Structure of 3469-20-3
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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. : | 3469-20-3 |
| Formula : | C20H15N |
| M.W : | 269.34 |
| SMILES Code : | C(N1)(C2=CC=CC=C2)=C(C3=CC=CC=C3)C4=C1C=CC=C4 |
| MDL No. : | MFCD00022698 |
| InChI Key : | GYGKJNGSQQORRG-UHFFFAOYSA-N |
| Pubchem ID : | 77020 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H317 |
| Precautionary Statements: | P280 |
| Num. heavy atoms | 21 |
| Num. arom. heavy atoms | 21 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 0.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 89.17 |
| TPSA ? Topological Polar Surface Area: Calculated from |
15.79 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.8 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.34 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.5 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.28 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.67 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.72 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-5.48 |
| Solubility | 0.000888 mg/ml ; 0.0000033 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-5.42 |
| Solubility | 0.00101 mg/ml ; 0.00000377 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-8.32 |
| Solubility | 0.0000013 mg/ml ; 0.0000000048 mol/l |
| Class? Solubility class: Log S scale |
Poorly 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) |
Yes |
| 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) |
Yes |
| 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) |
Yes |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.15 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
| 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 |
2.0 |
| 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) |
2.45 |
* 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.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | With toluene-4-sulfonic acid; at 140℃;Neat (no solvent); | General procedure: Aryl aldehyde (1.0 mmol), Precatalyst B (0.029 g) and DBU (0.114 g) were triturated together in an agate morlar for 45 minutes at 55 oC. Then, TsOH (0.344 g) and aryl amines (0.5 mmol) were added into and the mixture was kept at 140 oC. Upon completion, monitored by TLC, the reactant was cooled to room temperature and was purified by column chromatography (silica gel, mixtures of ethyl acetate/petroleum ether, 1:20, v/v) to afford the desired pure product. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93% | With sulfuric acid; In ethanol;Reflux; Inert atmosphere; | Example 53. Synthesis of 2,3-diphenyl-1 H-indole. Phenyl hydrazine (10.2 mL, 0.52 mol, 1 eq), 2-phenylacetophenone (20.3 g, 0.52 mol, 1 eq) and concentrated sulfuric acid (1 1.0 mL, 1.04 mol, 2 eq) were added with 100 mL ethanol in a 500 mL two neck flask. The reaction mixture was refluxed overnight under inert atmosphere. Completion of the reaction was monitored by thin layer chromatography (TLC) using as diluent ethyl acetate: heptane 1 :9. After cooling, the mixture was precipitated in 1 .5L ice in water and filtered. The obtained solid was recrystallized in water:ethanol (1 :2) to yield 2,3-diphenyl-1 H- indole as brown crystals (25.94 g, 0.096 mmol, 93 percent). Bruto formula: C2oH15N Molecular weight: 269.35 g mol"1 LC-MS (m/z): 270.1 [MH]+ RF. value (ethyl acetate:heptane 1 :9): 0.30 1H-NMR (300 MHz, DMSO-d6): delta (ppm) = 7.04 (t, 1 H, NH-C-CH-CH-CH), 7.16 (t, 1 H, NH-C-CH- CH), 7.25-7.44 (m, 8H, ArH) 7.45-7.51 (m, 4H, ArH), 1 1 .56 (s, 1 H, NH) 13C-NMR (125 MHz, DMSO-d6): delta (ppm) = 1 1 1 .40 (CH), 1 13.21 (C), 1 18.48 (CH), 1 19.61 (CH), 121 .89 (CH), 125.95 (CH), 127.38 (CH), 127.89 (C), 128.08 (CH), 128.37 (CH), 128.51 (CH), 129.66 (CH), 132.39 (C), 133.99 (C), 135.21 (C), 136.02 (C) Example 54. Synthesis of 3-(4-nitrophenyl)-2-phenyl-1 H-indole (1 st method) |
| 74% | With Amberlite® IR 120; In ethanol; at 80℃; for 12h; | General procedure: A mixture of the carbonyl compound (5, 1.0 mmol), arylhydrazine (6, 1.2 mmol), and the solid acid (7, Amberlite, 1.5 g, obtained from Aldrich Chemical Co.) was refluxed in absolute ethanol (10 ml) for 8 h. The reaction was monitored by thin-layer chromatography(TLC), and upon completion the mixture was cooled to room temperature, the catalyst filtered off, and the product was washed thoroughly with ethylacetate (30 ml). The combined organics were washed with water, dried (Na2SO4), and concentrated in vacuo. The resulting residue was chromatographed on a silicagel column eluting with ethylacetate?hexane mixtures to obtain the purified indole (8). This was fully characterized by infrared, 400-MHz 1H NMR, high-resolution mass spectrometry, and melting point (solids). |

A329244 [5054-94-4]
(2,3-Dimethyl-1H-indol-5-yl)methanamine
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