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[ CAS No. 1684-40-8 ] {[proInfo.proName]}

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Chemical Structure| 1684-40-8
Chemical Structure| 1684-40-8
Structure of 1684-40-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1684-40-8 ]

CAS No. :1684-40-8 MDL No. :MFCD00012657
Formula : C13H15ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZUFVXZVXEJHHBN-UHFFFAOYSA-N
M.W : 234.72 Pubchem ID :2723754
Synonyms :
Tacrine (hydrochloride);Tacrine HCl;Hydroaminacrine;C.I. 970

Calculated chemistry of [ 1684-40-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.31
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 70.54
TPSA : 38.91 Ų

Pharmacokinetics

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) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.51
Log Po/w (WLOGP) : 3.51
Log Po/w (MLOGP) : 2.6
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.97
Solubility : 0.0252 mg/ml ; 0.000107 mol/l
Class : Soluble
Log S (Ali) : -4.01
Solubility : 0.0229 mg/ml ; 0.0000976 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.46
Solubility : 0.00823 mg/ml ; 0.0000351 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.15

Safety of [ 1684-40-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1684-40-8 ]

* 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 [ 1684-40-8 ]

[ 1684-40-8 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 1684-40-8 ]
  • [ 112964-98-4 ]
  • [ 130073-99-3 ]
  • [ 130073-98-2 ]
  • 2
  • [ 4549-31-9 ]
  • [ 1684-40-8 ]
  • bis(7)-tacrine [ No CAS ]
  • 3
  • 5-chloromethyl-1-azabicyclo<3.3.0>octane hydrochloride [ No CAS ]
  • [ 1684-40-8 ]
  • 9-<(1-azabicyclo<3.3.0>octan-5-yl)methylamino>-1,2,3,4-tetrahydroacridine [ No CAS ]
  • 4
  • [ 67-56-1 ]
  • [ 1684-40-8 ]
  • (9-amino-5,6,7,8-tetrahydro-acridin-4-yl)-methanol [ No CAS ]
  • 5
  • [ 52824-42-7 ]
  • [ 1684-40-8 ]
  • 2-[7-(1,2,3,4-tetrahydro-acridin-9-ylamino)-heptyl]-isoindole-1,3-dione [ No CAS ]
  • 6
  • [ 17702-83-9 ]
  • [ 1684-40-8 ]
  • 2-[8-(1,2,3,4-tetrahydro-acridin-9-ylamino)-octyl]-isoindole-1,3-dione [ No CAS ]
  • 7
  • [ 1684-40-8 ]
  • tacrine dihydrate [ No CAS ]
  • 8
  • [ 637-59-2 ]
  • [ 1684-40-8 ]
  • [ 1440523-97-6 ]
YieldReaction ConditionsOperation in experiment
59% General procedure: Powdered potassium hydroxide (1.27 g, 22.6 mmol) was added to a solution of 7-MEOTA (2.00 g, 7.6 mmol) or THA(2.00 g, 8.5 mmol) in DMSO (30 mL) under nitrogen atmosphere.The mixture was vigorously stirred at room temperaturefor 2 hours. Subsequently, (3-bromopropyl)benzene (15mmol) or (bromomethyl)cyclohexane (15 mmol) was added dropwise and the stirring was continued for further 48 hours at the room temperature under nitrogen atmosphere. The endof reaction was determined with triethylamine-saturated TLC, mobile phase hexane/ethyl-acetate (1:1). When the reaction was finished, water (100 mL) was poured into reaction mixture and the water phase was extracted with ethylacetate(3100 mL). The combined ethyl-acetate extractswere dried over anhydrous sodium sulphate, filtered and the solvent was evaporated under reduced pressure. Evaporation of the solvent gave an oily residue that was purified by triethylamine-pretreated silica gel via column chromatography.The mobile phase hexane/ethyl-acetate (1:1) was usedfor purification. The pure product was isolated as brown crystals [13-16]. N-3-(Phenylpropyl)-1,2,3,4-Tetrahydroacridin-9-Amoniumchloride (1) Yield: 59.0 %; m.p. 195.6 - 196.8 C; 1H NMR spectrum(300 MHz, methanol-d4) delta (ppm): 1.87-1.94 (m, 4H), 2.11-2.20 (m, 2H), 2.54 (t, J = 5.87 Hz, 2H), 2.74 (t, J = 7.34 Hz,2H), 2.97 (t, J = 6.36 Hz, 2H), 3.93 (t, J = 6.85 Hz, 2H),7.12-7.25 (m, 5H), 7.44 (ddd, J = 1.22, 6.85, 8.80 Hz, 1H),7.74 (dd, J = 1.47, 8.56 Hz, 1H), 7.79 (ddd, J = 1.22, 6.84,8.31 Hz, 1H), 8.18 (d, J = 8.80 Hz, 1H); 13C NMR spectrum(75 MHz, methanol-d4) delta (ppm): 21.77, 22.91, 24.76, 29.23,32.81, 33.90, 48.39, 112.74, 116.84, 120.00, 126.17, 126.37,127.18, 129.54, 129.55, 133.97, 139.66, 142.14, 151.44,157.85; ESI-MS: m/z 317.0 [M]+ (calculated for:[C22H25N2]+ 317.2); EA: calculated 74.88 % C, 7.14 % H,7.94 % N; found 74.56 % C, 7.34 % H, 7.85 % N logP =5.49 ± 0.72 (calc. value) [17].
  • 9
  • [ 1684-40-8 ]
  • [ 2550-36-9 ]
  • [ 1440523-98-7 ]
YieldReaction ConditionsOperation in experiment
48.1% General procedure: Powdered potassium hydroxide (1.27 g, 22.6 mmol) was added to a solution of 7-MEOTA (2.00 g, 7.6 mmol) or THA(2.00 g, 8.5 mmol) in DMSO (30 mL) under nitrogen atmosphere.The mixture was vigorously stirred at room temperaturefor 2 hours. Subsequently, (3-bromopropyl)benzene (15mmol) or (bromomethyl)cyclohexane (15 mmol) was added dropwise and the stirring was continued for further 48 hours at the room temperature under nitrogen atmosphere. The endof reaction was determined with triethylamine-saturated TLC, mobile phase hexane/ethyl-acetate (1:1). When the reaction was finished, water (100 mL) was poured into reaction mixture and the water phase was extracted with ethylacetate(3100 mL). The combined ethyl-acetate extractswere dried over anhydrous sodium sulphate, filtered and the solvent was evaporated under reduced pressure. Evaporation of the solvent gave an oily residue that was purified by triethylamine-pretreated silica gel via column chromatography.The mobile phase hexane/ethyl-acetate (1:1) was usedfor purification. The pure product was isolated as brown crystals [13-16].
  • 10
  • [ 4509-90-4 ]
  • [ 1684-40-8 ]
  • C18H21BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2h; To a solution of 40 mg tetrahydroacridine hydrochloride(0.170 mmol) in DMF (3 mL) were added 5-bromovaleryl chloride(68 lL, 0.510 mmol) and Et3N (35 lL, 0.340 mmol). This mixturewas stirred at room temperature for 2 h. Then, Et2O (10 mL) andaqueous Na2CO3 solution (1 M, 10 mL) were added, and the mixturewas stirred. The organic phase was separated, and the aqueousphase was extracted with diethyl ether (3 15 mL). The combinedorganic extracts were dried with anhydrous Na2SO4 and filtered.After removing the solvent, 34 mg of corresponding bromo-amidewas obtained (55%). After that 27 mg of this product (0.070 mmol)was redissolved in DMF (2 mL), solanocapsine (30.0 mg,0.070 mmol) and KI (27.0 mg, 0.210 mmol) were added. The reactionmixture was stirred for 48 h at room temperature. CH2Cl2(10 mL) and aqueous Na2CO3 solution (0.1 M, approximatelypH = 11, 10 mL) were added, and the mixture was stirred. Theorganic phase was separated, and the aqueous phase was extractedwith CH2Cl2 (3 15 mL) and dried with anhydrous Na2SO4. Afterremoving the solvent, the residue was purified by preparative-TLC using a CH2Cl2:MeOH:Et3N (9.7:0.2:0.1) to obtain 19.0 mg ofcompound 24 (39%) as a yellow amorphous solid;[a]25D : +15.2(c 1.07, MeOH), IR (film) mmax: 3478.9, 3357.5, 3247.5, 3056.6,2927.4, 2854.1, 1648.8, 1575.6, 1565.9, 1500.4, 1444.4, 1376.9,1303.6, 1280.5, 1265.1, 1170.6, 1112.7, 1079.9, 1004.7, 759.8,736.7, 701.9 cm1. 1H NMR (CDCl3, 400.13 MHz): 7.90 dd (1H,J = 8.4, 0.7 Hz, H-170), 7.71 dd (1H, J = 8.4, 0.7 Hz, H-150), 7.56 ddd(1H, J = 8.4, 6.8, 1.2 Hz, H-160), 7.36 ddd (1H, J = 8.4, 6.8, 1.2 Hz,H-140), 4.47 ddd (1H, J = 16.9, 9.7, 7.2 Hz, H-16), 3.04 m (2H, H2-90),3.03 m (1H, H2-26a), 2.64 m (1H, H-3), 2.61 m (2H, H2-120), 2.56 m(2H, H2-10), 2.16 brt (1H, J = 11.8 Hz, H2-26b), 2.08 m (1H, H2-4a0),2.00 m (1H, H-22), 1.95 m (1H, H-25), 1.95 m (4H, H2-100, 110),1.82 m (1H, H2-4a), 1.82 m (1H, H2-24a), 1.79 m (1H, H-20), 1.68 m(1H, H2-7a), 1.67 m (1H, H2-1a), 1.63 m (2H, H2-2), 1.58 m (2H,H2-15), 1.49 m (1H, H2-11a), 1.42 m (1H, H2-12a), 1.38 m (1H,H-5), 1.34 m (1H, H-8), 1.33 m (1H, H2-11b), 1.27 m (2H, H2-20),1.26 m (2H, H2-6), 1.25 m (1H, H2-12b), 1.23 m (1H, H2-7b), 1.21 m(1H, H2-4b), 1.20 m (1H, H2-24b), 1.19 m (2H, H2-30), 1.11 m (1H,H-9), 1.07 m (1H, H-14), 1.02 m (1H, H2-4b0), 0.96 m (1H, H2-1b),0.95 d (3H, J = 6.7 Hz, H3-21), 0.85 d (3H, J = 6.4 Hz, H3-27), 0.77 s(3H, H3-19), 0.75 s (3H, H3-18), 0.70 m (1H, H-17). 13C NMR (CDCl3100.03 MHz): 168.1 (CO, C-50), 158.3 (C, C-80), 146.5 (C, C-60), 146.3(C, C-180), 128.6 (CH, C-170), 128.3 (CH, C-160), 123.9 (CH, C-140),119.5 (CH, C-150), 1 17.1 (C, C-130), 110.3 (C, C-70), 96.2 (C, C-23),74.4 (CH, C-16), 68.9 (CH, C-22), 60.5 (CH, C-14), 54.9 (CH, C-5),54.9 (CH2, C-26), 54.8 (CH, C-17), 50.8 (CH, C-3), 46.3 (CH2, C-10),46.0 (CH2, C-24), 45.6 (CH, C-9), 41.6 (C, C-13), 39.2 (CH2, C-40),39.2 (CH2, C-12), 39.0 (CH2, C-4), 38.9 (CH2, C-30), 37.4 (CH2, C-1),34.9 (CH, C-8), 32.9 (CH, C-20), 35.4 (C, C-10), 33.6 (CH, CH2-90),32.2 (CH2, C-7), 31.5 (CH2, C-2), 29.8 (CH, C-25), 28.9 (CH2, C-20),28.5 (CH2, C-6), 28.1 (CH2, C-15), 23.5 (CH, CH2-120), 22.5 (CH,CH2-100, 110), 20.2 (CH2, C-11), 18.7 (CH3, C-27), 15.1 (CH3, C-21),13.4 (CH3, C-18), 12.3 (CH3, C-19). HRESIMS m/z[M+H]+ 711.5240(calcd for C45H67N4O3, 711.5208).
  • 11
  • [ 1684-40-8 ]
  • [ 321-64-2 ]
  • 12
  • [ 1684-40-8 ]
  • [ 365533-87-5 ]
  • 13
  • [ 1684-40-8 ]
  • N-(7-(3,4-dihydro-1H-pyrido[3,4-b]indol-2(9H)-yl)heptyl)-1,2,3,4-tetrahydroacridin-9-amine [ No CAS ]
  • 14
  • [ 2468126-85-2 ]
  • [ 1684-40-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In water at 31.84℃; for 48h;
  • 15
  • [ 1684-40-8 ]
  • [ 6115-67-9 ]
YieldReaction ConditionsOperation in experiment
63 mg With N-chloro-succinimide In methanol; dichloromethane at 20℃; for 1h; Step 1: In a first step, 125mg of tetrahydroacridine hydrochloride (0.63mmol) were placed in a reaction flask. Then a solution of 86mg of N-chlorosuccinimide (0.63mmol) in a mixture of DCM (2mL) and MeOH (0.5mL) was added to this first flask, and the reaction was kept under stirring at room temperature. After 1h of reaction, 67mg of Na2CO3 (0.63mmol) were added. The mixture was concentrated to dryness until evaporation of the organic solvent, redissolved with H2O (10mL) and extracted with DCM (3x 10mL). The organic layers were combined, dried with anhydrous Na2SO4. The reaction mixture (138mg) was purified by column chromatography, using a sequential elution of DCM: MeOH (20%). The fractions corresponding to the elution with DCM: MeOH (97: 3%) were combined and 63mg (0.27mmol), assumed as chloro-tetrahydroacridine were obtained.
  • 16
  • [ 95983-89-4 ]
  • [ 1684-40-8 ]
  • [ 2640579-58-2 ]
YieldReaction ConditionsOperation in experiment
9.5 mg With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 5h; Step 4: 80mg of the activated linker were dissolved in 3mL of dry DMF, with 12mg of KOH. Then, 18mg of tetrahydroacridine hydrochloride (0.09mmol) were added and placed under stirring for 5h at room temperature. Then an aqueous solution of saturated Na2CO3 (5mL) was added and extracted with diethyl ether (5x 10mL). The organic phases were combined, dried with anhydrous Na2SO4 and evaporated under reduced pressure. After that, 307mg of reaction mixture were recovered and subjected to flash chromatography using hexane and DCM as solvents to remove tosylate-excess and a solution of DCM-MeOH (20%) for the elution of the compound of interest. This was subjected to purification by preparative TLC, and 9.5mg of product were recovered (that was assumed as the coupling product by its polarity in TLC).
  • 17
  • [ 624-76-0 ]
  • [ 1684-40-8 ]
  • [ 684238-90-2 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 20h; Step 1: 80mg (0.4mmol) of tetrahydroacridine hydrochloride were placed in a reaction flask and dissolved in 3mL of dry DMF. 32µL of iodoethanol (0.4mmol) were added and then 0.64mmol (36mg) of KOH. The reaction mixture was vigorously stirred for 20h (at room temperature),and then 5mL of H2O were added and partitioned with diethyl ether (5×10mL). The organic layers were combined, dried with anhydrous Na2SO4 and evaporated under reduced pressure. The resulting solid (67mg) was used as recovered in Step 3.
  • 18
  • [ 6165-76-0 ]
  • [ 1684-40-8 ]
  • N-(prop-2-yn-1-yl)-1,2,3,4-tetrahydroacridin-9-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h; Step 2: Moreover, 145mg (0.73mmol) of tetrahydroacridine hydrochloride were placed in a reaction flask and dissolved in 3mL of dry DMF, 140µL of tosylated propargyl alcohol (0.8mmol) were added and then 1.36mmol (76mg) of KOH. The reaction mixture was vigorously stirred for 3h, and then 5mL of H2O were added and partitioned with diethyl ether (5×10mL). The organic layers were combined, dried with anhydrous Na2SO4 and evaporated under reduced pressure. 86mg of impure tacrine derivative were recovered.
  • 19
  • [ 111-24-0 ]
  • [ 1684-40-8 ]
  • [ 490025-48-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 24h; Step 1: 80mg of tetrahydroacridine (0.4mmol) were dissolved in 2mL of dry DMSO and 42mg of KOH (0.64mmol) were added with stirring. Then, 60µL (0.43mmol) of 1,5-dibromopentane were added, and the reaction mixture was stirred at room temperature for 24h. After that, the reaction mixture was diluted with H2O (10mL) and extracted with AcOEt (4×8mL). The combined organic layers were washed with H2O (3×15mL), dried with anhydrous Na2SO4 and evaporated under reduced pressure.
Same Skeleton Products
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[ 1684-40-8 ]

Chemical Structure| 321-64-2

A295785[ 321-64-2 ]

1,2,3,4-Tetrahydroacridin-9-amine

Reason: Free-salt