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CAS No. : | 952-23-8 | MDL No. : | MFCD00066867 |
Formula : | C13H12ClN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PBBGTVBGXBUVLT-UHFFFAOYSA-N |
M.W : | 245.71 | Pubchem ID : | 197873 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 14 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 75.02 |
TPSA : | 64.93 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.93 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.63 |
Log Po/w (WLOGP) : | 3.37 |
Log Po/w (MLOGP) : | 2.06 |
Log Po/w (SILICOS-IT) : | 2.01 |
Consensus Log Po/w : | 2.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.63 |
Solubility : | 0.0576 mg/ml ; 0.000235 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.64 |
Solubility : | 0.0558 mg/ml ; 0.000227 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.67 |
Solubility : | 0.00531 mg/ml ; 0.0000216 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | 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 |
---|---|---|
With hydrogenchloride; phosphoric acid; sodium nitrite 1.) 0 deg C, 1 min, 2.) 0 deg C, 48 h; Yield given. Multistep reaction. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride at 180 - 190℃; for 44h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium azide; sodium nitrite 1.) 0 deg C, 1 min, 2.) 0 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium azide; trifluoroacetic acid; sodium nitrite at -5 - 0℃; for 1.25h; | |
With sodium azide; trifluoroacetic acid; sodium nitrite 1.) 0-5 deg C, 5 min; 2.) 15 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; tetrafluoroboric acid; sodium nitrite 1) H2O, 0 deg C, 30 min, 2) H2O, 0 deg C, 2 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With iodine; potassium iodide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-Bromosuccinimide; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Photochem. Verhalten; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium azide In acetic acid at 90℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / N-bromosuccinimide, aq. AcOH 2: 28 percent / N-bromosuccinimide, glacial AcOH / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3 3,6-Di-(β-D-galactopyranosyl-amino)-acridine EXAMPLE 3 3,6-Di-(β-D-galactopyranosyl-amino)-acridine In a round-bottom flask with a volume of 3 l provided with a reflux condenser and a mixer 60.0 g (0.33 mole) of D-galactose and 36.9 g (0.15 mole) of 3,6-diaminoacridine-hydrochloride are suspended in a mixture of 1350 ml of ethanol and 150 ml of water under heavy stirring. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.5 g (52.8%) | With hydrogenchloride In water; acetone | 7 3,6-Di-(α-D-ribopyranosyl-amino)-acridine EXAMPLE 7 3,6-Di-(α-D-ribopyranosyl-amino)-acridine Under stirring 2.46 g (10-2 mole) of 3,6-diamino-acridine-hydrochloride and 3.3 g (2.2*10-2 mole) of D-ribose are suspended in a mixture of 90 ml acetone and 10 ml of water. 0.5 ml of concentrated hydrochloric acid are added to the suspension heated to 45° C. After 2-3 minutes a clear solution is formed and after further 4-5 minutes the precipitate begins to separate. 25 minutes after the addition of the acid and liquid phase is separated, the precipitate is dissolved in 20 ml of water and the solution is poured into 200 ml of acetone. This reprecipitation is repeated twice. The product is filtered and dried. Yield: 2.5 g (52.8%), melting point: 180°-190° C., [α]D =+141° (c=1.20, dimethylformamide); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water; | EXAMPLE 6 3,6-Di-(alpha-L-rhamnopyranosyl-amino)-acridine 2.46 g (10-2 mole) of 3,6-diamino-acridine-hydrochloride and 4.0 g (2.2*10-2 mole) of <strong>[10030-85-0]L-rhamnose-monohydrate</strong> are suspended in a mixture of 10 ml of water and 90 ml of ethanol. The reaction mixture is stirred intensively and heated to a temperature of 70 C. After the addition of 0.5 ml or concentrated hydrochloric acid the mixture is stirred at the given temperature for another 90 minutes, while shining, flocculent crystals separate. The mixture is left to stand at room temperature for 12 hours and then it is filtered. 3.6 g (71.8%) of product are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; nitric acid; iron(II) sulfate In water at 25℃; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: potassium carbonate / acetone / 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: potassium carbonate / acetone / 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h 3.1: potassium carbonate / acetone / 5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h 3.1: potassium carbonate / acetone / 5 h / Reflux 4.1: pyridine; copper(II) acetate monohydrate / methanol / 96 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h 3.1: potassium carbonate / acetone / 5 h / Reflux 4.1: pyridine; copper(II) acetate monohydrate / methanol / 96 h / 45 °C 5.1: sodium hydroxide / N,N-dimethyl-formamide; toluene / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetone / 72 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: potassium carbonate / acetone / 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 24 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 24 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetone / 72 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 24 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Stage #1: proflavine hydrochloride; methyl chloroformate In acetone for 72h; Reflux; Stage #2: With sodium methylate In methanol | 2 General information 4.2 (6-Amino-3-acridinyl)carbamic acid methyl ester To a suspension of 3,6-diaminoacridine hydrochloride (3 g, 12.21 mmol) in dry acetone (100 mL), freshly distilled methyl chloroformate (9.4 mL, 122.1 mmol) was added. The reaction mixture was refluxed for 72 h and then concentrated up to dryness. The residue thus obtained was dissolved in methanol and the solution was basified with sodium methoxide in methanol. The crude product obtained after concentrating the solution in vacuo was purified by flash column (Ø=6 cm) chromatography by using acetone-ethyl acetate-triethylamine (5/5/1, v/v/v) as eluent, affording 2.25 g (69%) of product; mp 163-165 °C (hexane-dichloromethane). Found: C, 67.52; H, 4.85; N, 15.91. C15H13N3O2 requires C, 67.41; H, 4.90; N, 15.72; IR (KBr): ν 3334, 3215, 1717, 1645, 1551, 1488, 1462, 1398, 1318 cm-1; 1H NMR (DMSO-d6) δ 10.00 (s, 1H, NH), 8.51 (s, 1H, H-9), 8.06 (d, J=2.1 Hz, 1H, H-4), 7.83 (d, J=9.1 Hz, 1H, H-8), 7.72 (d, J=9.1 Hz, 1H, H-1), 7.41 (dd, J=9.1, 2.1 Hz, 1H, H-7), 6.99 (dd, J=9.1, 2.1 Hz, 1H, H-2), 6.84 (d, J=2.1 Hz, 1H, H-5), 6.22 (br s, 2H, NH2), 3.72 (s, 3H, CO2CH3); 13C NMR (DMSO-d6): δ 154.2, 151.6, 151.1, 149.8, 140.5, 135.0, 129.6, 129.3, 120.7, 120.2, 117.6, 112.4, 103.0, 52.0; MS (EI) (calcd for C15H13N3O2, 267.28) m/z 267 (M+, 82%), 235 (100), 208 (24), 181 (20), 153 (7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In water at 40℃; | 1 Synthesis of 3,6-Diamino-4,5-diiodoacridine DDA was synthesized based on a literature procedure (Martin, R. F., Aust. J. Chem., 1979, 32(12), 2637-2646). A round-bottom flask was charged with Proflavine HCl (1.4 g, 5.70 mmol) in water (150 mL). The solution was heated to 40° C. then solid NaHCO3 was added until a pH of 10 was achieved. The suspension was filtered and a yellow solid was isolated. A round-bottom flask was charged with the yellow solid (1.0 g, 4.79 mmol), potassium iodide (1.982 g, 11.946 mmol), Chloramine-T (3.366 g, 11.946 mmol), and dimethylformamide (20 mL) then reacted at ambient conditions for 1 hour. The resulting suspension was poured into water and the product was extracted with 3×50 mL of ethyl acetate. The ethyl acetate fractions were combined, reacted with sodium thiosulfate (25 mg), dried over anhydrous MgSO4, and evaporated using a rotary evaporator. To remove the p-toluene sulfonamide impurity, the resulting solid was dissolved in 250 mL of dichloromethane and excess ptoluenesulfonic acid monohydrate (1.26 g, 7.34 mmol) was added. After one hour of equilibration a dark red solid was isolated (608 mg 28% yield). 1H NMR spectroscopy verified the spectrum of the isolated solid matched the previously reported spectrum for DDA. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triethylamine In ethanol at 79℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / ethanol / 8 h / 79 °C 2: triethylamine / acetonitrile / 24 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 6 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 0 - 75 °C / Inert atmosphere 2.2: 75 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / 72 h / Inert atmosphere 2: phosphorus pentoxide / 5.5 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 6 h / 100 °C 2: sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 5 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / 72 h / Inert atmosphere 2: sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 5 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 6 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 0 - 75 °C / Inert atmosphere 2.2: 75 °C / Inert atmosphere 3.1: sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium tetrahydroborate for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 100℃; for 6h; |
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