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[ CAS No. 871361-88-5 ] {[proInfo.proName]}

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Chemical Structure| 871361-88-5
Chemical Structure| 871361-88-5
Structure of 871361-88-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 871361-88-5 ]

CAS No. :871361-88-5 MDL No. :MFCD05025493
Formula : C18H16N2O Boiling Point : -
Linear Structure Formula :- InChI Key :CYVVJSKZRBZHAV-UNZYHPAISA-N
M.W : 276.33 Pubchem ID :6018993
Synonyms :

Calculated chemistry of [ 871361-88-5 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 83.86
TPSA : 42.85 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 2.92
Log Po/w (WLOGP) : 3.48
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 4.29
Consensus Log Po/w : 3.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.68
Solubility : 0.0572 mg/ml ; 0.000207 mol/l
Class : Soluble
Log S (Ali) : -3.48
Solubility : 0.0913 mg/ml ; 0.00033 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.78
Solubility : 0.000454 mg/ml ; 0.00000164 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.66

Safety of [ 871361-88-5 ]

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 [ 871361-88-5 ]

* 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 [ 871361-88-5 ]

[ 871361-88-5 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 872-85-5 ]
  • [ 108-94-1 ]
  • 2,6-bis((pyridin-4-yl)methylene)cyclohexanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydroxide In water monomer at 25℃; for 10h;
75% With hydrogenchloride; acetic acid In water monomer at 20℃; for 24h; Synthesis of A and B General procedure: Synthesis of A and B 4-Pyridinecarboxaldehyde (2.14 g, 0.02 mol) was added to a solution of cyclohexanone (0.98 g, 0.01 mol) or N-methyl-4-piperidone (1.13 g, 0.01 mol) and glacial acetic acid (20 mL). Dry hydrogen chloride gas was passed through this mixture for 45 min, during which time a clear solution was obtained. After stirring at room temperature for about 24 h, the mixture was added into 100 mL water, and then aqueous ammonia was added until the pH of the system was adjusted to about 7. The system was filtered and subsequently washed by water to provide a yellow precipitate A or B.
69% With hydrogenchloride; acetic acid at 25 - 30℃; 4.2. Synthesis of curcumin analogs General procedure: A total of 61 curcumin analogs were synthesized as previously described with modification [35]. A mixture of the appropriate aldehyde (0.01 mol) and the ketone (0.005 mol) was dissolved in glacial acetic acid saturated with anhydrous hydrogen chloride and heated in a water bath at 25-30 °C for 2 h. After standing for 2d, the mixture was treated with cold water and filtered. The solid obtained was then washed and dried. The crude product was recrystallized from appropriate solvents (methanol or ethanol). Fourteen of the compounds studied were synthesized and characterized earlier in our laboratory [35]. The compounds described in Ref. [35] and their labeling in Ref. [35] are given in parenthesis in Table 1. Prior synthesis of additional curcumin-related compounds described in the literature are indicated below by providing appropriate references.
63% With potassium hydroxide In ethanol; water monomer at 20℃; for 2h; 4.2.1. Synthesis of 2a and 2b (2E,5E)2,5Bis(pyridine4methylene)cyclopentanone ( 2a) and(2E,6E)2,6bis(pyridine4methylene)cyclohexanone ( 2b) weresynthesized by modification from reported procedures [14]. 4-pyridinecarboxaldehyde (1.00 mL, 0.01 mol) was added a solutionof KOH (catalytic amount) in water (3 mL) and ethanol (1 mL).Cyclopentanone or cyclohexanone (0.5 molar equivalent) wasadded and the reaction mixture was stirred at ambient temperaturefor 2 h. The precipitated obtained was collected, dried andweighed.
50% With potassium hydroxide In ethanol at 40℃;
With sodium hydroxide In water monomer at 5 - 25℃; for 10h; General method for the chemical synthesis of compounds1-3 General procedure: The chemical synthesis was performed as previouslydescribed [24]. Briefly, Pyridine aldehyde (4 mmol) andcyclohexanone (2 mmol) were mixed in 20 ml distilledwater. The solution was then stirred in 2 ml of ice-coldSodium hydroxide (10%) for 10 h. Further, the solution wasneutralized with dilute HCl leading to the formation of aprecipitate that was filtered carefully. Ethanol was used torecrystallize the precipitate and the pure compound wasrecovered by column chromatography using ethyl acetate/hexane solution [25].

  • 2
  • [ 871361-88-5 ]
  • [ 108-46-3 ]
  • [ 1629904-93-3 ]
YieldReaction ConditionsOperation in experiment
92% In methanol; dichloromethane at 20℃; Co-crystal 1 A CH2Cl2 and CH3OH solution (10 mL, 1:1, v/v) of A (27.6 mg,0.1 mmol) with resorcinol (11.0 mg, 0.1 mmol) was kept at room temperature. Upon slow evaporation of the solvent about 7 days,yellow crystals 1 were obtained. Yield: 92%. IR (KBr Pellet cm1):3047(m), 2939(m), 2730(m), 2607(m), 1673(m), 1595(s),1543(m), 1422(m), 1309(m), 1273(s), 1220(s), 1182(m), 1166(m),1144(s), 1008(m), 837(m), 763(m). 1H NMR (300 MHz, DMSO,25 C, TMS, ppm): 9.12 (s, 2H, AOH), 8.64 (d, J = 5.8, 4H, AC5H4N7.54 (s, 2H, ACCH), 7.48 (d, J = 5.8, 4H, AC5H4N), 6.89 (m, 1H,AC6H4), 6.17 (t, 2H, AC6H4), 6.15 (s, 1H, AC6H4), 2.90 (t, 4H,ACH2), 1.73 (m, 2H, ACH2). Elemental analysis (%) calcd. forC24H22N2O3 (386.44): C 74.59, H 5.74, N 7.25; Found: C 74.43, H5.81, N 7.19.
  • 3
  • [ 871361-88-5 ]
  • [ 108-73-6 ]
  • [ 1629904-94-4 ]
YieldReaction ConditionsOperation in experiment
88% In methanol; dichloromethane at 20℃; Co-crystal 2 A CH2Cl2 and CH3OH solution (10 mL, 1:1, v/v) of A (27.6 mg,0.1 mmol) with 1,3,5-benzenetriol (12.6 mg, 0.1 mmol) was keptat room temperature. Upon slow evaporation of the solvent about4 days, yellow crystals 2 were obtained. Yield: 88%. IR (KBr Pelletcm1): 3047(m), 2939(br), 2774(br), 2624(br), 1665(m), 1597(s),1542(m), 1492(m), 1419(s), 1274(s), 1167(s), 1146(s), 1002(s),824(s), 730(m). 1H NMR (300 MHz, DMSO, 25 C, TMS, ppm):8.91 (s, 3H, AOH), 8.64 (d, J = 5.8, 4H, AC5H4N), 7.54 (s, 2H,ACCH), 7.48 (d, J = 5.8, 4H, AC5H4N), 5.64 (s, 3H, AC6H3), 2.90(t, 4H, ACH2), 1.73 (m, 2H, ACH2). Elemental analysis (%) calcd.for C24H22N2O4 (402.44): C 71.63, H 5.51, N 6.96; Found: C 71.51,H 5.57, N 6.89.
  • 4
  • [ 871361-88-5 ]
  • [ 123-31-9 ]
  • [ 1629904-96-6 ]
YieldReaction ConditionsOperation in experiment
75% In methanol; dichloromethane at 20℃; Co-crystal 4 A CH2Cl2 and CH3OH solution (10 mL, 1:1, v/v) of A (27.6 mg,0.1 mmol) with hydroquinone (11.0 mg, 0.1 mmol) was kept atroom temperature. Upon slow evaporation of the solvent about10 days, yellow crystals 4 were obtained. Yield: 75%. IR (KBr Pelletcm1): 3065(m), 2936(m), 2702(m), 2601(m), 1677(m), 1597(s),1543(m), 1472(s), 1422(s), 1368(s), 1271(s), 1255(s), 1215(s), 1168(s), 1144(s), 1009(s), 856(s), 830(s), 763(m). 1H NMR(400 MHz, DMSO, 25 C, TMS, ppm): 8.64 (d, J = 5.8, 4H, AC5H4N),8.60 (s, 2H, C6H6O2), 7.54 (s, 2H, ACCH), 7.48 (d, J = 5.8, 4H, AC5-H4N), 6.54 (s, 4H, C6H6O2), 2.90 (t, 4H, ACH2), 1.73 (m, 2H,ACH2).8.91 (s, 3H, AOH), 8.67 (d, J = 5.9, 4H, AC5H4N), 7.54 (s,2H, ACCH), 7.51 (d, J = 5.9, 4H, AC5H4N), 5.64 (s, 3H, AC6H3),2.93 (t, 4H, ACH2), 2.49 (s, 3H, ANCH3). Elemental analysis (%)calcd. for C24H22N2O3 (386.44): C 74.59, H 5.74, N 7.25; Found: C74.38, H 5.84, N 7.14.
  • 5
  • [ 871361-88-5 ]
  • [ 121-91-5 ]
  • [ 1629904-97-7 ]
YieldReaction ConditionsOperation in experiment
81% In methanol; dichloromethane Co-crystal 5 A CH2Cl2 and CH3OH solution (10 mL, 1:1, v/v) of A (27.6 mg,0.1 mmol) with isophthalic acid (16.6 mg, 0.1 mmol) was kept atroom temperature. Upon slow evaporation of the solvent about10 days, yellow crystals 5 were obtained. Yield: 81%. IR (KBr Pelletcm1): 2948(m), 1928(br), 1687(s), 1599(s), 1417(m), 1316(s),1272(s), 1241(s), 1163(s), 1141(s), 1014(s), 968(s), 839(m),735(m). 1H NMR (400 MHz, DMSO, 25 C, TMS, ppm): 13.26 (s,2H, ACOOH), 8.64 (d, J = 5.8, 4H, AC5H4N), 8.48 (s, 1H, AC6H4),8.17 (d, 2H, AC6H4), 7.64 (m, 1H, AC6H4), 7.54 (s, 2H, ACCH),7.48 (d, J = 5.8, 4H, AC5H4N), 2.90 (t, 4H, ACH2), 1.73 (m, 2H,ACH2). Elemental analysis (%) calcd. for C26H22N2O5 (442.46): C70.57, H 5.01, N 6.33; Found: C 70.76, H 5.06, N 6.12.
  • 6
  • [ 871361-88-5 ]
  • [ 762-04-9 ]
  • [ 1931947-64-6 ]
YieldReaction ConditionsOperation in experiment
58.7% With sodium ethanolate In ethanol at 20℃; for 24h; Inert atmosphere; Diethyl 3-oxo-1,5-diphenylpenta-1,4-dien-1-ylphosphonate(11). General procedure: Diethyl phosphonate, 0.2 mL, and a solution of sodium ethoxide (1-2 drops) were added to a solution of 0.5 g of 1,5-diphenylpenta-1,4-dien-3-one in 10 mL of ethanol. The mixture was kept for 24 h at room temperature, the solvent was distilled off under reduced pressure, and the residue was washed several times with diethyl ether. Yield 64.8%.
  • 7
  • [ 871361-88-5 ]
  • [ CAS Unavailable ]
  • [ 2375186-07-3 ]
YieldReaction ConditionsOperation in experiment
82% In dichloromethane for 24h; Reflux; 4.2.3. Synthesis of 4a and 4b Compound 1 (50 mg, 82 mmol) and 2a or 2b (1 molar equivalent)were added to 40 mL of dichloromethane and the mixturewas refluxed for 24 h. The solvent was removed under reducedpressure and the product recrystallized from hexane and dichloromethaneto afford 4a or 4b, respectively.
  • 8
  • [ 871361-88-5 ]
  • [ CAS Unavailable ]
  • [ 2375185-96-7 ]
YieldReaction ConditionsOperation in experiment
80% In dichloromethane for 24h; Reflux; 4.2.2. Synthesis of 3a and 3b Compound 1 (50 mg, 82 mmol) and 2a or 2b (2 molar equivalent)were added to 40 mL of dichloromethane and the mixturewas refluxed for 24 h. The solvent was removed under reducedpressure and the product recrystallized from hexane and dichloromethaneto afford 3a or 3b, respectively.
  • 9
  • [ 871361-88-5 ]
  • [ 74-88-4 ]
  • [ 2500955-76-8 ]
YieldReaction ConditionsOperation in experiment
99% In acetonitrile at 20℃; for 84h; General method for the chemical synthesis of compounds1A, 2A and 3A General procedure: The compounds were synthesized as per theprotocol described elsewhere [26]. Brief ly,2,6-Bis(pyridinylmethylene)cyclohexanone (2 mmol) derivativeswere dissolved in acetonitrile (10 ml) and immediatelycooled to 5 °C in a 25 ml round bottom flask. 5 ml of MethylIodide solution was injected into the flask using a syringe.The entire mixture was stirred first at 5 °C for 12 h, followedby RT for 72 h. The compound precipitate was filtered andwashed with little acetonitrile.
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