24410-19-3|Pyrido[2,3-d]pyrimidin-4(1H)-one| Ambeed

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Quality Control of [ 24410-19-3 ] Purity: 97% SDS Specification

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Product Details of [ 24410-19-3 ]

CAS No. :	24410-19-3
Formula :	C₇H₅N₃O
M.W :	147.13
SMILES Code :	C1=CC=C2C(=N1)NC=NC2=O
MDL No. :	MFCD08234707
InChI Key :	XKEBMWRWBWRQAO-UHFFFAOYSA-N
Pubchem ID :	135440277

Safety of [ 24410-19-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 24410-19-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	40.16
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.64 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.76
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	-0.03
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.32
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.	0.35
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	1.63
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.41
Solubility	5.78 mg/ml ; 0.0393 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.	-0.75
Solubility	26.1 mg/ml ; 0.177 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	-2.84
Solubility	0.212 mg/ml ; 0.00144 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	No
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.	-7.22 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)	1.48

Application In Synthesis of [ 24410-19-3 ]

* 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 [ 24410-19-3 ]

[ 24410-19-3 ] Synthesis Path-Downstream 1~35

1
[ 5345-47-1 ]
[ 77287-34-4 ]
[ 24410-19-3 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 3911 - 3913.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1713 - 1726.
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 2794 - 2809.
[4]Journal of Medicinal Chemistry,2013,vol. 56,p. 9482 - 9495.
[5]Journal of the Chemical Society,1956,p. 1045,1053.
[6]ACS Medicinal Chemistry Letters,2020,vol. 11,p. 83 - 89.

2
[ 24410-19-3 ]
[ 78159-02-1 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1823 - 1835.
[2]Journal of the American Chemical Society,1955,vol. 77,p. 2256,2259.

3
[ 24410-19-3 ]
[ 28732-79-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With trichlorophosphate; In water;	EXAMPLE 8 4-chloro-pyrido[2,3-d]pyrimidine A mixture of <strong>[24410-19-3]pyrido[2,3-d]pyrimidin-4(3H)-one</strong> (1.471 g, 10 mM) and POCl3 (16 ml) is stirred for 1 h at reflux. The excess of POCl3 is removed under vacuum. Then dichloromethane and iced water is added and the mixture stirred until the black solid dissolves. The organic layer is separated, washed with bicarbonate solution, dried over Na2 SO4 and then evaporated to dryness. The yellow residue is recrystallized from toluene/hexane to give almost pure title compound in 70% yield. mp 137 C.
	With trichlorophosphate; In water;	Preparation 3 4-Chloropyrido[2,3-d]pyrimidine A mixture of 17.8 g of Pyrido[2,3-d]pyrimidin4(3H)one and 200 mL of POCl3 was stirred under reflux for one hour. Excess POCl3 was removed under vacuum, and then CH2 Cl2, ice, and water were added. A black solid dissolved slowly. The organic layer was then separated, washed with aqueous NaHCO3, and dried over Na2 SO4. Solvent was then removed under vacuum to leave a yellow solid, which was recrystallized from toluene/hexane. M.P. 137 dec.
	With pyridine; trichlorophosphate; In toluene; at 180℃; for 2h;Sealed tube;	General procedure: Chlorination was carried out using a literature protocol with minor modifications. In summary, pyridopyrimidinone 36 (1.0eq), dry toluene (~1.0mL per 1.0mmol 36), and pyridine (1.0 eq) were mixed in the pressure vessel. POCl3 (5.0eq) was added with stirring. The tube was then sealed and heated at 115 C (in the case of 36iii) or at 180 C (in the case of 36i-ii) for ~2h. The reaction was cooled, concentrated in vacuo, diluted with EtOAc, and washed with cold NaHCO3 solution, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel chromatography (24 g column, 2%-85% EtOAc in hexanes with 0.1% Et3N) and used immediately in the next step. Isolated yields were typically?30-65%.

References: [1]Patent: US5965563,1999,A .
[2]Archiv der Pharmazie,1990,vol. 323,p. 513 - 515.
[3]Journal of the American Chemical Society,1955,vol. 77,p. 2256,2259.
[4]Patent: US5034393,1991,A .
[5]ChemMedChem,2014,vol. 9,p. 2516 - 2527.
[6]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1713 - 1726.
[7]ACS Medicinal Chemistry Letters,2020,vol. 11,p. 83 - 89.

4
[ 37891-04-6 ]
[ 24410-19-3 ]

References: [1]Journal of the Chemical Society,1956,p. 1045,1053.

5
[ 5050-41-9 ]
[ 24410-19-3 ]
3-(2-N-pyrolidynylethyl)-pyrido<2,3-d>pyrimidin-4(3H)-one [ No CAS ]

References: [1]Acta poloniae pharmaceutica,1994,vol. 51,p. 143 - 148.

6
[ 3240-94-6 ]
[ 24410-19-3 ]
3-(2-N-morpholinylethyl)-pyrido<2,3-d>pyrimidin-4(3H)-one [ No CAS ]

References: [1]Acta poloniae pharmaceutica,1994,vol. 51,p. 143 - 148.

7
[ 1932-03-2 ]
[ 24410-19-3 ]
3-(2-N-piperidinylethyl)-pyrido<2,3-d>pyrimidin-4(3H)-one [ No CAS ]

References: [1]Acta poloniae pharmaceutica,1994,vol. 51,p. 143 - 148.

8
[ 24410-19-3 ]
[ 107-99-3 ]
3-(2-N,N-dimethylaminoethyl)-pyrido<2,3-d>pyrimidin-4(3H)-one [ No CAS ]

References: [1]Acta poloniae pharmaceutica,1994,vol. 51,p. 143 - 148.

11
[ 24410-19-3 ]
[ 304665-10-9 ]
3-benzyloxy-2-[2-hydroxy-3-(4-oxo-4H-pyrido[2,3-d]pyrimidin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1854 - 1858.

12
[ 24410-19-3 ]
[ 35740-82-0 ]
C₁₇H₁₁ClN₄O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 4237 - 4246.

13
[ 24410-19-3 ]
3-[3-(3-hydroxy-piperidin-2-yl)-2-oxo-propyl]-3H-pyrido[2,3-d]pyrimidin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1854 - 1858.

14
[ 24410-19-3 ]
3-benzyloxy-2-[2-oxo-3-(4-oxo-4H-pyrido[2,3-d]pyrimidin-3-yl)-propyl]-piperidine-1-carboxylic acid benzyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1854 - 1858.

15
[ 24410-19-3 ]
[ 171178-49-7 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1823 - 1835.

16
[ 24410-19-3 ]
N-Benzylpyrido[2,3-d]pyrimidin-4-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1823 - 1835.

17
[ 24410-19-3 ]
4-(3-bromoanilino)pyrido[2,3-d]pyrimidine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1823 - 1835.

18
[ 24410-19-3 ]
[ 130015-66-6 ]

References: [1]Archiv der Pharmazie,1990,vol. 323,p. 513 - 515.

19
[ 24410-19-3 ]
[ 130015-64-4 ]

References: [1]Archiv der Pharmazie,1990,vol. 323,p. 513 - 515.

20
[ 24410-19-3 ]
[ 130015-65-5 ]

References: [1]Archiv der Pharmazie,1990,vol. 323,p. 513 - 515.

21
[ 24410-19-3 ]
[ 130015-63-3 ]

References: [1]Archiv der Pharmazie,1990,vol. 323,p. 513 - 515.

22
[ 7463-30-1 ]
[ 24410-19-3 ]