2CH); 71.1 (2C, 2CH2); 119.7 (4C, A+A0, C3, C5); 123.6 (2C, A+A0,
C1); 134.3 (4C, A+A0, C2, C6); 140.6 (2C, A+A0, C4); 154.4 (2C,
2C@O). MS (m/z% abundance): 544 (M+Å, 21), 470 (28), 272 (62),
198 (41), 172 (87), 57 (100). Elemental Analysis for
4.1.2.10.
Bis(4-chlorophenyl)
(diselanediyldibenzene-4,1-
diyl)biscarbamate hydrochloride (2j). From 4-chlorophenyl
chloroformate. Yellow solid; mp: 165–166 °C. Yield: 2%. IR (KBr)
cmꢀ1: 3368 (N–H), 1724 (C@O), 819 (Se–Se). 1H NMR (400 MHz,
CDCl3) d: 7.28 (d, 4H, B+B0, H3+H5, J3–2 = J5–6 = 8.4 Hz); 7.47–7.49
(m, 8H, A+A0, H3+H5, B+B0, H2+H6); 7.58 (d, 4H, A+A0, H2+H6,
J2–3 = J6–5 = 8.4 Hz); 10.45 (s, 2H, 2NH). 13C NMR (100 MHz,
CDCl3) d: 120.2 (4C, A+A0, C3, C5); 124.2 (2C, A+A0, C1); 125.3 (4C,
B+B0, C2, C6); 130.3 (4C, B+B0, C3, C5); 130.9 (2C, B+B0, C4); 134.4
(4C, A+A0, C2, C6); 140.3 (2C, A+A0, C4); 150.1 (2C, B+B0, C1); 154.3
(2C, 2C@O). MS (m/z% abundance): 396 (55), 198 (100), 396 (55),
128 (80). Elemental Analysis for C26H18Cl2N2O4Se2ꢁHCl, Calcd/
Found (%): C: 45.38/45.22; H: 2.79/2.61; N: 4.30/4.07.
C
22H28N2O4Se2, Calcd/Found (%): C: 48.72/48.44; H: 5.20/4.94; N:
5.16/5.10.
4.1.2.6. Diallyl (diselanediyldibenzene-4,1-diyl)biscarbamate
(2f).
From allyl chloroformate. Yellow solid; mp: 108 °C.
Yield: 34%. IR (KBr) cmꢀ1: 3348 (N–H), 2924 (C–H), 1704 (C@O),
814 (Se–Se). 1H NMR (400 MHz, CDCl3) d: 4.61 (d, 4H, 2CH2,
JCH2–CH = 5.4 Hz); 5.30–5.33 (m, 4H, 2CH2@); 5.94–5.97 (m, 2H,
2CH); 7.43 (d, 4H, A+A0, H3+H5, J3–2 = J5–6 = 8.8 Hz); 7.52 (d, 4H,
A+A0, H2+H6, J2–3 = J6–5 = 8.8 Hz); 9.90 (s, 2H, 2NH). 13C NMR
(100 MHz, CDCl3) d: 65.7 (2C, 2CH2); 118.6 (2C, 2CH2@); 119.8
(4C, A+A0, C3, C5); 123.7 (2C, A+A0, C1); 134.1 (4C, A+A0, C2, C6);
134.3 (2C, 2CH); 140.4 (2C, A+A0, C4); 153.9 (2C, 2C@O). MS (m/
z% abundance): 512 (M+Å, 26), 256 (48), 213 (41), 172 (22), 156
(98), 92 (36), 41 (100). Elemental Analysis for C20H20N2O4Se2,
Calcd/Found (%): C: 47.07/46.57; H: 3.95/3.72; N: 5.49/5.50.
4.1.2.11.
Bis(4-fluorophenyl)
(diselanediyldibenzene-4,1-
diyl)biscarbamate (2k). From 4-fluorophenyl chloroformate.
Yellow solid; mp: 174–175 °C. Yield: 2%. IR (KBr) cmꢀ1: 3333 (N–
H), 1723 (C@O), 820 (Se–Se). 1H NMR (400 MHz, CDCl3) d: 7.25–
7.27 (m, 8H, B+B0, H2+H3+H5+H6); 7.47 (d, 4H, A+A0, H3+H5,
J3–2 = J5–6 = 8.4 Hz); 7.56 (d, 4H, A+A0, H2+H6, J2–3 = J6–5 = 8.4 Hz);
4.1.2.7. Diphenyl (diselanediyldibenzene-4,1-diyl)biscarbamate
(2g).
From phenyl chloroformate, prepared with phenol and
13
10.42 (s, 2H, 2NH). C NMR (100 MHz, CDCl3) d: 117.2 (4C, B+B0,
trichloromethylchloroformate in toluene as solvent and with
DMAP as catalyst according to the literature.44 Yellow solid; mp:
167 °C. Yield: 7%. IR (KBr) cmꢀ1: 3317 (N–H), 1718 (C@O), 820
C3, C5, J2C–F = 24 Hz); 120.2 (4C, A+A0, C3, C5); 124.3 (2C, A+A0, C1);
134.2 (4C, A+A0, C2, C6); 136.1 (4C, B+B0, C2, C6); 140.4 (2C, A+A0,
1
(Se–Se). H NMR (400 MHz, CDCl3) d: 7.23–7.25 (m, 6H, B+B0,
C4); 152.1 (2C, B+B0, C1); 154.3 (2C, 2C@O); 162.1 (2C, B+B0, C4, J1C–F
=
H2+H4+H6); 7.49–7.55 (m, 8H, A+A0, H2+H6, B+B0, H3+H5); 7.57 (d,
4H, A+A0, H3+H5, J3–2 = J5–6 = 8.8 Hz); 10.4 (s, 2H, 2NH). 13C NMR
(100 MHz, CDCl3) d: 120.1 (2C, A+A0, C1); 122.8 (8C, A+A0, C3, C5,
B+B0, C2, C6); 126.4 (2C, B+B0, C4); 130.3 (4C, B+B0, C3, C5); 134.3
(4C, A+A0, C2, C6); 139.9 (2C, A+A0, C4); 151.3 (2C, 2C@O); 152.5
(2C, B+B0, C1). MS (m/z% abundance): 396 (60), 198 (100), 94
(83). Elemental Analysis for C26H20N2O4Se2, Calcd/Found (%): C:
53.62/53.30; H: 3.46/3.22; N: 4.81/4.75.
241 Hz). MS (m/z% abundance): 396 (55), 198 (100), 112 (86).
Elemental Analysis for C26H18F2N2O4Se2, Calcd/Found (%): C: 50.50/
49.75; H: 2.93/2.71; N: 4.53/4.50.
4.1.2.12.
Dibenzyl
(diselanediyldibenzene-4,1-diyl)bis-
carbamate (2l). From benzyl chloroformate. Yellow solid; mp:
158 °C. Yield: 24%. IR (KBr) cmꢀ1: 3359 (N–H), 1708 (C@O), 814
(Se–Se). 1H NMR (400 MHz, CDCl3) d: 5.16 (s, 4H, 2CH2); 7.34–
7.40 (m, 12H, A+A0, H3+H5, B+B0, H2+H3+H5+H6); 7.56 (d, 4H,
A+A0, H2+H6, J2–3 = J6–5 = 8.4 Hz); 9.95 (s, 2H, 2NH). 13C NMR
(100 MHz, CDCl3) d: 66.8 (2C, 2CH2); 119.7 (4C, A+A0, C3, C5);
123.8 (2C, A+A0, C1); 128.9 (10C, B+B0, C2, C3, C4, C5, C6); 134.4
4.1.2.8.
Bis(4-methoxyphenyl)
(diselanediyldibenzene-4,1-
diyl)biscarbamate (2h).
From 4-methoxyphenyl chloroformate,
prepared with 4-methoxyphenol and trichloromethylchlorofor-