A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Characterization
2.1.1. ICP Analysis of the Mn-Supported Nano-Catalyst
2.1.2. FT-IR Spectroscopy of the Mn-Supported Nano-Catalyst
2.1.3. XRD Analysis of the Mn-Supported Nano-Catalyst
2.1.4. EDX Analysis of the Mn-Supported Nano-Catalyst
2.1.5. SEM and TEM Analysis of the Mn-Supported Nano-Catalyst
2.1.6. Thermal Properties of the Mn-Supported Nano-Catalyst
2.1.7. VSM Analysis of the Mn-Supported Nano-Catalyst
3. Experimental
3.1. General
3.2. Preparation of the Mn-Supported Nano-Catalyst
3.3. General Procedure for the Synthesis of Indazolophthalazinetriones
3.4. Optimization
- The synthesis of indazolophthalazinetriones carried out in the absence of Fe3O4@SiO2@CPTMS@MBOL@Mn: reaction efficiency was very low (trace).
- The reaction was done in the presence of (Fe3O4@SiO2@CPTMS@MBOL) and no product was observed.
3.5. Synthesis of Diverse Indazolophthalazinetriones (2a–j)
3.6. Characterization of the Products
3.7. The Plausible Mechanism
3.8. Comparison of Catalytic Activity
3.9. Reusability of the Mn-Supported Nano-Catalyst
3.10. Antibacterial Properties
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Solvent | Catalyst (mg) | Temperature (°C) | Time (min) | Yield (%) |
---|---|---|---|---|---|
1 | EtOH/H2O | 10 | 80 | 15 | 71 |
2 | EtOH/H2O | 20 | 80 | 15 | 82 |
3 | EtOH/H2O | 30 | 80 | 15 | 74 |
4 | EtOH/H2O | 40 | 80 | 15 | 74 |
5 | EtOH | 20 | 80 | 15 | 90 |
6 | H2O | 20 | 80 | 15 | 76 |
7 | Toluene | 20 | 80 | 15 | 53 |
8 | DMF | 20 | 80 | 15 | 49 |
9 | EtOH | 20 | 60 | 15 | 72 |
10 | EtOH | 20 | 40 | 15 | 37 |
11 | EtOH | 20 | rt | 15 | 21 |
12 | ETOH | 10 | 80 | 15 | 73 |
13 | ETOH | 30 | 80 | 15 | 81 |
14 | ETOH | 40 | 80 | 15 | 83 |
Entry | RCHO (1a-j) | Products (2a-j) | Time (min) | Yield % | M.P. °C, Found (Lit.) [37] |
---|---|---|---|---|---|
1 | 10 | 85 | 202–206 (206–208) | ||
2 | 10 | 91 | 260–263 (262–264) | ||
3 | 10 | 85 | 256–259 (258–260) | ||
4 | 10 | 93 | 267–270 (269–271) | ||
5 | 10 | 91 | 219–222 (219–221) | ||
6 | 15 | 90 | 224–227 (226–228) | ||
7 | 15 | 71 | 219–221 (220–221) | ||
8 | 20 | 82 | 249–251 (251–252) | ||
9 | 25 | 55 | 143–146 (145–147) | ||
10 | 20 | 83 | 228–230 (229–231) |
Refs. | Yield (%) | Time (min) | T b (°C) | Solvent a | Catalyst | Entry |
---|---|---|---|---|---|---|
[38] | 90 | 40 | 70 | SF | MNPs-guanidine (0.03 g) | 1 |
[39] | 86 | 30 | 80 | H2O | β-Cyclodextrin | 2 |
[40] | 66 | 60 | 100 | SF | [Simp]3PW12O40 (0.03 g) | 3 |
[41] | 70 | 60 | 100 | SF | PTA@Fe3O4/EN-MIL-101 (0.02 g) | 4 |
[42] | 86 | 40 | 100 | SF | Fe3O4@Silica sulfuric acid (0.075 g) | 5 |
[43] | 90 | 30 | 100 | SF | MNPs-PSA (0.03) | 6 |
[44] | 86 | 30 | Reflux | EtOH | H2SO4 (0.015 %mmole) in EtOH/H2O | 7 |
[45] | 87 | 30 | 80 | SF | MnFe2O4@SiO2@NH-NH2-PTA (0.03 g) | 8 |
[46] | 94 | 150 | 50 | PEG | CAN (5 %mol) | 9 |
PW c | 90 | 15 | Reflux | EtOH | Fe3O4@SiO2@CPTMS@MBOL@Mn (0.02 g) | 10 |
Microorganisms | Standard | Blank | Zone of Inhabitation (mm) |
---|---|---|---|
Tetracycline (10 mg/mL) | DMSO | the Mn catalyst | |
MIC (mg/mL) | 8 | - | 8 |
Gram (+) | |||
Bacillus thuringiensis | 30 | - | 10 |
Bacillus cereus | 36 | - | 20 |
Staphylococcus aureus | 30 | - | 5 |
Gram (−) | 25 | - | 20 |
Pseudomonas aeruginosa Serratia marcescens | 20 | - | 30 |
Escherichia coli | 22 | - | 15 |
Klebsiella pneumoniae | 25 | - | 5 |
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Ariannezhad, M.; Habibi, D.; Heydari, S.; Khorramabadi, V. A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity. Chemistry 2021, 3, 783-799. https://doi.org/10.3390/chemistry3030056
Ariannezhad M, Habibi D, Heydari S, Khorramabadi V. A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity. Chemistry. 2021; 3(3):783-799. https://doi.org/10.3390/chemistry3030056
Chicago/Turabian StyleAriannezhad, Maryam, Davood Habibi, Somayyeh Heydari, and Vahideh Khorramabadi. 2021. "A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity" Chemistry 3, no. 3: 783-799. https://doi.org/10.3390/chemistry3030056