70033-61-3|5-Hydroxy-2-(hydroxymethyl)-1-phenylpyridin-4(1H)-one| Ambeed

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Quality Control of [ 70033-61-3 ] Purity: 95% SDS Specification

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Product Details of [ 70033-61-3 ]

CAS No. :	70033-61-3
Formula :	C₁₂H₁₁NO₃
M.W :	217.22
SMILES Code :	O=C1C=C(CO)N(C2=CC=CC=C2)C=C1O
MDL No. :	MFCD27991853
InChI Key :	JFSCKVXXRWUABD-UHFFFAOYSA-N
Pubchem ID :	12468238

Safety of [ 70033-61-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 70033-61-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	12
Fraction Csp3	0.08
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	60.19
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	62.46 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.84
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.88
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.21
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.43
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.12
Solubility	1.65 mg/ml ; 0.00758 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.7
Solubility	4.3 mg/ml ; 0.0198 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.89
Solubility	0.282 mg/ml ; 0.0013 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.05 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.01

Application In Synthesis of [ 70033-61-3 ]

* 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 [ 70033-61-3 ]

[ 70033-61-3 ] Synthesis Path-Downstream 1~16

1
[ 501-30-4 ]
[ 62-53-3 ]
[ 70033-61-3 ]

Yield	Reaction Conditions	Operation in experiment
49%		5-Hydroxy-2-hydroxymethyl-1-phenyl-pyridin-4-one (214) (Looker, J. H.; Cliffton, M. D. Convenient preparative methods for N-aryl-γ-pyridones from γ-pyrones. J. Hetero. Chem. 1986, 23, 5). To a suspension of kojic acid (1.421 g, 10.00 mmol) in diluted hydrochloric acid (0.52 mL of concentrated hydrochloric acid diluted with 25 mL of water) was added aniline (1.40 mL, 15.4 mmol). The resulting mixture was heated under reflux for 20 h. The mixture, while warn (60 C.), was washed with dichloromethane two times and the organic phase was discarded. The aqueous phase was neutralized with solid sodium carbonate, upon which much off-white precipitate appeared. The mixture stood in a hood overnight. The crude product was isolated by filtration and purified by recrystallization with methanol to give a pale solid (1.064 g, 49%). Mp: 236-238 C. (lit.85 237-240 C.). 1H NMR (d6-DMSO): δ 4.20 (2H, s), 6.47 (1H, s), 7.35 (1H, s), 7.5-7.6 (5H, m). 13C NMR (d6-DMSO): δ 70.9, 102.5, 114.8, 118.2, 118.9, 130.5, 138.7, 146.7, 165.3, 179.5.

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 5 - 8.
[2]Patent: US2007/232663,2007,A1 .Location in patent: Page/Page column 10.
[3]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 1879 - 1880.
[4]Canadian Journal of Chemistry,1999,vol. 77,p. 1249 - 1261.
[5]Journal of Medicinal Chemistry,2013,vol. 56,p. 9802 - 9806.

3
[ 70033-61-3 ]
[ 18162-48-6 ]
[ 951161-02-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With 1H-imidazole; In N,N-dimethyl-formamide;	5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-1-phenyl-1H-pyridin-4-one (215). Pyridone 214 (0.773 g, 3.56 mmol) and imidazole (509 mg, 7.47 mmol) were dissolved in DMF (15 mL). tert-Butyldimethylsilyl chloride (1.127 g, 7.478 mmol) was added portionwise. The mixture was stirred overnight. The mixture was then diluted with EtOAc. The solution was washed with water and brine. The organic layer was dried over Na2SO4 and the solvent removed under vacuum. After flash column chromatography, the desired product was obtained as a light yellow solid (812 mg, 73%). Mp: 254-255 C. 1H NMR (CDCl3): δ -0.06 (6H, s), 0.82 (9H, s), 4.18 (2H, s), 6.36 (1H, br s), 6.67 (1H, s), 7.21 (1H, s), 7.25-7.32 (2H, m), 7.46-7.52 (3H, m). 13C NMR (CDCl3): δ -5.4, 18.4, 25.9, 61.6, 111.9, 122.7, 127.0, 130.0, 141.1, 147.0, 147.5, 172.1. IR (KBr): 3312, 3156, 2975, 2847, 1615, 1507, 1176, 1043 cm-1. Anal. Calcd. for C18H25NO3Si: C, 65.22; H, 7.60. Found: C, 65.20; H, 7.61.

References: [1]Patent: US2007/232663,2007,A1 .Location in patent: Page/Page column 10-11.

4
[ 70033-61-3 ]
ammonium dimolybdate [ No CAS ]
[ 244187-62-0 ]

References: [1]Canadian Journal of Chemistry,1999,vol. 77,p. 1249 - 1261.

5
[ 70033-61-3 ]
2-((benzo[d]oxazol-2-ylthio)methyl)-5-hydroxy-1-phenylpyridin-4(1H)-one [ No CAS ]