523993-95-5

Basic information

• Product Name: methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate
• Synonyms: methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate
• CAS NO: 523993-95-5
• Molecular Weight: 362.406
• Mol File: 523993-95-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate(523993-95-5)
• EPA Substance Registry System: methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate(523993-95-5)

Safety Data

• Hazardous Substances Data: 523993-95-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 45754-12-9 2,3-bis(chloromethyl)-pyridine 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 605-38-9 dimethyl 2,3-pyridinedicarboxylate 
• 38070-79-0 2,3-bis(hydroxymethyl)pyridine 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 

Relevant articles and documents

Synthesis and structure-activity relationships of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids as HB-EGF shedding inhibitors

HB-EGF Shedding inhibitors have been expected to become effective medicines for skin diseases caused by the proliferation of keratinocytes. In order to discover novel HB-EGF shedding inhibitors and clarify their structure-activity relationships, 5,6,7,8-tetrahydronaphthylidine-based hydroxamic acid and 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids have been synthesized. Among the synthesized compounds, the ethoxyethoxy derivative 3o and the methoxypropoxy derivative 3p exhibited much more potent HB-EGF shedding inhibitory activity than CGS 27023A. The structural modification of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids enabled us to establish the following structure-activity relationships; the existences of the hydroxamic acid, the sulfonamide, and the phenyl moieties are crucial for a potent HB-EGF shedding inhibitory activity, and the stereochemistry of the alpha carbon of hydroxamic acid is also important. In addition, from the comparison of their HB-EGF shedding inhibitory activities with their MMPs inhibitory activities, we found that the S1′ pocket of the responsible enzyme for HB-EGF shedding is deep unlike that of MMP-1.