Synthesis and Antibacterial Activities of Novel Imidazo[2,1-b]-1,3,4-thiadiazoles
Abstract
:1. Introduction
2. Results and Discussion
Cpd. No. | IR (cm−1) | 1H-NMR Chemical Shift (δ/ppm) * | ||||||
---|---|---|---|---|---|---|---|---|
C=N | C=N | C=N | C=C | C-S-C | ArH | Imidazole proton | Triazole proton | |
(thiadiazole ring) | (imidazole ring) | (triazole ring) | (imidazole ring) | (thiadiazole ring) | (m) | (s, 1H) | (s, 1H) | |
5a | 1638 | 1594 | 1534 | 1490 | 690 | 7.33–8.14 (10H) | 8.07 | 8.33 |
5b | 1635 | 1595 | 1532 | 1490 | 669 | 7.61–8.84 (9H) | 7.50 | 8.46 |
5c | 1634 | 1594 | 1536 | 1490 | 669 | |||
5d | 1629 | 1527 | 1540 | 1844 | 690 | |||
5e | 1631 | 1555 | 1528 | 1488 | 669 | |||
5f | 1626 | 1600 | 1529 | 1488 | 669 | 7.42–8.11 (8H) | 8.06 | 8.50 |
5g | 1651 | 1601 | 1538 | 1486 | 690 | |||
5h | 1649 | 1565 | 1533 | 1487 | 671 | |||
5i | 1652 | 1599 | 1533 | 1485 | 670 | |||
6a | 1640 | 1597 | 1545 | 1489 | 662 | 7.25–8.14 (10H) | 8.41 | |
6b | 1641 | 1594 | 1522 | 1487 | 669 | 7.44–8.15 (9H) | 8.42 | |
6c | 1637 | 1595 | 1524 | 1488 | 669 | 7.42–8.14 (9H) | 8.41 | |
6d | 1632 | 1549 | 1526 | 1436 | 686 | 7.35–8.06 (9H) | 8.42 | |
6e | 1632 | 1552 | 1522 | 1486 | 669 | 7.57–8.03 (8H) | 8.42 | |
6f | 1628 | 1545 | 1521 | 1686 | 669 | 7.42–8.04 (8H) | 8.42 | |
6g | 1645 | 1550 | 1510 | 1488 | 686 | 7.36–8.10 (9H) | 8.42 | |
6h | 1642 | 1568 | 1519 | 1487 | 672 | 7.49–8.09 (8H) | 8.41 | |
6i | 1641 | 1585 | 1522 | 1488 | 672 | 7.42–8.09 (8H) | 8.41 | |
7a | 1634 | 1595 | 1532 | 1488 | 663 | 7.37–8.15 (10H) | 8.43 | |
7b | 1640 | 1594 | 1527 | 1489 | 668 | 7.42–8.14 (9H) | 8.41 | |
7c | 1636 | 1596 | 1530 | 1489 | 669 | 7.43–8.14 (9H) | 8.41 | |
7d | 1642 | 1547 | 1522 | 1486 | 685 | |||
7e | 1633 | 1565 | 1535 | 1485 | 671 | 7.58–8.03 (8H) | 8.41 | |
7f | 1633 | 1565 | 1521 | 1487 | 671 | 7.43–8.03 (8H) | 8.42 | |
7g | 1639 | 1545 | 1509 | 1488 | 685 | 7.39–8.11 (9H) | 8.42 | |
7h | 1640 | 1595 | 1555 | 1487 | 669 | 7.49–8.09 (8H) | 8.41 | |
7i | 1639 | 1598 | 1565 | 1486 | 670 | 7.43–8.10 (8H) | 8.41 |
Cpd. No. | M | I | II | III |
---|---|---|---|---|
5a | 33 | 2 | 11 | 8 |
5b | 100,78 | 10 | 70 | 5 |
5g | 21 | 5 | 36 | 4 |
5i | 29 | 24 | 40 | 4 |
6a | 69 | 100 | 34 | 18 |
6d | 7 | 57 | 100 | 12 |
6f | 8 | 40 | 8 | 7 |
6g | 22 | 100 | 29 | 19 |
6i | 5 | 35 | 34 | 1 |
7a | 100 | 73 | 22 | 18 |
7e | 39 | 16,15 | 44,46 | 2 |
7g | 46 | 100 | 18 | 57 |
7i | 14 | 36 | 18 | 1 |
Biological screening: antimicrobial activity tests
Test microorganisms | S | C | Ps | E |
---|---|---|---|---|
Test compounds | Average inhibition zone diameter in mms | |||
Imepenam | 30 | - | 30 | 26 |
Ampicillin | 30 | - | - | - |
Clotrimazole | - | 40 | - | - |
2 | - | 18 | 22 | 17 |
3 | - | 18 | 22 | 16 |
4 | - | 18 | 22 | 16 |
5a | - | 18 | 22 | 17 |
5b | - | 18 | 22 | 18 |
5c | - | 18 | 22 | 16 |
5d | - | 18 | 22 | 20 |
5e | - | 18 | 22 | 16 |
5f | - | 18 | 22 | 18 |
5g | - | 18 | 22 | 16 |
5h | - | 19 | 22 | 18 |
5i | - | 18 | 23 | 16 |
6a | - | 19 | 22 | 17 |
6b | - | 18 | 23 | 16 |
6c | - | 18 | 22 | 17 |
6d | - | 18 | 23 | 17 |
6e | - | 18 | 22 | 16 |
6f | - | 18 | 22 | 17 |
6g | - | 18 | 22 | 17 |
6h | - | 18 | 22 | 20 |
6i | - | 18 | 22 | 16 |
7a | - | 18 | 22 | 19 |
7b | - | 18 | 26 | 19 |
7c | - | 18 | 22 | 16 |
7d | - | 18 | 22 | 16 |
7e | - | 19 | 22 | 17 |
7f | - | 19 | 22 | 17 |
7g | - | 19 | 22 | 16 |
7h | - | 18 | 22 | 17 |
7i | - | 18 | 22 | 16 |
8 | - | 18 | 22 | 19 |
DMF | - | 18 | 22 | 16 |
3. Experimental
3.1. General
3.2.1. 2-Amino-5-(2-aryl-2H-1,2,3-triazol-4-yl)-1,3,4-thiadiazoles (2-4)
3.2.2. 6-Aryl-2-(2-aryl-2H-1,2,3-triazol-4-yl)imidazo[2,1-b]-1,3,4-thiadiazoles 5a-i
3.2.3. 6-Aryl-2-(2-aryl-2H-1,2,3-triazol-4-yl)-5-haloimidazo[2,1-b]-1,3,4-thiadiazoles 6a-i and 7a-i
Cpd. No. | Mp (°C) | Yield (%) | Formula | Calcd. % | Found % | ||||
---|---|---|---|---|---|---|---|---|---|
C | H | N | C | H | N | ||||
5a | 225-226 | 60 | C18H12N6S | 62.77 | 3.51 | 24.40 | 62.50 | 3.42 | 24.43 |
5b | 253-254 | 62 | C18H11BrN6S | 51.07 | 2.62 | 19.85 | 51.00 | 2.32 | 19.92 |
5c | 257-258 | 61 | C18H11ClN6S | 57.07 | 2.93 | 22.18 | 57.11 | 2.86 | 22.20 |
5d | 285-286 | 61 | C18H11BrN6S | 51.07 | 2.62 | 19.85 | 51.15 | 2.40 | 20.06 |
5e | 281-282 | 60 | C18H10 Br2N6S | 43.05 | 2.01 | 16.73 | 43.07 | 2.00 | 16.81 |
5f | 276-277 | 66 | C18H10BrClN6S | 47.23 | 2.20 | 18.36 | 47.31 | 2.12 | 18.02 |
5g | 279-280 | 58 | C18H11ClN6S | 57.07 | 2.93 | 22.18 | 57.10 | 2.92 | 22.21 |
5h | 267-268 | 55 | C18H10BrClN6S | 47.23 | 2.20 | 18.36 | 47.19 | 2.26 | 18.41 |
5i | 271-272 | 58 | C18H10 Cl2N6S | 52.31 | 2.44 | 20.33 | 52.40 | 2.40 | 20.21 |
6a | 221-222 | 80 | C18H11BrN6S | 51.07 | 2.62 | 19.85 | 51.12 | 2.42 | 20.03 |
6b | 261-262 | 80 | C18H10 Br2N6S | 43.05 | 2.01 | 16.73 | 43.12 | 2.00 | 16.92 |
6c | 255-256 | 80 | C18H10BrClN6S | 47.23 | 2.20 | 18.36 | 47.21 | 2.15 | 18.38 |
6d | 265-266 | 82 | C18H10 Br2N6S | 43.05 | 2.01 | 16.73 | 43.05 | 2.01 | 16.73 |
6e | 246-247 | 76 | C18H9 Br3N6S | 37.21 | 1.56 | 14.46 | 37.22 | 1.81 | 14.51 |
6f | 248-249 | 80 | C18H9Br2ClN6S | 40.29 | 1.69 | 15.66 | 40.01 | 1.81 | 15.62 |
6g | 257-258 | 80 | C18H10BrClN6S | 47.23 | 2.20 | 18.36 | 47.12 | 2.25 | 18.39 |
6h | 259-260 | 80 | C18H9Br2ClN6S | 0.29 | 1.69 | 15.66 | 40.42 | 1.72 | 15.52 |
6i | 237-238 | 80 | C18H9 BrCl2N6S | 43.93 | 1.84 | 17.08 | 43.90 | 1.87 | 16.90 |
7a | 270-271 | 85 | C18H11IN6S | 45.97 | 2.36 | 17.87 | 45.82 | 2.39 | 17.85 |
7b | 251-252 | 83 | C18H10BrIN6S | 39.37 | 1.84 | 15.30 | 39.40 | 1.90 | 15.21 |
7c | 251-252 | 82 | C18H10ClIN6S | 42.83 | 2.00 | 16.65 | 42.90 | 2.03 | 16.82 |
7d | 273-274 | 85 | C18H10BrIN6S | 39.37 | 1.84 | 15.30 | 39.21 | 1.61 | 15.42 |
7e | 251-252 | 80 | C18H9Br2IN6S | 34.42 | 1.44 | 13.38 | 34.50 | 1.49 | 13.42 |
7f | 243-244 | 85 | C18H9BrClIN6S | 37.04 | 1.55 | 14.40 | 37.24 | 1.52 | 14.43 |
7g | 285-286 | 82 | C18H10ClIN6S | 42.83 | 2.00 | 16.65 | 42.72 | 1.95 | 16.62 |
7h | 255-256 | 84 | C18H9BrClIN6S | 37.04 | 1.55 | 14.40 | 36.92 | 1.61 | 14.41 |
7i | 253-254 | 80 | C18H9Cl2IN6S | 40.10 | 1.68 | 15.59 | 40.20 | 1.72 | 15.51 |
3.2.4. 5-Formyl-6-phenyl-2-(2-phenyl-2H-1,2,3-triazol-4-yl)imidazo[2,1-b]-1,3,4-thiadiazole (8)
3.3. Antibacterial Activity Tests
4. Conclusions
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Atta, K.F.M.; Farahat, O.O.M.; Ahmed, A.Z.A.; Marei, M.G. Synthesis and Antibacterial Activities of Novel Imidazo[2,1-b]-1,3,4-thiadiazoles. Molecules 2011, 16, 5496-5506. https://doi.org/10.3390/molecules16075496
Atta KFM, Farahat OOM, Ahmed AZA, Marei MG. Synthesis and Antibacterial Activities of Novel Imidazo[2,1-b]-1,3,4-thiadiazoles. Molecules. 2011; 16(7):5496-5506. https://doi.org/10.3390/molecules16075496
Chicago/Turabian StyleAtta, Kamal F. M., Omaima O.M. Farahat, Alaa Z. A. Ahmed, and Mohamed G. Marei. 2011. "Synthesis and Antibacterial Activities of Novel Imidazo[2,1-b]-1,3,4-thiadiazoles" Molecules 16, no. 7: 5496-5506. https://doi.org/10.3390/molecules16075496