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CAS No. : | 3918-92-1 | MDL No. : | MFCD00020423 |
Formula : | C14H20N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GJNDXQBALKCYSZ-RYUDHWBXSA-N |
M.W : | 264.32 | Pubchem ID : | 6993120 |
Synonyms : |
H-Val-Phe-OH;Valylphenylalanine
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 72.54 |
TPSA : | 92.42 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -9.45 cm/s |
Log Po/w (iLOGP) : | 1.2 |
Log Po/w (XLOGP3) : | -2.16 |
Log Po/w (WLOGP) : | 0.78 |
Log Po/w (MLOGP) : | 1.15 |
Log Po/w (SILICOS-IT) : | 1.23 |
Consensus Log Po/w : | 0.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.11 |
Solubility : | 341.0 mg/ml ; 1.29 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.75 |
Solubility : | 1480.0 mg/ml ; 5.62 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -2.74 |
Solubility : | 0.481 mg/ml ; 0.00182 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.59 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 40℃; incubated with protease from Streptomyces cellulosae; pH 7.0; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 40℃; incubated with protease from Streptomyces cellulosae; pH 7.0; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water at 30℃; Peptidamidase aus dem Flavedo von Orangen; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
α-MAPI-O; Trypsin; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28.8% | With hydrogenchloride In various solvent(s) at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylamine In 1,2-dimethoxyethane; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In methanol for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Z-Val-OCO2iBu; (S)-Phe ester salt With 4-methyl-morpholine In dichloromethane at -15 - 20℃; Stage #2: With hydrogen In methanol for 24h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-methylmorpholine / CH2Cl2 / 0.33 h / -15 °C 2.1: N-methylmorpholine / CH2Cl2 / -15 - 20 °C 2.2: H2 / Pd/C / methanol / 24 h / 4654.46 Torr | ||
Multi-step reaction with 3 steps 1: N-methyl morpholine / CH2Cl2 / 0.33 h / -15 °C 2: N-methyl morpholine / CH2Cl2 / -15 - 20 °C 3: H2 / Pd/C / methanol / 24 h / 4654.33 Torr | ||
Multi-step reaction with 3 steps 1: N-methylmorpholine / CH2Cl2 / 0.33 h / -15 °C 2: N-methylmorpholine / CH2Cl2 / 1 h / -15 °C 3: H2 / Pd/C / methanol / 24 h / 4654.33 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-methyl morpholine / CH2Cl2 / -15 - 20 °C 2: H2 / Pd/C / methanol / 24 h / 4654.33 Torr | ||
Multi-step reaction with 2 steps 1: N-methylmorpholine / CH2Cl2 / 1 h / -15 °C 2: H2 / Pd/C / methanol / 24 h / 4654.33 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / Et3N / 1,2-dimethoxy-ethane; H2O / 20 °C 2: 22 percent / H2 / Pd/C / methanol / 3 h / 25 °C / 1551.49 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In water CuCO3 added to aq. soln. of dipeptide; after stirring, excess carbonate filtered off; blue soln. concentrated by slow evaporation until formation of crystals; crystals separated by filtration; washed with small portions of 1:2 water-acetone; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In water at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-Fmoc L-Phe With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: Fmoc-Val-OH Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 0.25 h / 0 °C 1.2: 24 h / 20 °C 2.1: sodium hydroxide / methanol / 10 h 3.1: trifluoroacetic acid / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 10 h 2: trifluoroacetic acid / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 0.25 h / 0 °C 1.2: 24 h / 20 °C 2.1: sodium hydroxide / methanol / 10 h 3.1: trifluoroacetic acid / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82 %Chromat. | Stage #1: L-phenylalanine; (S)-4-isopropyloxazolidine-2,5-dione With potassium hydroxide In water at 0 - 2℃; for 0.233333h; Flow reactor; Stage #2: With sulfuric acid In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In ethanol | 2.1 Synthesis of the complexes and analytical characterization General procedure: Heteroleptic Cu-dipeptide-necuproine complexes where L-dipeptide: Gly-Val, Gly-Leu, Gly-Phe, Ala-Gly, Ala-Phe, Val-Phe, Phe-Ala or Phe-Phe were obtained as follows (Fig. 1). 0.1mmol of dipeptide were dissolved in the minimum volume of warm water (10-50mL) and 0.1mmol of CuSO4·5H2O was added. The pH was adjusted to 7 with a 0.1M NaOH solution. A solution of 0.1mmol of neo in 5mL of ethanol was added, while stirring. The compounds were isolated by evaporation at 40-50°C, until blue crystals were formed. Yield 60-70%. Crystals suitable for X-ray analysis were obtained by slow evaporation of solvent at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 60 - 80℃; for 1h; | [Cu(dipeptide)(tmp)] complexes General procedure: A solution of [Cu(dipeptide)] precursor with general formula[Cu(dipeptide)] was firstly obtained by dissolving thecorresponding dipeptide in the minimum volume of H2O.To this solution, a 50% excess of CuCO3was added andstirred at 60-80 °C for 1 h. The CuCO3that was not solubilizedwas filtered off. The resulting blue solution wasevaporated at 60-80 °C until an adequate amount of solidis obtained which was then filtered off, washed with coldH2Oand air dried, as described by Facchin et al. [23]. Theadequate amount of solid (0.1 mmol) was dissolved in hotH2Oto make 50 mL of a 2 mM, solution (0.1 mmol). Itwas mixed under stirring at 60 °C with 10 mL of a 0.01 Methanolic solution of tmp (0.1 mmol). The dipeptidesused were: Gly-Gly, l-Gly-Phe, l-Ala-Gly, l-Ala-Phe, l-Val-Phe, l-Phe-Ala, and l-Phe-Phe. In all cases a darkblue-green solid was obtained after evaporation at 25 °C.Yield: 50-70%. Figure 1 presents a scheme of the syntheticprocedure and of the proposed coordination of thecomplexes. Blue prismatic crystals were obtained for[Cu(Gly-Gly)(tmp)]·6H2O by recrystallization in 95%ethanol. Recrystallization tests for the remaining ternarycomplexes were unsuccessful.The obtained solids correspond to the general formula[Cu(l-dipeptide)(tmp)]·xCH3CH2OHxH2O, where thedipeptide acts as a - 2 anion, making neutral complexesof the following formulas and elemental compositions.[Cu(Gly-Gly)(tmp)]·6H2O C1 Calc. for C20H34CuN4O9/Found: %C: 44.64/44.68, %N: 10.41/10.25, %H: 6.36/6.20;[Cu(l-Gly-Phe)(tmp)]·CH3CH2OH·2H2O C2 Calc./Found(C29H38CuN4O6) %C: 57.84/57.39, %N: 9.30/8.96, %H:6.36/5.90; [Cu(l-Ala-Gly)(tmp)]·3.5H2O C3 Calc./Found(C21H31CuN4O6.5) %C: 49.75/49.75, %N: 11.05/11.12,%H: 6.16/5.99; [Cu(l-Ala-Phe)(tmp)]·3H2O C4 Calc./Found (C28H36CuN4O6) %C: 57.18/57.52, %N: 9.52/9.40,%H: 6.17/6.07; [Cu(l-Val-Phe)(tmp)]·CH3CH2OH C5Calc./Found (C32H40CuN4O4) %C: 63.19/63.58, %N:9.21/8.79, %H: 6.62/6.15; [Cu(l-Phe-Ala)(tmp)]·3.5H2OC6 Calc./Found (C28H37CuN4O6.5) %C: 56.31/56.15, %N:9.38/9.29, %H: 6.24/6.34; [Cu(l-Phe-Phe)(tmp)]·2H2OC7 Calc./Found (C34H38CuN4O5) %C: 63.19/63.60, %N:8.67/8.59, %H: 5.93/5.74. Only complexes C1, C3 and C4are soluble in water to mM concentrations, all the complexesare soluble in DMSO and DMSO/water mixtures. | |
at 60 - 80℃; for 1h; | [Cu(dipeptide)(tmp)] complexes General procedure: A solution of [Cu(dipeptide)] precursor with general formula[Cu(dipeptide)] was firstly obtained by dissolving thecorresponding dipeptide in the minimum volume of H2O.To this solution, a 50% excess of CuCO3was added andstirred at 60-80 °C for 1 h. The CuCO3that was not solubilizedwas filtered off. The resulting blue solution wasevaporated at 60-80 °C until an adequate amount of solidis obtained which was then filtered off, washed with coldH2Oand air dried, as described by Facchin et al. [23]. Theadequate amount of solid (0.1 mmol) was dissolved in hotH2Oto make 50 mL of a 2 mM, solution (0.1 mmol). Itwas mixed under stirring at 60 °C with 10 mL of a 0.01 Methanolic solution of tmp (0.1 mmol). The dipeptidesused were: Gly-Gly, l-Gly-Phe, l-Ala-Gly, l-Ala-Phe, l-Val-Phe, l-Phe-Ala, and l-Phe-Phe. In all cases a darkblue-green solid was obtained after evaporation at 25 °C.Yield: 50-70%. Figure 1 presents a scheme of the syntheticprocedure and of the proposed coordination of thecomplexes. Blue prismatic crystals were obtained for[Cu(Gly-Gly)(tmp)]·6H2O by recrystallization in 95%ethanol. Recrystallization tests for the remaining ternarycomplexes were unsuccessful.The obtained solids correspond to the general formula[Cu(l-dipeptide)(tmp)]·xCH3CH2OHxH2O, where thedipeptide acts as a - 2 anion, making neutral complexesof the following formulas and elemental compositions.[Cu(Gly-Gly)(tmp)]·6H2O C1 Calc. for C20H34CuN4O9/Found: %C: 44.64/44.68, %N: 10.41/10.25, %H: 6.36/6.20;[Cu(l-Gly-Phe)(tmp)]·CH3CH2OH·2H2O C2 Calc./Found(C29H38CuN4O6) %C: 57.84/57.39, %N: 9.30/8.96, %H:6.36/5.90; [Cu(l-Ala-Gly)(tmp)]·3.5H2O C3 Calc./Found(C21H31CuN4O6.5) %C: 49.75/49.75, %N: 11.05/11.12,%H: 6.16/5.99; [Cu(l-Ala-Phe)(tmp)]·3H2O C4 Calc./Found (C28H36CuN4O6) %C: 57.18/57.52, %N: 9.52/9.40,%H: 6.17/6.07; [Cu(l-Val-Phe)(tmp)]·CH3CH2OH C5Calc./Found (C32H40CuN4O4) %C: 63.19/63.58, %N:9.21/8.79, %H: 6.62/6.15; [Cu(l-Phe-Ala)(tmp)]·3.5H2OC6 Calc./Found (C28H37CuN4O6.5) %C: 56.31/56.15, %N:9.38/9.29, %H: 6.24/6.34; [Cu(l-Phe-Phe)(tmp)]·2H2OC7 Calc./Found (C34H38CuN4O5) %C: 63.19/63.60, %N:8.67/8.59, %H: 5.93/5.74. Only complexes C1, C3 and C4are soluble in water to mM concentrations, all the complexesare soluble in DMSO and DMSO/water mixtures. |