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CAS No. : | 157716-52-4 | MDL No. : | |
Formula : | C25H52NO4P | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SZFPYBIJACMNJV-UHFFFAOYSA-N |
M.W : | 461.66 | Pubchem ID : | 148177 |
Synonyms : |
KRX-0401;NSC 639966;NKA17;D21266
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 20 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 138.51 |
TPSA : | 68.4 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.14 cm/s |
Log Po/w (iLOGP) : | -1.35 |
Log Po/w (XLOGP3) : | 8.42 |
Log Po/w (WLOGP) : | 7.68 |
Log Po/w (MLOGP) : | 0.38 |
Log Po/w (SILICOS-IT) : | 6.58 |
Consensus Log Po/w : | 4.34 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.69 |
Solubility : | 0.0000949 mg/ml ; 0.000000206 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -9.73 |
Solubility : | 0.000000087 mg/ml ; 0.0000000002 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.92 |
Solubility : | 0.00000552 mg/ml ; 0.000000012 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 4.76 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
48% | In chloroform at 20℃; for 24h; Inert atmosphere; | General Procedure for the Preparation of pro-APLs General procedure: Pro-APLs were prepared according to a previously reportedprocedure (26). Briefly, electrophilic reagent and APL werestirred in refluxing dry CHCl3 for 24 h under argon. Volatilewas distilled off and the residue was purified by flash chromatography(CH2Cl2/MeOH 10:0 to 7:3) to yield thecorresponding pro-APL. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | In chloroform for 24h; Inert atmosphere; Reflux; | General Procedure for the Preparation of pro-APLs General procedure: Pro-APLs were prepared according to a previously reportedprocedure (26). Briefly, electrophilic reagent and APL werestirred in refluxing dry CHCl3 for 24 h under argon. Volatilewas distilled off and the residue was purified by flash chromatography(CH2Cl2/MeOH 10:0 to 7:3) to yield thecorresponding pro-APL. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | In chloroform for 24h; Inert atmosphere; Reflux; | General Procedure for the Preparation of pro-APLs General procedure: Pro-APLs were prepared according to a previously reportedprocedure (26). Briefly, electrophilic reagent and APL werestirred in refluxing dry CHCl3 for 24 h under argon. Volatilewas distilled off and the residue was purified by flash chromatography(CH2Cl2/MeOH 10:0 to 7:3) to yield thecorresponding pro-APL. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | Stage #1: 1-octadecanol With triethylamine; trichlorophosphate In diethyl ether at 0 - 20℃; for 16h; Stage #2: 4-hydroxy-1,1-dimethylpiperidinium p-toluenesulphonate With dmap; triethylamine In chloroform at 20℃; for 48h; Stage #3: With water In tetrahydrofuran for 6h; Reflux; | Perifosine (P) Phosphorus oxychloride (864 μL, 9.2 mmol) was addedto 1-octadecanol (2.50 g, 9.2 mmol) in anhydrous Et2O(100 mL) at 0°C, followed by dropwise addition of triethylamine(1.29 mL, 9.2 mmol). The reaction mixturewas stirred at rt. for 16 h, filtered and the filtrate wasreduced under vacuum. The dry residue was dissolvedin anhydrous CHCl3 (100 mL) and N,N-dimethyl-4-hydroxypiperidinium tosylate (2.78 g, 9.24 mmol), triethylamine(3.00 mL, 21.5 mmol), and 4-DMAP (65 mg,0.53 mmol) in CHCl3 (100 mL) were introduced in thereaction flask and allowed to react for 2 d at rt. Thereaction mixture was then reduced under vacuum, suspendedin THF (100 mL) and refluxed with H2O(2 mL) for 6 h. The crude mixture was reduced undervacuum and the residue was directly purified by flashchromatography (CHCl3/MeOH/NH4OH 28% 10:6:1)to yield perifosine (0.70 g, 16%). Rf: 0.2 (CH2Cl2/MeOH/H2O 75:22:3). 1H-NMR (400 MHz,MeOD/CDCl3 1:1) δ 0.85 (t, J = 6.5 Hz, 3H); 1.24(m, 30H); 1.59 (m, 2H); 2.10 (m, 4H); 3.09 (s, 3H);3.16 (s, 3H); 3.25-3.53 (m, 4H); 3.82 (m, 2H); 4.40(m, 1H). 13C-NMR (100.7 MHz, MeOD/CDCl3 1:1) δ14.3; 23.2; 26.4; 27.2 (2C); 29.9; 30.0; 30.2 (10C); 31.5;32.5; 55.4 (2C); 59.2 (2C); 65.0; 66.6. 31P-NMR(162 MHz; MeOD/CDCl3 1:1) δ - 0.40. IR ν 479;720; 846; 919; 994; 1062; 1124; 1156; 1225; 1468;2848; 2916. HR-MS (ESI+) m/z [M + Na]+ calcd forC25H52NNaO4P+ 484.3526, found 484.3528. |