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CAS No. : | 22994-85-0 | MDL No. : | |
Formula : | C12H12N4O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CULUWZNBISUWAS-UHFFFAOYSA-N |
M.W : | 260.25 | Pubchem ID : | 31593 |
Synonyms : |
Ro 71051;Ro 07-1051;Rochagan.;NSC 299972;Radanil;Benznidazol
|
Chemical Name : | N-Benzyl-2-(2-nitro-1H-imidazol-1-yl)acetamide |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
, in which the chemical compound is a nitroimidazole derivative selected from the group consisting of 2-methyl-5-nitroimidazole-1-ethanol (Metronidazole); 1-[2-(ethylsulphonyl)ethyl]-2-methyl-5-nitroimidazole (Tinidazole); 4-[2-(5-nitroimidazol-1-yl)ethyl]morpholine (Nimorazole); 1-chloro-3-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol (Omidazole); and N-benzyl-2-(2-nitroimidazol-1-yl)acetamide (Benznidazole). | ||
In a fourth preferred embodiment, the chemical compound having IKCa inhibitory activity for use according to the invention is a nitroimidazole derivative selected from the group consisting of 2-methyl-5-nitroimidazole-1-ethanol (Metronidazole); 1-[2-(ethylsulphonyl)ethyl]-2-methyl-5-nitroimidazole (Tinidazole); 4-[2-(5-nitroimidazol-1-yl)ethyl]morpholine (Nimorazole); 1-chloro-3-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol (Omidazole), and N-benzyl-2-(2-nitroimidazol-1-yl)acetamide (Benznidazole). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In aq. phosphate buffer at 37℃; for 24h; | General procedure for nucleophilic thiol addition to nitroaromatic compounds for NOA and GC measurements. General procedure: In a 10 mL septum sealed round bottom flask, the nitroaromatic antibiotic (0.1 mmol) and 2-aminoethanethiol (45 mg, 0.40 mmol) in phosphate buffer (e.g. PBS buffer, 100 mM, pH = 7.4) (2 mL) were stirred at 37 °C for one day. Subsequent experiments were done with glutathione. In a 10 mL septum sealed round bottom flask, the nitroaromatic antibiotic (0.1 mmol) and glutathione (123 mg, 0.40 mmol) in phosphate buffer (e.g. PBS buffer, 100 mM, pH = 7.4) (2 mL) were stirred at 37 °C for one day. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate In aq. phosphate buffer; ethanol at 37℃; for 24h; | General procedure for sodium borohydride mediated reduction of nitroaromatic compounds for NOA and GC measurements General procedure: In a 10 mL septum sealed round bottom flask, the nitroaromatic antibiotic (0.1 mmol) and NaBH4 (15.13 mg, 0.4 mmol) in phosphate buffer (e.g. PBS buffer, 100 mM, pH = 7.4)/EtOH mixture (2 mL) were stirred at 37 °C for one day. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23 % | at 20℃; | [CuCl2(BZN)(H2O)]·1/2CH3CN (2) A solution of copper chloride (0.17mmol) in acetonitrile (20mL) was added to a round-bottom flask containing benznidazole (0.33mmol) dissolved in 20mL acetonitrile. The mixture was stirred under room temperature for 30min. The initially yellow solution turned green. Then, the solvent was evaporated to of its volume and sat it in the fridge for 3h. A green solid precipitated which was filtered through cannula and dried under vacuum. Yield: 23%. Elemental analyses calcd. (%) for: C25H27N9O7Cl2.Cu C: 36.04; H: 3.61; N: 14.55, found: C: 36.26; H: 4.44; N: 14.08. IR [cm-1 (assign)]: 3297 (NH), 3120 (C-H aromatic), 1533 (C=N), 1502 (C=C), 1676 (C=O), 1369 (NO2/NO3). Λm (Ω-1.cm2.mol-1): 24.32. λmax nm in DMSO (, M-1cm-1): 323(23154). EPR experimental data: giso=2.138, in solid sample at 77K. |
23 % | at 20℃; | [CuCl2(BZN)(H2O)]·1/2CH3CN (2) A solution of copper chloride (0.17mmol) in acetonitrile (20mL) was added to a round-bottom flask containing benznidazole (0.33mmol) dissolved in 20mL acetonitrile. The mixture was stirred under room temperature for 30min. The initially yellow solution turned green. Then, the solvent was evaporated to of its volume and sat it in the fridge for 3h. A green solid precipitated which was filtered through cannula and dried under vacuum. Yield: 23%. Elemental analyses calcd. (%) for: C25H27N9O7Cl2.Cu C: 36.04; H: 3.61; N: 14.55, found: C: 36.26; H: 4.44; N: 14.08. IR [cm-1 (assign)]: 3297 (NH), 3120 (C-H aromatic), 1533 (C=N), 1502 (C=C), 1676 (C=O), 1369 (NO2/NO3). Λm (Ω-1.cm2.mol-1): 24.32. λmax nm in DMSO (, M-1cm-1): 323(23154). EPR experimental data: giso=2.138, in solid sample at 77K. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71 % | In acetonitrile at 20℃; Inert atmosphere; Darkness; Schlenk technique; | [Ag(PPh3)2(BZN)2]NO3·H2O (3) [Ag(PPh3)2]NO3 (0.18mmol) was dissolved in dried acetonitrile (30mL) and added to a Schlenk tube containing benznidazole (0.36mmol) dissolved in acetonitrile (30mL). The reaction was stirred for 3h at room temperature under inert atmosphere and protected from light. The transparent solution became pale yellow. After the reaction was complete, the solvent was evaporated and a pale-yellow solid was obtained. Yield: 71%. Elemental analyses calcd. (%) for:C60H56N9O10Ag: C: 58.45; H: 4.58; N: 10.22. found: C: 58.65; H: 4.49; N: 10.86. IR [cm-1 (assign)]: 3266 (NH), 3035-3105 (C-H aromatic), 1561 (C=N), 1654 (C=O), 1350 (NO2/NO3), 1150 (C-P), 694 (P-Ph). (Ω-1.cm2.mol-1): 27.70. λmax nm in DMSO (, M-1cm-1): 328 (24168). 1H NMR (DMSO-d6) [δppm, (integral, assignation)]: 4.34 (H9, 2H, J=5.8Hz); 5.18 (H6, 2H, s); 7.20 (H5, 2H, s); 7.54-7.24 (PPh3, H11, H12, H13, H14, H15, 19H);7.65 (H4, 1H, J=1.0Hz); 8.84 (N-H, 1H, J=5.9Hz).13C NMR (DMSO-d6): 42.27 (C9), 51.61 (C6), 126.95-133.51(C4, C5, C11, C12, C13, C14, C15, CPPh3), 138.87 (C2), 138.87 (C10), 145.07 (C2), 165.68 (C7)· 31P{1H}-NMR (DMSO-d6): 9.04 (PPh3). |
71 % | In acetonitrile at 20℃; Inert atmosphere; Darkness; Schlenk technique; | [Ag(PPh3)2(BZN)2]NO3·H2O (3) [Ag(PPh3)2]NO3 (0.18mmol) was dissolved in dried acetonitrile (30mL) and added to a Schlenk tube containing benznidazole (0.36mmol) dissolved in acetonitrile (30mL). The reaction was stirred for 3h at room temperature under inert atmosphere and protected from light. The transparent solution became pale yellow. After the reaction was complete, the solvent was evaporated and a pale-yellow solid was obtained. Yield: 71%. Elemental analyses calcd. (%) for:C60H56N9O10Ag: C: 58.45; H: 4.58; N: 10.22. found: C: 58.65; H: 4.49; N: 10.86. IR [cm-1 (assign)]: 3266 (NH), 3035-3105 (C-H aromatic), 1561 (C=N), 1654 (C=O), 1350 (NO2/NO3), 1150 (C-P), 694 (P-Ph). (Ω-1.cm2.mol-1): 27.70. λmax nm in DMSO (, M-1cm-1): 328 (24168). 1H NMR (DMSO-d6) [δppm, (integral, assignation)]: 4.34 (H9, 2H, J=5.8Hz); 5.18 (H6, 2H, s); 7.20 (H5, 2H, s); 7.54-7.24 (PPh3, H11, H12, H13, H14, H15, 19H);7.65 (H4, 1H, J=1.0Hz); 8.84 (N-H, 1H, J=5.9Hz).13C NMR (DMSO-d6): 42.27 (C9), 51.61 (C6), 126.95-133.51(C4, C5, C11, C12, C13, C14, C15, CPPh3), 138.87 (C2), 138.87 (C10), 145.07 (C2), 165.68 (C7)· 31P{1H}-NMR (DMSO-d6): 9.04 (PPh3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65 % | In acetonitrile at 20℃; Inert atmosphere; Schlenk technique; | [Cu(PPh3)2(BZN)2]NO3·2H2O (4) [Cu(PPh3)2]NO3 (0.15mmol) dissolved in dried acetonitrile (30mL) was added to a Schlenk tube containing benznidazole (0.30mmol) dissolved in acetonitrile (30mL). The reaction was stirred for 3h. at room temperature under inert atmosphere. The color of the solution changed from transparent to pale yellow. Then, the solvent was evaporated, and a pale orange solid was obtained. Yield: 65%. Elemental analyses calcd. (%) for: C60H58N9O11Cu: C: 59.72; H: 4.84; N: 10.45. found: C: 59.83; H: 4.70; N: 11.03. IR [cm-1 (assign)]: 3275 (NH), 3060-3125 (C-H aromatic), 1535 (C=N), 1658 (C=O), 1358 (NO2/ NO3), 1157 (C-P), 693 (P-Ph). Λm (Ω-1.cm2.mol-1): 33.79. λmax nm in DMSO (, M-1cm-1): 322 (19835). 1H NMR (DMSO-d6) [δppm, (integral, assignation)]: 4.34 (H9, 4H, J=5.8Hz); 5.18 (H6, 4H, s), 7.20 (H5, 2H, J=1.4Hz); 7.48-7.29 (PPh3, H11, H12, H13, H14, H15, 19H); 7.66 (H4, 1H, J=1.4Hz); 8.84 (H8, 1H, J=6.1Hz). 13C NMR (DMSO-d6): 42.65 (C9), 51.87 (C6),127,28-133.59 (C4, C5, C11, C12, C13, C14, C15, CPPh3), 139.20 (C10), 145.31 (C2), 166.00 (C7)· 31P{1H}- NMR (DMSO-d6): -3.78(PPh3). |
65 % | In acetonitrile at 20℃; Inert atmosphere; Schlenk technique; | [Cu(PPh3)2(BZN)2]NO3·2H2O (4) [Cu(PPh3)2]NO3 (0.15mmol) dissolved in dried acetonitrile (30mL) was added to a Schlenk tube containing benznidazole (0.30mmol) dissolved in acetonitrile (30mL). The reaction was stirred for 3h. at room temperature under inert atmosphere. The color of the solution changed from transparent to pale yellow. Then, the solvent was evaporated, and a pale orange solid was obtained. Yield: 65%. Elemental analyses calcd. (%) for: C60H58N9O11Cu: C: 59.72; H: 4.84; N: 10.45. found: C: 59.83; H: 4.70; N: 11.03. IR [cm-1 (assign)]: 3275 (NH), 3060-3125 (C-H aromatic), 1535 (C=N), 1658 (C=O), 1358 (NO2/ NO3), 1157 (C-P), 693 (P-Ph). Λm (Ω-1.cm2.mol-1): 33.79. λmax nm in DMSO (, M-1cm-1): 322 (19835). 1H NMR (DMSO-d6) [δppm, (integral, assignation)]: 4.34 (H9, 4H, J=5.8Hz); 5.18 (H6, 4H, s), 7.20 (H5, 2H, J=1.4Hz); 7.48-7.29 (PPh3, H11, H12, H13, H14, H15, 19H); 7.66 (H4, 1H, J=1.4Hz); 8.84 (H8, 1H, J=6.1Hz). 13C NMR (DMSO-d6): 42.65 (C9), 51.87 (C6),127,28-133.59 (C4, C5, C11, C12, C13, C14, C15, CPPh3), 139.20 (C10), 145.31 (C2), 166.00 (C7)· 31P{1H}- NMR (DMSO-d6): -3.78(PPh3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83 % | In acetonitrile Reflux; Darkness; | [Ag(BZN)2]NO3·H2O (1) AgNO3 (0.19mmol) was dissolved in 20mL acetonitrile and then was added to a solution of benznidazole (0.38mmol) in 30mL acetonitrile. The mixture was stirred under reflux for 2h in a round-bottom flask protected from light. The initially transparent solution became pale-yellow. The solvent was evaporated, and the residual-yellow oil was stirred in ethyl ether for 12h until a pale-yellow solid was formed. It was then centrifuged and dried under vacuum. Yield: 83%. Elemental analyses calcd. (%) for C24H26N9O10Ag: C: 40.68; H: 3.67; N: 17.80, found: C: 40.65; H: 3.65; N: 17.02. IR (cm-1 (assign): 3273 (NH), 3035-3155 (C-Haromatic), 1656 (C=O), 1550(C=N), 1361(NO2/NO3). Λm (Ω-1.cm2.mol-1): 24.20. λmax nm in DMSO (, M-1cm-1): 328 (16113). 1H NMR (DMSO-d6) [δppm, (assignation, integral)]: 4.34 (H9, 2H, J=5.9Hz); 5.18 (H6, 2H, s); 7.21 (H5, 1H, s); 7.32-7.25 (H12, H13, H14 3H, m); 7.36-7.33 (H11, H15 2H, m); 7.66 (H4, 1H, J=1.4Hz); 8.84 (H8, 1H, J=5.9Hz). 13C NMR (DMSO-d6): 42.32 (C9), 51.60 (C6), 126.97-128.83 (C4, C5, C11, C12, C13, C14, C15), 138.88 (C10), 145.29 C2, 165.69 (C7). |
83 % | In acetonitrile Reflux; Darkness; | [Ag(BZN)2]NO3·H2O (1) AgNO3 (0.19mmol) was dissolved in 20mL acetonitrile and then was added to a solution of benznidazole (0.38mmol) in 30mL acetonitrile. The mixture was stirred under reflux for 2h in a round-bottom flask protected from light. The initially transparent solution became pale-yellow. The solvent was evaporated, and the residual-yellow oil was stirred in ethyl ether for 12h until a pale-yellow solid was formed. It was then centrifuged and dried under vacuum. Yield: 83%. Elemental analyses calcd. (%) for C24H26N9O10Ag: C: 40.68; H: 3.67; N: 17.80, found: C: 40.65; H: 3.65; N: 17.02. IR (cm-1 (assign): 3273 (NH), 3035-3155 (C-Haromatic), 1656 (C=O), 1550(C=N), 1361(NO2/NO3). Λm (Ω-1.cm2.mol-1): 24.20. λmax nm in DMSO (, M-1cm-1): 328 (16113). 1H NMR (DMSO-d6) [δppm, (assignation, integral)]: 4.34 (H9, 2H, J=5.9Hz); 5.18 (H6, 2H, s); 7.21 (H5, 1H, s); 7.32-7.25 (H12, H13, H14 3H, m); 7.36-7.33 (H11, H15 2H, m); 7.66 (H4, 1H, J=1.4Hz); 8.84 (H8, 1H, J=5.9Hz). 13C NMR (DMSO-d6): 42.32 (C9), 51.60 (C6), 126.97-128.83 (C4, C5, C11, C12, C13, C14, C15), 138.88 (C10), 145.29 C2, 165.69 (C7). |
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