73154-79-7

Basic information

• Product Name: <2-(acetylamino)-2-carbomethoxyethyl>sulfenyl chloride
• Synonyms: <2-(acetylamino)-2-carbomethoxyethyl>sulfenyl chloride
• CAS NO: 73154-79-7
• Molecular Weight: 211.669
• Mol File: 73154-79-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: <2-(acetylamino)-2-carbomethoxyethyl>sulfenyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: <2-(acetylamino)-2-carbomethoxyethyl>sulfenyl chloride(73154-79-7)
• EPA Substance Registry System: <2-(acetylamino)-2-carbomethoxyethyl>sulfenyl chloride(73154-79-7)

Safety Data

• Hazardous Substances Data: 73154-79-7(Hazardous Substances Data)

Upstream product

• 7652-46-2 Ac-Cys-OMe 

Downstream Products

• 78774-18-2 (R)-2-Acetylamino-3-(2-chloro-propylsulfanyl)-propionic acid methyl ester 
• 73154-78-6 (R)-2-Acetylamino-3-(2-chloro-cyclohexylsulfanyl)-propionic acid methyl ester 
• 109064-76-8 cCmES)-OMeZ-Lys(Z)-Trp( 

Relevant articles and documents

Analgesic Dipeptide Derivatives. 3. Synthesis and Structure-Activity Relationships of o-Nitrophenyl-Modified Analogues of the Analgesic Compound H-Lys-Trp(NPS)-OMe

A series of analogues of the analgesic dipeptide derivative H-Lys-Trp(NPS)-OMe has been designed to determine the influence of the (2-nitrophenyl)sulfenyl (NPS)moiety on the activity.The syntheses and antinociceptive effects of these analogues of general formula H-Lys-Trp(R)-OMe sulfenyl (AacCmES) (13); R = sulfenyl (AacPS) (17); R = tert-butylsulfenyl (t-BuS) (23); R = (2-carbomethoxyethyl)sulfenyl (CmES) (24)> are described.Reaction of Z-Lys(Z)-Trp-OMe (3) with PS-, CmPS-, pNPS-, DNPS-, and AacCmES-Cl afforded the corresponding 2-(sulfenyl)tryptophan derivatives, which on treatment with boron-tris(trifluoroacetate)/trifluoroacetic acid or trimethylsilyl iodide in acetonitrile (Me3SiI/CH3CN) provided 9-13, respectively.Sulfenylation of 3 with NPS-Cl gave Z-Lys(Z)-Trp(NPS)-OMe, which, on catalytic hydrogenation of the nitro group using 10percent Pd/C followed by acetylation of the resulting amino function and removal of the protecting Z group, gave 17.Condensation of 2-(ter-butylsulfenyl)- and 2-tryptophan methyl ester, obtained by reaction of methyl 3a -hydroxy-1,2,3,3a,8,8a-hexahydropyrroloindole-2-carboxylate with the corresponding thiol, with Z-Lys(Z)-OSu afforded Z-Lys(Z)-Trp(t-BuS)-OMe and Z-Lys(Z)-Trp(CmES)-OMe, which on treatment with Me3SiI/CH3CN provided 23 and 24, respectively.Intracerebroventricular administration of 10 elicited a naloxone-reversible antinociceptive effect in mice similar to that of H-Lys-Trp(NPS)-OMe.No analgesia was however found with the phenylsulfenyl or acyclic sulfenyl substituted dipeptides 9, 11, and 17 or 13, 23, and 24.The Trp(DNPS)-containing analogue was neurotoxic.Structure-activity studies indicate that the role of the NPS and CmPS moieties could be related to the adoption of a preferential active conformation.