Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus
Abstract
:Introduction
Results and Discussion
Biological activities
Experimental
General
Antibacterial activity
Conclusions
References
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Sample Availability: Samples are available from the authors. |
Comp. No. | M.P. (T/oC)a | Molecular Formula (MW) | Analysis (%) Found/calculated | ||
---|---|---|---|---|---|
C | H | N | |||
1 | 108-110a | C14H10O2 (210.23) | 79.95 (79.98) | 4.78 (4.79) | - |
2 | 172-174a | C20H16N2O (300.35) | 79.96 (79.98) | 5.35 (5.37) | 9.30 (9.33) |
3 | 180-182a | C22H14N2O2 (338.36) | 78.00 (78.09) | 4.12 (4.17) | 8.20 (8.28) |
4a | 185-187a | C25H14N4O (386.40) | 77.65 (77.71) | 3.60 (3.65) | 14.47 (14.50) |
4b | 292-294b | C25H16N4O2 (404.42) | 74.20 (74.25) | 3.95 (3.99) | 13.78 (13.85) |
4c | 265-267a | C25H16N4OS (420.49) | 71.35 (71.41) | 3.80 (3.84) | 13.25 (13.32) |
5 | 350-352a | C26H16N4O4 (448.43) | 69.60 (69.64) | 3.55 (3.60) | 12.35 (12.49) |
6a | 280-282c | C22H16N4O (352.39) | 74.90 (74.98) | 4.50 (4.58) | 15.85 (15.90) |
6b | 190-192d | C29H24N4O (444.53) | 78.29 (78.36) | 5.35 (5.44) | 12.55 (12.60) |
6c | 220-222d | C25H22N4O2 (410.47) | 73.10 (73.15) | 5.32 (5.40) | 13.60 (13.65) |
6d | 228-230b | C23H17N5OS (411.48) | 67.09 (67.13) | 4.12 (4.16) | 16.95 (17.02) |
6e | 345-347e | C25H17N5O2 (419.43) | 71.50 (71.59) | 4.05 (4.09) | 16.67 (16.70) |
7a | 174-176d | C29H23N3O (429.51) | 81.00 (81.09) | 5.32 (5.40) | 9.70 (9.78) |
7b | 170-172d | C29H22ClN3O (463.96) | 75.00 (75.07) | 4.70 (4.78) | 9.00 (9.06) |
8 | 260-262b | C36H22N2O3 (530.57) | 81.40 (81. 49) | 4.12 (4.18) | 5.25 (5.28) |
10 | 218-220c | C32H22N4O2 (494.54) | 77.70 (77.72) | 4.35 (4.48) | 11.30 (11.33) |
12 | 208-210a | C31H24N4O4 (516.55) | 72.00 (72.08) | 4.60 (4.68) | 10.80 (10.85) |
13 | 260-262b | C34H20N44O4 (548.55) | 74.40 (74.44) | 3.60 (3.67) | 10.18 (10.21) |
14 | 271-273c | C25H17N5O2S (451.50) | 66.45 (66.50) | 3.72 (3.80) | 15.45 (15.51) |
15 | 220-222c | C26H19N5OS (449.53) | 69.42 (69.47) | 4.23 (4.26) | 15.54 (15.85) |
16 | 255-257c | C27H21N5O3S (495.55) | 65.38 (65.44) | 4.23 (4.27) | 14.00 (14.13) |
Comp. No. | m/z (intensity/%) | |||||||
---|---|---|---|---|---|---|---|---|
M+ | 336 | 310 | 232 | 193 | 139 | 77 | Other peaks | |
1 | 210 (32) | 139(100) | 168(3), 113(11), 89(15), 63(38). | |||||
3 | 338 (100) | 310 (20) | 139 (15) | 77 (62) | 234 (1), 208 (1), 167 (1) | |||
4b | 404 (100) | 232 (1) | 193 (3) | 139 (12) | 77 (67) | 360 (25), 283 (4), 257 (3), | ||
4c | 420 (35) | 310 (1) | 193 (8) | 139 (15) | 77 (58) | 386(100), 281(2) | ||
5 | 448 (100) | 139 (7) | 77 (34) | 338 (14), 290 (11), 22 4(5), 181 (3) | ||||
6a | 352 (100) | 336 (66) | 139 (30) | 77 (44) | 168 (20) | |||
6b | 428 (100) | 336 (60) | 139 (13) | 77 (64) | 351 (1), 284 (15), 176 (11) | |||
6c | 394 (100) | 336 (29) | 139 (5) | 77 (20) | 352 (10), 309 (2), 232 (3), 180 (1) | |||
6d | 411 (1) | 336 (100) | 77 (32) | 308 (2), 233 (2), 20 (1), 181 (1) | ||||
7b | 530 (65) | 336 (100) | 232 (5) | 139 (41) | 77 (28) | 258 (4), 195 (16) | ||
8 | 447 (100) | 336 (7) | 310 (2) | 233 (3), 207 (5), 141 (15), 76 (64) | ||||
10 | 494 (100) | 310 (2) | 193 (5) | 139 (8) | 77 (31) | 466 (2), 386 (25), 233 (4) | ||
12 | 516 (2) | 193 (13) | 139 (5) | 77 (16) | 386 (100), 323 (12), 254 (4), | |||
13 | 548 (2) | 310 (5) | 139 (11) | 482 (15), 414 (9), 268 (12), 215 (25), 162 (23), 71 (60) | ||||
16 | 495 (45) | 336(100) | 232 (3) | 193(4) | 77 (40) | 453 (18), 394 (29), 306 (4) |
Comp. No. | Inhibition zone diameter (mm per 200 mcg sample) | |||||
---|---|---|---|---|---|---|
(BS) ACTC 10400 | (SA) NCTC 7447 | (EC) NCTC 10410 | (PA) ATCC 10415 | (CA) IMRU 3669 | (AN) ATCC 6275 | |
2 | ++ ve | ++ ve | ++ ve | ++ ve | - ve | - ve |
14 | +++ ve | +++ ve | +++ ve | +++ ve | +++ ve | +++ ve |
Neomycin (30 µg mL–1) | +++ ve | +++ ve | +++ ve | +++ ve | +++ ve | +++ ve |
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El-Wahab, A.H.F.A.; Al-Fifi, Z.I.A.; Bedair, A.H.; Ali, F.M.; Halawa, A.H.A.; El-Agrody, A.M. Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus. Molecules 2011, 16, 307-318. https://doi.org/10.3390/molecules16010307
El-Wahab AHFA, Al-Fifi ZIA, Bedair AH, Ali FM, Halawa AHA, El-Agrody AM. Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus. Molecules. 2011; 16(1):307-318. https://doi.org/10.3390/molecules16010307
Chicago/Turabian StyleEl-Wahab, Ashraf H. F. Abd, Zarrag Isa A. Al-Fifi, Ahmed H. Bedair, Fawzy M. Ali, Ahmed H. A. Halawa, and Ahemed M. El-Agrody. 2011. "Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus" Molecules 16, no. 1: 307-318. https://doi.org/10.3390/molecules16010307