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[ CAS No. 578-95-0 ] {[proInfo.proName]}

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Chemical Structure| 578-95-0
Chemical Structure| 578-95-0
Structure of 578-95-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 578-95-0 ]

CAS No. :578-95-0 MDL No. :MFCD00005019
Formula : C13H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :FZEYVTFCMJSGMP-UHFFFAOYSA-N
M.W : 195.22 Pubchem ID :2015
Synonyms :

Calculated chemistry of [ 578-95-0 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.07
TPSA : 32.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.98
Log Po/w (WLOGP) : 2.68
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 3.63
Consensus Log Po/w : 2.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.62
Solubility : 0.047 mg/ml ; 0.000241 mol/l
Class : Soluble
Log S (Ali) : -3.33
Solubility : 0.0906 mg/ml ; 0.000464 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.29
Solubility : 0.00101 mg/ml ; 0.00000516 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 578-95-0 ]

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:

Application In Synthesis of [ 578-95-0 ]

* 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.

  • Upstream synthesis route of [ 578-95-0 ]
  • Downstream synthetic route of [ 578-95-0 ]

[ 578-95-0 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 578-95-0 ]
  • [ 1207-69-8 ]
YieldReaction ConditionsOperation in experiment
89% for 12 h; Reflux; Inert atmosphere A magnetically stirred solution of 9-acridanone (4.01 g, 21 mmol) in phosphorus oxychloride (105 mL, 1.13 mol) was brought to reflux for 12 h. The solution was cooled to rt, added slowly to cracked ice (650 g), and made slightly alkaline with concentrated ammoniumhydroxide. A light tan solid was collected by filtration, washed with water, and air dried for 24 h. Flash chromatography (silica gel/75percent hexane, 20percent THF, 5percent triethylamine) afforded 3.97 g (89percent yield)of 10 as fine yellow needles which was identical to material prepared by method A as judged by TLC, mp, and spectral data.
86% at 105℃; for 3 h; Inert atmosphere Add 3 mmol of acridone to a two-necked flask equipped with a condenser and a stir bar, fill with N2, add 6 ml of P0C13 in a nitrogen atmosphere, and reflux at 105 ° C for 3 h. After the reaction is completed, cool to room temperature. The reaction solution was slowly dropped into ice water while stirring, and a mixture of ice, concentrated aqueous ammonia and chloroform (volume ratio 1:1:1) was added to the above liquid, and the chloroform layer was separated and dried (anhydrous magnesium sulfate). Filtration gave a pale yellow liquid, which was purified by column chromatography using ethyl acetate: petroleum ether.White needle crystals were obtained with strong fluorescence. Intermediate Compound 1, yield 86percent.
47 g With thionyl chloride In N,N-dimethyl-formamide A mixture of 50 g (0.25 mol) of intermediate (d) and 35 g of thionyl chloride and 200 g of N, N-dimethylformamide,After completion of the reaction, the reaction mixture was poured into ice water, filtered and dried to obtain 47 g of a yellow solid powdery intermediate ()
Reference: [1] Pharmaceutical Sciences, 1997, vol. 3, # 5-6, p. 235 - 239
[2] European Journal of Inorganic Chemistry, 1999, # 3, p. 557 - 563
[3] Heterocycles, 2014, vol. 88, # 1, p. 535 - 546
[4] Patent: CN108640873, 2018, A, . Location in patent: Paragraph 0022; 0023
[5] Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 926 - 935
[6] Justus Liebigs Annalen der Chemie, 1893, vol. 276, p. 48
[7] Organic Syntheses, 1942, vol. 22, p. 5
[8] Chemische Berichte, 1900, vol. 33, p. 3770
[9] Patent: CN103755634, 2016, B, . Location in patent: Paragraph 0040
[10] Patent: WO2008/10984, 2008, A2, . Location in patent: Page/Page column 22
  • 2
  • [ 10026-13-8 ]
  • [ 578-95-0 ]
  • [ 10025-87-3 ]
  • [ 1207-69-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 276, p. 48
  • 3
  • [ 578-95-0 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1278,1281
  • 4
  • [ 578-95-0 ]
  • [ 611-64-3 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1278,1281
  • 5
  • [ 917-64-6 ]
  • [ 142-96-1 ]
  • [ 578-95-0 ]
  • [ 611-64-3 ]
  • [ 6267-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1278,1281
  • 6
  • [ 109392-90-7 ]
  • [ 5336-90-3 ]
  • [ 578-95-0 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 17, p. 5189 - 5196
  • 7
  • [ 79-11-8 ]
  • [ 578-95-0 ]
  • [ 38609-97-1 ]
YieldReaction ConditionsOperation in experiment
95.7% at 20 - 25℃; for 12 h; Ionic liquid The synthesis method comprises the following steps:29.2 g of [Pmim] OH ionic liquid was added in a three-necked flask equipped with a condensing reflux at room temperature,19.5g acridone, stirring evenly after adding 11.3 g of chloroacetic acid, the control temperature of 25 stirring reaction 12h after standing at room temperatureThe residue was then washed with 25 ml of methanol and dried to give 24.2 g of acridone acetate (yield: 95.7percent).
93.5% With tetrabutylammomium bromide; sodium hydroxide In water; N,N-dimethyl-formamide at 80℃; for 3 h; 39percent acridone (2 mol),N-tetrabutylammonium bromide (TBAB) 19.34g (0.06mol),265 g (2.8 mol) of chloroacetic acid was added to a 1000 mL three-necked flask.Add 500 mL of organic solvent DMF and stir at 80 ° C to dissolve.Further, 100 mL of a 60 wtpercent NaOH aqueous solution was added, and after heating at 80 ° C for 3 hours,The reaction was stopped, allowed to cool to room temperature, and the reaction system was poured into 300 mL of ice water.A large amount of yellow solid precipitates were precipitated, allowed to stand overnight, suction filtered, and washed with ice water.That is, a wet intermediate is obtained; 500 mL of a 30 wtpercent NaOH aqueous solution is added to the wet intermediate,Dissolve and stir at room temperature, filter, and wash with 100 mL of 30 wtpercent NaOH aqueous solution.Combine the washing solution, add concentrated hydrochloric acid to adjust the pH value between 4 and 5.There is a large amount of yellow solid precipitates, Allow to stand overnight, suction filtration, wash with ice water,Drying, 474 g of acridinone acetate product was obtained, and the yield was 93.5percent.The purity by HPLC was 99.2percent.
Reference: [1] Patent: CN104592115, 2017, B, . Location in patent: Paragraph 0016; 0017; 0018
[2] Patent: CN108456166, 2018, A, . Location in patent: Paragraph 0030; 0044; 0045; 0047; 0050; 0051; 0072
[3] Acta Poloniae Pharmaceutica - Drug Research, 2010, vol. 67, # 2, p. 211 - 214
  • 8
  • [ 105-36-2 ]
  • [ 578-95-0 ]
  • [ 38609-97-1 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 1, p. 94 - 97
[2] Organic Preparations and Procedures International, 2000, vol. 32, # 3, p. 284 - 287
  • 9
  • [ 578-95-0 ]
  • [ 38609-97-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2007, vol. 42, # 6, p. 752 - 771
  • 10
  • [ 578-95-0 ]
  • [ 106-89-8 ]
  • [ 150389-84-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 6, p. 2423 - 2427
[2] Chemical Communications, 2011, vol. 47, # 15, p. 4472 - 4474
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 19, p. 3071 - 3079
  • 11
  • [ 2516-33-8 ]
  • [ 578-95-0 ]
  • [ 150389-84-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 11, p. 3973 - 3979
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