Structure of 17024-12-3
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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. : | 17024-12-3 |
| Formula : | C14H9I |
| M.W : | 304.13 |
| SMILES Code : | IC1=CC2=CC=CC=C2C3=CC=CC=C31 |
| MDL No. : | MFCD00192230 |
| InChI Key : | CBFIPOTVFMLMFQ-UHFFFAOYSA-N |
| Pubchem ID : | 259286 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 15 |
| Num. arom. heavy atoms | 14 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 0 |
| Num. H-bond acceptors | 0.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 74.17 |
| TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.7 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.07 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.6 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.03 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.01 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.48 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-5.61 |
| Solubility | 0.000746 mg/ml ; 0.00000245 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-4.81 |
| Solubility | 0.00469 mg/ml ; 0.0000154 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.68 |
| Solubility | 0.0000628 mg/ml ; 0.000000207 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
| 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) |
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) |
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 |
-4.56 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 |
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) |
2.52 |
* 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 |
|---|---|---|
| 85% | General procedure: Aryl bromide (10 mmol) was dissolved in dry THF (30 mL) and cooled to -78 C under anargon atmosphere. n-Butyllithium (1.6 M in n-hexane; 7.5 mL; 12 mmol) was addeddropwise. After 15 minutes a solution of I2 (3.81 g; 15 mmol) in dry THF (10 mL) was addedand the reaction mixture was allowed to warm to room temperature overnight.For workup the reaction mixture was concentrated in vacuo. H2O was added to the residueand it was extracted with DCM (3x). The combined organic phases were washed withsaturated Na2S2O5 solution and H2O. After drying over MgSO4 and concentration underreduced pressure, the crude product was purified by column chromatography. | |
| With iodine; magnesium; In tetrahydrofuran; at -10 - 50℃; for 5h; | A small amount of iodine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added to 14 g of magnesium having a shaved form (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 230 ml of THF which was dried and distilled while heating at 50C and stirring to activate magnesium, and then a solution prepared by dissolving 129 g of 9-bromophenanthrene (manufactured by Tokyo Kasei Kogyo Co., Ltd.) in one liter of THF which was dried and distilled was dropwise added thereto in one hour. After finishing dropwise adding, the solution was stirred at 50C for 2 hours and cooled down to - 10C, and then 250 g of iodine was added little by little. The temperature was returned to a room temperature, and then stirring was continued for 2 hours. Water 100 ml was added to the above reaction liquid, and it was extracted with ethyl acetate. The ethyl acetate layer was extracted with a caustic soda aqueous solution, and after the aqueous layer was washed with hexane, it was acidified with hydrochloric acid and then extracted with ethyl acetate. After the extract was concentrated under reduced pressure, the resulting viscous liquid was dissolved again in a caustic soda aqueous solution and precipitated with an acid to obtain 91 g of 9-iodophenanthrene. |
[ 7652-46-2 ]
[ 17024-12-3 ]
[ 17024-12-3 ]
[ 197231-94-0 ]
[ 85-01-8 ]


[ 17024-12-3 ]

[ 17024-12-3 ]
[ 259263-69-9 ]
[ 17024-12-3 ]
[ 259263-71-3 ]
[ 17024-12-3 ]
[ 259263-70-2 ]
[ 17024-12-3 ]
[ 265137-02-8 ]
[ 17024-12-3 ]
[ 83469-21-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 90% | With 1,4-diaza-bicyclo[2.2.2]octane;palladium diacetate; In acetonitrile; at 80℃; for 4h; | Synthesis of 1-[5-(1 ,1 ,3,3-tetramethylisoindolin-2-yloxylyl)-2-[9-(phenanthryl)]acetylene; 205 2079-lodophenanthrene (59 mg, 0.194 mmol), DABCO (62.5 mg, 0.557 mmol, 3 equiv) and Pd(OAc)2 (1 mg, 2.5 mol %) was dissolved in dry MeCN (1 cm3). 5-ethynyl- 1,1,3,3-tetramethylisoindolin-2-yloxyl 205 (50 mg, 0.233 mmol, 1.2 equiv) was added and mixture heated at 80 0C under argon for 4 h. Subsequently the solvent was removed under reduced pressure and the residue taken up in CHCI3 (~1 ml) ensuring the DABCO remained undissolved. Purification of the resulting solution by column chromatography (SiO2, eluant:10 % EtOAc, 90 % n-Hexane) gave 1 -[5-(1 , 1,3,3- tetramethylisoindolin-2-yloxylyl)-2-[9-(phenanthryl)]acetylene, 207 (68 mg, 0.175 mmol, 90 %). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium t-butanolate;bis-triphenylphosphine-palladium(II) chloride; In xylene; at 130℃; for 12h; | Mixed under argon flow were 50 g of 4-bromoaniline (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 265 g of <strong>[17024-12-3]9-iodophenanthrene</strong>, 84 g of sodium t-butoxide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 11 g of bis(triphenylphosphine)palladium dichloride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 4.5 liter of xylene, and they were reacted at 130C for 12 hours. Water was added to the reaction liquid, and the mixture was filtered through celite, followed by carrying out separation thereof with toluene. The oil layer was concentrated under reduced pressure to obtain crystal. This was refined through a column and then dissolved in toluene, and hexane was added thereto to reprecipitate crystal. It was filtered and then dried to obtain 101 g of N,N-di(phenantho-9-yl)-4-bromoaniline (B6). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Mixed under argon flow were 100 g of N,N'-diacetyl-4,4'-benzidine (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 337 g of <strong>[17024-12-3]9-iodophenanthrene</strong>, 204 g of anhydrous potassium carbonate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4.7 g of copper powder (manufactured by Hiroshima Wako Co., Ltd.) and 750 ml of decalin, and they were reacted at 190C for 3 days. After cooling, 2 liter of toluene was added thereto to filter an insoluble matter. The matter filtered was dissolved in 4.5 liter of chloroform to filter off an insoluble matter, and then the filtrate was treated with activated carbon and concentrated under reduced pressure. Acetone 3 litter was added when the solution became slurry in the middle of concentration, and crystal deposited was filtered and dried. This was suspended in a mixture of 2 liter of ethylene glycol and 20 ml of water, and 110 g of a 85 % potassium hydroxide aqueous solution was added thereto, followed by carrying out reaction at 120C for 12 hours. After left cooling down to a room temperature, the reaction liquid was injected to 4 liter of water and treated with activated carbon, and then it was concentrated under reduced pressure. Acetone was added when the solution became slurry, and crystal deposited was filtered and dried to obtain 116 g of N,N'-bis(phenantho-9-yl)-4,4'-benzidine (A3). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium t-butanolate;bis-triphenylphosphine-palladium(II) chloride; In xylene; at 130℃; for 12h; | Mixed under argon flow were 73 g of 4-bromodiphenylamine (A4), 135 g of <strong>[17024-12-3]9-iodophenanthrene</strong>, 34 g of sodium t-butoxide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4 g of bis(triphenylphosphine)palladium dichloride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 1.5 liter of xylene, and they were reacted at 130C for 12 hours. Water was added to the reaction liquid, and the mixture was filtered through celite, followed by carrying out separation thereof with toluene. The oil layer was concentrated under reduced pressure to obtain crystal. This was refined through a column and then dissolved in toluene, and hexane was added thereto to reprecipitate crystal. It was filtered and then dried to obtain 82 g of N-(4-bromophenyl)-N-phenyl-9-aminophenanthrene (B3). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 66% | A 500 mL three-necked round-bottomed flask equipped with a mechanical stirrer, reflux condenser, and inert gas in- and outlet was charged with quinidine (QD-1, 12.8g, 39.5 mmol, 1.2 eq). The flask was flushed for 30 min with a gentle stream of argon. Anhydrous dimethyl sulfoxide (130 mL, freshly distilled in presence of CaHz) was added, and the reaction mixture was stirred at room temperature until all the quinidine was dissolved. Sodium hydride (60% oil dispersion, 2.0g, 1.5 eq. ) was added in small portions yielding an orange, slightly cloudy solution of the corresponding sodium alkoxide. Upon addition of pyridine (6.4 mL, 2.4 eq. ) and copper (I) g, 1.2 eq. ) to the reaction mixture at room temperature, the color of the reaction mixture was changed from orange to dark green. After 30 min all of the precipitate dissolved, and a clear solution was formed. 9- iodophenanthrene (10.0 g, 32.9 mmol), was added, and the reaction mixture was kept at 113 C for 70 h (oil bath, temperature: 120 C). The reaction mixture was allowed to cool to room temperature. Water (100 mL), methylene chloride(100 mL), and diethyl ether (100 mL) were successively added to the brown solution followed by ethylenediaminetetraacetate disodium salt dehydrate (20 g) and concentrated aqueous ammonia solution (20 mL, 29%, w/w). The argon inlet was removed, and a gentle stream of air was flushed through the well-agitated reaction mixture for about 1 h. The reaction mixture was transferred to a separatory funnel and the turquoise blue aqueous phase separated from the dark brown organic phase. The aqueous layer was washed twice with methylene chloride (100 mL), and the combined organic phases were extracted three times with aqueous ammonia solution (200 mL, 5%, w/w) until the aqueous phase remained colorless. Then the organic layer was washed with HCl aq (1 N 2 x 50 mL) twice and washed with H20 three times (3 x 50 mL) to remove the left QD. The organic layer was washed with NH40H to neutralize the salt and dried over Na2S04 and the solvent was removed in vacuo to yield the crude product. The crude product was dissolved in ethyl ether (300 mL) and treated with HCI (IN in Et20) until no further precipitates was generated. The precipitates were collected and dissolved in CH2C12 and basified with NH40H and dried over Na2S04 and the solvent in vacuo to give yellowish foam QD-PHN (5.6g, 66% yield). [alpha]D23 = + 310.7(C 0.89 EtOH) (at)HNMR (CDC13, 400 Hz) 6 8.65-8.71 (m, 2H), 8.61 (d, J = 4.8 Hz, 1H), 8.52(d, J = 8 Hz, 1H), 8.07 (d, J= 9.2 Hz, 1H), 7.70-7.75 (m, 2H), 7.55 (d, 2.4 Hz, 1H), 7.38-7.46(m, 5H), 6.66 (s, 1H), 6.35 (br, 1H), 6.12-6.21 (m, 1H), 5.18(d, J=10.4 Hz, 1H), 5.12 (m, 1H), 4.03 (s, 3H), 3.32-3.42 (m, 2.97-3.06 (m, 2.79-2.87 (m, 1H),2.44-2.50(t, J= 10 Hz, 1H), 2.34-3.25 (m, 1H), 1.97 (br, 1H), 1.55-1.62 (m, 3H). ¹3CNMR:(CDCl3, 100Hz): 158.1, 150.4, 147.71, 144.7, 143.7, 140.3, 132.3, 132.2, 131.5, 127.5,127.3, 126.8, 126.7, 126.6,126.4, 124.5,122.8, 122.7,122.3, 121.8, 118.2, 114.7, 104.8, 100.8, 78.8, 60.5, 55.8, 50.2, 49.9, 39.6, 27.8, 26.5, 22.1. IR: 3062, 2935, 2863, 1622, 1594, 1507, 1454, 1226, 1117, 750. |
[ 17024-12-3 ]
[ 7787-58-8 ]
[ 5142-75-6 ]

[ 17024-12-3 ]

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