M. Babu et al. / European Journal of Medicinal Chemistry 47 (2012) 608e614
613
minimum amount of water and an aqueous solution of NaOAc in
6.4.7. 3-(3,4-Methylenedioxyphenyl)- 4-phenyl-5-benzyl-1,3,4,5,
minimum amount of water were added and the reaction mixture
was refluxed for 4 h on a water bath and the course of the reaction
was followed by TLC. After completion of the reaction, excess of
alcohol was evaporated and the resulting residue was treated with
iceewater. The compounds (3ael) that separated were filtered,
dried and crystallised from ethanol.
5a,6,7,8,9,9a-decahydroisoxazolo[4,3-c]quinoline (3g)
IR (KBr): 3210 (NeH str.), 3064 (aromatic CeH str.) cmꢀ1; 1H NMR
(300 MHZ, CDCl3):
4.5 (s, 1H, eNeCH
6.9e7.5 (m, 13H, AreH), 8.7 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3):
24.3, 25.3, 30.2, 33.1, 55.2 (eNeCH24), 56.2 (eNeCH ), 64.2, 82.4
d
1.0e2.4 (m,10H, 4CH2 &2CH), 3.5(s,2H, NeCH24),
4), 5.4 (s, 1H, OeCHAr), 6.1 (s, 1H, eOeCH2eOe),
4
(OeCHAr), 104.4 (eOeCH2eO), 127.4, 128.8, 133.4, 137.2, 138.1, 145.4.
6.4.1. 3,4-Diphenyl-5-benzyl-1,3,4,5,5a,6,7,8,9,9a-decahydroisoxazolo
[4,3-c]quinoline (3a)
6.4.8. 3-(1H-indol-2-yl)-4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,9,9a-
IR (KBr): 3290 (NeH str.), 2924 (aromatic CeH str.) cmꢀ1
;
1H
1.1e1.5 (m, 10H, 4CH2 & 2CH), 3.6 (s, 2H,
NeCH24), 4.2 (s, 1H, NeCH ), 5.4 (s, 1H, OeCHAr), 7.1e7.4 (m, 15H,
AreH), 8.5 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3): 23.3, 27.5, 31.9,
38.4, 56.1 (eNeCH24), 62.1 (eNeCH ), 67.5, 84.7 (OeCHAr), 113.9,
125.2, 128.7, 129.2, 137.4, 143.9; DEPT-135 (75 MHZ, CDCl3): 23.35
(Y), 26.62 (Y), 34.58 (Y), 38.45 (Y), 55.34 (Y) (NeCH24), 61.23 ([)
(NeCH ), 67.52 ([), 83.55 ([) (OeCHAr), 123.01 ([), 125.94 ([),
decahydroisoxazolo-[4,3-c]quinoline (3h)
NMR (300 MHZ, CDCl3):
d
1H NMR (300 MHZ, CDCl3):
2H, NeCH24), 4.1 (s, 1H, NeCH4
d
1.0e2.5 (m,10H, 4CH2 & 2CH), 3.4 (s,
), 5.1 (s, 1H, OeCHAr), 7.0e7.6 (m,
15H, AreH), 8.9 (s,1H, eNH),10.4 (s,1H, eNH of indole); 13C NMR (75
4
4
MHZ, CDCl3): 24.3, 25.3, 30.2, 33.1, 55.6 (eNeCH24), 56.2 (eNeCH
64.2, 82.4 (OeCHAr), 127.4, 128.8, 133.4, 137.2, 138.1, 145.4.
4),
d
4
6.4.9. 3-(3,4-dimethoxyphenyl)-4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,
127.75 ([), 128.71 ([), 129.02 ([).
9,9a-decahydroisoxazolo[4,3-c]quinoline (3i)
IR (KBr): 3330 (NeH str.), 3072 (aromatic CeH str.) cmꢀ1; 1H NMR
6.4.2. 3-(2-chlorophenyl)-4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,9,9a-
(300 MHZ, CDCl3):
NeCH24), 3.9 (s, 6H, 2ꢃ OeCH3), 4.2 (s, 1H, NeCH
OeCHAr), 6.8e7.3 (m, 13H, AreH), 8.5 (s,1H, eNH);13C NMR (75 MHZ,
d
1.0e2.5 (m, 10H, 4CH2 & 2CH), 3.5 (s, 2H,
decahydro- isoxazolo[4,3-c]quinoline (3b)
4), 5.1 (s, 1H,
IR (KBr): 3310 (NeH str.), 2921(aromatic CeH str.) cmꢀ1 1H
;
NMR (300 MHZ, CDCl3):
NeCH24), 4.4 (s, 1H, NeCH
AreH), 8.7 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3): 24.4, 25.2, 30.8,
d
1.0e2.5 (m, 10H, 4CH2 & 2CH), 3.6 (s, 2H,
CDCl3): 24.3, 25.3, 30.2, 33.1, 55.12, 55.4 (eNeCH24), 56.2 (eNeCH
64.2, 82.4 (OeCHAr), 127.4, 128.8, 133.4, 137.2, 138.1, 145.4.
4),
4), 5.2 (s, 1H, OeCHAr), 7.2e7.8 (m, 14H,
33.7, 56.4 (eNeCH24), 60.2 (eNeCH
4
), 64.3, 82.6 (OeCHAr), 127.5,
6.4.10. 3-(4-nitrophenyl)-4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,9,9a-
128.2.
decahydro-isoxazolo[4,3-c]quinoline (3j)
IR (KBr): 3240 (NeH str.), 3045 (aromatic CeH str.) cmꢀ1 1H
;
6.4.3. 3-(3-nitrophenyl)-4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,9,9a-
decahydro-isoxazolo-[4,3-c]quinoline (3c)
NMR (300 MHZ, CDCl3):
NeCH24), 4.1(s, 1H, NeCH
AreH), 9.2 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3): 24.3, 25.3, 30.2,
d
1.0e2.6 (m, 10H, 4CH2 & 2CH), 3.6 (s, 2H,
4
), 5.2 (s, 1H, OeCHAr), 7.2e8.2 (m, 14H,
IR (KBr): 3280 (NeH str.), 2929 (aromatic CeH str.) cmꢀ1 1H
;
NMR (300 MHZ, CDCl3):
NeCH24), 4.2 (s, 1H, NeCH
AreH), 8.7 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3): 24.3, 25.5, 34.7,
d
1.0e2.7 (m, 10H, 4CH2 & 2CH), 3.6 (s, 2H,
33.1, 55.4 (eNeCH24), 56.7 (eNeCH4), 64.2, 82.4 (OeCHAr), 127.4,
128.8, 133.4, 137.2, 138.1, 145.4.
4
), 5.4 (s, 1H, OeCHAr), 7.2e8.2 (m, 14H,
37.4, 56.2 (eNeCH24), 59.2 (eNeCH
4
), 64.3, 82.4 (OeCHAr), 127.1,
6.4.11. 3-(pyridin-2-yl-4-phenyl-5-benzyl-)-1,3,4,5,5a,6,7,8,9,9a-
128.0, 133.6, 137.8, 138.3, 145.1.
decahydro-isoxazolo-[4,3-c]quinoline (3k)
1H NMR (300 MHZ, CDCl3):
d
1.0e2.5 (m, 10H, 4CH2 & 2CH), 3.6
(s, 2H, NeCH24), 4.1 (s, 1H, NeCH ), 5.2 (s, 1H, OeCHAr), 7.1e8.4
(m, 14H, AreH), 8.7 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3): 24.3,
6.4.4. 3-(4-methoxyphenyl)-4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,
9,9a-decahydro-isoxazolo[4,3-c]quinoline (3d)
4
IR (KBr): 3385 (NeH str.), 3161 (aromatic CeH str.) cmꢀ1
;
1H
25.3, 30.2, 33.1, 55.4 (eNeCH24), 56.2 (eNeCH
(OeCHAr), 127.4, 128.8, 133.4, 137.2, 138.1, 145.4.
4), 64.2, 82.4
NMR (300 MHZ, CDCl3):
d 1.0e2.5 (m, 10H, 4CH2 & 2CH), 3.5 (s, 2H,
NeCH24), 3.9 (s, 3H, OeCH3), 4.3 (s, 1H, eNeCH4), 5.2 (s, 1H,
OeCHAr), 6.9e7.4 (m, 14 H, AreH), 8.6 (s, 1H, eNH); 13C NMR (75
MHZ, CDCl3): 24.5, 25.6, 30.7, 33.5, 55.23 (OeCH3), 55.7 (eNeCH24),
6.4.12. 3-(pyridin-3-yl)- 4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,9,9a-
decahydro-isoxazolo-[4,3-c]quinoline (3l)
57.2 (eNeCH
4
), 64.2, 82.3 (OeCHAr), 127.4, 128.5, 133.8, 137.6,
IR (KBr): 3290(NeH str.), 3038 (aromatic CeH str.) cmꢀ1 1H
;
138.3, 145.4.
NMR (300 MHZ, CDCl3):
NeCH24), 4.3 (s, 1H, NCH
AreH), 8.6 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3): 24.3, 25.3, 30.2,
d
1.0e2.5 (m, 10H, 4CH2 & 2CH), 3.5 (s, 2H,
4
), 5.2 (s, 1H, OeCHAr), 7.2e8.6 (m, 14H,
6.4.5. 3-(4-chlorophenyl)-4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,9,9a-
decahydro-isoxazolo[4,3-c]quinoline (3e)
33.1, 55.4(eNeCH24), 56.2 (eNeCH4), 64.2, 82.4 (OeCHAr), 127.4,
128.8, 133.4, 137.2, 138.1, 145.4.
IR (KBr): 3250 (NeH str.), 3080(aromatic CeH str.) cmꢀ1
;
1H
NMR (300 MHZ, CDCl3):
eNeCH24), 4.3 (s, 1H, eNeCH
14H, AreH), 8.8 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3): 24.4, 25.1,
d
1.0e2.6 (m, 10H, 4CH2 & 2CH), 3.4 (s, 2H,
4
), 5.3 (s, 1H, OeCHAr), 7.2e7.4 (m,
6.5. Antibacterial assay
30.2, 33.1, 55.3 (eNeCH24), 56.6 (eNeCH
126.4, 125.8, 134.3, 137.4, 138. 3, 143.4.
4
), 64.2, 83.4 (OeCHAr),
Discs measuring 6.25 mm in diameter were punched from
Whatmann no. 1 filter paper. Batches of 10 discs were dispensed to
each screw capped bottle and sterilized by dry heat at 140 ꢁC for an
hour. The test compounds were prepared with a concentration of
0.5% using methanol. The discs of each concentration were placed
in triplicate in meat peptone agar medium and seeded with fresh
bacterial culture separately and incubated at 37 ꢁC for 24 h. The
6.4.6. 3-(furan-2-yl)-4-phenyl-5-benzyl-1,3,4,5,5a,6,7,8,9,9a-
decahydro-isoxazolo-[4,3-c]quinoline (3f)
IR (KBr): 3382 (NeH str.), 2996 (aromatic CeH str.)cmꢀ1 1H
;
NMR (300 MHZ, CDCl3):
NeCH24), 4.7 (s, 1H, eNeCH
13H, AreH), 8.6 (s, 1H, eNH); 13C NMR (75 MHZ, CDCl3): 24.3, 25.3,
d
1.0e2.5 (m, 10H, 4CH2 & 2CH), 3.5 (s, 2H,
4
), 5.5 (s, 1H, OeCHAr), 6.6e7.4 (m,
zone of inhibition was measured in millimetres using 10 mg/mL
concentrations of synthesized compounds (3ael); methanol was
used both as a solvent and as a control. No zone of inhibition was
observed in control (i.e. in methanol).
30.2, 33.1, 55.4 (eNeCH24), 56.2 (eNeCH4), 64.2, 82.4 (OeCHAr),
127.4, 128.8, 133.4, 137.2, 138.1, 145.4.