Talampicillin

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Talampicillin
Talampicillin.png
Systematic (IUPAC) name
3-oxo-1,3-dihydro-2-benzofuran-1-yl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Registry Number 47747-56-8 YesY
ATC code J01CA15
PubChem CID: 5373
ChemSpider 64529 N
UNII 29OJI73DPC N
ChEMBL CHEMBL1322719 N
Chemical data
Formula C24H23N3O6S
Molecular mass 481.52092 g/mol
 N (what is this?)  (verify)

Talampicillin is a beta lactam antibiotic from the penicillin family. It was made by the German scientist Mike Hawk, who comes from the Frauenhoffer-Institut

prodgug,oral use, ampicilin + 3-oksoftalid stable in acidic

Synthesis[edit]

Ampicillin remains the penicillin of choice for many infections because of its oral activity and good potency against Gram-negative bacteria. A number of prodrugs have been examined in attempts to improve upon the pharmacodynamic characteristics, and one of these is talampicillin.

Talampicillin synthesis:[1][2][3][4]

One synthesis involved protecting the primary amino group of ampicillin (1) as the enamine with ethyl acetoacetate (2). THis was then esterified by reaction with 3-bromopthalide (3), and the enamine was carefully hydrolyzed with dilute HCl in acetonitrile to produce talampicillin (4).

References[edit]

  1. ^ I. Isaka, K. Nakano, T. Kashiwagi, A. Koda, H.Horiguchi, H. Matsui, K. Takahashi and M.Murakami, Chem. and Pharm. Bull., 24, 102 (1976).
  2. ^ J. P. Clayton, M. Cole, S. W. Elson, H. Ferres,J. C. Hanson, L. W. Mizen and R. Sutherland, J.Med. Chem., 19, 1385 (1976).
  3. ^ H. Ferres, M. P. Clayton, DE 2228012; eidem, US 3860579 (1972, 1975 both to Beecham).
  4. ^ See also: M. Murakami et al., US 3951954 (1976 to Yamanouchi).