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[ CAS No. 74258-86-9 ] {[proInfo.proName]}

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Chemical Structure| 74258-86-9
Chemical Structure| 74258-86-9
Structure of 74258-86-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 74258-86-9 ]

CAS No. :74258-86-9 MDL No. :MFCD00869538
Formula : C20H26N2O5S Boiling Point : -
Linear Structure Formula :- InChI Key :FHHHOYXPRDYHEZ-COXVUDFISA-N
M.W : 406.50 Pubchem ID :71992
Synonyms :
DU-1219;Cetapril;Alaceprilum

Calculated chemistry of [ 74258-86-9 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 11
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 111.36
TPSA : 129.08 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 1.32
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 1.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.12
Solubility : 0.307 mg/ml ; 0.000755 mol/l
Class : Soluble
Log S (Ali) : -4.45
Solubility : 0.0144 mg/ml ; 0.0000354 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.59
Solubility : 0.104 mg/ml ; 0.000256 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.87

Safety of [ 74258-86-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 74258-86-9 ]

* 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 [ 74258-86-9 ]

[ 74258-86-9 ] Synthesis Path-Downstream   1~11

  • 2
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  • [ 129398-84-1 ]
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  • 5
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  • 7
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  • [ 74597-04-9 ]
  • [ 801293-47-0 ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In chloroform; at 0 - 20℃; for 5.0h; 1-[(25)-3-(ACETYLTHIO)-2-METHYL-1-OXOPROPYL]-L-PROLYL- L-phenylalanine (1.00 g, 0.025 Mol), 1-HYDROXY-3- bromomethylbenzene (0.463 g, 0.025 Mol) and 4- DIMETHYLAMINOPYRIDINE (0.060 g, 0.005 Mol) were dissolved in CHC13 (10 ml) and the solution was cooled to 0C. Dicyclohexylcarbodiimide (0.70 g, 0.033 Mol) was then added and the solution was slowly warmed to room temperature and stirred for 5 h. The crude material was concentrated and purified by flash chromatography eluting with EtOAc/n- Hexane 1: 1, affording 1-[(2S)-3-(ACETYLTHIO)-2-METHYL-1- OXOPROPYL]-L-PROLYL-L-PHENYLALANINE 3-bromomethyl phenyl ester (i. e. <strong>[74258-86-9]Alacepril</strong> 3-bromomethyl phenyl ester) (1.00 g) as a white powder. H-NMR (CDC13) : 7.30 (m, 7H), 6.98 (m, 2H), 4.98 (m, 1H), 4.66 (m, 1H), 4.45 (s, 2H), 3.45 (m, 3H), 3.28 (m, 2H), 3.09 (m, 1H), 3.07 (m, 1H), 2.78 (m, 1H), 2.34 (s, 3H), 2.00 (m, 4H), 1.01 (d, 3H).
  • 8
  • [ 74258-85-8 ]
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YieldReaction ConditionsOperation in experiment
100% With trifluoroacetic acid; In dichloromethane; at 20℃; for 1.0h; 1-[(2S)-3-(ACETYLTHIO)-2-METHYL-1-OXOPROPYL]-L-PROLYL- L-PHENYLALANINE tert-butyl ester (1.19 g, 0.025 Mol) was dissolved in a solution of trifluoroacetic ACID : CH2CL2 (1: 2,30 ml) and the reaction was stirred at room temperature for 1 hour. Then it was evaporated under reduced pressure affording 1-[(2S)-3-(ACETYLTHIO)-2-METHYL- 1-OXOPROPYL]-L-PROLYL-L-PHENYLALANINE as a clear oil (1.00 g, 100 %) that was used in the subsequent reaction without any further purification. 1H-NMR (CDC13) : 7.23 (m, 5H), 7.05 (d, 1H), 4.91 (m, 1H), 4.55 (m, 1H), 3.62 (m, 2H), 3.15 (m, 3H), 2.92 (m, 2H), 2.38 (s, 3H), 2.07 (m, 4H), 1.88 (m, 3H), 1.17 (d, 3H).
  • 9
  • [ 74258-86-9 ]
  • 1-(D-3-mercapto-2-methylpropanoyl)-L-prolyl-L-phenylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With calcium hydroxide; sodium hydroxide; In ethanol; water; EXAMPLE 23 1-(D-3-Mercapto-2-methylpropanoyl)-L-prolyl-L-phenylalanine 1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine (1.0 g) was suspended in water (20 ml) under argon. The pH of the suspension was maintained at 13 for 1.5 hours using 5 N sodium hydroxide. During this time, the suspension became clear to give a solution. The solution thus obtained was adjusted to pH 2 with concentrated sulfuric acid and extracted with dichloromethane. The organic layer was washed with water, dried and concentrated to give the title compound (0.75 g). The compound thus obtained (0.50 g) was dissolved in 50% ethanol, and calcium hydroxide (48 mg) was added. The solution was concentrated to dryness under reduced pressure. The residue was dissolved in water (50 ml) and the resulting solution was lyophilized to give the calcium salt of the title compound, m.p. 160-180 C. (decomposition). IR numaxKBr cm-1: 3380, 1600, 1410.
  • 10
  • [ 64805-64-7 ]
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YieldReaction ConditionsOperation in experiment
In sodium hydroxide; EXAMPLE 27 1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine To a solution of L-prolyl-L-phenylalanine (0.52 g) in 1 N sodium hydroxide (2 ml) cooled in an ice bath, 3-acetylthio-2-methylpropanoyl chloride (0.36 g) and 2 N sodium hydroxide (1 ml) were added with vigorous stirring. After 3 hours' stirring at room temperature, the solution was washed with diethyl ether, acidified, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was treated as in the third paragraph of Example 26 to give the title compound.
  • 11
  • 1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine tert-butyl ester [ No CAS ]
  • [ 74258-86-9 ]
YieldReaction ConditionsOperation in experiment
In methoxybenzene; trifluoroacetic acid; EXAMPLE 17 1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine 1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine tert-butyl ester (2.5 g) was dissolved in a mixture of anisole (18 ml) and trifluoroacetic acid (37 ml). The solution was allowed to stand at room temperature for one hour and then concentrated to dryness under reduced pressure. The residue was crystallized from diethyl ether. Crystals collected were recrystallized from ethanol/n-hexane to give the title compound (1.8 g), m.p. 155-156 C. [alpha]D25 =-81.3 (c=1.02, ethanol) IR numaxKBr cm-1: 3240, 1740, 1685, 1645, 1620.
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