4-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfamide Chemical Properties

Melting point:

209-214 °C

Density 

1.356±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in DMSO (up to 45 mg/ml).

pka

10.14±0.10(Predicted)

form 

Solid

color 

White

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

InChI

InChI=1S/C16H17ClN2O4S/c1-23-15-7-4-12(17)10-14(15)16(20)19-9-8-11-2-5-13(6-3-11)24(18,21)22/h2-7,10H,8-9H2,1H3,(H,19,20)(H2,18,21,22)

InChIKey

KVWWTCSJLGHLRM-UHFFFAOYSA-N

SMILES

C(NCCC1=CC=C(S(N)(=O)=O)C=C1)(=O)C1=CC(Cl)=CC=C1OC

CAS DataBase Reference

16673-34-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

23-24-25

Safety Statements 

24/25

WGK Germany 

1

HS Code 

2935909550

4-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfamide Usage And Synthesis

Description

NLRP3i (16673-34-0) is an NLRP3 inflammasome inhibitor which likely acts via interfering with the formation of the NLRP3 inflammasome complex and which exhibits promising?in vivo?protective activities in mouse acute myocardial infarction models. It blocks ASC aggregation, blocks the release of IL-1β and the activation of caspase-1 in macrophages expressing constitutively active NLRP3 but does not directly inhibit caspase-1.1,2?Limits infarct size after myocardial ischemia-reperfusion as well as leukocyte infiltration in a peritonitis model in mice.2

Chemical Properties

Light Yellow Solid

Uses

An impurity arising in the synthesis of Glyburide (G598350).

General Description

5-Chloro-2-methoxy-N-[2-(4-sulfamoylphenyl)ethyl]benzamide is an organic building block. It has been reported as an intermediate in the synthesis of glyburide. Synthesis of 5-chloro-2-methoxy-N-[2-(4-sulfamoylphenyl)ethyl]benzamide has been reported.

storage

Store at +4°C

References

1) Fulp?et al.?(2018),?Structural Insights of Benzenesulfonamide Analogues as NLRP3 Inflammasome Inhibitors: Design, Synthesis, and Biological Characterization; J. Med. Chem.,?61?5412 2) Marchetti?et al.?(2014),?A novel pharmacologic inhibitor of the NLRP3 inflammasome limits myocardial injury after ischemia-reperfusion in the mouse; J. Cardiovas. Pharmacol.,?63?316

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