Synthesis and Spectroscopic Identification of Certain Imidazole-Semicarbazone Conjugates Bearing Benzodioxole Moieties: New Antifungal Agents
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Crystal Structure of Compound 5e
2.3. Antifungal Activity of the Target Semicarbazones 5a–o
3. Experimental
3.1. General Information
3.2. Synthesis
3.2.1. General Procedure for the Synthesis of Semicarbazones 5a–n
3.2.2. Synthesis of (2E)-2-[1-(1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]hydrazine Carboxamide (5o)
3.3. Crystal Structure Determination of Compound 5e
3.4. Antifungal Activity of the Title Semicarbazones 5a–o
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the synthesized compounds are available from the corresponding authors. |
Compound No. | R | Compound No. | R | Compound No. | R | Compound No. | R |
5a | C6H5 | 5e | 4-OC2H5-C6H4 | 5i | 3-CH3-C6H4 | 5m | 3,4-Cl2-C6H3 |
5b | 4-Br-C6H4 | 5f | 4-F-C6H4 | 5j | 4-CH3-C6H4 | 5n | C6H9 |
5c | 3-Cl-C6H4 | 5g | 4-OCH3-C6H4 | 5k | 3-CF3-C6H4 | 5o | H |
5d | 4-Cl-C6H4 | 5h | 2-CH3-C6H4 | 5l | 2,4-Cl2-C6H3 |
O1—C1 | 1.362 (7) | N1—C13 | 1.366 (14) |
O1—C7 | 1.425 (7) | N2—C12 | 1.399 (18) |
O2—C6 | 1.376 (7) | N2—C13 | 1.293 (17) |
O2—C7 | 1.427 (6) | N3—N4 | 1.380 (7) |
O3—C14 | 1.229 (8) | N3—C8 | 1.294 (7) |
O4—C18 | 1.372 (7) | N4—C14 | 1.372 (8) |
O4—C21 | 1.430 (7) | N5—C14 | 1.345 (9) |
N1—C10 | 1.443 (11) | N5—C15 | 1.431 (8) |
N1—C11 | 1.366 (14) | ||
C1—O1—C7 | 105.0 (4) | N3—C8—C3 | 115.0 (4) |
C6—O2—C7 | 105.1 (4) | N3—C8—C9 | 125.8 (5) |
C18—O4—C21 | 118.5 (4) | N1—C10—C9 | 112.8 (5) |
C10—N1—C11 | 126.2 (8) | N1—C11—C12 | 107.5 (10) |
C10—N1—C13 | 128.4 (8) | N2—C12—C11 | 109.4 (12) |
C11—N1—C13 | 105.2 (9) | N1—C13—N2 | 113.3 (11) |
C12—N2—C13 | 104.5 (11) | N4—C14—N5 | 116.4 (6) |
N4—N3—C8 | 118.3 (4) | O3—C14—N4 | 119.5 (6) |
N3—N4—C14 | 117.6 (5) | O3—C14—N5 | 124.1 (6) |
C14—N5—C15 | 125.7 (6) | N5—C15—C20 | 117.9 (5) |
O1—C1—C6 | 110.4 (5) | N5—C15—C16 | 122.4 (6) |
O1—C1—C2 | 128.1 (4) | O4—C18—C17 | 126.2 (5) |
O2—C6—C5 | 129.5 (4) | O4—C18—C19 | 114.6 (5) |
O2—C6—C1 | 109.0 (4) | O4—C21—C22 | 106.5 (5) |
O1—C7—O2 | 107.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H1NA···O3 i | 1.01(6) | 1.87(6) | 2.857(6) | 167(5) |
N5—H1NB···N3 | 0.68(7) | 2.21(7) | 2.611(7) | 120(7) |
C5—H5A···O1 ii | 0.9300 | 2.5500 | 3.454(6) | 164.00 |
C9—H9A···O3 i | 0.9700 | 2.4200 | 3.182(7) | 135.00 |
C21—H21A···N2 iii | 0.9700 | 2.5700 | 3.500(13) | 160.00 |
Compound No. | Candida albicans | Candida tropicalis | Candida parapsilosis | Asperagillus niger | ||||
---|---|---|---|---|---|---|---|---|
DIZ ± SD * (mm) | MIC (µmol/mL) | DIZ ± SD * (mm) | MIC (µmol/mL) | DIZ ± SD * (mm) | MIC (µmol/mL) | DIZ ± SD * (mm) | MIC (µmol/mL) | |
5a | 14 ± 0.60 | 0.678 | 20 ± 0.90 | 0.339 | 11 ± 0.80 | 0.678 | 15 ± 0.50 | 0.678 |
5b | 12 ± 0.70 | > 1.12 | 18 ± 0.50 | > 1.12 | 15 ± 0.58 | >1.12 | 14 ± 0.40 | 0.561 |
5c | 14 ± 0.58 | 0.311 | 20 ± 0.90 | 0.311 | 16 ± 1.10 | 0.622 | 15 ± 0.50 | 0.622 |
5d | 14 ± 0.60 | 0.622 | 17 ± 0.50 | > 1.24 | 14 ± 0.40 | >1.24 | 0.0 ± 0.0 | >1.24 |
5e | 13 ± 0.40 | 0.607 | 22 ± 0.80 | 0.304 | 16 ± 0.12 | 0.304 | 13 ± 1.00 | 0.607 |
5f | 14 ± 0.60 | 0.648 | 17 ± 1.00 | > 1.30 | 14 ± 0.60 | 0.648 | 16 ± 1.10 | 0.648 |
5g | 14 ± 0.58 | 0.628 | 22 ± 0.50 | 0.314 | 12 ± 1.20 | 0.628 | 15 ± 0.50 | 0.628 |
5h | 14 ± 1.00 | 0.654 | 19 ± 0.50 | 0.654 | 18 ± 0.90 | 0.327 | 14 ± 1.00 | 0.654 |
5i | 13 ± 0.40 | 0.654 | 21 ± 1.00 | 0.327 | 17 ± 0.58 | 0.654 | 13 ± 0.40 | 0.654 |
5j | 13 ± 1.00 | 0.654 | 22 ± 1.00 | 0.327 | 17 ± 0.90 | 0.327 | 15 ± 0.58 | 0.654 |
5k | 12 ± 0.43 | 0.287 | 23 ± 0.50 | 0.287 | 15 ± 0.60 | 0.575 | 14 ± 0.80 | 0.575 |
5l | 14 ± 0.58 | 0.287 | 21 ± 1.00 | 0.574 | 14 ± 0.60 | 0.574 | 13 ± 0.40 | 0.574 |
5m | 11 ± 0.30 | 0.574 | 17 ± 0.80 | >1.15 | 16 ± 0.58 | >1.15 | 16 ± 0.80 | 0.574 |
5n | 14 ± 0.40 | 0.668 | 19 ± 1.00 | 1.34 | 19 ± 0.50 | >1.24 | 13 ± 1.00 | 0.668 |
5o | 14 ± 0.58 | 0.850 | 20 ± 0.90 | 0.850 | 15 ± 0.90 | 0.850 | 14 ± 0.10 | 0.850 |
Fluconazole | 18 ± 1.10 | 0.051 | 19 ± 1.00 | 0.045 | 19 ± 0.90 | 0.047 | ND | ND |
Ketoconazole | ND | ND | ND | ND | ND | ND | 29 ± 0.60 | 0.02 |
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Al-Wabli, R.I.; Al-Ghamdi, A.R.; Ghabbour, H.A.; Al-Agamy, M.H.; Attia, M.I. Synthesis and Spectroscopic Identification of Certain Imidazole-Semicarbazone Conjugates Bearing Benzodioxole Moieties: New Antifungal Agents. Molecules 2019, 24, 200. https://doi.org/10.3390/molecules24010200
Al-Wabli RI, Al-Ghamdi AR, Ghabbour HA, Al-Agamy MH, Attia MI. Synthesis and Spectroscopic Identification of Certain Imidazole-Semicarbazone Conjugates Bearing Benzodioxole Moieties: New Antifungal Agents. Molecules. 2019; 24(1):200. https://doi.org/10.3390/molecules24010200
Chicago/Turabian StyleAl-Wabli, Reem I., Alwah R. Al-Ghamdi, Hazem A. Ghabbour, Mohamed H. Al-Agamy, and Mohamed I. Attia. 2019. "Synthesis and Spectroscopic Identification of Certain Imidazole-Semicarbazone Conjugates Bearing Benzodioxole Moieties: New Antifungal Agents" Molecules 24, no. 1: 200. https://doi.org/10.3390/molecules24010200
APA StyleAl-Wabli, R. I., Al-Ghamdi, A. R., Ghabbour, H. A., Al-Agamy, M. H., & Attia, M. I. (2019). Synthesis and Spectroscopic Identification of Certain Imidazole-Semicarbazone Conjugates Bearing Benzodioxole Moieties: New Antifungal Agents. Molecules, 24(1), 200. https://doi.org/10.3390/molecules24010200