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[ CAS No. 915385-81-8 ] {[proInfo.proName]}

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Chemical Structure| 915385-81-8
Chemical Structure| 915385-81-8
Structure of 915385-81-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 915385-81-8 ]

CAS No. :915385-81-8 MDL No. :MFCD22666355
Formula : C23H25ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :CAOTVXGYTWCKQE-UHFFFAOYSA-N
M.W : 380.91 Pubchem ID :15604015
Synonyms :
Opaganib

Calculated chemistry of [ 915385-81-8 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.48
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 107.86
TPSA : 41.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.4
Log Po/w (XLOGP3) : 4.67
Log Po/w (WLOGP) : 4.74
Log Po/w (MLOGP) : 4.05
Log Po/w (SILICOS-IT) : 5.25
Consensus Log Po/w : 4.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.14
Solubility : 0.00274 mg/ml ; 0.0000072 mol/l
Class : Moderately soluble
Log S (Ali) : -5.28
Solubility : 0.002 mg/ml ; 0.00000526 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.79
Solubility : 0.00000623 mg/ml ; 0.0000000164 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.48

Safety of [ 915385-81-8 ]

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 [ 915385-81-8 ]

* 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 [ 915385-81-8 ]

[ 915385-81-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 3731-53-1 ]
  • [ 1057292-87-1 ]
  • [ 915385-81-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran 1 As an example, a process for the synthesis of Compound 62 is described in Scheme 1. The direct bromination of adamantane-1-carboxylic acid (1) in the presence of aluminum chloride (AlCl3) gave 3-bromide derivative (2) of 1 which was converted to (3) by the reaction of Friedel-Crafts reaction. 3 was reacted with thionyl chloride (SOCl2) to give 3-R-substituted-1-adamantanecarbonyl chlorides 4. By reaction 4 with a substituted amine, for example, 4-aminomethylpyridin (5), in THF, (6, also represented as Compound 62) and related amide compounds were obtained.
  • 2
  • [ 3731-53-1 ]
  • [ 1057292-88-2 ]
  • [ 915385-81-8 ]
YieldReaction ConditionsOperation in experiment
In toluene 1; 2 3 reacted with an equimolar amount of 1,1'-carbonyl diimidazole (CDI) to give intermediate 3-R-substituted-1-adamantanecarbonyl imidazole (4). By reaction of 4 with a substituted amine, the corresponding adamantylamide was obtained. For example, reaction of 3 with 4-aminomethylpyridine (5), in toluene, produced {3-(4-Chloro-phenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)-amide} (6 also represented as Compound 62) with a yield of 92.6% and a melting point of 128-130° C. 1H NMR(300 MHz, CDCl3) δ 1.72-2.25(m, 12H, Admant-CH), 4.44-4.46 (d, J=6 Hz, 2H, CH2-Py), 6.18 (m, 1H, HN), 7.13-7.15 (d, J=6 Hz, 2H, H-Py), 7.15-7.30 (m, 4H, H-Ph), 8.52-8.54 (d, J=6 Hz, 2H, H-Py); 13C NMR(300 MHz, CDCl3) δ 28.98, 35.73, 36.71, 38.77, 42.18, 42.37, 44.88, 122.38, 125.30, 126.57, 128.56, 129.26, 148.39, 150.20 177.76; MS m/z (rel intensity) 381.50 (MH+, 100), 383.41 (90), 384.35(80). Example 2 A Second Method for the Synthesis of Compound 62 A second method for the synthesis of Compound 62 and related adamantylamides is described in Scheme 2. 3-phenyl substituted intermediate (3) was prepared as described above. 3 reacted with 1,1'-carbonyldiimidazole (CDI) to give 3-R-substituted-1-adamantanecarbonylimidazole intermediate (4). By reaction of 4 with a substituted amine, for example 4-aminomethylpyridine 5, in toluene, 6 {3-(4-Chloro-phenyl)-adamantane-1-carboxylic acid(pyridin-4-ylmethyl)-amide} was obtained.
  • 3
  • [ CAS Unavailable ]
  • [ 56531-62-5 ]
  • [ 915385-81-8 ]
YieldReaction ConditionsOperation in experiment
83.99 % Stage #1: 3-(4-chlorophenyl)adamantane-1-carboxylic acid With oxalyl dichloride In toluene at 15 - 25℃; Large scale; Stage #2: 4-(aminomethyl)pyridine With triethylamine In toluene at 0 - 25℃; Large scale; 6.S2; 7.S2; 8.S2 Small test is carried out to step S2, and its test concrete operation is: The specific operation of the test is as follows: add 4kg of toluene to a 10L three-mouth bottle equipped with mechanical stirring and thermometer, open the stirring, add 1.5kg (5.16 moles) 3-(4-chlorophenyl)-1-adamantanecarboxylic acid and 753g oxalyl chloride (5.93 moles) in turn, keep warm 15~25 °C and stir for 2-3h, the system is concentrated under reduced pressure at 40 °C until no liquid is produced, add 1kg of toluene, stir evenly and continue to concentrate at 40 °C under reduced pressure until no liquid is released, The resulting white solid was dissolved with 4kg of toluene to form a slightly turbid solution, which was recorded as an acid chloride solution for backup.Add 1kg of toluene, 614g (5.67 moles) of 4-aminomethylpyridine and 574g (5.67 moles) of triethylamine to another 10L three-mouth bottle equipped with mechanical stirring and thermometer; Turn on stirring, the system is cooled to 0~10 °C, the acid chloride solution prepared in advance is added to the reaction system droplets, after the dropwise addition is completed, the system is heated at 15~25 °C for stirring for 2h, the reaction system is concentrated under reduced pressure at no more than 55 °C until no liquid is released, add 3.0kg 1.0% hydrochloric acid aqueous solution, stir at room temperature for 20min, stand, filter, recrystallize the filter cake with toluene, filter, obtain a white to light yellow solid filter cake, dry the filter cake in a blast drying box at 40 °C to constant weight, weigh, The white to off-white solid was 1.65kg, the liquid phase purity was 99.12%, and the yield was 83.99%.
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