Amfenac

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Amfenac
Amfenac.svg
Systematic (IUPAC) name
2-Amino-3-benzoylphenylacetic acid
2-Amino-3-benzoylbenzeneacetic acid
2-(2-amino-3-benzoyl-phenyl)acetic acid
Identifiers
CAS Registry Number 51579-82-9 YesY
ATC code None
PubChem CID: 2136
IUPHAR/BPS 7565
ChemSpider 2051 YesY
UNII 28O5C1J38A YesY
KEGG D07443 YesY
ChEBI CHEBI:75915 N
ChEMBL CHEMBL25146 YesY
Chemical data
Formula C15H13NO3
Molecular mass 255.27 g/mol
 N (what is this?)  (verify)

Amfenac (2-Amino-3-benzoylbenzeneacetic acid) is a non-steroidal anti-inflammatory drug with acetic acid moiety.

Synthesis[edit]

Amfenac synthesis:.[1][2]

The starting N-amino-2-indolone[3] (1) can be obtained by reduction of the N-nitrosation product of Oxindole[4] (2-indolone) itself. Reaction of this intermediate, which is in essence an N-acylhydrazine, with phenylacetone gives the corresponding hydrazone (2). The hydrazone is then treated with ethanolic hydrogen chloride; Fischer indole synthesis would in theory lead to the fused bicyclic indole (3). The observed product (4) can be rationalized by assuming that the labile bicyclic N-acyl indole opens to an ester in the presence of ethanolic HCl. Ozonation of the double bond in the heterocyclic ring then leads to N-acylated benzophenone 5, with the acetyl group arising from the ring atom bearing a methyl group. Acid hydrolysis of this intermediate removes both the amide and the ester to afford amfenac.

See also[edit]

  • Bromfenac (same structure as amfenac but with p-bromo)

References[edit]

  1. ^ Welstead, W. J.; Moran, H. W.; Stauffer, H. F.; Turnbull, L. B.; Sancilio, L. F. (1979). "Antiinflammatory agents. 1. Synthesis and antiinflammatory activity of 2-amino-3-benzoylphenylacetic acid". Journal of Medicinal Chemistry 22 (9): 1074–9. doi:10.1021/jm00195a012. PMID 490552.  edit
  2. ^ W. J. Welstead, H. W. Moran, DE 2324768  C.A. 80, 59708s (1974) and U.S. Patent 4,045,576 (1973, 1977 both to A. H. Robbins)
  3. ^ http://www.chemspider.com/Chemical-Structure.3003785.html?rid=c5857ec2-157a-48ff-9d99-8f8bf45881d0
  4. ^ http://www.chemspider.com/Chemical-Structure.284794.html?rid=13aff875-e7a5-4303-88fc-72a125fcad0c