EXCLI Journal 2017;16:1090-1098 – ISSN 1611-2156
Received: February 03, 2017, accepted: July 04, 2017, published: August 14, 2017
column chromatography to give pure com- 5H), 2.17 (m, 1H), 1.70 (m, 1H), 1.53-1.43
pound.
(m, 1H), 1.10 (d, J = 6.90 Hz, 1H), 1.04 (t, J
= 7.43 Hz, 2H), 0.95 (t, J = 7.39 Hz, 1H), 0.81
(d, J = 6.81 Hz, 2H); C-NMR (400 MHz,
CDCl3) δppm : 180.1, 161.1, 133.8, 128.2,
127.7, 126.1, 125.2, 117.5, 71.9, 37.2, 26.6,
25.9, 24.5, 13.9, 11.9; LRMS : (ES+) m/z =
243.3 (Fragmented ion).
(S)-3-isobutyl-3,4,6,7-tetrahydro-1H-
13
benzo[e][1,4]diazonine-2,5-dione (6a)
Molecular Formula : C15H20N2O2;Rf: 0.2
at 0.2: 9.8 ethyl acetate/DCM; Yield : 26 %;
1H-NMR (400 MHz, CDCl3) δppm : 8.24 (d,
J = 8.01 Hz, 1H), 7.38-7.09 (m, 4H), 4.20 (m,
1H), 3.02-2.95 (m, 2H), 2.88 (m, 2H), 2.05 (S)-3-methyl-3,4,6,7-tetrahydro-1H-
(m, 1H), 1.82 (m, 1H), 1.54 (m, 1H), 1.02 (m, benzo[e][1,4]diazonine-2,5-dione (6e)
J = 17.83, 6.64 Hz, 6H); 13C-NMR (100
Molecular Formula : C12H14N2O2; Rf: 0.2
MHz, CDCl3) δppm : 180.6, 160.6, 133.7, at 3 : 7 ethyl acetate/hexanes; Yield : 40 %;
128.3, 127.8, 126.2, 125.2, 117.5, 67.2, 40.7, 1H-NMR (400 MHz, CDCl3) δppm : 8.23 (d,
29.7, 25.9, 25.2, 23.2, 21.7; LRMS : (ES+) J = 8.13 Hz, 1H), 7.39-7.30 (m, 2H), 7.20 (d,
m/z = 242.8 (Fragmented ion).
J = 7.31 Hz, 1H), 7.15 (t, J = 7.46 Hz, 1H),
4.17 (m, 1H) , 2.95 (m, J = 7.47 Hz, 2H),
2.90-2.85 (m, 2H),1.34(d, 3H); 13C-NMR
(100 MHz, CDCl3) δppm : 178.5,161.2,
134.7, 128.3, 127.8, 125.2, 123.8, 115.5, 72.6,
30.7, 25.1, 18.8; LRMS : (ES+) m/z = 200.5
(Fragmented ion).
(S)-3-benzyl-3,4,6,7-tetrahydro-1H-
benzo[e][1,4]diazonine-2,5-dione (6b)
Molecular Formula : C18H18N2O2; Rf: 0.2
at 3 : 7 of ethyl acetate/hexanes; Yield : 10 %;
1H-NMR (400 MHz,CDCl3) δppm : 8.16 (d, J
= 8.15 Hz, 1H),7.32-7.07 (m, 9H), 4.50-4.44
(s, 1H),3.36 (m, 1H), 3.13 (m, 1H), 2.77 3,4,6,7-tetrahydro-1H-benzo[e][1,4]diazo-
(m,4H); 13C-NMR (100 MHz,CDCl3) δppm : nine-2,5-dione (6f)
179.2, 161.2, 136.0, 133.4, 129.5, 128.2,
Molecular Formula : C11H12N2O2; Rf:
128.1, 127.7, 126.7, 126.2, 125.3, 117.5, 69.2, 0.35 at 3 : 7 ethyl acetate/hexanes; Yield :
1
37.2, 29.7, 25.7, 25.7; LRMS : (ES+) m/z = 54 %; H-NMR (400 MHz, CDCl3) δppm :
276.7 (Fragmented ion).
8.20 (d, J = 8.12 Hz, 1H), 7.38-7.31 (m, 2H),
7.25 (d, J = 7.31 Hz, 1H), 7.14 (t, J = 7.55
Hz, 1H), 4.15 (d, 2H) , 2.93 (m, J = 7.47 Hz,
2H), 2.91-2.85 (m, 2H); 13C-NMR (100 MHz,
CDCl3) δppm : 180.5,165.2, 136.8, 129.1,
127.8, 124.7, 122.8, 112.5, 74.6, 38.7, 25.7;
LRMS : (ES+) m/z = 185.7 (Fragmented ion).
(S)-3-isopropyl-3,4,6,7-tetrahydro-1H-
benzo[e][1,4]diazonine-2,5-dione (6c)
Molecular Formula : C14H18N2O2; Rf: 0.3
at 3 : 7 ethyl acetate/hexanes; Yield : 46 %;
1H-NMR (400 MHz, CDCl3) δppm : 8.25 (d,
J = 8.13 Hz, 1H), 7.37-7.28 (m, 2H), 7.24 (d,
J = 7.31 Hz, 1H), 7.16 (t, J = 7.46 Hz, 1H),
4.10 (m, 1H) , 2.98 (m, J = 7.47 Hz, 2H),
2.95-2.87 (m, 2H), 2.45-2.37 (m, 1H), 0.90
(m, 6H); 13C-NMR (100 MHz, CDCl3) δppm
: 179.5,161.2, 133.7, 128.3, 127.8, 126.2,
125.2, 117.5, 73.6, 29.7, 26.1, 19.3, 16.8,
14.1; LRMS : (ES+) m/z = 228.7 (Fragmented
ion).
Antibacterial activity
The title compounds were subjected for
antibacterial activity, where Zone of inhibi-
tion (Pandey et al., 2010; Kirby and Bauer,
1996) and Minimum inhibitory concentration
(Sarker et al., 2007; Gibbons et al., 2002; Pra-
chayasittikul et al., 2010) test were conducted
against test organism Bacillus subtilis which
is a gram positive bacteria, by using Cup Plate
Method and Microtitre Plate Method respec-
tively.
(S)-3-sec-butyl-3,4,6,7-tetrahydro-1H-
benzo[e][1,4]diazonine-2,5-dione (6d)
Molecular Formula : C15H20N2O2; Rf : 0.5
at 3 : 7 ethyl acetate/hexanes; Yield :
10 %;1H-NMR (400 MHz, CDCl3) δppm :
8.26 (m, 1H), 7.29 (m, 3H), 7.15 (t, J = 7.47
Hz, 1H), 4.26-4.13 (d, 1H), 3.02-2.87 (m,
1093