Structure of 1643-30-7
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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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CAS No. : | 1643-30-7 |
Formula : | C9H9BrO2 |
M.W : | 229.07 |
SMILES Code : | O=C(O)CCC1=CC=C(Br)C=C1 |
MDL No. : | MFCD01310793 |
InChI Key : | NCSTWHYWOVZDOC-UHFFFAOYSA-N |
Pubchem ID : | 2735609 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 50.49 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.79 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.21 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.7 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.56 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.34 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.82 |
Solubility | 0.343 mg/ml ; 0.0015 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.63 |
Solubility | 0.54 mg/ml ; 0.00236 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.44 |
Solubility | 0.0832 mg/ml ; 0.000363 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 |
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) |
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 |
-6.13 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 |
0.56 |
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) |
1.21 |
* 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 sulfuric acid; acetic acid; In water; for 18h;Heating / reflux; | A mixture of a 60% suspension of sodium hydride in mineral oil (4.8 g, 120 mmol) in N, N-dimethylformamide (50 mL) at about 5 C was treated with diethyl malonate (36.4 mL, 240 mmol). The mixture was stirred for about 5 minutes, slowly treated with a solution of 4- bromobenzyl bromide (20.0 g, 80 mmol) in N, N-dimethylformamide (20 mL), stirred at room temperature overnight, diluted with water, and extracted with ethyl acetate. The combined organic extracts were dried (MgS04), filtered, and concentrated under high vacuum. The residue was dissolved in a mixture of acetic acid (46 mL), water (30 mL), and concentrated sulfuric acid (13 mL) and was heated to reflux for 18 hours. The reaction mixture was cooled, concentrated under high vacuum, and diluted with water. The formed crystalline solid was collected by filtration, washed with water and diethyl ether, and was dried under high vacuum to provide the desired product. MS (DCI-NH3) : m/z 246,248 (M+NH4) +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With Novozym 435; acylase I from Aspergillus melleus; amano lipase AK from pseudomonas fluorescens; lipase from wheat germ; papaine; In toluene; at 40℃; for 48h;Enzymatic reaction;Mechanism; | General procedure: To the solution of acid (1 mmol) in toluene (1 ml), the corresponding dialkyl carbonate (2 mmol) and enzymes (per 4 mg of each enzyme) were added in 5 ml vial. The reaction mixture was stirring for 24 or 48 h at 40 C in vortex mixture (Heidolph Promax 1020) equipped with incubator (Heidolph Inkubator 1000). After cooling, the mixture was washed with NaHCO3 (3×) and brine (1×). Organic solvent was removed under vacuum to obtain the product 2a-2r. |
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