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CAS No. : | 51264-14-3 | MDL No. : | MFCD00242748 |
Formula : | C21H19N3O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XCPGHVQEEXUHNC-UHFFFAOYSA-N |
M.W : | 393.46 | Pubchem ID : | 2179 |
Synonyms : |
acridinyl anisidide;m-AMSA;Acridinylanisidide, AMSA, Amsacrine, Amsidine, Amsidyl, CI 880, CI880, CI-880, m-AMSA, meta-Amsacrine
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 20 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 113.55 |
TPSA : | 88.7 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.85 cm/s |
Log Po/w (iLOGP) : | 2.93 |
Log Po/w (XLOGP3) : | 4.01 |
Log Po/w (WLOGP) : | 5.4 |
Log Po/w (MLOGP) : | 2.22 |
Log Po/w (SILICOS-IT) : | 2.78 |
Consensus Log Po/w : | 3.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.0 |
Solubility : | 0.0039 mg/ml ; 0.0000099 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.58 |
Solubility : | 0.00105 mg/ml ; 0.00000266 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -8.36 |
Solubility : | 0.0000017 mg/ml ; 0.0000000043 mol/l |
Class : | Poorly soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.94 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335-H351-H361 | 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 |
---|---|---|
78% | at 120℃; for 0.666667h; | 27 General procedure: The suitable starting heterocycle (1 mmol), the corresponding amine [1 equiv, except ethylenediamine (4 equiv), imidazole and benzimidazole (2 equiv)] and 2 equiv of phenol were charged in a pressure-tight microwave tube containing a stirring bar. The reaction mixture was submitted to microwave irradiation for 30-45 min at 120 °C, with an irradiation power of 150 W, using a CEM Discover SP focused microwave reactor. The crude mixture was diluted with 5 ml of a 10% KOH aqueous solution and stirred until a precipitate was formed. Filtration afforded a solid was dried overnight in the presence of P2O5 to give the pure final products ;Orange solid; mp: 234 °C; 1H NMR (250 MHz, acetone) δ 8.36 (br s, 1H), 8.04 (s, 2H), 7.55-7.49 (m, 4H), 7.09-7.03 (m, 3H), 6.92 (dd, J=8.3, 2.2 Hz, 1H), 6.70 (d, J=8.3 Hz, 1H), 3.70 (s, 3H), 3.01 (s, 3H) ppm; 13C NMR (63 MHz, acetone-d6) δ 150.3 (2C), 143.2 (broad signal, 2C), 134.0, 132.2 (4C), 128.2 (2C), 121.8, 121.8 (broad signal, 2C), 119.9, 115.8 (2C), 107.9 (2C), 56.4, 39.1 ppm; IR (NaCl): ν 3798, 3347, 1560, 1512, 1474, 1321, 1149, 730, 667 cm-1. Elemental analysis calcd (%) for C21H19N3S: C 64.10, H 4.87, N 10.68, S 8.15; found: C 64.39, H 4.98, N 10.85, S 8.29. |
With hydrogenchloride In methanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 36% 2: 16% 3: 21% | In acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 30℃; pH = 7.56 - 10.35; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 30℃; pH = 7.61 - 11.40; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 30℃; pH = 7.44 - 9.75; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 30℃; pH = 7.78 - 9.08; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 30℃; pH = 8.91 - 9.88; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With manganese(IV) oxide In ethyl acetate at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11025 g (75%) | 6 Production of Methanesulfon-m-anisidide, 4'-(9 acridinyl-amino)-(VI) EXAMPLE 6 Production of Methanesulfon-m-anisidide, 4'-(9 acridinyl-amino)-(VI) To a stirred suspension of methanesulfon-m-anisidide, 4'-(9-acridinylamino)-, monohydrochloride (V) (16100 g; 37.5 moles) in N,N-dimethylacetamide (25.0 l.) was added a solution of sodium hydroxide (1610 g; 40.25 moles) in water (400 l.) during 1.5 hours. The reaction mixture was diluted with water (80 l.), stirred at 40°-50° for 4 hours, then stored for 16 hours at room temperature. The product was collected on a filter, then washed with deionized water (20.0 l.) until the washings were neutral. The free base was dissolved in hot (70°-80°) N,N-dimethylformamide (51 l.), then water (24 l.) was added to the stirred solution until precipitation began. The mixture was stored for 15 hours at room temperature, then cooled to 10°. The precipitated solid was collected, washed with ethanol (4*4.0 l.), then dried in vacuo (40°) to give 11025 g (75%) of purified product; m.p., 230°-231°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.8% | With triethylamine In dichloromethane for 4h; | 1.4 Synthesis of Compound 4 Methanesulfonyl chloride (72.9 mg 0.63 mmol) was dissolved in 60 mL of dichloromethane,A catalytic amount (0.5 mL) of triethylamine was added dropwise,The above solution was added dropwise to compound 3 (200 mg 0.63 mmol)Reaction for 4 hours,Washed three times with saturated potassium carbonate solution,Spin dry organic solvents,The crude product was isolated from the column (eluent Vrai = 3: 1) to give compound 4 in a yield of 42.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Cooling with ice 1.2: 12 h / 20 °C 2.1: dichloromethane / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Cooling with ice 1.2: 12 h / 20 °C 2.1: dichloromethane / 6 h / 20 °C 3.1: hydrogenchloride / water; acetone / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41.4% | Stage #1: bis(trichloromethyl) carbonate; 4'-(9-acridinylamino) methanesulfon-m-anisidine With N-ethyl-N,N-diisopropylamine In dichloromethane Cooling with ice; Stage #2: 2-(2-(Pyridin-2-yl)disulfanyl)ethanol With dmap In dichloromethane at 20℃; for 12h; | 1.5 Synthesis of Compound 5 Compound 4 (180 mg 0.46 mmol) was dissolved in dry 30 mL of dichloromethane,A solution of DIPEA (236 mg, 1.84 mmol,Chinese name: Ν, Ν-diisopropylethylamine),Triphosgene (135 mg 0.46 mmol) was then dissolved in dry 30 mL of dichloromethane,In the ice bath conditions,Dropping into the solution dropwise,With TLC detection to complete reaction,Pyridine-2-dithioethanol (86 mg 0.46 mmo 1) was added dropwise,A small amount of DMAP (56.12 mg 0.46mo 1, Chinese name: 4-dimethylaminopyridine)Room temperature reaction overnight (reaction time 12h).The reaction product was washed with water,Separating the organic layer,And dried over anhydrous sodium sulfate,The crude product was subjected to column chromatography (eluent: Vflf = 100: 1)To give compound 5,Yield 41.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol; chloroform; water / 12 h / 20 °C / Cooling with ice 2: tin(ll) chloride; hydrogenchloride / water / 2 h / 100 °C 3: triethylamine / dichloromethane / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol; chloroform; water / 12 h / 20 °C / Cooling with ice 2: tin(ll) chloride; hydrogenchloride / water / 2 h / 100 °C 3: triethylamine / dichloromethane / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tin(ll) chloride; hydrogenchloride / water / 2 h / 100 °C 2: triethylamine / dichloromethane / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium chloride |
A580248[ 54301-15-4 ]
N-(4-(Acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide hydrochloride
Reason: Free-salt