53297-70-4|4-Amino-3-methylbenzenesulfonamide| Ambeed

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Quality Control of [ 53297-70-4 ] Purity: 97% SDS Specification

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Product Details of [ 53297-70-4 ]

CAS No. :	53297-70-4
Formula :	C₇H₁₀N₂O₂S
M.W :	186.23
SMILES Code :	C1=CC(=CC(=C1N)C)[S](N)(=O)=O
MDL No. :	MFCD00466840
InChI Key :	IGQGXIVCGKMRAM-UHFFFAOYSA-N
Pubchem ID :	143037

Safety of [ 53297-70-4 ]

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

Computational Chemistry of [ 53297-70-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	46.81
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	94.56 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.06
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	-0.18
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.31
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.	0.05
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	-0.3
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.19
Solubility	12.2 mg/ml ; 0.0653 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.	-1.35
Solubility	8.32 mg/ml ; 0.0447 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	-1.99
Solubility	1.89 mg/ml ; 0.0102 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.	-7.56 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	1.0 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)	1.66

Application In Synthesis of [ 53297-70-4 ]

* 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 [ 53297-70-4 ]

[ 53297-70-4 ] Synthesis Path-Downstream 1~35

1
[ 112-77-6 ]
[ 53297-70-4 ]
6-oleoylamino-toluenesulfonamide-⁽³⁾ [ No CAS ]

References: [1]Patent: US2169971,1937, .

2
[ 252562-03-1 ]
[ 53297-70-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; In ethanol; water; at 80℃;	A mixture of N-(2-methyl-4-sulfamoylphenyl)acetamide (5.1 g, 22.3 mmol), HCl (2 N, 76.5 ml) and EtOH (100 ml) was refluxed overnight. Then the mixture was neutralized with Na2CO3 (aq) to pH = 8. The mixture was extracted with EA (80 mL x 4), dried over Na2SO4, and concentrated to obtain 4-amino-3-methylbenzenesulfonamide as a pale solid (4.9 g, yield 100%).
100%	With hydrogenchloride; water; In ethanol;Reflux;	Compound 27-6 (0455) A mixture of 27-5 (5.1 g, 22.3 mmol), HCl (2 N, 76.5 ml) and EtOH (100 ml) was refluxed overnight. Then the mixture was neutralized with Na2CO3(aq) to PH=8. The mixture was extracted with EA (80 ml×4), dried over Na2SO4, and concentrated to give 27-6 as a pale solid (4.9 g, yield 100%).
93%		A round-bottom flask was equipped with a stir bar, a reflux condenser and nitrogen on demand. Into the flask were placed sulfonamide 465 (8.4 g, 36.80 mmol), ethyl alcohol (200 mL) and 2N hydrochloric acid (128 mL). The resulting mixture was allowed to heat to reflux overnight, after which time it was allowed to cool to RT and was neutralized with saturated, aqueous sodium bicarbonate. It was then poured into a separatory funnel containing water and ethyl acetate, the organic layer was collected, washed with water, brine, dried over MgSO4, filtered and the solvents were removed under reduced pressure to afford a tan solid (6.35 g, 93%), which was used without further purification. 1H NMR (DMSO-d6, 400 MHz) delta 2.06 (s, 3H), 5.54 (s, 2H), 6.58 (d, J= 12 Hz, 1H), 6.82 (s, 2H), 7.30 (d, J= 12 Hz, 1H), 7.33 (s, 1H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2338 - 2342.
[2]Patent: US9138427,2015,B2 .Location in patent: Page/Page column 304.
[3]Patent: EP1208091,2006,B1 .Location in patent: Page/Page column 8; 21.
[4]Collection of Czechoslovak Chemical Communications,1948,vol. 13,p. 161,165,169.
[5]Journal of Medicinal Chemistry,2004,vol. 47,p. 1175 - 1182.

3
[ 53297-70-4 ]
[ 111-92-2 ]
[ 75-36-5 ]
2-Methyl-benzene-1,4-disulfonic acid 4-(acetyl-amide) 1-dibutylamide [ No CAS ]

References: [1]Patent: DE2047384,1971, .
Chem.Abstr.,1971,vol. 75.

4
[ 53297-70-4 ]
[ 329944-30-1 ]
2-[4-chloro-2-(3-cyano-benzoyl)-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1175 - 1182.

5
[ 53297-70-4 ]
[ 675139-67-0 ]
GW₄₅₁₁ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1175 - 1182.

6
[ 436095-23-7 ]
[ 53297-70-4 ]
N-[4-(aminosulfonyl)-2-methylphenyl]-2-[(1-mesityl-1H-tetrazol-5-yl)thio]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; In chloroform; toluene; at 20 - 70℃; for 4.5h;	The compounds in Table 2 below were prepared in accordance with the procedures set forth in Example 1, Step 3 using either [(1-mesityl-1H-tetrazol-5-yl)thio]acetic acid (prepared as described in Example 1, Steps 2 and 3) or the appropriate counterpart and the appropriate amine in place of 2-chloro-3-aminopyridine.

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2748 - 2752.
[2]Patent: WO2005/115147,2005,A2 .Location in patent: Page/Page column 35-36.

7
[ 329943-23-9 ]
[ 53297-70-4 ]
2-[2-(3-cyano-benzoyl)-4-trifluoromethyl-phenoxy]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide [ No CAS ]