92379-10-7|3'-Hydroxy-[1,1'-biphenyl]-2-carboxylic acid| Ambeed

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Quality Control of [ 92379-10-7 ] Purity: 95% SDS Specification

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Product Details of [ 92379-10-7 ]

CAS No. :	92379-10-7
Formula :	C₁₃H₁₀O₃
M.W :	214.22
SMILES Code :	O=C(C1=CC=CC=C1C2=CC=CC(O)=C2)O
MDL No. :	MFCD04117371
InChI Key :	JIKAGDRSOLWVAB-UHFFFAOYSA-N
Pubchem ID :	2759300

Safety of [ 92379-10-7 ]

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

Computational Chemistry of [ 92379-10-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	60.86
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	57.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.37
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	2.53
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.76
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.	2.54
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	2.41
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.32

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.19
Solubility	0.14 mg/ml ; 0.000653 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.	-3.38
Solubility	0.0883 mg/ml ; 0.000412 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	-3.72
Solubility	0.0408 mg/ml ; 0.000191 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	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.	-5.81 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<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)	1.74

Application In Synthesis of [ 92379-10-7 ]

* 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 [ 92379-10-7 ]

[ 92379-10-7 ] Synthesis Path-Downstream 1~35

1
[ 67856-54-6 ]
[ 92379-10-7 ]

References: [1]Journal of medicinal chemistry,1964,vol. 7,p. 245 - 251.

2
[ 92379-10-7 ]
[ 77-78-1 ]
[ 38087-96-6 ]

References: [1]Journal of medicinal chemistry,1964,vol. 7,p. 245 - 251.

3
[ 92379-10-7 ]
6β-(3'-methoxy-biphenyl-2-carbonylamino)-penicillanic acid [ No CAS ]

References: [1]Journal of medicinal chemistry,1964,vol. 7,p. 245 - 251.

4
3'-Nitro-biphenyl-2-carboxylic acid; compound with cyclohexylamine [ No CAS ]
[ 92379-10-7 ]

References: [1]Journal of medicinal chemistry,1964,vol. 7,p. 245 - 251.

5
[ 38087-96-6 ]
[ 92379-10-7 ]

Yield	Reaction Conditions	Operation in experiment
	With boron tribromide; In dichloromethane;	Step C: Preparation of 2-(3'-hydroxyphenyl)benzoic acid 2-(3-Methoxyphenyl)benzoic acid from Step B (6.53 g, 28.6 mmol) was dissolved in dry CH2Cl2 (100 mL) under argon and cooled to -78 C. Boron tribromide (62.9 mL of a 1.0 M solution in CH2Cl2, 62.9 mmol) was added dropwise and the solution was stirred overnight and allowed to warm slowly to ambient temperature. The resulting mixture was cooled in an ice bath and quenched carefully with water (200 mL), then extracted with CH2Cl2 (3*250 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the titled product which was sufficiently pure for use in the next step.

References: [1]Patent: US6358985,2002,B1 .

6
[ 92379-10-7 ]
C₁₃H₇Br₃O₃ [ No CAS ]
C₁₃H₇Br₃O₃ [ No CAS ]

References: [1]Science,2010,vol. 328,p. 1251 - 1255.

7
[ 92379-10-7 ]
[ 1251854-46-2 ]

References: [1]Science,2010,vol. 328,p. 1251 - 1255.

8
[ 92379-10-7 ]
C₁₅H₁₁Br₃O₃ [ No CAS ]

References: [1]Science,2010,vol. 328,p. 1251 - 1255.
[2]Science,2010,vol. 328,p. 1251 - 1255.

9
[ 92379-10-7 ]
C₁₅H₁₁Br₃O₃ [ No CAS ]
C₁₅H₁₁Br₃O₃ [ No CAS ]

References: [1]Science,2010,vol. 328,p. 1251 - 1255.

10
[ 92379-10-7 ]
C₁₃H₇Br₃O₃ [ No CAS ]

References: [1]Science,2010,vol. 328,p. 1251 - 1255.

11
[ 67-56-1 ]
[ 92379-10-7 ]
[ 1251836-88-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With thionyl chloride; for 4.17h;Reflux;	Template A building blocks (Scheme 5): 3'-Hydroxybiphenyl-2-carboxylic acid (1 ) is commercially available. Methyl 3'-hydroxybiphenyl-2-carboxylate (2) Thionyl chloride (7.7 mL, 105 mmol) was added at 0C to a soln of 1 (4.5 g, 21.0 mmol) in MeOH (55 mL). The mixture was stirred for 10 min at 0C and then heated to reflux for 4 h. Evaporation of the volatiles, aqueous workup (EtOAc, sat. aq. NaHCOs soln; Na2S04) and FC (hexane/EtOAc 5:1 ) afforded the ester 2 (4.34 g, 90%). Data of 2: Ci4Hi203 (228.2). H-NMR (DMSO-d6): 9.52 (br. s, OH); 7.68 (dd, J = 1.1 , 7.6, 1 H); 7.59 (dt, J = 1 .5, 7.6, 1 H); 7.47 (dt, J = 1.3, 7.5, 1 H); 7.40 (dd, J = 0.9, 7.6, 1 H); 7.20 (t-like m, J = 8.0, 1 H); 6.75 (m, 1 H); 6.70 - 6.67 (m, 2 H); 3.59 (s, 3 H).
90%	With thionyl chloride; for 4.0h;Reflux;	Thionyl chloride (7.7 mE, 105 mmol) was added at0C. to a solnofl (4.5 g, 21.0 mmol) inMeOH (55 mE). The mixture was stirred for 10 mm at 0 C. and then heated to reflux for 4 h. Evaporation of the volatiles, aqueous workup (EtOAc, sat. aq. NaHCO3 soln; Na2504) and FC (hexane/ EtOAc 5:1) afforded the ester 2 (4.34 g, 90%).Data of 2: C14H1203 (228.2). ?H-NMR (DMSOd 5): 9.52 (br. s, OH); 7.68 (dd, J=1.1, 7.6, 1H); 7.59 (dt, J=1.5, 7.6, 1H); 7.47 (dt, J=1.3, 7.5, 1H); 7.40 (dd, J=0.9, 7.6, 1H);7.20 (t-like m, J=8.0, 1H); 6.75 (m, 1H); 6.70-6.67 (m, 2H);3.59 (s, 3H).

References: [1]Patent: WO2013/139697,2013,A1 .Location in patent: Page/Page column 119.
[2]Patent: US2015/51183,2015,A1 .Location in patent: Paragraph 0377; 0378.

12
[ 92379-10-7 ]
[ 1460301-40-9 ]