148332-36-9|[2,2':6',2''-Terpyridine]-4'-carboxylic acid| Ambeed

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Quality Control of [ 148332-36-9 ] Purity: 97% SDS Specification

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Product Details of [ 148332-36-9 ]

CAS No. :	148332-36-9
Formula :	C₁₆H₁₁N₃O₂
M.W :	277.28
SMILES Code :	O=C(C1=CC(C2=NC=CC=C2)=NC(C3=NC=CC=C3)=C1)O
MDL No. :	MFCD04114290
InChI Key :	ZYTWXMBGOUJDHJ-UHFFFAOYSA-N
Pubchem ID :	2762749

Safety of [ 148332-36-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 148332-36-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	21
Num. arom. heavy atoms	18
Fraction Csp3	0.0
Num. rotatable bonds	3
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	77.66
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	75.97 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.19
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	1.49
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.9
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.	-0.37
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	2.83
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.81

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.93
Solubility	0.323 mg/ml ; 0.00116 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.	-2.69
Solubility	0.563 mg/ml ; 0.00203 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	-5.69
Solubility	0.000571 mg/ml ; 0.00000206 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.93 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.	0.56

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<0.0
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)	2.55

Application In Synthesis of [ 148332-36-9 ]

* 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 [ 148332-36-9 ]

[ 148332-36-9 ] Synthesis Path-Downstream 1~36

1
[ 90050-70-7 ]
[ 17997-47-6 ]
[ 148332-36-9 ]
[ 148332-31-4 ]

References: [1]Synthesis,2000,p. 1138 - 1142.

2
(2R,5S,13R,16S)-5,16-Bis-(4-amino-butyl)-7,18-bis-(2,4-dimethoxy-benzyl)-2,13-diisobutyl-1,4,7,10,11,12,15,18,21,22-decaaza-tricyclo[18.2.1.1^9,12]tetracosa-9⁽²⁴⁾,10,20⁽²³⁾,21-tetraene-3,6,14,17-tetraone [ No CAS ]
[ 148332-36-9 ]
C₈₀H₉₀N₁₈O₁₀ [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 4503 - 4506.

3
[ 148332-36-9 ]
5'-DMTO-d(TGTGACG[2'-O-(4-aminobutyl)uridylyl]ATCACATT-LCAA-CPG (protected) [ No CAS ]
5'-HO-d(TGTGACG)-{2'-O-[N-(2,2':6',2''-terpyridine-4'-carbonyl)-4-aminobutyl]uridylyl}-d(ATCACATT)-OH [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 363 - 369.

4
[ 99-11-6 ]
[ 148332-36-9 ]

References: [1]Synthesis,2000,p. 1138 - 1142.

5
[ 2016-99-1 ]
[ 148332-36-9 ]

References: [1]Synthesis,2000,p. 1138 - 1142.

6
ammonium hexafluorophosphate [ No CAS ]
dichlorotetrakis(dimethylsulfoxide)ruthenium(II) [ No CAS ]
[ 148332-36-9 ]
bis(4'-carboxy-2,2':6',2''-terpyridine)ruthenium(II) bis(hexafluorophosphate) [ No CAS ]

References: [1]Inorganic Chemistry,2007,vol. 46,p. 638 - 651.

7
ammonium hexafluorophosphate [ No CAS ]
Ru⁽²⁺⁾*NC₅H₂(C₆H₄PO(OC₂H₅)2)(C₅H₄N)2*2Cl^(1-)*(CH₃)2SO=Ru(NC₅H₂(C₆H₄PO(OC₂H₅)2)(C₅H₄N)2)((CH₃)2SO)Cl₂ [ No CAS ]
[ 148332-36-9 ]
(Ru(NC₅H₂(C₆H₄PO(OC₂H₅)2)(C₅H₄N)2)(NC₅H₂(COOH)(C₅H₄N)2))⁽²⁺⁾*2PF₆^(1-)=(Ru(N₃C₁₅H₁₀C₆H₄PO(OC₂H₅)2)(N₃C₁₅H₁₀COOH))(PF₆)2 [ No CAS ]

References: [1]Inorganic Chemistry,2007,vol. 46,p. 638 - 651.

8
ruthenium(III) chloride trihydrate [ No CAS ]
[ 148332-36-9 ]
[ 1220636-36-1 ]

References: [1]Inorganic Chemistry,2010,vol. 49,p. 2202 - 2209.

9
[ 10049-08-8 ]
[ 148332-36-9 ]
[ 1220636-36-1 ]

References: [1]Inorganic Chemistry,2010,vol. 49,p. 7340 - 7352.

10
[ 148332-36-9 ]
C₁₆H₁₀ClN₃O [ No CAS ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 6737 - 6745.
[2]Chemical Communications,2019,vol. 55,p. 7752 - 7755.

11
[ 1926-80-3 ]
[ 148332-36-9 ]
[ 1332851-01-0 ]

References: [1]Chemistry - A European Journal,2011,vol. 17,p. 9478 - 9488.

12
[ 148332-36-9 ]
[ 1332851-02-1 ]

References: [1]Chemistry - A European Journal,2011,vol. 17,p. 9478 - 9488.

13
[ 148332-36-9 ]
[ 1332851-03-2 ]

References: [1]Chemistry - A European Journal,2011,vol. 17,p. 9478 - 9488.

14
[ 148332-36-9 ]
[ 717111-10-9 ]
[ 1332851-00-9 ]

References: [1]Chemistry - A European Journal,2011,vol. 17,p. 9478 - 9488.

15
[ 375382-77-7 ]
[ 148332-36-9 ]

References: [1]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 1667 - 1672.
[2]Inorganic Chemistry,2018,vol. 57,p. 4898 - 4905.
[3]Journal of Photochemistry and Photobiology A: Chemistry,2011,vol. 222,p. 203 - 209.
[4]Chemistry - A European Journal,2011,vol. 17,p. 9478 - 9488.
[5]Dalton Transactions,2017,vol. 46,p. 10029 - 10036.

16
[ 148332-36-9 ]
[Ru(II)(2,2':6',2''-terpyridine-4'-carboxylic acid)(2,2'-bipyridine)(D₂O)]⁽²⁺⁾ [ No CAS ]

References: [1]Inorganic Chemistry,2010,vol. 49,p. 2202 - 2209.

17
[ 148332-36-9 ]
[Ru(2,2':6',2''-terpyridine-4'-carboxylic acid)(2,2'-bipyridine)Cl]Cl*3H₂O [ No CAS ]

References: [1]Inorganic Chemistry,2010,vol. 49,p. 2202 - 2209.

18
[ 148332-36-9 ]
[Ru(2,2':6',2''-terpyridine-4'-carboxylic acid)(2,2'-bipyridine)(H₂O)](ClO₄)2*2H₂O [ No CAS ]

References: [1]Inorganic Chemistry,2010,vol. 49,p. 2202 - 2209.

19
[ 148332-36-9 ]
[Ru(2,2':6',2''-terpyridine-4'-carboxylic acid)(2,2'-bipyridine-4,4'-dicarboxylic acid)Cl]Cl*3H₂O [ No CAS ]

References: [1]Inorganic Chemistry,2010,vol. 49,p. 2202 - 2209.

20
[ 148332-36-9 ]
[Ru(2,2':6',2''-terpyridine-4'-carboxylic acid)(2,2'-bipyridine-4,4'-dicarboxylic acid)(H₂O)](ClO₄)2*4H₂O [ No CAS ]

References: [1]Inorganic Chemistry,2010,vol. 49,p. 2202 - 2209.

21
[ 67-56-1 ]
[ 148332-36-9 ]
[ 247058-06-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With thionyl chloride; at 60℃; for 16h;	Compound 8 (5.05 g, 18.2 mmol) was dispersed in 200 ml of dry methanol and cooled to 0°C. Thionyl chloride (7.93 ml, 13.0 g, 109 mmol) was added dropwise. After complete addition the mixture was heated for 60°C and stirred for 16 h. The solvent was removed under reduced pressure and 80 mlof saturated aqueous NaHCO3 solution was added. The mixture wasextracted with DCM (3x50 ml). The combined organic phases weredried over Na2SO4 and the solvent was removed underreduced pressure. The product was obtained as a white solid. Yield: 4.74 g(89percent) mp:208-209°C.1H-NMR(500 MHz, DMSO-d6): delta 8.86 (s, 2H), 8.76 (ddd, J = 4.7 Hz, 1.7 Hz, 0.9 Hz, 2H), 6.64 (dt, J = 7.9 Hz, 0.9 Hz, 2H), 8.04 (td, J = 7.8 Hz, 1.8 Hz, 2H), 7.54 (ddd, J = 7.5 Hz, 4.7 Hz, 1.1 Hz, 2H), 3.98 (s, 3H) 13C-NMR (126 MHz, DMSO-d6): delta165.0, 156.1, 154.0, 149.5, 139.3, 137.6, 124.9, 120.9, 119.3, 52.9HRMS (ESI, m/z): calcd for C17H14N3O2 [M+H]+: 292.1081; Found: 292.1079.
		General procedure: Typically, 2-(4-carboxyphenyl)-4,6-dipyrid-2-yltriazine (1.0 g,2.81 mmol) was heated to reflux in thionyl chloride (30 mL) for0.5 h, after which no solid suspension remained. The excess thionylchloride was removed by distillation and the residue was driedunder vacuum, dry methanol (60 mL) was added and the reactionmixture was heated to reflux until no solid suspension remained(2 h). The solution was cooled to room temperature and addedto H2O (300 mL) forming a voluminous precipitate of the methylester ligand which was isolated by filtration and dried in vacuowithout further purification. Typically, the ligand (0.25 g,0.68 mmol) was heated to reflux in DMF with RuCl3 (0.07 g,0.34 mmol) and AgNO3 (0.173 g, 1.02 mmol) after which the solutionwas filtered to remove AgCl(s). The filtrate was then decantedinto a solution of NH4PF6 (aq) (300 mL), and the resultant heavyprecipitate was isolated by filtration and washed with water, thendissolved in a minimal amount of acetonitrile for chromatographicpurification using silica and a 7:2 CH3CN/KNO3 (aq, sat) mixture aseluent. The collected fractions are combined, and to this addedNH4PF6 and enough DCM to effect a phase separation. After washingthe organic phase, the aqueous phase was discarded and theprocess repeated, with a final washing with water alone. Theorganic phase was dried and the residue taken up in a minimalamount of acetonitrile, then poured into H2O (300 mL) to give aheavy precipitate which was filtered and dried in vacuo. Yield:0.263 g (69percent), Rf = 0.55 (silica, 7:2 CH3CN/KNO3 (sat, aq) as eluent).1H NMR (400 MHz, CD3CN) d ppm 9.19 (d, J = 8.4 Hz, 4H), 9.14 (d,J = 7.7 Hz, 4H), 8.44 (d, J = 8.4 Hz, 4H), 8.16 (m, 4H), 7.73 (d,J = 5.3 Hz, 4H), 7.41 (m, 4H), 4.02 (s, 3H). ESI-MS: [M]2+ Cald. forC42H30N10O4Ru: 420.07475. Found: 420.07499.

References: [1]Journal of Photochemistry and Photobiology A: Chemistry,2011,vol. 222,p. 203 - 209.
[2]Tetrahedron Letters,2019,vol. 60,p. 906 - 910.
[3]Inorganic Chemistry,2018,vol. 57,p. 4898 - 4905.
[4]Inorganica Chimica Acta,2017,vol. 454,p. 208 - 215.

22
[ 7732-18-5 ]
[ 71-48-7 ]
[ 148332-36-9 ]
Co(2,2':6',2''-terpyridine-4'-carboxylate)2*4H₂O [ No CAS ]