Structure of 146224-62-6
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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. : | 146224-62-6 |
Formula : | C7H8N2O2 |
M.W : | 152.15 |
SMILES Code : | O=C(N)C1=CC=C(N)C(O)=C1 |
MDL No. : | MFCD16999380 |
InChI Key : | GLJFZIKVMDSXMY-UHFFFAOYSA-N |
Pubchem ID : | 21184836 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 40.96 |
TPSA ? Topological Polar Surface Area: Calculated from |
89.34 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.45 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.15 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.08 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.0 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.22 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.03 |
Solubility | 14.3 mg/ml ; 0.0941 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.27 |
Solubility | 8.14 mg/ml ; 0.0535 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.04 |
Solubility | 14.0 mg/ml ; 0.092 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 |
-7.33 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 |
2.0 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) |
1.0 |
* 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 |
---|---|---|
Example 104 Preparation of N-[4-aminocarbonyl-2-hydroxyphenyl]-N'-[2-bromophenyl] urea N-[4-Aminocarbonyl-2-hydroxyphenyl]-N'-[2-bromophenyl] urea was prepared from <strong>[146224-62-6]5-aminocarbonyl-2-amino phenol</strong> (304 mg, 0.50 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chlorides hexane(1/20) and filtering. (440 mg, 62%). 1 H NMR (CD3 OD): delta 8.09 (d, 1H), 7.91 (d, 1H), 7.60 (d, 1H), 7.45 (m, 3H), 7.00 (d, 1H). | ||
In hexane; | Example 104 Preparation of N-[4-aminocarbonyl-2-hydroxyphenyl]-N'-[2-bromophenyl]urea N-[4-Aminocarbonyl-2-hydroxyphenyl]-N'-[2-bromophenyl]urea was prepared from <strong>[146224-62-6]5-aminocarbonyl-2-amino phenol</strong> (304 mg, 0.50 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chloride/hexane (1/20) and filtering. (440 mg, 62%). 1H NMR (CD3OD): d 8.09 (d, 1H), 7.91 (d, 1H), 7.60 (d, 1H), 7.45 (m, 3H), 7.00 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Representative compounds of the present invention are: ... 4-(morpholino-carbonyl)-o-phenylene-diamine hydrochloride; 4-[(4-morpholino)hydrazino-carbonyl]-o-phenylenediamine; 4-(1-piperidinylamino-carbonyl)-o-phenylenediamine dihydrochloride; 4-amino-3-hydroxybenzoic acid; 4-amino-3-hydroxybenzamide; 3,4-diaminobenzamide; 3,4-diaminobenzhydrazide; 3,4-diamino-N,N-bis(1-methylethyl)benzamide; ... | ||
The structures of compounds 29 to 34 are given in Table 4, below. ... Compound 29: 2-hydroxy-4-(amino-carbonyl)aniline; 2-hydroxy-4-(methylhydrazino-carbonyl) aniline; 2-hydroxy-4-[1-(morpholino)amino-carbonyl]aniline; ... | ||
The structures of compounds 29 to 34 are given in Table 4, below. ... Compound 29: 2-hydroxy-4-(amino-carbonyl)aniline; 2-hydroxy-4-(methylhydrazino-carbonyl)aniline; 2-hydroxy-4-[1-(morpholino)aminocarbonyl]aniline; ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; | Example 104 Preparation of N-[4-aminocarbonyl-2-hydroxyphenyl]-N'-[2-bromophenyl]urea N-?4-Aminocarbonyl[-2-hydroxyphenyl]-N'-[2-bromophenyl] urea was prepared from <strong>[146224-62-6]5-aminocarbonyl-2-amino phenol</strong> (304 mg, 0.50 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chloride/hexane(1/20) and filtering. (440 mg, 62%). 1 H NMR (CD3 OD): d 8.09 (d, 1H), 7.91 (d, 1H), 7.60 (d, 1H), 7.45 (m, 3H), 7.00 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 16.0h;Inert atmosphere; | General procedure: A mixture of d1-d14 (1.0 equiv), Pd2(dba)3 (0.1 equiv), Xantphos (0.2 equiv), Cs2CO3 (1.5 equiv) in dioxane was heated to 110 C under N2 for 16 hours. After cooling to room temperature, the mixture was washed with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography on a silica gel column to give corresponding product e1-e17. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iron; acetic acid; at 60.0℃; for 2.0h; | General procedure: To a solution of c1-c14 (1.0 equiv) in acetic acid, iron powder was added (5.0 equiv) slowly. Then the mixture was reacted over 2 h at 60 C. After completed, the reaction was cooled to room temperature and the iron filings was filtrated off and neutralized with sodium bicarbonate saturated aqueous solution. Then the solution was washed by ethyl acetate, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography on a silica gel column to give corresponding product d1-d14. |