402-71-1

Basic information

• Product Name: Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-
• Synonyms: Benzenesulfonamide,N-[3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-, (S)-;p-Toluenesulfonamide, N-[a-(chloroacetyl)phenethyl]-, L- (8CI);L-1-Chloro-3-tosylamidyl-4-phenyl-2-butanone;L-1-Chloro-4-phenyl-3-p-tolylsulfonamidobutan-2-one;L-1-Tosylamide-2-phenylethylchloromethyl ketone;L-1-Tosylamido-2-phenylethylchloromethyl ketone;L-Tolylsulfonylphenylalanyl chloromethyl ketone;N-Tosyl-L-phenylalaninechloromethane;N-Tosyl-L-phenylalanylchloromethane;N-Tosylphenylalanine chloromethylketone;N-a-Tosyl-L-phenylalanylchloromethane;Tosylphenylalanylchloromethane;a-N-Tosyl-L-phenylalanine chloromethyl ketone
• CAS NO: 402-71-1
• Molecular Formula: C17H18ClNO3S
• Molecular Weight: 351.8477
• EINECS: 206-954-6
• Product Categories: Apoptosis Inhibitors
• Mol File: 402-71-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 106-108 °C(lit.)
• Boiling Point: 509.9 °C at 760 mmHg
• Flash Point: 262.2 °C
• Appearance: white crystalline powder
• Density: 1.278 g/cm³
• Vapor Pressure: 1.63E-10mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: ?20°C
• Solubility: DMSO: >10?mg/mL stable for several months at 4°C.
• PKA: 8.71±0.50(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• BRN: 2895215
• CAS DataBase Reference: Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-(402-71-1)
• EPA Substance Registry System: Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-(402-71-1)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36
• RIDADR: UN 3335
• WGK Germany: 3
• RTECS: XT5613500
• F: 10-19-21
• TSCA: Yes
• Hazardous Substances Data: 402-71-1(Hazardous Substances Data)

Usage

Description

Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methylis a complex organic compound with a specific molecular structure. It is characterized by its white crystalline powder form and is derived from the benzenesulfonamide class of compounds. This molecule possesses a unique arrangement of functional groups, including a chloro, oxo, and phenylmethyl moiety, which contribute to its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methylis used as a proteinase inhibitor with apoptotic function for the development of therapeutic agents. Its application is based on its ability to induce caspase-dependent apoptosis in certain cell lines, such as Epstein-Barr virus (EBV)-transformed human B cell lines. Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methylpromotes the release of pro-apoptotic proteins from mitochondria, down-regulation of anti-apoptotic proteins, and caspase-dependent cleavage of two anti-apoptotic proteins. Additionally, it facilitates the dephosphorylation of p53 on serine residues, which is crucial for its apoptotic activity.
Used in Biochemical Research:
In the field of biochemical research, Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methylcan be utilized as an irreversible inhibitor of serine protease chymotrypsin and certain cysteine proteases, such as bromelain, ficin, and papain. Its inhibitory properties make it a valuable tool for studying the mechanisms and regulation of these proteases, which are involved in various biological processes.
Used in Cell Cycle Regulation Studies:
Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methylhas been shown to inhibit the mitogen-induced activation of pp70s6k, a mitogen-regulated serine/threonine kinase involved in the G1 to S phase transition of the cell cycle. This makes it a potential candidate for use in research aimed at understanding and modulating cell cycle progression, which is essential for the development of novel cancer therapeutics and other applications related to cell growth and division.

Biochem/physiol Actions

Blocks the LPS- or cytokine-induced activation of nuclear factor κB (NFκB), which, in turn, blocks the induction of iNOS and COX-2 transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli. Also blocks apoptosis initiated by Taxol (in MCF-7 human breast carcinoma cells).

Safety Profile

Experimental reproductive effects. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx, SOx, and Cl-.

References

1) Bond and Butler, (1987) Intracellular proteases; Annu. Rev. Biochem., 56 333 2) Grammer and Blenis (1996) The serine protease inhibitors, tosylphenylalanine chloromethylketone and tosyllysine chloromethylketone, potently inhibit pp70s6k activation; J. Biol. Chem., 271 23650

InChI:InChI=1/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1