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Chemical Structure| 35303-76-5 Chemical Structure| 35303-76-5
Chemical Structure| 35303-76-5

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4-(2-Aminoethyl)benzenesulfonamide

CAS No.: 35303-76-5

4.5 *For Research Use Only !

Cat. No.: A690542 Purity: 98%

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Product Citations

Product Details of [ 35303-76-5 ]

CAS No. :35303-76-5
Formula : C8H12N2O2S
M.W : 200.26
SMILES Code : O=S(C1=CC=C(CCN)C=C1)(N)=O
MDL No. :MFCD00010301
InChI Key :FXNSVEQMUYPYJS-UHFFFAOYSA-N
Pubchem ID :169682

Safety of [ 35303-76-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405
Class:8
UN#:3259
Packing Group:

Calculated chemistry of [ 35303-76-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 49.92
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

94.56 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.03
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.17
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.92
Log Po/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.

0.12
Log Po/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

-0.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.36

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.12
Solubility 15.3 mg/ml ; 0.0762 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.

-1.36
Solubility 8.73 mg/ml ; 0.0436 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

-2.42
Solubility 0.763 mg/ml ; 0.00381 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.

-7.64 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

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)

1.62

Application In Synthesis [ 35303-76-5 ]

* 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 [ 35303-76-5 ]

[ 35303-76-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 97-08-5 ]
  • [ 35303-76-5 ]
  • 4-Chloro-3-nitro-N-[2-(4-sulfamoyl-phenyl)-ethyl]-benzenesulfonamide [ No CAS ]
  • 2
  • [ 75-44-5 ]
  • [ 52430-43-0 ]
  • [ 35303-76-5 ]
  • [ 52430-44-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine; sodium acetate; In water; acetone; benzene; (a) 4-(beta-N'-2-quinolyl-N'-methylureidoethyl)-benzene-sulfonamide 76.5 Grams of <strong>[52430-43-0]2-methylaminoquinoline</strong> were mixed in 600 ml of absolute benzene with 39.5 g of pyridine and, while cooling with ice and stirring, treated with 49 g of phosgene. Stirring was continued for 1 hour, the salt precipitated was suction-filtered and washed well with benzene. The filtrate was evaporated, the residue taken up in 100 ml of acetone and added dropwise, while stirring and cooling with ice, to a mixture which contained in 290 ml of water 0.36 mol of 4-(beta-aminoethyl)-benzenesulfonamide and 0.72 mol of sodium acetate and was mixed with 290 ml of acetone. Stirring was continued for about 1 hour, the mixture was mixed with water, suction-filtered and recrystallized from ethanol - dimethylformamide. The reaction product obtained melted at 185-187 C.
  • 3
  • [ 617-89-0 ]
  • [ 35661-38-2 ]
  • [ 35661-60-0 ]
  • [ 71989-28-1 ]
  • [ 79-08-3 ]
  • [ 104091-08-9 ]
  • Nα-fmoc-N(im)-trityl-D-histidine [ No CAS ]
  • N-FMOC-O-tert-butyl-D-threonine [ No CAS ]
  • [ 35303-76-5 ]
  • C46H67N11O15S2 [ No CAS ]
  • 4
  • [ 21286-54-4 ]
  • [ 35303-76-5 ]
  • [ 1286246-07-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere; General procedure: Reactions of (1R)-(-)-10-camphorsulfonyl chloride 1 and (1S)-(+)-10-camphorsulfonyl chloride 2 (0.3 g,1.0 equiv) with amino derivatives 3 - 7 (1.0 equiv) were carried out at 0 C to room temperature in Schotten-Baumann conditions under nitrogen atmosphere, in the presence of a stoichiometric amount of dropwised dry TEA (1.0 equiv for 3, 5, 6 and 2.0 equiv for 4, 7), in dry DMF as solvent (2 ml). When complete (monitoring by TLC), reactions were quenched with crushed ice, extracted with ethyl acetate (20 ml), washed with 1 N HCl (2 x 10 ml) and brine (2 x 10 ml). The collected organic phase was dried on anhydrous Na2SO4, filtered and evaporated under vacuum. The crude was purified by silica gel column chromatography eluting with n-hexane/ethyl acetate or DCM/methanol to afford compounds 8-17 as white solids in medium yields.
  • 5
  • [ 32703-79-0 ]
  • [ 35303-76-5 ]
  • 4-(2-(5-(tert-butyl)-1,3-dioxoisoindolin-2-yl)ethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With sodium acetate; acetic anhydride; acetic acid; for 12h;Reflux; General procedure: A mixture of 4-(2-aminoethyl)benzenesulfonamide (0.5 g,2.5 mmol), anhydrous sodium acetate (0.41 g, 5.0 mmol) and anacid anhydride (2.5 mmol) was stirred in glacial acetic acid(15 mL). The mixture was heated under reflux for 12 h and thereaction was monitored with the help of TLC. After completion ofreaction the solvent was removed under reduced pressure andthe crude solid obtained was washed with water, dried and recrystallisedfrom an appropriate solvent.
  • 6
  • phenyl 3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate [ No CAS ]
  • [ 35303-76-5 ]
  • [ 119018-29-0 ]
YieldReaction ConditionsOperation in experiment
85% In tetrahydrofuran; at 20℃; 3-Ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate(1; 1.349 g, 5.5 mmol) and 4-(2-aminoethyl)benzenesulfonamide(1.001 g, 5 mmol) were dissolved in THF (40 mL), and themixture was stirred at r.t. over night. After completion of thereaction (TLC), the solvent was evaporated under reduced pressure,and the crude product was purified by crystallization(EtOAc) to give a white solid yield: 1.495 g, (85%); mp 183-185 C.1H NMR (400 MHz, DMSO-d6): delta = 8.37 (t, J = 5.2 Hz, 1 H), 7.45(d, J = 7.8 Hz, 2 H), 7.43 (d, J = 7.8 Hz, 2 H), 7.32 (s, 2 H), 4.17 (s, 2H), 3.49 (q, J = 6.0 Hz, 2 H), 2.88 (t, J = 6.5 Hz, 2 H), 2.18 (q, J = 7.3Hz, 2 H), 2.01 (s, 3 H), 0.97 (t, J = 7.4 Hz, 3 H). 13C NMR (100MHz, DMSO-d6): delta = 172.3, 152.5, 152.1, 143.8, 142.6, 132.3,129.5, 126.2, 52.3, 40.6, 35.5, 16.4, 13.3, 13.2. HRMS (ESI): m/z[M + Na]+ calcd for C16H21N3NaO4S: 374.1150; found: 374.1140.
85.5% In isopropyl alcohol; for 6h;Reflux; The compound Kappa 5.0g, 4-(2-aminoethyl)benzenesulfonamide 4.08g and isopropanol 50g were heated under reflux for 6 h (4-(2-aminoethyl)benzenesulfonamide remaining 0.79%), cooled to After drying at 25 C, filtration and 50 C, 6.12 g of compound I was obtained. The purity of the solution was 98.66% by HPLC, the impurity was 0.60%, and the impurities V and VI were not detected. The yield was 85.5%.
  • 7
  • C24H30N4O6S [ No CAS ]
  • [ 35303-76-5 ]
  • [ 119018-29-0 ]
YieldReaction ConditionsOperation in experiment
93.6% With propionic acid; In isopropyl alcohol; for 7.5h;Reflux; 10.0 g of the compound, 8.16 g of 4-(2-aminoethyl)benzenesulfonamide, 3.02 g of propionic acid and 50 g of isopropanol were heated under reflux for 7.5 h, cooled at 25 C, filtered and dried at 50 C to give the compound 113.52 g. , the yield was 94.4%, the purity of the HPLC method was 99.63%, the impurity was 0.06%, and the impurities V and VI were not detected.
 

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