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CAS No. : | 1268524-71-5 | MDL No. : | MFCD22124456 |
Formula : | C23H25ClN4O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DNVXATUJJDPFDM-QGZVFWFLSA-N |
M.W : | 456.99 | Pubchem ID : | 49871818 |
Synonyms : |
(−)-JQ1
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.39 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 128.62 |
TPSA : | 97.61 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.64 cm/s |
Log Po/w (iLOGP) : | 4.17 |
Log Po/w (XLOGP3) : | 4.85 |
Log Po/w (WLOGP) : | 4.83 |
Log Po/w (MLOGP) : | 3.63 |
Log Po/w (SILICOS-IT) : | 6.6 |
Consensus Log Po/w : | 4.81 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.78 |
Solubility : | 0.000757 mg/ml ; 0.00000166 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.63 |
Solubility : | 0.000106 mg/ml ; 0.000000232 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.64 |
Solubility : | 0.0000103 mg/ml ; 0.0000000226 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.64 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
82 % ee | at 20 - 90℃; for 2 h; | In a 500mL two neck round-bottomed flask equipped with a magnetic stir bar was dissolved amide 5 (3.40g, 8.13mmol) in THF (60mL) and cooled to −78°C. While stirring at −78°C, potassium tert-butoxide (1.0M solution in THF, 8.95mL, 8.94mmol, 1.10equiv) was added. The reaction mixture was warmed to −10°C and stirred for 30min. The reaction mixture was cooled to −78°C and diphenyl chlorophosphate (2.02mL, 9.76mmol) was added to the reaction mixture. The resulting mixture was warmed to −10°C and stirred at this temperature for 45min. Acetylhydrazide (0.90, 12.20mmol, 1.50equiv) was added to the reaction mixture. The reaction mixture was stirred at room temperature. After 1h, 1-butanol (70mL) was added to the reaction mixture, which was heated to 90°C. After 1h, all solvents were removed under reduce pressure. The residue was dissolved in CH2Cl2 and washed with saturated aq. NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain crude (+)-JQ1, which was purified by flash column chromatography on silica gel (0–100percent ethyl acetate in hexanes) to afford (+)-JQ1 (3.04g, 82percent) as a white solid and with a 91:9 er (determined with Supercritical Fluid Chromatography (SFC) using the CHIRALPAK AS-H column, CO2–EtOH (3:1), 210nm, tR (R-enantiomer) 1.62min, tR (S-enantiomer) 3.51min). This product was further purified by preparative SFC using a CHIRALPAK AS-H column to obtain (+)-JQ1 (S-enantiomer) with >99percent ee. The spectral data of (+)-JQ1 matched with those described in the literature6 with the exception of the optical rotation. [α]D22 +41 (c 0.50, CHCl3), (Lit. [α]D22 +55 (c 0.50, CHCl3);12 (−)-JQ1: >99percent ee, [α]D22 −39 (c 0.55, CHCl3), (Lit. [α]D22 −55 (c 0.50, CHCl3).6 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82 % ee | at 20 - 90℃; for 2 h; | In a 500mL two neck round-bottomed flask equipped with a magnetic stir bar was dissolved amide 5 (3.40g, 8.13mmol) in THF (60mL) and cooled to −78°C. While stirring at −78°C, potassium tert-butoxide (1.0M solution in THF, 8.95mL, 8.94mmol, 1.10equiv) was added. The reaction mixture was warmed to −10°C and stirred for 30min. The reaction mixture was cooled to −78°C and diphenyl chlorophosphate (2.02mL, 9.76mmol) was added to the reaction mixture. The resulting mixture was warmed to −10°C and stirred at this temperature for 45min. Acetylhydrazide (0.90, 12.20mmol, 1.50equiv) was added to the reaction mixture. The reaction mixture was stirred at room temperature. After 1h, 1-butanol (70mL) was added to the reaction mixture, which was heated to 90°C. After 1h, all solvents were removed under reduce pressure. The residue was dissolved in CH2Cl2 and washed with saturated aq. NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain crude (+)-JQ1, which was purified by flash column chromatography on silica gel (0–100percent ethyl acetate in hexanes) to afford (+)-JQ1 (3.04g, 82percent) as a white solid and with a 91:9 er (determined with Supercritical Fluid Chromatography (SFC) using the CHIRALPAK AS-H column, CO2–EtOH (3:1), 210nm, tR (R-enantiomer) 1.62min, tR (S-enantiomer) 3.51min). This product was further purified by preparative SFC using a CHIRALPAK AS-H column to obtain (+)-JQ1 (S-enantiomer) with >99percent ee. The spectral data of (+)-JQ1 matched with those described in the literature6 with the exception of the optical rotation. [α]D22 +41 (c 0.50, CHCl3), (Lit. [α]D22 +55 (c 0.50, CHCl3);12 (−)-JQ1: >99percent ee, [α]D22 −39 (c 0.55, CHCl3), (Lit. [α]D22 −55 (c 0.50, CHCl3).6 |