122 Letters in Drug Design & Discovery, 2013, Vol. 10, No. 2
Kumar et al.
(E)-1-(7-benzylidene-3-phenyl-3,3a,4,5,6,7-hexahydro-2H-
(E)-1-(7-(3-nitrobenzylidene)-3-(3-nitrophenyl)-3,3a,4,5,6-
indazol-2-yl)ethanone (A1):
,7-hexahydro-2H-indazol-2-yl) ethanone (A6):
1
Yellow powder, mp 130-1320 C. H NMR (CDCl3, 300
Yellow powder, mp 90-920C.1H NMR (CDCl3, 300
MHz, 25 °C): 7.61-7.25 (m, 10H), 6.31 (s, 1H, =CH), 4.72
(d, 1H), 2.67 (m, 1H), 2.12 (s, 3H, CH3), 1.81-1.42 (m, 6H).
13C NMR (CDCl3, 75 MHz, 25 °C): 166.9, 154.4, 141.7,
136.0, 134.9, 131.9, 128.5, 127.6, 127.1, 127.9, 126.3, 70.2,
41.8, 27.5, 24.8, 23.7. ESI-MS: m/z: (M+, %) 330.14 (M+
6%), 329(97%), 200(100%). Elemental analysis found
(Calc.) for C22H22N2O: C, 79.97 (79.65); H, 6.71 (6.73); N,
8.48(8.45).
MHz, 25 °C): 8.29-7.54 (m, 8H), 6.42 (s, 1H, =CH), 4.4 (d,
1H), 2.63 (m, 1H), 2.02 (s, 3H, CH3), 1.81-1.43 (m, 6H). 13
C
NMR (CDCl3, 75 MHz, 25 °C): 167.5, 154.6, 146.8, 146.2,
140.4, 136.1, 135.3, 134.6, 134.2, 129.5, 129.3, 128.7, 123.8,
122.7, 121.7, 120.7, 69.7, 42.8, 27.8, 24.5, 23.4. ESI-MS:
m/z: 420(M+ 12%),.418(100%). Elemental analysis found
(Calc.) for C22H20 N4O5 : C, 62.85(62.60); H,4.79 (4.80); N,
13.33(13.28) .
(E)-1-(7-(3-methoxybenzylidene)-3-(3-methoxyphenyl)-3,3-
a,4,5,6,7-hexahydro-2H-indazol-2-yl)ethanone (A7):
(E)-1-(7-(2-chlorobenzylidene)-3-(2-chlorophenyl)-3,3a,4,-
5,6,7-hexahydro-2H-indazol-2-yl)ethanone (A2):
Yellow powder, mp 110-1120 C.1H NMR (CDCl3, 300
MHz, 25 °C): 7.49-6.21 (m,8 H), 6.11 (s, 1H, =CH), 4.1 (d,
1H), 3.75 (s, 6H), 2.68 (m, 1H), 2.04 (s, 3H, CH3), 1.78 -1.32
(m, 6H). 13C NMR (CDCl3, 75 MHz, 25 °C): 169.5, 161.5,
160.4, 155.6, 142.5, 136.0, 134.8, 128.6, 126.5, 120.8, 120.4,
112.5, 112.0, 111.5, 71.2, 55.8, 42.8, 27.1, 24.5, 23.4. ESI-
MS: m/z: 390((M+ 8%), 389(26%), 212(100%). Elemental
analysis found (Calc.) for C24H26N2O3 : C, 73.82(73.63); H,
6.71(6.72); N, 7.17(7.16).
Yellow powder, mp 102-1040C.1H NMR (CDCl3, 300
MHz, 25 °C): 7.72-7.20 (m, 8H), 6.69 (s, 1H, =CH), 4.5 (d,
1H), 2.67 (m, 1H), 2.02 (s, 3H, CH3), 1.85-1.43 (m, 6H). 13
C
NMR (CDCl3, 75 MHz, 25 °C): 166.5, 154.6, 141.5, 136.5
134.7, 133.5, 133.1, 130.7, 129.5, 129.3, 129.3, 128.2, 127.1,
127.0, 126.6, 126.4, 65.9, 42.4, 23.3. ESI-MS: m/z: (M+, %)
398.07. (M+ 9%), 397(22%), 220(100%). Elemental analysis
found (Calc.) for C22H20Cl2N2O : C, 66.17(66.43); H,
5.05(5.03); N, 7.02(7.30).
(E)-1-(7-(2,3,4-trimethoxybenzylidene)-3-(2,3,4-trimethoxy-
phenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl)ethanone
(A8):
(E)-1-(7-(3-hydroxybenzylidene)-3-(3-hydroxyphenyl)-3,-
3a,4,5,6,7-hexahydro-2H-indazol-2-yl)ethanone (A3):
Yellow powder, mp 166-1680 C.1H NMR (CDCl3, 300
MHz, 25 °C): 7.52-6.51 (m, 8 H), 6.31 (s, 1H, =CH), 5.30 (s,
2H), 4.6 (d, 1H), 2.55 (m, 1H), 2.32 (s, 3H, CH3), 1.75-1.37
(m, 6H). 13C NMR (CDCl3, 75 MHz, 25 °C): 167.2, 158.9,
156.6, 155.5, 140.7, 135.6, 135.1, 131.7, 130.4, 129.7, 121.8,
120.4, 115.6, 113.4, 113.2, 22.2. ESI-MS: m/z: (M+, %) 362
(M+ 7%),361(96%), 221( 100%). Elemental analysis found
(Calc.) for C22H22N2O3 : C, 72.91(72.71); H,6.12 (6.09); N,
7.73(7.76).
Yellow powder, mp 210-2120 C.1H NMR ( CDCl3 , 300
MHz, 25 °C): 7.47 -6.25 (m,4 H), 6.59 (s, 1H, =CH), 4.4 (d,
1H), 3.75 (s, 9H), 2.68 (m, 1H), 2.04 (s, 3H, CH3), 1.80-1.35
(m, 6H). 13C NMR (CDCl3, 75 MHz, 25 °C): 168.5, 156.8,
155.9, 152.9, 151.1, 149.1, 142.3, 141.6, 136.0, 135.7, 132.7,
122.7, 121.4, 119.6, 108.2, 106.8, 104.7, 65.3, 61.7, 60.8,
60.3, 56.1, 43.1, 27.8, 24.5, 23.4. ESI-MS: m/z: 510(M+
12%), 507(20%), 215(100%). Elemental analysis found
(Calc.) for C28H34N2O7: C, 65.87(65.92); H, 6.71(6.70); N,
5.49(5.48).
(E)-1-(7-(4-chlorobenzylidene)-3-(4-chlorophenyl)-3,3a,4,-
5,6,7-hexahydro-2H-indazol-2-yl)ethanone (A4):
(E)-1-(7-(4-(dimethylamino)benzylidene)-3-(4-(dimethyla-
mino)phenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-
yl)ethanone (A9) :
Yellow powder, mp 126-1280 C.1H NMR (CDCl3, 300
MHz, 25 °C): 7.66-7.58 (m,8 H), 6.27 (s, 1H, =CH), 4.2 (d,
Yellow powder, mp 150-1520 C.1H NMR (CDCl3, 300
MHz, 25 °C): 7.64 -6.56 (m,10 H), 6.25 (s, 1H, =CH), 4.7 (d,
1H), 3.78 (s, 12 H), 2.68 (m, 1H), 2.54 (s, 3H, CH3), 1.81-
1.36 (m, 6H). 13C NMR (CDCl3, 75 MHz, 25 °C): 167.5,
154.6, 151.3, 149.3, 133.7, 132.1, 131.4, 128.7, 124.7, 112.7,
111.7, 72.9, 41.3, 26.8, 24.5, 23.4. ESI-MS: m/z: 416(M+ 9
%), 415(21%), 221(100%). Elemental analysis found (Calc.)
for C26H32N4O: C, 74.97(74.96); H, 7.74(7.72); N,
13.45(13.43).
1H), 2.65 (m, 1H), 2.01 (s, 3H, CH3), 1.77-1.45 (m, 6H). 13
C
NMR (CDCl3, 75 MHz, 25 °C): 168.5, 155.6, 139.7, 136.0,
133.3, 131.5, 129.0, 128.6, 128.4, 70.9, 42.8, 27.8, 24.5,
21.4. ESI-MS: m/z: (M+,%) 398 (M+ 12%),
397(47%),229(100%). Elemental analysis found (Calc.) for
C22H20 Cl2N2O2 : C, 63.62(63.36); H,4.85 (4.86); N,6.75
(6.77).
(E)-1-(7-(2,4-dichlorobenzylidene)-3-(2,4-dichlorophenyl)-
3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl)ethanone (A5):
Synthesis of E-7-(substituted benzylidene)-2-phenyl-3-
(substituted phenyl)-3, 3a, 4,5,6,7 hexahydro 2H inda-
zoles (B1-B5)
Yellow powder, mp 152-1540 C.1H NMR (CDCl3 , 300
MHz, 25 °C): 7.71-7.02 (m, 6H), 6.56 (s, 1H, =CH), 4.7 (d,
1H), 2.66 (m, 1H), 2.02 (s, 3H, CH3), 1.85-1.23 (m, 6H). 13
C
In the first step, the dibenzylidene cycloheaxanones were
synthesized as reported. The synthesized dibenzylidene
cycloheaxanon(1.2 mmol) from first step was dissolved in
glacial acetic acid (5 mL) and phenyl hydrazine (1.5mml)
was added to the solution. The solution was refluxed for 12
hours and monitored by TLC. Solvent was removed in
vacuum and recrystallized with ethlyl alcohol. The
NMR (CDCl3, 75 MHz, 25 °C): 163.5, 152.6, 150.1, 137.6,
136.8, 132.4, 132.1, 131.4, 131.0, 130.3, 127.9, 126.8, 126.5,
125.2, 120.8, 75.8, 42.1, 27.9, 24.3, 23.1. ESI-MS: m/z: (M+,
%) 468(M+ 12%), 467(22%), 221(100%). Elemental analysis
found (Calc.) for C22H18 Cl4N2O : C, 56.44(56.66); H,3.88
(3.83); N, 5.98 (5.96).