Structure of 14437-03-7
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 14437-03-7 |
Formula : | C9H11NO4S |
M.W : | 229.25 |
SMILES Code : | O=C(OC)NS(=O)(C1=CC=C(C)C=C1)=O |
MDL No. : | MFCD00453717 |
InChI Key : | KNVDHKOSDVFZTO-UHFFFAOYSA-N |
Pubchem ID : | 84437 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 53.78 |
TPSA ? Topological Polar Surface Area: Calculated from |
80.85 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.71 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.78 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.12 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.74 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.12 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.78 |
Solubility | 3.76 mg/ml ; 0.0164 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.06 |
Solubility | 2.0 mg/ml ; 0.00874 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.85 |
Solubility | 0.328 mg/ml ; 0.00143 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) |
Yes |
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 |
-7.14 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 |
0.0 |
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 |
0.0 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) |
2.3 |
* 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 |
---|---|---|
90% | at 120℃; for 0.333333h;Sealed tube; Microwave irradiation; | General procedure: The 4-substituted methyl (phenylsulfonyl)carbamate was dissolved in the chosen alcohol (2 mL) in a microwave vial, which was closed using an aluminum open-top seal with PTFE-faced septum. The reaction mixture was heated under microwave irradiation at 100-120 oC for 20-60 min. The crude reaction mixture was concentrated under reduced pressure and the residue was purified using silica gel column chromatography to yield the desired (aryl)carbamate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | General procedure: A solution of a 4-subsituted benzenesulfonamide in dry dichloromethane was placed on an ice bath and cooledto 0 °C after which trimethylamine was added dropwise. The mixture was stirredat 0 °C for 10 min before methyl chloroformate was added dropwise. Afterstirring for an additional 30 min at 0 °C, the ice bath was removed and the reaction mixture was allowed to warm to room temperature over 2 h. The reaction mixture was diluted with dichloromethane, washed with 1 M HCl (aq.),water, and brine in sequence, dried with MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to yield the desired 4-substituted methyl(phenylsulfonyl)carbamate. |
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