1261080-59-4|Methyl 2-acetylthiazole-5-carboxylate| Ambeed

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Quality Control of [ 1261080-59-4 ] Purity: 97% SDS Specification

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Product Details of [ 1261080-59-4 ]

CAS No. :	1261080-59-4
Formula :	C₇H₇NO₃S
M.W :	185.20
SMILES Code :	O=C(C1=CN=C(C(C)=O)S1)OC
MDL No. :	MFCD22665896
InChI Key :	GZQHBNUKAZKLMJ-UHFFFAOYSA-N
Pubchem ID :	78358133

Safety of [ 1261080-59-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 1261080-59-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	5
Fraction Csp3	0.29
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	43.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.5 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.88
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	1.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.13
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.	-0.57
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	2.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.16

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.83
Solubility	2.74 mg/ml ; 0.0148 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.53
Solubility	0.547 mg/ml ; 0.00296 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-1.71
Solubility	3.64 mg/ml ; 0.0196 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	No
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.	-6.61 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	1.0
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)	2.6

Application In Synthesis of [ 1261080-59-4 ]

* 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 [ 1261080-59-4 ]

[ 1261080-59-4 ] Synthesis Path-Downstream 1~32

1
[ 14527-44-7 ]
[ 75-07-0 ]
[ 1261080-59-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tert.-butylhydroperoxide; ferrous(II) sulfate heptahydrate; sulfuric acid; In water; at 25.0℃;	A solution of FeSO4·7H2O (33.4 g, 120 mmol) in 80 ml H2O and 70% tert-butyl hydroperoxide (12 ml, 120 mmol) were added to a stirred and cooled (10-20 ) mixture of the methyl-thiazole-5-carboxylate 6 (2.86 g, 20 mmol), 4 M H2SO4 (10 ml), and the 40% aldehyde (13.22 g, 120 mmol) separately and simultaneously. The reaction mixture was stirred at room temperature (25 ) for 1 h, extracted with EtOAc and washed with saturated Na2S2O3 solution and brine. After drying over anhydrous Na2SO4 and removing the solvent, a crude material was obtained. The material was purified by column chromatography (PE:EtOAc, 50:1, v/v) to afford compound 7 (2.97 g, 80%) as pale yellow solid. MS (ESI) m/z 186.0 [M+H]+. 1H NMR (400 Hz, CDCl3) δ 8.50 (s, 1H), 3.95 (s, 3H), 2.73 (s, 3H) .
80%	With tert.-butylhydroperoxide; ferrous(II) sulfate heptahydrate; sulfuric acid; In water; at 20.0℃; for 2.25h;Inert atmosphere;	At 0 C ice bath,5-thiazole methyl ester 1a(2.86g, 20mmol)Dissolved in 10ml of 4M sulfuric acid solution (2.0 eq),FeSO4 7H2O (33.4 g, 6.0 eq) was added in that order.40% aqueous acetaldehyde solution (13.22 g, 6.0 eq), protected under N2 70% t-BuOOH (12 ml, 6.0 eq) was slowly added dropwise via a constant pressure funnel.After 15 minutes, the drop is completed.Transfer to room temperature for 2 h, extract with EA (60 ml x 3),Wash the saturated FeSO4 solution twice,Water, saturated NaHCO3 solution,Wash the saturated saline once,Dry anhydrous Na2SO4,Evaporate the solvent under reduced pressure.Column chromatography separation (PE: EA = 50: 1 v/v) gave a pale yellow odorous solid 1b(2.97g, 80%).

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1208 - 1212.
[2]Patent: CN101921268,2016,B .Location in patent: Paragraph 0074; 0077-0081.

2
[ 1261080-59-4 ]
[ 1357194-14-9 ]