Structure of 98-71-5
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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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CAS No. : | 98-71-5 |
Formula : | C6H8N2O3S |
M.W : | 188.20 |
SMILES Code : | NNC1=CC=C(C=C1)S(O)(=O)=O |
MDL No. : | MFCD00025097 |
InChI Key : | IOMZCWUHFGMSEJ-UHFFFAOYSA-N |
Pubchem ID : | 66825 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338-P304+P340-P405-P501 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 43.51 |
TPSA ? Topological Polar Surface Area: Calculated from |
100.8 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
-0.19 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-4.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.11 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.49 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.24 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
1.6 |
Solubility | 7540.0 mg/ml ; 40.1 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
3.02 |
Solubility | 198000.0 mg/ml ; 1050.0 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.44 |
Solubility | 6.8 mg/ml ; 0.0361 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 |
-10.66 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 |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
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) |
2.05 |
* 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 |
---|---|---|
82% | With hydrogenchloride; In ethanol; water; at 20℃; for 8h;Heating / reflux; | To a stirred suspension of p-hydrazino-benzenesulfonic acid (42 g, 0.223 mol) in ethanol (450 ml) 6N hydrochloric acid (74 ml, 0.446 mol) was added at room temperature, followed by addition of 4,4,4-trifluoro-l-(4-methyl-phenyl)-butane-l,3- dione (51.45 g, 0.223 mol). The obtained suspension was refluxed for 8 h, then concentrated in vacuo. The residue was dissolved in water (300 ml) and extracted with ethyl acetate (2 x 200 ml). The combined organic layers were washed with water (1 x 100 ml) and brine (1 x 100 ml), dried over MgSO4, decolorized, filtered and concentrated in vacuo. The obtained crystalline product was recrystallized from diisopropyl ether (300 ml) to yield 70.12 g (82 percent) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Example 8. Preparation of 2,3-dimethyl-3-(4-carboxybutyl)-5-sulfoindolenyne, potassium salt (compound 8) A mixture of phenylhydrazine-p-sulphonic acid (compound 7) (1.8 g; 9.7 mmole), 6-methyl-7-oxooctane acid (compound 5) (2.0 g; 11.6 mmole), and glacial acetic acid (15 mL) was refluxed under stirring for 8 h, then an additional amount of acetic acid was added and treated with activated carbon. The solvent was removed and the residue was dissolved in methanol (10 mL). To solution obtained, there are added dropwise the solution of potassium hydroxide (600 mg; 10,56 mmole) in methanol (7 mL), isopropyl alcohol (15 mL), and diethyl ether (2 mL). The precipitate formed was collected by filtration and dried in vacuum desiccator over P2O5. 2,3-Dimethyl-3-(4-carboxybutyl)-5-sulfoindolenyne, potassium salt (compound 8) was obtained with yield of 3.47 g (83%), λmax 258 nm. Mass-spectrum (MALDI) (C15H19NO5S): found m/z 327.2, calculated m/z 325.38. 1H-NMR (D2O), δ (ppm): 0.45-0.7 (2H, m, CH2CH2CH2CH2COOH); 1.31 (3H, s, 3-CH3); 1.36 (2H, m, CH2CH2CH2CH2COOH); 1.88-2.14 (4H, m, CH2CH2CH2CH2COOH); 7.53 (1H, d, ArH), 7.8 (2H, m, ArH) |
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