177913-49-4

Basic information

• Product Name: 2,4-Cyclohexadiene-1-carboxylic acid, 5-acetyl-4-amino-1-hydroxy-, methyl ester
• CAS NO: 177913-49-4
• Molecular Formula: C10H13NO4
• Molecular Weight: 211.218
• Mol File: 177913-49-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,4-Cyclohexadiene-1-carboxylic acid, 5-acetyl-4-amino-1-hydroxy-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Cyclohexadiene-1-carboxylic acid, 5-acetyl-4-amino-1-hydroxy-, methyl ester(177913-49-4)
• EPA Substance Registry System: 2,4-Cyclohexadiene-1-carboxylic acid, 5-acetyl-4-amino-1-hydroxy-, methyl ester(177913-49-4)

Safety Data

• Hazardous Substances Data: 177913-49-4(Hazardous Substances Data)

Upstream product

• 22600-30-2 methyl 5-amino-2-furoate 
• 78-94-4 methyl vinyl ketone 

Downstream Products

• 960324-79-2 3-acetyl-4-methanesulfonylaminobenzoic acid 
• 111714-47-7 3-acetyl-4-aminobenzoic acid methyl ester 

Relevant articles and documents

Solid-phase parallel synthesis and SAR of 4-amidofuran-3-one inhibitors of cathepsin S: Effect of sulfonamides P3 substituents on potency and selectivity

Highly potent and selective 4-amidofuran-3-one inhibitors of cathepsin S are described. The synthesis and structure-activity relationship of a series of inhibitors with a sulfonamide moiety in the P3 position is presented. Several members of the series show sub-nanomolar inhibition of the target enzyme as well as an excellent selectivity profile and good cellular potency. Molecular modeling of the most interesting inhibitors describes interactions in the extended S3 pocket and explains the observed selectivity towards cathepsin K.

CATHEPSIN S INHIBITORS

Compounds of the formula (I) where R1 is C1-C4 straight or branched alkyl, optionally substituted with up to three substituents selected from halo and hydroxy; R2 is halo, hydroxy, methyloxy, or C1-C2 alkyl, which alkyl is optionally substituted with up to three halogens or an hydroxy or a methyloxy; D is - C3-C7 alkylene-, thereby defining a cycloalkyl ring; E is -C(=O)-, -S(=O)m-, -NRdS(=O)m-, -NRaC(=O)-, -OC(=O)-, R3 is an optionally substituted carbocyclic or heterocyclic ring R10 is H, ORc, SRc or together with the gem H is =O or (ORc)2; Ra is independently selected from H, C1-C4 alkyl; have utility in the inhibition of cathepsin S and are thus useful pharmaceuticals against disorders such as autoimmune disorders and chronic pain.

Synthesis of polysubstituted anilines using the Diels-Alder reaction of methyl 5-aminofuroate

Methyl 5-aminofuroate undergoes a facile [4+2]-cycloaddition with a variety of dienophiles to afford ring opened cycloadducts which are readily dehydrated using BF3·OEt2 to give polysubstituted anilines.