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[ CAS No. 165668-41-7 ] {[proInfo.proName]}

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Chemical Structure| 165668-41-7
Chemical Structure| 165668-41-7
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Product Details of [ 165668-41-7 ]

CAS No. :165668-41-7 MDL No. :MFCD00945325
Formula : C14H12ClN3O4S2 Boiling Point : -
Linear Structure Formula :- InChI Key :SETFNECMODOHTO-UHFFFAOYSA-N
M.W : 385.85 Pubchem ID :216468
Synonyms :
E 7070

Calculated chemistry of [ 165668-41-7 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 91.42
TPSA : 138.88 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.7
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 4.24
Log Po/w (MLOGP) : 0.62
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 1.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.54
Solubility : 0.111 mg/ml ; 0.000289 mol/l
Class : Soluble
Log S (Ali) : -4.29
Solubility : 0.0196 mg/ml ; 0.0000508 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.89
Solubility : 0.000493 mg/ml ; 0.00000128 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.87

Safety of [ 165668-41-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 165668-41-7 ]

* 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 [ 165668-41-7 ]

[ 165668-41-7 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 6960-42-5 ]
  • [ 165668-41-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 93 percent / N-chlorosuccinimide; aq. HCl / tetrahydrofuran / 5 h / 20 °C 2: Fe; aq. NH4Cl / propan-2-ol / 2 h / 60 °C 3: pyridine / 3 h / 20 °C
  • 3
  • [ 165669-14-7 ]
  • [ 165668-41-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Fe; aq. NH4Cl / propan-2-ol / 2 h / 60 °C 2: pyridine / 3 h / 20 °C
YieldReaction ConditionsOperation in experiment
A list of specific examples of the sulfonamide derivative or the sulfonic acid ester derivative represented by the general formula (I) or the pharmacologically acceptable salt, or the hydrate thereof is as follows: Compound 1 ... 3-Chloro-N-(3-formyl-1H-indol-7-yl)benzenesulfonamide 3-Chloro-N-(3-cyano-1H-indol-7-yl)benzenesulfonamide 6-Chloro-N-(3-cyano-1H-indol-7-yl)-3-pyridinesulfonamide N-(3-Chloro-1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide 3-Chloro-N-(8-imidazo[1,2-a]pyridinyl)benzenesulfonamide hydrochloride N-(3,4-Dichloro-1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide N-(3-Chloro-1H-indol-7-yl)-4-(methylthio)benzenesulfonamide ...
S.11 N-(3-Chloro-1H-indole-7-yl)-4-sulfamoylbenzenesulfonamide The resulting compound was chlorinated using N-chlorosuccinimide in dichloromethane, to give 349 mg of the title compound. Melting point: started coloring partially in a black color from a temperature close to 220° C. and decomposed gradually from a temperature close to 240° C. (recrystallized from ethanol-n-hexane). 1H-NMR(DMSO-d6) δ (ppm): 6.75(1H, d, J=7.6 Hz), 6.96(1H, dd, J=8.0, 7.6 Hz), 7.29(1H, d, J=7.6 Hz), 7.50(1H, d, J=2.8 Hz), 7.58(2H, s), 7.90-7.98(4H, m), 10.23(1H, s), 11.07-11.17(1H, m)
N-(3-Chloro-1H-indole-7-yl)-4-sulfamoylbenzenesulfonamide The product was chlorinated in the same manner as in Example 2a, to give 349 mg of the title compound. Melting point: started coloring partially in a black color from a temperature close to 220° C. and decomposed gradually from a temperature close to 240° C. (recrystallized from ethanol/n-hexane). 1H-NMR(DMSO-d6) δ (ppm): 6.75(1H, d, J=7.6 Hz), 6.96(1H, dd, J=8.0, 7.6 Hz), 7.29(1H, d, J=7.6 Hz), 7.50(1H, d, J=2.8 Hz), 7.58(2H, s), 7.90-7.98(4H, m), 10.23(1H, s), 11.07-11.17(1H, m)
  • 5
  • [ 165669-28-3 ]
  • [ 165668-41-7 ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; 1.4 (4) N-(3-chloro-1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide (α-type crystal); [Show Image] 860 mg (6.5 mmol) of 7-amino-1H-indole obtained in the above (3) was dissolved in 5 ml of tetrahydrofuran, 5 ml of pyridine was added to the solution, and the mixture was ice cooled. After the mixture was stirred at 0°C for 10 minutes, 1.83 g of 4-sulfamoylbenzenesulfonyl chloride (7.16 mmol) obtained in Reference Example 2 was added thereto and the resultant mixture was stirred at room temperature. After addition of ethyl acetate and IN hydrochloric acid, the organic layer was separated and washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride successively. The organic layer was dried over magnesium sulfate, and the solvent was distilled under reduced pressure. The residue was purified by silica column chromatography (hexane/ethyl acetate = 1.5/1 to 1/1) to give 1.812 g of N-(1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide. 1.812 g (5.17 mmol) of this compound was dissolved in a mixed solvent of 150 ml of dichloromethane and 12 ml of dimethylformamide, and then 718 mg (5.27 mmol) of N-chlorosuccinimide was added to the solution while being stirred in a nitrogen atmosphere. After stirring at room temperature for 1 hour, an aqueous sodium thiosulfate solution and ethyl acetate were added thereto. The organic layer was separated and washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride successively. The organic layer was dried over magnesium sulfate and the solvent was distilled under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1 to 2/1) to give 1.926 g of the title compound. The compound began to be discolored partially black around the melting point of 220°C, and was gradually decomposed around 240°C (recrystallized from ethanol-n-hexane). 1H-NMR(DMSO- d6).δ(ppm):6.75(1H,d,J=7.6Hz),6.96(1H,dd,J=8.0,7.6Hz),7. 29(1H,d,J=7.6Hz),7.50(1H,d,J=2.8Hz),7.58(2H,s),7.90-7.98(4H,m),10.23(1H,s),11.07-11.17(1H,m)
With N-chloro-succinimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; 1 Example 1; N-(3-chloro-1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide (β-type crystal); [Show Image] 860 mg (6.5 mmol) of 7-amino-1H-indole obtained in (3) of Reference Example 1 was dissolved in 5 ml of tetrahydrofuran, 5 ml of pyridine was added to the reaction solution, and the reaction solution was ice cooled. After the reaction solution was stirred at 0°C for 10 minutes, 1.83 g of 4-sulfamoylbenzenesulfonyl chloride (7.16 mmol) obtained in Reference Example 2 was added to the reaction solution and the resultant mixture was stirred at room temperature. After addition of ethyl acetate and 1N hydrochloric acid to the reaction solution, the organic layer was separated and washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride successively. The organic layer was dried over magnesium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by silica column chromatography (hexane/ethyl acetate = 1.5/1 to 1/1) to give 1.812 g of N-(1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide. 1.812 g (5.17 mmol) of this compound was dissolved in a mixed solvent of 150 ml of dichloromethane and 12 ml of dimethylformamide, and then 718 mg (5.27 mmol) of N-chlorosuccinimide was added to the solution while being stirred in a nitrogen atmosphere. After stirring at room temperature for 1 hour, an aqueous sodium thiosulfate solution and ethyl acetate were added thereto. The organic layer was separated and washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride successively. The organic layer was dried over magnesium sulfate and the solvent was distilled under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1 to 2/1) to give 1.926 g of the title compound. 99.91 mg of N-(3-chloro-1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide was dissolved in 100 ml of a mixed solvent of isopropanol-water (1:1) and the solvent was evaporated at room temperature at ordinary pressure in the dark to give β-type crystal (49.12 mg). 1H-NMR(DMSO-d6).δ(ppm):6.75(1H,d,J=7.6Hz),6.96(1H,dd,J=8.0,7.6Hz),7. 29(1H,d,J=7.6Hz),7.50(1H,d,J=2.8Hz),7.58(2H,s),7.90-7.98(4H,m),10.23(1H,s),11.07-11.17(1H,m)
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