402-17-5|2-Nitro-5-(trifluoromethyl)phenol| Ambeed

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Quality Control of [ 402-17-5 ] Purity: 95% SDS Specification

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Product Details of [ 402-17-5 ]

CAS No. :	402-17-5
Formula :	C₇H₄F₃NO₃
M.W :	207.11
SMILES Code :	OC1=CC(C(F)(F)F)=CC=C1[N+]([O-])=O
MDL No. :	MFCD08282785
InChI Key :	FVKYLHATVWKUMW-UHFFFAOYSA-N
Pubchem ID :	14091690

Safety of [ 402-17-5 ]

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

Computational Chemistry of [ 402-17-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	6.0
Num. H-bond donors	1.0
Molar Refractivity	42.29
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.58
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	2.34
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.47
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.	1.37
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	0.27
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.	-2.78
Solubility	0.341 mg/ml ; 0.00165 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.	-3.37
Solubility	0.0891 mg/ml ; 0.00043 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	-2.1
Solubility	1.66 mg/ml ; 0.00802 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.	-5.9 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	2.0 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)	1.64

Application In Synthesis of [ 402-17-5 ]

* 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 [ 402-17-5 ]

[ 402-17-5 ] Synthesis Path-Downstream 1~35

1
[ 402-17-5 ]
[ 454-82-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h;Inert atmosphere;	Step-b: Synthesis of 2-amino-5-(trifluoromethyl)phenol To a solution of 2-nitro-5-(trifluoromethyl)phenol (1.0 g, 4.83 mmol) in methanol (15 mL) was added 10% Pd/C (100 mg) under nitrogen atmosphere. The reaction mixture was stirred under hydrogen balloon for 16 h. The reaction mixture was filtered through a celite bed and the filtrate was concentrated under vacuum to afford the title compound (850 mg, 99%); 1H NMR (400 MHz, DMSO-d6): δ 9.58 (bs, 1H), 6.88 (s, 1H), 6.86 (s, 1H), 6.66 (d, J=7.8 Hz, 1H), 5.18 (s, 2H); LC-MS: m/z 178.0 (M+1)+.
	With stannous chloride; sodium hydrogencarbonate; In ethanol;	b) Preparation of 2-amino-5-trifluoromethylphenol 2-Amino-5-trifluoromethylphenol was prepared by treating <strong>[402-17-5]2-nitro-5-trifluoromethylphenol</strong> (500 mg, 2.41 mmol) with a solution of SnCl2 (3.5 g, mmol) in EtOH at 23 C. for 12 h. The mixture was concentrated to 50 mL and adjusted to pH7 using saturated sodium bicarbonate. The reaction mixture was partitioned between H2 O and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting colorless oil(370 mg, 87%) was used without further purification. 1H NMR (CDCl3): 7.6 (s, 1H), 7.39(d, 1H, J=8.5 Hz), 7.08(d, 1H, J=8.5 Hz)
	With stannous chloride; sodium hydrogencarbonate; In ethanol;	b)Preparation of 2-amino-5-trifluoromethylphenol 2-Amino-5-trifluoromethylphenol was prepared by treating <strong>[402-17-5]2-nitro-5-trifluoromethylphenol</strong> (500 mg, 2.41 mmol) with a solution of SnCl2 (3.5g, mmol) in EtOH at 23 C. for 12 h. The mixture was concentrated to 50 mL and adjusted to pH 7 using saturated sodium bicarbonate. The reaction mixture was partitioned between H2 O and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting colorless oil(370 mg, 87%) was used without further purification. 1H NMR (CDCl3): 7.6 (s, 1H), 7.39(d, 1H, J =8.5 Hz), 7.08(d, 1H, J=8.5 Hz)

With sodium hydrogencarbonate; In ethanol;

b) Preparation of 2-amino-5-trifluoromethylphenol 2-Amino-5-trifluoromethylphenol was prepared by treating <strong>[402-17-5]2-nitro-5-trifluoromethylphenol</strong> (500 mg, 2.41 (M mol) with a solution of SnCl2(3.5 g, mmol) in EtOH at 23 C for 12 h. The mixture was concentrated to 50 mL and adjusted to pH 7 using saturated sodium bicarbonate. The reaction mixture was partitioned between H2O and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting colorless oil(370 mg, 87%) was used without further purification. 1H NMR (CDCl3): 7.6 (s, 1H), 7.39(d, 1H, J=8.5 Hz), 7.08(d, 1H, J=8.5 Hz)

References: [1]Patent: US10766888,2020,B1 .Location in patent: Page/Page column 62.
[2]Chemistry - A European Journal,2011,vol. 17,p. 9076 - 9082.
[3]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119.
[4]Journal of the Chemical Society,1954,p. 3846,3849.
[5]Patent: US5886044,1999,A .
[6]Patent: US5780483,1998,A .
[7]Patent: US6262113,2001,B1 .

2
[ 402-54-0 ]
[ 402-17-5 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 4979 - 4981.
[2]Journal of Organic Chemistry,1998,vol. 63,p. 4199 - 4208.
[3]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6628 - 6639.

3
[ 98-17-9 ]
[ 402-17-5 ]

Yield	Reaction Conditions	Operation in experiment
26.1%	With nitric acid; acetic acid; at 20 - 40℃; for 1h;	General procedure: An appropriate phenol (3) (150 mmol) was dissolved in glacial acetic acid (50 mL), and the solution was stirred and maintained at 40 C. Then, a solution containing 11 mL of 65% HNO3 and 30 mL of glacial acetic acid was added drop wise over 15 min. The mixture was stirred at r.t. for 45 min and poured into ice-water (400 mL). The aqueous mixture was extracted four times with CHCl3 (100 mL). Next, the organic phases were collected, dried with Na2SO4, evaporated and purified by column chromatography (4a, 4c, 4e) or crystallisation from ethanol (4b). Compound 4d was used for the next step without further purification [17].
16%	With nitric acid; acetic acid; In water; at 0 - 20℃; for 17.5h;	To a solution of 3-(trifluoromethyl)phenol (5.0 g, 30.86 mmol) in acetic acid (50 mL) was added 60% aqueous nitric acid (3.5 mL) dropwise at 0 C. Then the mixture was stirred at this temperature for 1.5 h and stirring was continued at RT for 16 h. The mixture was poured into ice water (80 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was purified by combiflash column chromatography using 5% ethyl acetate in hexane as eluent to afford the titled compound (1.0 g, 16%); 1H NMR (400 MHz, DMSO-d6): δ 11.75 (bs, 1H), 8.06 (d, J=8.3 Hz, 1H), 7.41 (d, J=1.4 Hz, 1H), 7.32 (dd, J=1.4 Hz, J=8.3 Hz, 1H); LC-MS: m/z 206.0 (M-1)-.
	With nitric acid; In water; at 0℃; for 1h;	The subtitle compound was prepared by using 3-(l,l,l-trifluoromethyl)phenol (5.0g)which was cooled to 0 C and 65% nitric acid (6ml) was added dropwise. After the addition,the mixture was kept at 0 C for 1 hour. This was diluted with saturated sodium acetatesolution, extracted with ethyl acetate, dried and concentrated under reduced pressure to givean oil. Yield 3.67gMS: ESI (+ve) 206 (M+l)

	With nitric acid; In water; at 20℃; for 1h;	Reference Production Example 9 To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol. [Show Image] 1H-NMR (CDCl3) δ: 10.59 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.48-7.46 (m, 1H), 7.27-7.23 (m, 1H)
	With nitric acid; at 20℃; for 1h;	Reference Production Example 9To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol.1H-NMR (CDCl3) δ: 10.59 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.48-7.46 (m, 1H), 7.27-7.23 (m, 1H)2-amino-5-trifluoromethylphenol was obtained according to the same manner as that of Reference Production Example 1, using 2-nitro-5-trifluoromethylphenol instead of 4-propyl-2-nitrophenol.1H-NMR (CDCl3+DMSO-d6) δ: 9.03 (br s, 1H), 7.01 (d, J=1.8 Hz, 1H), 6.95-6.91 (m, 1H), 6.71-6.66 (m, 1H), 4.13 (br s, 2H)A mixture of 1.30 g of 2-amino-5-trifluoromethylphenol, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80 C. for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of N-(2-hydroxy-4-trifluoromethylphenyl)isonicotinamide.1H-NMR (DMSO-d6) δ: 8.82-8.76 (m, 2H), 7.98-7.93 (m, 1H), 7.89-7.85 (m, 2H), 7.23-7.17 (m, 2H)
		Reference Production Example 9To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol.1H-NMR (CDC13) δ: 10.59 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.48-7.46 (m, 1H), 7.27-7.23 (m, 1H)
	With nitric acid; at 20℃; for 1h;	To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol.-NMR (CDC13) δ: 10.59 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.48-7.46 (m, 1H), 7.27-7.23 (m,1H)
		To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol.1 H-NMR (CDC13) δ: 10.59 (s, IH), 8.25 (d, J=8.8 Hz, IH), 7.48-7.46 (m, IH), 7.27-7.23 (m,IH)
	With nitric acid; In water; acetic acid; at 20℃; for 4h;	Reference Production Example 9To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol.1H-NMR (CDC13) δ: 10.59 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.48-7.46 (m, 1H), 7.27-7.23 (m,1H)
	With nitric acid; at 20℃; for 1h;	Reference Production Example 9To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol.1 H-NMR (CDC13) δ: 10.59 (s, IH), 8.25 (d, J=8.8 Hz, IH), 7.48-7.46 (m, IH), 7.27-7.23 (m,IH)

References: [1]Organic Letters,2008,vol. 10,p. 3025 - 3028.
[2]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119.
[3]Chemistry - A European Journal,2011,vol. 17,p. 9076 - 9082.
[4]Chemistry - A European Journal,2021,vol. 27,p. 7561 - 7571.
[5]Patent: US10766888,2020,B1 .Location in patent: Page/Page column 62.
[6]Journal of Organic Chemistry,1991,vol. 56,p. 1788 - 1800.
[7]Patent: WO2006/5909,2006,A1 .Location in patent: Page/Page column 52.
[8]Patent: EP2274983,2011,A1 .Location in patent: Page/Page column 123.
[9]Patent: US2011/39843,2011,A1 .Location in patent: Page/Page column 77.
[10]Patent: WO2011/40629,2011,A1 .Location in patent: Page/Page column 204.
[11]Patent: WO2011/49220,2011,A1 .Location in patent: Page/Page column 203.
[12]Patent: WO2011/49221,2011,A1 .Location in patent: Page/Page column 204.
[13]Patent: WO2011/49223,2011,A1 .Location in patent: Page/Page column 203.
[14]Patent: WO2011/49222,2011,A1 .Location in patent: Page/Page column 207.
[15]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6842 - 6851.

4
[ 2417-72-3 ]
[ 402-17-5 ]
[ 907587-46-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6628 - 6639.
[3]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

5
[ 402-17-5 ]
[ 107-30-2 ]
[ 209688-18-6 ]

Yield	Reaction Conditions	Operation in experiment
	In argon; N,N-dimethyl-formamide;	REFERENCE EXAMPLE 19 2-nitro-5-Trifluoromethylphenyl Methoxymethyl Ether To a solution of <strong>[402-17-5]2-nitro-5-trifluoromethylphenol</strong> (400 mg) in DMF (4.0 ml), sodium hydride (77 mg) was added at 0 C. in a stream of argon. The mixture was stirred for 30 minutes After stirring, methoxymethyl chloride (147 μl) was added dropwise thereto. The mixture was stirred for 20 minutes. The reaction mixture was quenched by iced water and extracted with ethyl acetate. The layer containing ethyl acetate was washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt=20:1) to give the title compound (353 mg) having the following physical data. TLC: Rf 0.44 (hexane:AcOEt=10:1).

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.
[2]Patent: US6448290,2002,B1 .

6
[ 402-11-9 ]
[ 402-17-5 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 473 - 476.

7
[ 402-17-5 ]
[ 907587-49-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6628 - 6639.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.
[3]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

8
[ 402-17-5 ]
[ 209685-47-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6628 - 6639.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

9
[ 402-17-5 ]
[ 907587-58-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6628 - 6639.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

10
[ 402-17-5 ]
4-[2-(benzenesulfonyl-isobutyl-amino)-5-trifluoromethyl-phenoxymethyl]-benzoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6628 - 6639.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5562 - 5577.

11
[ 402-17-5 ]
[ 209688-19-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

12
[ 402-17-5 ]
[ 913078-70-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

13
[ 402-17-5 ]
[ 913078-69-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

14
[ 402-17-5 ]
[ 913078-76-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

15
[ 402-17-5 ]
[ 913078-87-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

16
[ 402-17-5 ]
[ 913078-78-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

17
[ 402-17-5 ]
[ 913078-88-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

18
[ 402-17-5 ]
[ 913078-71-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

19
[ 402-17-5 ]
[ 913078-86-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

20
[ 402-17-5 ]
[ 913078-77-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7121 - 7137.

21
[ 402-17-5 ]
[ 909896-99-7 ]