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CAS No. : | 15098-69-8 | MDL No. : | MFCD00038892 |
Formula : | C28H53N3O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HRLHJTYAMCGERD-MERQFXBCSA-N |
M.W : | 527.74 | Pubchem ID : | 12017189 |
Synonyms : |
|
Num. heavy atoms : | 37 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.89 |
Num. rotatable bonds : | 15 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 148.2 |
TPSA : | 125.99 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.06 cm/s |
Log Po/w (iLOGP) : | 5.9 |
Log Po/w (XLOGP3) : | 3.47 |
Log Po/w (WLOGP) : | 5.9 |
Log Po/w (MLOGP) : | 2.91 |
Log Po/w (SILICOS-IT) : | 1.34 |
Consensus Log Po/w : | 3.91 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.31 |
Solubility : | 0.026 mg/ml ; 0.0000492 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.8 |
Solubility : | 0.000841 mg/ml ; 0.00000159 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.79 |
Solubility : | 0.862 mg/ml ; 0.00163 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.87 |
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 |
---|---|---|
65% | Stage #1: VRX-480773; N,N'-bis(tert-butyloxycarbonyl)-L-lysine dicyclohexylamine salt With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 14h; Stage #2: With hydrogenchloride In 1,4-dioxane at 20℃; for 14h; | A 25 mL round-bottomed flask was charged with 2-[5-bromo-4-(4-cyclopropyl- naphthalen-l-yl)-4H-[l,2,4]triazol-3-ylsulfanyl]-N-(2-chloro-4-sulfamoylphenyl)acetamide (50 mg, 0.085 mmol), EDC (35 mg, 0.18 mmol), Boc-Lys(Boc)-OH DCHA (47 mg, 0.09 mmol) in the mixture of 5 niL THF and 5 mL methylene chloride. To the mixture was added DMAP (16 mg, 0.13 mmol) in one portion. The reaction mixture was stirred at RT for 14 h. The solvents were evaporated under reduced pressure yielding thick oily residue. The residue was dissolved in 5mL 4.0 M HCl in dioxane. The reaction was stirred at RT for 14 h. The solvent was evaporated under reduced pressure yielding thick oily residue. The residue was washed successively with 10 mL methylene chloride and 10 mL ether yielding the title compound as a light yellow solid (44 mg, 65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; | |
78% | With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; | (S)-Di-tert-butyl(6-oxo-6-((2-(2-pyridyldithio)ethyl)amino)hexane-1,5-diyl)dicarbamate (7) [21]. N,N′-Di-boc-l-lysine dicyclohexylammonium salt (1.52g, 2.89mmol), 3 (707mg, 3.18mmol) and TSTU (955.9mg, 3.18mmol) were dissolved in 35mL anhydrous DMF. DIPEA (1.49g, 1.96mL, 11.55mmol) was added to the initially prepared solution and the reaction mixture was stirred for 4hat room temperature in an argon atmosphere. Afterwards, the suspension was diluted with 250mL ethyl acetate and the organic layer was washed three times with 0.2M hydrochloric acid. The clear solution was dried with magnesium sulfate and the solvent was removed in vacuo. Subsequently, the residue was purified by silica gel column chromatography using ethyl acetate/hexane (3:1) as eluent, to obtain the product as colorless oil (1.16g, 2.25mmol, 78%). 1H NMR (300MHz, DMSO-d6): δ=8.52-8.43 (1H, m, NCH), 8.05 (1H, t, J=5.4Hz, CHCONH), 7.88-7.70 (2H, m, SCCHCH), 7.31-7.18 (1H, m, NCHCH), 6.82 (1H, d, J=7.8Hz, CHNH), 6.75 (1H, t, J=5.4Hz, OCONH), 3.89-3.73 (1H, m, CHNH), 3.47-3.19 (2H, m, CH2CH2S), 2.98-2.77 (4H, m, CH2CH2S, OCONHCH2), 1.58-1.17 (6H, m, CHCH2CH2CH2), 1.36 (18H, s, 6xCH3); 13C NMR (75MHz, DMSO-d6): δ=172.3, 159.0, 155.5, 155.3, 149.6, 137.8, 121.2, 119.3, 77.9, 77.3, 54.4, 39.6, 37.7, 37.5, 31.6, 29.2, 28.3, 28.2, 22.8; m/z (MALDI-TOF): 536.93 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.5% | With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; | TAEA-(W(Boc)K(Boc)-Boc)3 (3-K). TAEA-(W(Boc)K(Boc)-Boc)3 (3-K). (0427) Without further purification, 2 (0.696 mmol, 699 mg) was dissolved in DMF (25 mL) and Boc-Lys(Boc)-OH.DCHA (2.3 mmol, 1.21 g), HBTU (2.3 mmol, 872.4 mg), HOBT (2.3 mmol, 310.8 mg), DIEA (4.6 mmol, 801.6 μL), were added to the reaction mixture which was stirred for 4 h at room temperature. The solvent was evaporated and EtOAc (40 mL) was added. The solution was then washed with saturated KHSO4 (1×20 mL), saturated NaHCO3 (1×20 mL), and saturated NaCl (1×20 mL). After drying over Na2SO4, the solvent was evaporated in vacuum to give a yellow oil which was purified by flash chromatography to give 3-K (1.06 g, 76.5%). (0428) ESI-MS: m/z=Found 1991.2 (M+H+); Calcd 1991.4 |