Structure of 5370-25-2
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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. : | 5370-25-2 |
Formula : | C6H5BrOS |
M.W : | 205.07 |
SMILES Code : | CC(=O)C1=CC=C(Br)S1 |
MDL No. : | MFCD00014528 |
InChI Key : | IGBZCOWXSCWSHO-UHFFFAOYSA-N |
Pubchem ID : | 79335 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H312-H315-H319-H332 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 42.21 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.31 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.04 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.64 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.71 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.54 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.49 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.48 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.12 |
Solubility | 0.156 mg/ml ; 0.000759 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.24 |
Solubility | 0.117 mg/ml ; 0.000572 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.86 |
Solubility | 0.283 mg/ml ; 0.00138 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) |
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 |
-5.68 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) |
2.25 |
* 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 |
---|---|---|
In toluene; at 150℃; for 48h; | EXAMPLE 58; A mixture of the commercially available ketone (1.64 g), methyl triphenylphosphoranylidene acetate (2.8 g), and 20 mL of toluene was heated at 150 0C for 2 days. The mixture was purified by Biotage (5% ethyl acetate in hexane) to afford the enoate (cis:trans=l:l) as a white solid. The hydrolysis of this enoate, and the subsequent amide formation, followed the procedures described in the Examples above to provide a yellow oil. A solution of the bromide (1.24 g), hexamethyl ditin (1.6 g) in 10 mL of THF was degassed with argon, and to this solution was added Pd(PPh3)4 (151 mg). The mixture was heated at 80 0C overnight. The resulting stannane mixture was used directly for the subsequent Stille coupling, following procedures described in the above Examples. Following similar procedures as described in EXAMPLE 54, after hydrogenation, conversion of the amino group to the hydroxyl group, and hydrolysis, the desired product was obtained as a brown oil. 1H NMR (acetone-d6, 500 MHz) δ 11.3 (IH, s), 8.75 (IH, d), 8.13 (IH, d), 8.10 (IH, d), 7.63 (IH, d), 7.60 (IH, t), 7.33 (IH, d), 7.25 (IH, dd), 7.16 (IH, t), 6.91 (IH, d), 3.68 (IH, m), 2.83 (IH, dd), 2.75 (IH, dd), 1.45 (3H, d); LCMS m/z 383 (M++l). |
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