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[ CAS No. 51264-14-3 ] {[proInfo.proName]}

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Chemical Structure| 51264-14-3
Chemical Structure| 51264-14-3
Structure of 51264-14-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51264-14-3 ]

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

Calculated chemistry of [ 51264-14-3 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.94

Safety of [ 51264-14-3 ]

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:

Application In Synthesis of [ 51264-14-3 ]

* 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.

  • Downstream synthetic route of [ 51264-14-3 ]

[ 51264-14-3 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 1207-69-8 ]
  • [ 57165-06-7 ]
  • [ 349459-07-0 ]
YieldReaction ConditionsOperation 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;
  • 2
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ 51264-14-3 ]
  • [ 117252-55-8 ]
  • [ 117252-56-9 ]
YieldReaction ConditionsOperation in experiment
1: 36% 2: 16% 3: 21% In acetonitrile
  • 3
  • [ 52-90-4 ]
  • [ 51264-14-3 ]
  • [ 57165-06-7 ]
  • [ 1255771-61-9 ]
YieldReaction ConditionsOperation in experiment
In methanol at 30℃; pH = 7.56 - 10.35;
  • 4
  • [ 616-91-1 ]
  • [ 51264-14-3 ]
  • [ 57165-06-7 ]
  • [ 1255771-68-6 ]
YieldReaction ConditionsOperation in experiment
In methanol at 30℃; pH = 7.61 - 11.40;
  • 5
  • [ 76946-74-2 ]
  • [ 51264-14-3 ]
  • [ 57165-06-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In methanol at 30℃; pH = 7.44 - 9.75;
  • 6
  • [ 51264-14-3 ]
  • [ 60-23-1 ]
  • [ 57165-06-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In methanol at 30℃; pH = 7.78 - 9.08;
  • 7
  • [ 51264-14-3 ]
  • [ 60-24-2 ]
  • [ 57165-06-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In methanol at 30℃; pH = 8.91 - 9.88;
  • 8
  • [ 51264-14-3 ]
  • [ 87764-57-6 ]
YieldReaction ConditionsOperation in experiment
With manganese(IV) oxide In ethyl acetate at 20℃; for 1h;
YieldReaction ConditionsOperation 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°.
  • 10
  • [ 124-63-0 ]
  • [ 110004-27-8 ]
  • [ 51264-14-3 ]
YieldReaction ConditionsOperation 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%.
  • 11
  • [ 51264-14-3 ]
  • [ 1680246-03-0 ]
YieldReaction ConditionsOperation 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
  • 12
  • [ 51264-14-3 ]
  • [ 1680246-04-1 ]
YieldReaction ConditionsOperation 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
  • 13
  • [ 32315-10-9 ]
  • [ 111625-28-6 ]
  • [ 349459-07-0 ]
  • C29H26N4O5S3 [ No CAS ]
YieldReaction ConditionsOperation 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%.
  • 14
  • [ 97-52-9 ]
  • [ 51264-14-3 ]
YieldReaction ConditionsOperation 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
  • 15
  • [ 1207-69-8 ]
  • [ 51264-14-3 ]
YieldReaction ConditionsOperation 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
  • 16
  • [ 132445-56-8 ]
  • [ 51264-14-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tin(ll) chloride; hydrogenchloride / water / 2 h / 100 °C 2: triethylamine / dichloromethane / 4 h
YieldReaction ConditionsOperation in experiment
With potassium chloride
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