Molecules 2017, 22, 794
16 of 22
(
3
m, 4H, CHarom),3.57 (q, 4H, J = 6.6 Hz, 2
H, NCH ), 1.84 (quin, 4H, J = 6.9 Hz, 2
C(O)), 160.68 (C(O)), 154.33, 147.82, 134.57, 130.70, 125.62, 119.54, 118.87, 116.59, 53.18 (C-N), 49.66
×
NCH ), 2.51 (dd, 4H, J = 6.9, 6.9 Hz, 2
×
CH NH), 2.28 (s,
2
2
13
×
CH CH CH ) ppm; C-NMR (151 MHz, CDCl )
δC: 161.99
3
2
2
2
3
(
(
1
CH ), 37.00 (C-N
), 24.18 ppm; Anal. Calcd. (%) for C H N O
×
HCl
×
1 / H O: C, 58.43, H,
3
amide
27 29
3
6
2
2
5
.99, N, 7.57. Found (%): C, 57.98, H, 5.59, N, 7.59.
N,N'-[Azanediylbis(propane-3,1-diyl)]bis(2-oxo-2H-chromene-3-carboxamide) (13d). Creamy solid. Yield:
◦
1
6
2.1%; M.p. 189.0–191.0 C; H-NMR (600 MHz, DMSO-d )
δ
H: 8.83 (s, 2H, CHarom), 8.77 (t, 2H,
6
J = 5.6 Hz,
2
×
CONH), 7.96 (dd, 2H, J = 7.8, 1.4 Hz, CHarom), 7.73 (ddd, 2H, J = 8.1, 7.6, 1.6 Hz, CHarom),
7
2
2
.48 (d, 2H, J = 8.1 Hz, CHarom), 7.43 (td, 2H, J = 7.6, 7.6, 0.6 Hz, CHarom), 3.41 (q, 4H, J = 6.8 Hz
,
× NCH ), 2.59 (t, 4H, J = 6.7 Hz, 2 × CH NH), 1.76–1.62 (brs, 1H, NH), 1.69 (quin, 4H, J = 6.7 Hz
,
2
2
13
× CH CH CH2) ppm
;
C-NMR (151 MHz, DMSO-d )
δ
C: 162.12 (C(O)), 161.63 (C(O)), 154.33,
2
2
6
147.86, 134.61, 130.72, 125.64, 119.50, 118.87, 116.60, 45.20 (C-N), 36.84 (C-Namide), 26.32 ppm; Anal.
1
Calcd. (%) for C H N O
N, 7.23.
×
HCl
×
1 / H O: C, 53.34, H, 5.34, N, 7.18. Found (%): C, 53.38, H, 4.97,
26
27
3
6
2
2
N,N -[Piperazine-1,4-diylbis(propane-3,1-diyl)]bis(1H-indole-2-carboxamide) (14a). Creamy solid. Yield
'
◦
1
5
8
2.9%; M.p. 246.0 C with decomp.; H-NMR (600 MHz, DMSO-d )
δ
H: 11.51 (brs, 2H, NHindole),
6
.45 (t, 2H, J = 5.5 Hz, 2
×
CONH), 7.77 (d, 2H, J = 8.0, CHarom.), 7.43 (dd, 2H, J = 8.1, 1.0 Hz,
CHarom.), 7.14 (dt, 2H, J = 8.2, 7.0, 1.0 Hz, CHarom.), 7.43 (s, CHindole), 7.02 (dt, 2H, J = 8.0, 7.0, 0.6 Hz,
CHarom.), 3.34–3.27 (m, 4H, CH N), 2.20–2.47 (cluster, 12H, 2
×
CH2piperazine
,
2 × NCH2), 1.68 (quin,
2
4
H, J = 6.9 Hz, 2 × CH CH CH ) ppm; 13C-NMR (151 MHz, DMSO-d )
δ
: 161.81 (C(O)), 136.92,
2
2
2
6
C
1
32.06, 127.52, 123.78, 121.92, 120.20, 112.77, 103.23, 54.41 (s, 4
×
C
), 48.72 (C-Npiperazine), 36.48
piperazine
×
1
(
1
C-Namide), 24,30 ppm; Anal. Calcd. (%) for C H N O
3.06. Found (%): C, 52.23, H, 6.38, N, 13.06.
×
2HBr
1 / H O: C, 52.26, H, 6.11, N,
28
34
6
2
2
2
N,N
'
-[(Butane-1,4-diylbis(oxy))bis(propane-3,1-diyl)]bis(1H-indole-2-carboxamide) (14b). Creamy solid.
◦
1
Yield 43.9%; M.p. 182.3–183.1 C; H-NMR (600 MHz, DMSO-d )
δ
H: 11.52 (brs, 2H, NHindole), 8.41 (t,
CONH), 7.61 (d, 2H, J = 8.4 Hz, CHarom.), 7.43 (d, 2H, J = 7.8 Hz, CHarom.), 7.17 (dt,
H, J = 8.4, 7.0, 1.2 Hz, CHarom.), 7.10 (s, CHindole), 7.03 (dt, 2H, J = 7.8, 7.0, 0.8 Hz, CHarom.), 3.44 (t, 4H,
CH O and 2 NCH ), 1.79 (quin, 4H, J = 6.6 Hz,
6
2
2
H, J = 6.0 Hz, 2
×
J = 6.6, 6.0 Hz, CH N), 3.40–3.34 (cluster, 8H, 2
×
×
2
2
2
1
3
2
(
×
NCH CH ), 1.57–1.55 (m, 4H, 2
×
CH CH O) ppm; C-NMR (151 MHz, DMSO-d )
δ
C: 161.81
2
2
2
2
6
C(O)), 136.92, 132.06, 127.52, 123.78, 121.92, 120.20, 112.77, 103.23, 69.71 (O-C
.
), 68.09 (Cprop.-O), 37.
but
1
9
9 (C-Namide), 27.67, 25.95 ppm; Anal. Calcd. for C H N O
×
HCl
×
/ H O, (%): C, 62.94, H, 7.04,
2 2
28
34
4
4
N, 15.29. Found (%): C, 62.93, H, 6.70, N, 15.30.
N,N
'-[(Methylazanediyl)bis(propane-3,1-diyl)]bis(1H-indole-2-carboxamide) (14c). Creamy solid. Yield
◦
1
5
2.0%; M.p. 205.3–207.0 C; H-NMR (600 MHz, DMSO-d )
δ
H: 11.52 (brs, 2H, NHindole), 8.50 (t, 2H,
CONH), 7.60 (d, 2H, J = 7.8 Hz, CHarom.), 7.44 (d, 2H, J = 8.4 Hz, CHarom.), 7.17 (dd,
H, J = 8.4, 7.2 Hz, CHarom.), 7.09 (s, CHindol ), 7.03 (dd, 2H, J = 7.8, 7.2 Hz, CHarom.), 3.36–3.33 (m, 4H,
6
J = 5.4 Hz, 2
×
2
2
2
e
× NCH ), 2.40 (dd, 4H, J = 7.2, 7.2 Hz, 2 × CH NCH ), 2.19 (s, 3H, NCH ), 1.85 (quin, 4H, J = 7.2 Hz,
2
2
3
3
13
×
CH CH CH ) ppm; C-NMR (151 MHz, DMSO-d )
δ
C: 161.81 (C(O)), 136.92, 132.06, 127.52,
2
2
2
6
1
23.78, 121.92, 120.20, 112.77, 103.23, 56.02 (C-N), 42.19 (CH ), 38.45 (C-Namide), 27.16 ppm; Anal. Calcd.
3
1
(%) for C H N O × / H O: C, 68.16; H, 6.86; N, 15.90. Found (%): C, 67.94; H, 6.88; N, 16.00.
25
29
5
2
2
2
N,N'-[Azanediylbis(propane-3,1-diyl)]bis(1H-indole-2-carboxamide) (14d). Creamy solid. Yield 42.8%; M.p.
◦
1
1
84.3–186.1 C; H-NMR (600 MHz, DMSO-d )
δ
H: 11.52 (brs, 2H, NHindol
× CONH), 7.60 (d, 2H, J = 7.8 Hz, CHarom.), 7.44 (d, 2H, J = 8.4 Hz, CHarom.), 7.17 (dd, 2H, J = 8.4
.8 Hz, CHarom.), 7.09 (s, 2H, CHindol
× NCH2, NH), 2.61 (t, 4H, J = 7.0 Hz, 2
e
), 8.50 (t, 2H, J = 5.4 Hz
,
6
2
7
2
,
e
), 7.03 (dd, 2H, J = 7.8, 7.8 Hz, CHarom.), 3.39–3.28 (m, 4H,
CH NH), 1.71 (quin, 4H, J = 7.0 Hz, 2 CH CH CH )
×
×
2
2
2
2
13
ppm; C-NMR (151 MHz, DMSO-d6)
δ : 161.81 (C(O)), 136.93, 132.11, 127.53, 123.76, 121.93, 120.19,
C
1
6
12.77, 103.28, 45.36 (C-N), 36.43 (C-Namide), 26.56 ppm; Anal. Calcd. (%) for C H N O
2
2.94; H, 7.04; N, 15.29. Found (%): C, 62.93; H, 6.80; N, 15.30.
×
HCl: C,
24
27
5