Methanone derivatives as antimycobacterial agents 893
EI-MS (m/z): 439 (M+1); Cal/Ana: [C (71.22) 71.20, H
(5.06) 5.07, N (12.78) 12.80].
cm−1: 3322 (NH2), 3040 (CH), 1592 (C=N), 1672 (C=O),
1320 (C-N). 1H NMR (DMSO-d6) ppm: 2.36 (2H, m, CH2),
3.82 (12H, s, OCH3), 3.09 (1H, m, CH), 5.16-(1H, d, CH),
6.6-7.55 (9H, m, aromatic), EI-MS (m/z): 484 (M+1);
Cal/Ana: [C (69.55) 69.54, H (5.21) 5.22, N (8.69) 8.67].
3,4-Dimethoxyphenyl-6,7-dimethoxy-3-(4-pyridyl)-2,3,3a,
4-tetrahydroindeno[1,2-c]pyrazol-2-ylmethanone (4h) IR:
(KBr) cm−1: 3040 (CH), 1592 (C=N), 1672 (C=O), 1320
(C-N), 788 (C-Cl). 1H NMR (DMSO-d6) ppm: 2.36 (2H, m,
CH2), 3.82 (12H, s, OCH3), 3.09 (1H, m, CH), 5.16-(1H, d,
CH), 6.6–7.25 (5H, m, aromatic), 7.6–8.35 (4H, m, pyri-
dine), EI-MS (m/z): 460 (M+1); Cal/Ana: [C (67.96) 67.98,
H (5.48) 5.46, N (9.14) 9.16].
6,7-Dimethoxy-3-(4-pyridyl)-2,3,3a,4-tetrahydroindeno[1,2-c]
pyrazol-2-yl-3-methoxyphenylmethanone (4o) IR: (KBr)
cm−1: 3040 (CH), 1592 (C=N), 1672 (C=O), 1320 (C-N), 788
(C-Cl). 1H NMR (DMSO-d6) ppm: 2.36 (2H, m, CH2), 3.82
(9H, s, OCH3), 3.09 (1H, m, CH), 5.16-(1H, d, CH), 6.6–7.25
(6H, m, aromatic), 7.6–8.45 (4H, m, pyridine), EI-MS
(m/z): 430 (M+1); Cal/Ana: [C (69.92) 69.94, H (5.40) 5.42,
N (9.78) 9.76].
3-(2- Chlorophenyl)-6,7- dimethoxy-2,3,3a,4-tetra-
h y d r o i n d e n o [ 1 , 2 - c ] p y ra z o l - 2 - y l - 3 , 4 - d i m e t h ox y -
phenylmethanone (4i) IR: (KBr) cm−1: 3040 (CH), 1592
(C=N), 1672 (C=O), 1320 (C-N), 788 (C-Cl). 1H NMR
(DMSO-d6) ppm: 2.36 (2H, m, CH2), 3.82 (12H, s, OCH3),
3.09 (1H, m, CH), 5.16-(1H, d, CH), 6.6–7.55 (9H, m,
aromatic), EI-MS (m/z): 493 (M+1); Cal/Ana: [C (65.79)
65.80, H (5.11) 5.13, N (5.68) 5.66].
3 - ( 2 - C h l o r o p h e n y l ) - 6 , 7 - d i m e t h o x y - 2 , 3 , 3 a ,
4-tetrahydroindeno[1,2- c]pyrazol-2-yl-3-methoxy-
phenylmethanone (4p) IR: (KBr) cm−1: 3040 (CH), 1592
(C=N), 1672 (C=O), 1320 (C-N), 788 (C-Cl). 1H NMR
(DMSO-d6) ppm: 2.36 (2H, m, CH2), 3.82 (9H, s, OCH3),
3.09 (1H, m, CH), 5.16-(1H, d, CH), 6.6–7.55 (10H, m,
aromatic), EI-MS (m/z): 463 (M+1); Cal/Ana: [C (67.46)
67.48, H (5.01) 5.03, N (6.05) 6.06].
3,4-Dimethoxyphenyl-3-(4-fluorophenyl)-6,7-dimethoxy-2,
3,3a,4-tetrahydroindeno[1,2-c]pyrazol-2-ylmethanone
(4j) IR: (KBr) cm−1: 3040 (CH), 1592 (C=N), 1672
(C=O), 1320 (C-N), 770 (C-F). 1H NMR (DMSO-d6)
ppm: 2.36 (2H, m, CH2), 3.82 (12H, s, OCH3), 3.09 (1H,
m, CH), 5.16-(1H, d, CH), 6.6–7.55 (9H, m, aromatic),
EI-MS (m/z): 477 (M+1); Cal/Ana: [C (68.06) 68.08, H
(5.29) 5.27, N (5.88) 5.86].
3 - ( 4 - F l u o r o p h e n y l ) - 6 , 7 - d i m e t h o x y - 2 , 3 , 3 a ,
4-tetrahydroindeno[1,2- c]pyrazol-2-yl-3-methoxy-
phenylmethanone (4q) IR: (KBr) cm−1: 3040 (CH), 1592
(C=N), 1672 (C=O), 1320 (C-N), 770 (C-F). 1H NMR
(DMSO-d6) ppm: 2.36 (2H, m, CH2), 3.82 (9H, s, OCH3),
3.09 (1H, m, CH), 5.16-(1H, d, CH), 6.6–7.55 (10H, m,
aromatic), EI-MS (m/z): 447 (M+1); Cal/Ana: [C (69.94)
69.02, H (5.19) 5.17, N (6.27) 6.26].
3,4-Dimethoxyphenyl-3-(3,4- dimethoxyphenyl)-6,
7-dimethoxy-2,3,3a,4-tetrahydroindeno[1,2-c]pyrazol-2-
ylmethanone (4k) IR: (KBr) cm−1: 3322 (NH2), 3040 (CH),
1592 (C=N), 1672 (C=O), 1320 (C-N). 1H NMR (DMSO-d6)
ppm: 2.36 (2H, m, CH2), 3.82 (18H, s, OCH3), 3.09 (1H, m,
CH), 5.16-(1H, d, CH), 6.6–7.55 (8H, m, aromatic), EI-MS
(m/z): 519 (M+1); Cal/Ana: [C (67.17) 67.18, H (5.83) 5.84,
N (5.40) 5.41].
3 - ( 3 , 4 - D i m e t h ox y p h e ny l ) - 6 , 7 - d i m e t h ox y- 2 , 3 , 3 a ,
4-tetrahydroindeno[1,2- c]pyrazol-2-yl-3-methoxy-
phenylmethanone (4r) IR: (KBr) cm−1: 3322 (NH2), 3040
(CH), 1592 (C=N), 1672 (C=O), 1320 (C-N). 1H NMR
(DMSO-d6) ppm: 2.36 (2H, m, CH2), 3.82 (15, s, OCH3),
3.09 (1H, m, CH), 5.16-(1H, d, CH), 6.6–7.55 (9H, m,
aromatic), EI-MS (m/z): 489 (M+1); Cal/Ana: [C (68.84)
68.86, H (5.78) 5.80, N (5.73) 5.75].
6 , 7 - D i m e t h o x y - 3 - ( 4 - m e t h o x y p h e n y l ) - 2 , 3 , 3 a ,
4-tetrahydroindeno[1,2-c]pyrazol-2-yl-3,4-dimethoxy-
phenylmethanone (4l) IR: (KBr) cm−1: 3322 (NH2), 3040
(CH), 1592 (C=N), 1672 (C=O), 1320 (C-N). 1H NMR
(DMSO-d6) ppm: 2.36 (2H, m, CH2), 3.82 (15H, s, OCH3),
3.09 (1H, m, CH), 5.16-(1H, d, CH), 6.6–7.55 (9H, m,
aromatic), EI-MS (m/z): 489 (M+1); Cal/Ana: [C (68.84)
68.82, H (5.78) 5.76, N (5.73) 5.71].
6 , 7 - D i m e t h o x y - 3 - ( 4 - m e t h o x y p h e n y l ) - 2 , 3 , 3 a ,
4-tetrahydroindeno[1,2- c]pyrazol-2-yl-3-methoxy-
phenylmethanone (4s) IR: (KBr) cm−1: 3322 (NH2), 3040
(CH), 1592 (C=N), 1672 (C=O), 1320 (C-N). 1H NMR
(DMSO-d6) ppm: 2.36 (2H, m, CH2), 3.82 (12H, s, OCH3),
3.09 (1H, m, CH), 5.16-(1H, d, CH), 6.6–7.55 (10H, m,
aromatic), EI-MS (m/z): 459 (M+1); Cal/Ana: [C (70.73)
70.75, H (5.72) 5.74, N (6.11) 6.13].
3,4-Dimethoxyphenyl-6,7-dimethoxy-3-phenyl-2,3,3a,
4-tetrahydroindeno[1,2-c]pyrazol-2-ylmethanone (4m) IR:
(KBr) cm−1: 3322 (NH2), 3040 (CH), 1592 (C=N), 1672
(C=O), 1320 (C-N). 1H NMR (DMSO-d6) ppm: 2.36 (2H, m,
CH2), 3.82 (12H, s, OCH3), 3.09 (1H, m, CH), 5.16-(1H, d,
CH), 6.6–7.55 (10H, m, aromatic), EI-MS (m/z): 459 (M+1);
Cal/Ana: [C (70.73) 70.72, H (5.72) 5.73, N (6.11) 6.13].
6,7-Dimethoxy-3-phenyl-2,3,3a,4-tetrahydroindeno[1,2-c]
pyrazol-2-yl-3-methoxyphenyl methanone (4t) IR: (KBr)
cm−1: 3322 (NH2), 3040 (CH), 1592 (C=N), 1672 (C=O),
1320 (C-N). 1H NMR (DMSO-d6) ppm: 2.36 (2H, m, CH2),
3.82 (9H, s, OCH3), 3.09 (1H, m, CH), 5.16-(1H, d, CH),
6.6–7.55 (11H, m, aromatic), EI-MS (m/z): 429 (M+1);
Cal/Ana: [C (72.88) 72.86, H (5.65) 5.63, N (6.54) 6.53].
4-[2-(3,4-Dimethoxybenzoyl)-6,7-dimethoxy-2,3,3a,4-tetra-
hydroindeno[1,2-c]pyrazol-3-yl]benzonitrile (4n) IR: (KBr)
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