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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 5351-69-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 5351-69-9 |
Formula : | C7H9N3S |
M.W : | 167.23 |
SMILES Code : | NNC(NC1=CC=CC=C1)=S |
MDL No. : | MFCD00007615 |
InChI Key : | KKIGUVBJOHCXSP-UHFFFAOYSA-N |
Pubchem ID : | 730679 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H300 |
Precautionary Statements: | P264-P301+P310 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅱ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 49.05 |
TPSA ? Topological Polar Surface Area: Calculated from |
82.17 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.55 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.76 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.66 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.13 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.87 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.99 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.56 |
Solubility | 4.59 mg/ml ; 0.0275 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.07 |
Solubility | 1.44 mg/ml ; 0.0086 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.29 |
Solubility | 0.866 mg/ml ; 0.00518 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.78 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.89 |
* 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 |
---|---|---|
With potassium carbonate; In pyridine; ethanol; | Example 5 3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]-4-phenyl-1,2,4-triazole (Compound 5) The title compound was prepared by the general method described by Potts, K.T.(1961) Chem. Rev. 61:87. 4-Phenyl-3-thiosemicarbazide (4.18 g) (Aldrich) was dissolved in 50 mL of pyridine and treated with 2.71 g of ethyl chloroformate at 0° C. The reaction was stirred for 2 hours and then refluxed for 18 hours. Evaporation of the solvent and trituration with water gave 2.5 g of 3-hydroxy-5-mercapto-4-phenyl-1,2,4-triazole. 3-Hydroxy-5-mercapto-4-phenyl-1,2,4-triazole (1.93 g) was stirred in 10 mL of ethanol with 1.1 equivalent of potassium carbonate in 10 mL ethanol for one hour and then reacted with 2.09 g of <strong>[3034-48-8]<strong>[3034-48-8]2-bromo-5-nitrothiazol</strong>e</strong> as in Example 1. Crystallization from ethanol and water gave 0.6 g of 3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]-4-phenyl-1,2,4-triazole, a dark yellow solid, M.P. 188-190° C. | |
With potassium carbonate; In pyridine; ethanol; | Example 5 3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]-4-phenyl-1,2,4-triazole (Compound 5) The title compound was prepared by the general method described by Potts, K. T.(1961) Chem. Rev. 61:87. 4-Phenyl-3-thiosemicarbazide (4.18 g) (Aldrich) was dissolved in 50 mL of pyridine and treated with 2.71 g of ethyl chloroformate at 0° C. The reaction was stirred for 2 hours and then refluxed for 18 hours. Evaporation of the solvent and trituration with water gave 2.5 g of 3-hydroxy-5-mercapto-4-phenyl-1,2,4-triazole. 3-Hydroxy-5-mercapto-4-phenyl-1,2,4-triazole (1.93 g) was stirred in 10 mL of ethanol with 1.1 equivalent of potassium carbonate in 10 mL ethanol for one hour and then reacted with 2.09 g of <strong>[3034-48-8]<strong>[3034-48-8]2-bromo-5-nitrothiazol</strong>e</strong> as in Example 1. Crystallization from ethanol and water gave 0.6 g of 3-hydroxy-5-[(5-nitrothiazol-2-yl)mercapto]-4-phenyl-1,2,4-triazole, a dark yellow solid, M.P. 188°-190° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol; for 3h;Reflux; | The ligand was prepared by the following method. A solution of <strong>[2631-77-8]3,5-diodosalicylaldehyde</strong> (1 mmol, 0.4 g) in methanol (15 ml) was added dropwise to a solution of 4-phenylthiosemicarbazide (1 mmol, 0.17 g) in methanol (15 ml) with stirring at reflux. After being stirred for 3 h, the resulting white solids were removed by filtration, washed with cold ethanol and dried in vacuo over anhydrous CaCl2. M.p: 192 C, Yield: 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 12h; | General procedure: A carboxylic acid (0.33mmol), a 4-phenyl-3-thiosemicarbazide (0.33mmol), and EDCI (182mg, 1.0mmol) were mixed in CH2Cl2 (15mL), and the reaction mixture was stirred at room temperature for 12h. The organic layer was washed three times with saturated NaHCO3, dried over MgSO4, filtered, and concentrated. Chromatography (5:95 MeOH/DCM, silica gel) of the residue afforded the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.9% | In methanol; at 60℃; for 24h; | (1) 10 mmol of <strong>[32974-92-8]2-acetyl-3-ethylpyrazine</strong> was dissolved in 20 ml of methanol,Stirring at 60 C for 15 min to prepare a solution;(2) taking 10 mmol of 4-phenylthiosemicarbazide dissolved in 20 ml of methanol,The solution prepared in the step (1) is dropwise added to a methanol solution containing 4-phenylthiosemicarbazide, and the reaction mixture is stirred under reflux at 60 C for 24 hours to obtain a pale yellow precipitate.After the reaction, the mixture was cooled to room temperature, poured into a beaker and evaporated, and the resulting precipitate was filtered.Wash 3 times with absolute ethanol,After drying, the ligand L3 is obtained;Yield: 85.9%, |
85.9% | In methanol; at 65℃; for 3h; | General procedure: The ligands L1-L4 were synthesized by reflux method. Shown in Scheme 1, 5mM of 2-Acetyl-3-ethylpyrazine and thiosemicarbazides (L1), 5mM of 2-Acetyl-3-ethylpyrazine and 4-methylthiosemicarbazide (L2), 5mM of 2-Acetyl-3-ethylpyrazine and 4-phenylthiosemicarbazide (L3), and 5mM of 2-Acetyl-3-ethylpyrazine and 3-pyrrolethiosemicarbazide (L4) were stirred in CH3OH for 3 h at 65C. The ligands were precipitated and filtered. L1-L4 were characterized by infrared spectroscopy, electrospray ionization mass spectrometry (ESI-MS), 1H NMR, and 13C NMR (Supplementary Figs S4- S31). |
(1) Dissolving 10 mmol of <strong>[32974-92-8]2-acetyl-3-ethylpyrazine</strong> in 20 mL of methanol,Stir at 60 C for 15 min,Then 20mL, 10mmola 4-phenyl-3-thiosemicarbazone methanol solution is added dropwise to the above solution,After stirring at 60 C for 12 h,After cooling to room temperature, pour into the beaker and evaporate.The pale yellow crystal obtained above was filtered and washed with methanol three times.Get ligand (L3),; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20%; 5%; 45% | With triethylamine; In ethanol; at 50℃; for 3h; | General procedure: A solution of 1a-d (1.0 mmol) and 2a (1.0 mmol) was stirred with gentle heating at 50 C in dry ethanol containing 0.5 mL triethylamine till consumption of starting materials. After reaction completion, the solvent was removed und vacuum and the residue was subjected to PLC using toluene/EtOAc (10:1) to give different zones. |