Novel Microwave-Assisted Synthesis of the Immunomodulator Organotellurium Compound Ammonium Trichloro(dioxoethylene-O,O')tellurate (AS101)
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Experimental Procedure
3.1.1. AS101 Obtention by Method A
- Found (%): C, 7.70; H, 2.58; N, 4.49. C2H8Cl3NO2Te.
- Calculated (%): C, 7.85; H, 2.37; N, 4.42.
- IR (Golden-Gate): v = 3183 (NH): 1390 (NH4+): 1019: 894 cm−1.
- NMR-1H (DMSO-d6, δ, ppm): 4.36 (s, 4H, CH2): 7.16 (t, 4H, J = 50 Hz, NH4+).
- NMR-13C (DMSO-d6, δ, ppm): 68.13.
- EM (m/z): 292 (M+-NH4,1), 290 (M+–NH4+,1), 260 (M+–NH4+–Cl [Te130, 2Cl35],7), 258 (M+–NH4+–Cl [Te128, 2Cl35],13), 256 (M+–NH4+–Cl [Te126, 2Cl35],13), 254 (9), 224 (42), 223 (35), 221 (19), 200 (36), 198 (27), 196 (14), 190 (69), 188 (63), 186 (37), 165 (21), 163 (18), 161 (11), 146 (5), 130 (25), 128 (23), 126 (13).
3.1.2. AS101 Obtention by Method B
- Found (%): C, 7.81; H, 2.33; N, 4.45. C2H8Cl3NO2Te.
- Calculated (%): C, 7.70; H, 2.58; N, 4.49.
- IR (Golden-Gate): 3198 (NH): 1399 (NH4+): 1017: 889 cm−1.
- NMR-1H (DMSO-d6, δ, ppm): 4.36 (s, 4H, CH2): 7.16 (s, 4H, NH4+).
- NMR-13C (DMSO-d6, δ, ppm): 68.10.
- EM (m/z): 292 (M+–NH4+,1), 290 (M+–NH4+,1), 260 (M+–NH4+–Cl [Te130,2Cl35], 11), 258 (M+–NH4+–Cl [Te128, 2Cl35],20), 256 (M+–NH4+–Cl [Te126, 2Cl35],21), 254 (14), 224 (52), 223 (43), 221 ( 23), 200 (46), 198 (36), 196 (18), 190 (100), 188 (92), 186 (54), 165 (27), 163 (23), 161 (14), 146 (7), 130 (32), 128 (30), 126 (18).
3.2. 1H-NMR and 13C-NMR Analysis
3.3. MS Analysis
3.4. Infrared Spectroscopy (FTIR)
3.5. Optimization of MAOS AS101 Procedure
3.6. Statistical Analyses
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Key | High level (+) | Low level (−) | Unit | |
---|---|---|---|---|
Method A | ||||
Power | X1a | 90 | 50 | watt |
Pressure | X2a | 7 | 3 | bar |
Time | X3a | 30 | 10 | minute |
Method B | ||||
Power | X1b | 80 | 50 | watt |
Temperature | X2b | 120 | 80 | °C |
Time | X3b | 20 | 10 | minute |
X1a | X2a | X3a | X1b | X2b | X3b | Yield Method A | Yield Method B | |
---|---|---|---|---|---|---|---|---|
1 | + | + | + | + | − | − | 73.5 ± 2.1 | 20.0 ± 4.2 |
2 | − | + | + | − | + | − | 78.5 ± 0.7 | 34.5 ± 2.1 |
3 | − | − | + | + | − | + | 67.0 ± 2.8 | 38.0 ± 5.7 |
4 | + | − | − | + | + | − | 53.0 ± 1.4 | 45.0 ± 0.3 |
5 | − | + | − | + | + | + | 78.5 ± 0.7 | 36.5 ± 0.7 |
6 | + | − | + | − | + | + | 75.5 ± 0.7 | 31.0 ± 2.8 |
7 | + | + | − | − | − | + | 53.0 ± 1.4 | 33.0 ± 1.4 |
8 | − | − | − | − | − | − | 0 | 0 |
Source | Sum of squares | df | Mean square | F value | p value Prob > F |
---|---|---|---|---|---|
X1a | 7.99 | 1 | 7.99 | 1.57 | 0.2452 |
X2a | 449.122 | 1 | 449.122 | 88.36 | <0.0001 |
X3a | 1128.12 | 1 | 1128.12 | 221.94 | <0.0001 |
X1a* X2a | 4.74 | 1 | 4.74 | 0.93 | 0.3624 |
X1a* X3a | 149.51 | 1 | 149.51 | 29.41 | <0.0001 |
X2a* X3a | 64.52 | 1 | 64.52 | 12.69 | 0.0074 |
Total error | 40.66 | 8 | 5.08 | ||
Cor total | 1846.32 | 15 | |||
X1b | 8.57 | 1 | 8.57 | 0.29 | 0.6048 |
X2b | 4.98 | 1 | 4.98 | 0.17 | 0.6921 |
X3b | 7.54 | 1 | 7.54 | 0.26 | 0.6269 |
X1b* X2b | 455.07 | 1 | 455.07 | 15.40 | 0.0044 |
X1b* X3b | 592.31 | 1 | 592.31 | 20.05 | 0.0021 |
X2b* X3b | 155.68 | 1 | 155.68 | 5.27 | 0.0505 |
Total error | 236.35 | 8 | 29.54 | ||
Cor total | 1472.22 | 15 |
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Vázquez-Tato, M.P.; Mena-Menéndez, A.; Feás, X.; Seijas, J.A. Novel Microwave-Assisted Synthesis of the Immunomodulator Organotellurium Compound Ammonium Trichloro(dioxoethylene-O,O')tellurate (AS101). Int. J. Mol. Sci. 2014, 15, 3287-3298. https://doi.org/10.3390/ijms15023287
Vázquez-Tato MP, Mena-Menéndez A, Feás X, Seijas JA. Novel Microwave-Assisted Synthesis of the Immunomodulator Organotellurium Compound Ammonium Trichloro(dioxoethylene-O,O')tellurate (AS101). International Journal of Molecular Sciences. 2014; 15(2):3287-3298. https://doi.org/10.3390/ijms15023287
Chicago/Turabian StyleVázquez-Tato, M. Pilar, Alberto Mena-Menéndez, Xesús Feás, and Julio A. Seijas. 2014. "Novel Microwave-Assisted Synthesis of the Immunomodulator Organotellurium Compound Ammonium Trichloro(dioxoethylene-O,O')tellurate (AS101)" International Journal of Molecular Sciences 15, no. 2: 3287-3298. https://doi.org/10.3390/ijms15023287