Structure of 28394-58-3
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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. : | 28394-58-3 |
Formula : | C9H8Cl2O2 |
M.W : | 219.06 |
SMILES Code : | O=C(OCC)C1=CC=C(Cl)C(Cl)=C1 |
MDL No. : | MFCD06204554 |
Boiling Point : | No data available |
InChI Key : | YONQPSPHUKKUEJ-UHFFFAOYSA-N |
Pubchem ID : | 11481387 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 52.55 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.65 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.15 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.17 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.38 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.32 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.33 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.96 |
Solubility | 0.0242 mg/ml ; 0.000111 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.41 |
Solubility | 0.00852 mg/ml ; 0.0000389 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.12 |
Solubility | 0.0167 mg/ml ; 0.0000762 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
Yes |
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 |
-4.69 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.67 |
* 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 |
---|---|---|
61% | With sodium cyanide In N,N-dimethyl-formamide at 50℃; for 1 h; Molecular sieve | General procedure: Aldehyde 1 (1.0 mmol; 1.0 equiv.) and 4 Å molecular sieves (300 mg) were added to a mixture of DMF (3.0 mL) and an appropriate alcohol (or a thiol) (3.0 mL). To the above solution was added sodium cyanide (1.5 mmol; 1.5 equiv). The reaction mixture was stirred in an open flask at 50 C and monitored by TLC. After the complete consumption of 1, the mixture was poured into water (25 mL) and extracted with diethyl ether (5 × 10 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated. The crude mixture was further purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent to furnish the desired ester compound 3. The aqueous layer was acidified with HCl, extracted with ether, and concentrated to yield the corresponding carboxylic acid 6, which was sufficiently pure needing no further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | for 120 h; Reflux | General procedure: Sulfonimidate 1 (0.859 g, 3.00 mmol) and 2-bromobenzoic acid (0.601 g, 3.00 mmol) were refluxed in THF (25 mL) for 5 d. TLC analysis (hexane–EtOAc, 6:1) showed that most of 1 had been converted into the sulfonamide 2. The mixture was concentrated by rotary evaporation and pentane (5 mL) was added. The pentane solution was removed by pipet and treated with NaH to precipitate any unreacted acid and residual 2. This solution was pipet filtered, concentrated in vacuo and purified by Kugelrohr distillation; yield: 0.32 g (47percent). IR and 1H NMR spectra were identical to published spectra. |
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