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CAS No. : | 737-86-0 | MDL No. : | MFCD00763290 |
Formula : | C14H14N4O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 286.29 | Pubchem ID : | - |
Synonyms : |
PIH;NSC 77674
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 76.32 |
TPSA : | 107.7 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) : | -7.24 cm/s |
Log Po/w (iLOGP) : | 1.63 |
Log Po/w (XLOGP3) : | 1.14 |
Log Po/w (WLOGP) : | 0.59 |
Log Po/w (MLOGP) : | -0.56 |
Log Po/w (SILICOS-IT) : | 1.77 |
Consensus Log Po/w : | 0.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.43 |
Solubility : | 1.07 mg/ml ; 0.00375 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.0 |
Solubility : | 0.289 mg/ml ; 0.00101 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.9 |
Solubility : | 0.036 mg/ml ; 0.000126 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.76 |
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: |
* 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 |
---|---|---|
Specific examples of compounds of Formula (I) above include: pyridoxal benzoyl hydrazone (PBH), pyridoxal isonicotinoyl hydrazone (PIH), pyridoxal phenylacetyl hydrazone (PPH), 3-hydroxyisonicotinaldehyde benzoyl hydrazone (HBH), salicylaldehyde benzoyl hydrazone (SBH); ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In methanol byproducts: H2O; mixing solns. of metal chloride and hydrazone, room temp.; stirring at pH 2 (HCl), 4h; digesting on a water bath, 0.5h; cooling to room temp.; filtration; washing (cold methaanol); drying (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In water mixing solns. of metal chloride, hydrazone and KOH; adjusting pH to 7; digesting on a water bath, 0.5h; cooling; filtration; washing (water); drying (room temp.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In water mixing solns. of metal chloride, hydrazone and KOH; adjusting pH to 7; digesting on a water bath, 0.5h; cooling; filtration; washing (water); drying (room temp.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol byproducts: H2O; mixing solns. of metal chloride and hydrazone, room temp.; stirring at pH 2 (HCl), 4h; digesting on a water bath, 0.5h; cooling to room temp.; filtration; washing (cold methaanol); drying (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In methanol byproducts: H2O; mixing solns. of metal chloride and hydrazone, room temp.; stirring at pH 2 (HCl), 4h; digesting on a water bath, 0.5h; cooling to room temp.; filtration; washing (cold methaanol); drying (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In water mixing solns. of metal chloride, hydrazone and KOH; adjusting pH to 7; digesting on a water bath, 0.5h; cooling; filtration; washing (water); drying (room temp.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In methanol byproducts: H2O; mixing solns. of metal chloride and hydrazone, room temp.; stirring at pH 2 (HCl), 4h; digesting on a water bath, 0.5h; cooling to room temp.; filtration; washing (cold methaanol); drying (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In water mixing solns. of metal chloride, hydrazone and KOH; adjusting pH to 7; digesting on a water bath, 0.5h; cooling; filtration; washing (water); drying (room temp.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In water mixing solns. of metal chloride, hydrazone and KOH; adjusting pH to 7; digesting on a water bath, 0.5h; cooling; filtration; washing (water); drying (room temp.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In methanol byproducts: H2O; mixing solns. of metal chloride and hydrazone, room temp.; stirring at pH 2 (HCl), 4h; digesting on a water bath, 0.5h; cooling to room temp.; filtration; washing (cold methaanol); drying (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol soln. of CuCl2*2H2O in EtOH added to a hot soln. of pyridoxal hydrazone, mixt. heated under reflux for 30 min; soln. concentrated, cooled, filtered, washed with EtOH and ether, dried in vac. over P2O5; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With NaOH In methanol dissolution of ligand in a soln. containing NaOH in methanol, addn. of FeCl3*6H2O in methanol; filtn., standing for 24 h, pptn. after 1 h, collection, washing with MeOH/ether and ether, drying in air, elem. anal., elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol addn. of solid hydrazone to a soln. of FeCl3*6H2O in abs. MeOH with continuous stirring, soln. clears in about 2 min, forming a solid, stirring for ca. 20 min; collection of solid, washing with MeOH and ether, drying in air, recrystn. from MeOH/ether, elem. anal.; | |
In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water addn. of 1 equiv Na2S2O4 to soln. of PIH and FeSO4*7H2O (2:1 molar ratio) in H2O (stirring, pH 7.0), left to stand (overnight); pptn.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water PIH and FeSO4*7H2O in H2O stirred (2:1 molar ratio, N2, pH 6.0); pptn. on short standing; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With HCl In potassium hydroxide aq. KOH; V2O5 (5 mmol) suspnd. in aq. KOH (5 mmol), stirred at 50°C for 2 h, filtered, ligand (5 mmol) in aq. KOH added, stirred, soln. pH adjusted to 7.5 (HCl), stirred for 2 h, pptd.; filtered off, washed (water, acetone), crystd., filtered off, washed (MeOH), dried, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In methanol methanolic soln. of metal compd. (2 mmol) added to soln. of ligand (2 mmol), refluxed for 5 h, cooled to room temp., ppt. filtered off, washed (water), dried, suspnd. in methanol, O2 bubbled for 24 h at 40°C with occasional shaking; ppt. filtered off, washed (methanol), dried, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In methanol byproducts: Hacac; methanolic soln. of metal compd. (2 mmol) added to soln. of ligand (2 mmol), refluxed for 5 h, cooled to room temp.; ppt. filtered off, washed (water), dried, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium acetate In ethanol; water for 1h; Reflux; Inert atmosphere; | |
63% | In methanol for 1h; Reflux; | 2 2.2 Synthesis of ligand pyridoxal isonicotinoyl hydrazone (HL) The ligand HL was prepared by refluxing an equimolar mixture of pyridoxal hydrochloride and isonicotinoyl hydrazide. The amount of pyridoxal hydrochloride (0.204 g, 1 mmol) was dissolved at room temperature in methanol (10 mL). Paralelly, the corresponding amount of isonicotinoyl hydrazide (0.137 g, 1 mmol) was dissolved in the same solvent (10 mL). The pale yellow mixture formed by the two methanolic solutions was refluxed for one hour. Afterwards, it was left to cool at room temperature. The resulting orange precipitate was filtered, washed with alcohol and dried in vacuum. In order to obtain the orange single crystals suitable for X-ray diffraction, a certain amount of solid ligand was re-dissolved in a mixture methanol:DMSO (3:1, v/v). After the slow evaporation of the obtained solution the single crystals were isolated and filtered. Yield: 63%; M. wt: 322.5 g/mol; Anal. Calc. for C14H15N4O3Cl: C, 52.09; H, 4.65; N, 17.36; Cl, 11.00. Found: C, 52.85, H, 4.30, N, 17.08, Cl, 10.57%. Main IR peaks (KBr, cm-1): The condensation of the two reagents with the formation of the hydrazone HL is confirmed by the appearance in the IR spectrum of the signal at 1605 cm-1. This signal is typical for the vibration of the azomethine bond [25,26]; ν(OH) 3595, 3247; ν(C=O)1685; ν(C=N) 1605; ν(Ar-OH) 1267; ν(N-NH) 1093; ν(CH2-OH) 1029. 1H NMR (DMSO-d6, δ (ppm), J (Hz)): The formation of the azomethine group is emphasized by the presence of the signal at δ 9.18 ppm in the 1H NMR spectrum. 2.63 (s, 3H, CH3); 4.77 (s, 2H, CH2-OH); 7.85 (d, 2H, H-2, H-6); 8.03 (d, 2H, H-3, H-5); 8.17 (s, 1H, OH); 8.86 (s, 1H, NH); 9.18 (s, 1H, CH=N). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | for 5h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In acetonitrile for 16h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In methanol for 4h; Reflux; | Synthesis of dioxidovanadium complexes General procedure: A mixture of [VO(acac)2] (0.05 g, 0.2 mmol) and the appropriateligand (0.2 mmol) in methanol (20 mL) was refluxed for 4 h and the precipitate formed during the reaction was filtered, washed withmethanol and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium hydroxide In methanol for 3h; Reflux; | 3.1 2.3.1 Synthesis of complex [CuLCl(H2O)2] (1) To a solution of ligand pyridoxal isonycotinoyl hydrazone (0.286 g, 1 mmol) in methanol (25 mL) was added a solution of CuCl2·2H2O (0.17 g, 1 mmol) in methanol (15 mL). The pH of the solution was adjusted by adding dropwise an alcoholic solution of NaOH. The mixture was refluxed for 3 h. The dark green solid obtained was filtered, washed with alcohol and dried in vacuum. The complex is soluble in pyridine, slightly soluble in DMSO and insoluble in methanol and ethanol. Yield: 71%; M.wt.: 420.5 g/mol. Anal. calc. for CuC14H17N4O5Cl: C, 39.95; H, 4.04; N, 13.31; Cu, 15.21. Found: C, 39.36; H, 4.32; N, 13.08; Cu, 15.36%. Main IR peaks (KBr, cm-1): 3418, ν(OH); 1611, ν(C=O); 1583, ν(C=N); 1217, ν(Ar-OH); 1095, ν(N-NH); 1029, ν(CH2-OH). μeff = 1.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In methanol Reflux; Heating; | 3.2 2.3.2 Synthesis of complex [CuL(OAc)](H2O) (2) A solution of Cu(OAc)2·H2O (0.199 g, 1 mmol) in methanol (10 mL) was added to a warm solution of HL (0.286 g, 1 mmol) in methanol (10 mL). The mixture was refluxed for 3-4 h. A solid brown precipitate was isolated and dried. Complex 2 is soluble in pyridine, slightly soluble in DMSO and DMF and insoluble in alcohols. Yield: 78%; M.wt.: 427 g/mol. Anal. Calc. for CuC16H18N4O6: C, 44.96; H, 4.44; N, 13.11; Cu, 14.98. Found: C, 45.31; H, 4.01; N, 12.25; Cu, 14.10%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol for 3h; Reflux; Heating; | 4 2.3.4 Synthesis of complex [CuL(NO3)](H2O) (4) Complex 4 was prepared in a similar fashion as complex 2. To a warm solution of ligand (0.286 g, 1 mmol) dissolved in methanol was slowly added a solution of Cu(NO3)2·3H2O (0.241 g, 1 mmol). The resulting solution was heated under continuos stirring for 3 h. A brown solid was obtained. Finally, it was filtered, washed with alcohol and dried. Complex 4 is soluble in pyridine and insoluble in alcohols, acetonitrile or acetone. Yield: 85%; M. wt.: 430 g/mol. Anal. Calc. for CuC14H15N5O7: C, 39.06; H, 3.48; N, 16.27; Cu, 14.88. Found: C, 39.55; H, 3.02; N, 16.20; Cu, 14.49%. Main IR peaks (KBr, cm-1): 3349, ν(OH); 1606, ν(C=O); 1575, ν(C=N); 1207, ν(Ar-OH); 1089, ν(N-NH); 1030, ν(CH2-OH); 1090, ν(O-NO2); 1280, 1430, ν(NO3). μeff = 1.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In methanol; chloroform at 50℃; for 5h; | 2.3.3 Synthesis of complex [CuL(OAcac)] (3) This complex was synthesized by refluxing a 1:1 mixture of ligand and copper(II) acetylacetonate. The Cu(acac)2 (0.261g, 1mmol) was dissolved in a small volume of chloroform (5mL) and resulting solution was added to a methanolic solution of corresponding amount of ligand HL (0.286g, 1mmol). The mixture was heated at 50°C for 5h. Once the solution was left to cool at room temperature a brown solid compound was isolated, washed with a chloroform:methanol mixture and dried. The obtained complex is soluble in pyridine and slightly soluble in DMSO. Yield: 60%; M.wt.: 448g/mol. Anal. Calc. for CuC19H20N4O5: C, 50.89; H, 4.46; N, 12.50; Cu, 14.28. Found: C, 51.25; H, 4.18; N, 11.37; Cu, 13.77%. Main IR peaks (KBr, cm-1): 3324, ν(OH); 1606, ν(C=O); 1560, ν(C=N); 1204, ν(Ar-OH); 1092, ν(N-NH); 1025, ν(CH2-OH). μeff=1.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | for 3h; Reflux; | 2.3.5 Synthesis of complex [CuL2](H2O) (5) Complex 5 was prepared by stirring at reflux temperature a 2:1 mixture of ligand HL (0.286 g, 1 mmol) and CuSO4·5H2O (0.249 g, 1 mmol). After one hour a solid green compound was obtained. The mixture was stirred for another 2h in order to increase the yield of complex formation. Afterwards, the obtained compound was filtered and dried. The novel complex is soluble in pyridine. Complex 5 is soluble in pyridine and insoluble in alcohols. Yield: 65%; M.wt.: 654. Anal. Calc. for CuC28H28N8O7: C, 51.37; H, 4.28; N, 17.12; Cu, 9.78. Found: C, 51.74; H, 3.96; N, 16.94; Cu, 9.63%. Main IR peaks (KBr, cm-1): 3349, ν(OH); 1606, ν(C=O); 1575, ν(C=N); 1207, ν(Ar-OH); 1100, ν(N-NH); 1030, ν(CH2-OH). μeff=1.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With phosphonic Acid In ethanol at 40℃; for 2h; | N-((3-Hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)iso-nicotinohydrazide diphosphite (4) A mixture of imine 3 and a two-fold excess of phosphorous acid in ethyl alcohol was heated for 2 h at 40°C. The precipitate was separated and dried in vacuo. Colorless solid: yield 85%; mp 203-206°C. 1H NMR (400 MHz, DMSO-d6): δ=2.45 (s, 3H, CH3); 4.64 (s, 2H, OCH2); 6.73 (d, JPH = 640.0 Hz, 1H, PH); 7.89 (d, J = 6.0 Hz, 2H, Py); 8.0 (s, 1H, CHarom); 8.83 (d, J = 6.0 Hz, 2H, Py); 9.0 (s, 1H, CH). 31P NMR (161.9 MHz, DMSO-d6): δ=1.3 (JPH = 640.0 Hz). Anal. Calcd. for C14H20N4O9P2: C, 37.33; H, 4.44; N, 12.44; P, 13.77. Found: C, 37.59; H, 4.68; N, 12.41; P, 13.69%. MALDI-MS: 268 [M+H- 2H3PO3]+. |