Structure of 1122-10-7
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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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Sarah M. West ; Duyen K. Tran ; Jiajie Guo ; Shinya E. Chen ; David S. Ginger ; Samson A. Jenekhe
Abstract: In this work, we show how N-alkyl substitution affects the chain conformation, electronic structure, and optical and charge transport properties of π-conjugated ladder poly(pyrrolobenzothiazines)s (LPBTs). We found that the π-conjugated backbones of the LPBTs have a donor–acceptor motif, which enabled a small bandgap of 1.5 eV that is unchanged by N-alkyl substitution. We found that partial protonation of the LPBTs in acid solutions resulted in increased backbone flexibility evidenced by thermochromism in solution and planar/nonplanar chain conformational variation with degree of protonation that we saw in density functional theory (DFT) calculations. The average field-effect hole mobility increased from 1.3 × 10[–3] cm2/(V s) in LPBT-Me to 3.1 × 10[–3] cm2/(V s) in LPBT, which can be explained by the increased crystallinity and decreased lattice disorder in LPBT. The results of our investigations of the solution and solid-state properties of the two ladder poly(pyrrolobenzothiazine)s provide new insights into the structure–property relationships of π-conjugated ladder polymers.
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CAS No. : | 1122-10-7 |
Formula : | C4HBr2NO2 |
M.W : | 254.86 |
SMILES Code : | BrC1=C(Br)C(=O)NC1=O |
MDL No. : | MFCD00185696 |
InChI Key : | BIKSKRPHKQWJCW-UHFFFAOYSA-N |
Pubchem ID : | 14279 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 41.61 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.17 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.94 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.1 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.26 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.69 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.91 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.11 |
Solubility | 1.96 mg/ml ; 0.00771 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.66 |
Solubility | 5.55 mg/ml ; 0.0218 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.5 |
Solubility | 0.81 mg/ml ; 0.00318 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 |
-7.07 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 |
1.0 |
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 |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.45 |
* 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.
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