Structure of 16803-97-7
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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.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
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| CAS No. : | 16803-97-7 |
| Formula : | C12H13N3O2S |
| M.W : | 263.32 |
| SMILES Code : | O=S(C1=CC=C(N)C=C1)(NC2=CC=C(N)C=C2)=O |
| English Name : | 4-Amino-N-(4-aminophenyl)benzenesulfonamide |
| MDL No. : | MFCD00082174 |
| InChI Key : | LWOAIKNLRVQTFT-UHFFFAOYSA-N |
| Pubchem ID : | 768320 |
| Num. heavy atoms | 18 |
| Num. arom. heavy atoms | 12 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 3 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 3.0 |
| Molar Refractivity | 72.36 |
| TPSA ? Topological Polar Surface Area: Calculated from |
106.59 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.05 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.4 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.56 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.04 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.06 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.22 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-2.65 |
| Solubility | 0.59 mg/ml ; 0.00224 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-3.24 |
| Solubility | 0.151 mg/ml ; 0.000572 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.18 |
| Solubility | 0.0176 mg/ml ; 0.0000667 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 |
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) |
Yes |
| 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 |
-6.91 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 |
1.0 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) |
2.43 |
* 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 ammonium hydroxide; copper(l) chloride at 160℃; Hydrieren des Reaktionsprodukts an Raney-Nickel in Methanol; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With nickel Hydrogenation; | ||
| With zinc Reduktion; | ||
| With sodium dithionite; sodium carbonate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 140℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride | ||
| With sodium hydroxide | ||
| With hydrogenchloride |
| With hydrogenchloride In water Reflux; | Synthesis of 4-amino-N-arylbenzenesulfonamide (1-8) General procedure: A mixture of acetanilide-4-sulfonyl chloride (0.02 mole)and 4-substituted phenylamine (0.02 mole) was dissolvedin dry ether (50 mL), and the resulting solution wasstirred for 1 h. The product was filtered and recrystallizedfrom chloroform after the excess solvent was removed bydistillation.[29] To the isolated solid product (taken in a RBflask) was added 20 mL of water and 10 mL of concentratedhydrochloric acid with stirring. The mixture was refluxedfor 30-45 with constant stirring and then allowed to cool toroom temperature. Neutralization with 10% sodium bisulfitesolution (slight excess). Followed by cooling in ice resultedin the separation of solid, which was isolated by filtration.The obtained solid product was washed with a little amountof ice-cold water dried to give 1-8.[30] |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium hydroxide |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 140℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 140℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 140℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 140℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| at 140℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium acetate anschliessendes Hydrieren an Raney-Nickel und Erwaermen mit wss. Natronlauge; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium acetate anschliessendes Erwaermen mit wss. Natronlauge und Behandeln des Reaktionsprodukts mit Zink und Saeure; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium acetate anschliessendes Hydrieren an Raney-Nickel und Erwaermen mit wss. Natronlauge; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With Copper; potassium carbonate at 180℃; Erwaermen des Reaktionsprodukts mit wss. Natronlauge; |