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Vince lactam

Vince lactam

Vince lactam is the commercial name given to the bicyclic molecule γ-lactam 2-azabicyclo[2.2.1]hept-5-en-3-one. This lactam is a versatile chemical intermediate used in organic and medicinal chemistry. It is used as a synthetic precursor for three drugs (approved or in clinical trials). It is named after Robert Vince who has used the structural features of this molecule for the preparation of carbocyclic nucleosides. Vince's work with this lactam eventually led to his synthesis of abacavir. Peramivir synthesis is also dependent on Vince lactam starting material.

Vince lactam has been extensively used for the preparation of various carbocyclic nucleosides with medicinal applications in mind, including carbocyclic puromycin (I), carbocyclic Ara-A (II), carbovir (III) and guanine as well as azaguanine carbocyclic derivatives (IV)

Prepared Carbocyclic Nucleoside Analogs by Using Vince Lactam

Vince lactam is also an intermediate in the synthesis of various nucleoside analogs such as difluoro guanosine derivatives (V), carbocyclic oxanosine and related derivatives (VI), and precursors for azidocarbonucleosides (VII). The lactam has found several applications in targeting an array of different diseased conditions by providing various non-nucleoside therapeutic molecules as well. Some well known examples include scaffolds for the preparation of glycosidase inhibitors (VIII) and GABA-AT inhibitors (IX).

Prepared Nucleoside and non-nucleoside molecules with applications by using Vince Lactam

References

References

  1. Singh, R.; Vince, R. ''Chem. Rev.'' '''2012,''' ''112'' (8), pp 4642–4686; {{doi. 10.1021/cr2004822."2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics"
  2. Rouhi, A. M.. (July 14, 2003). "Simplifying Syntheses Is Always A Key Goal". [[C&EN]].
  3. Holt-Tiffin, K. E. ''Chimica Oggi'' '''2009''', ''27'', 23-25.
  4. "Robert Vince, Ph.D.". Center for Drug Design, [[University of Minnesota]].
  5. Daluge, S.; Vince, R. ''J. Org. Chem.'' '''1978''', ''43'', 2311-2320.
  6. Vince, R.; Hua, M. ''"Synthesis of carbovir and abacavir from a carbocyclic precursor"'' [[Current Protocols]] in nucleic acid chemistry Ed. Beaucage, S. L. '''2006''', Chapter 14 Unit 14.4. {{doi. 10.1002/0471142700.nc1404s25.
  7. Vince, R. ''"A brief history of the development of Ziagen"'' ''Chemtracts'' '''2008''', ''21'', 127-134.
  8. Vince, R.; Daluge, S.; Brownell, J. ''J. Med. Chem.'' '''1986''', ''29'', 2400.
  9. Daluge, S.; Vince, R. ''J. Org. Chem.'', '''1978''', ''43'', 2311-2320.
  10. Vince, R.; Hua, M. ''J. Med. Chem.'' '''1990''', ''33'', 17.
  11. Peterson, M. L.; Vince, R. ''J. Med. Chem.'' '''1990''', ''33'', 1214-1219.
  12. Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C. ''Tetrahedron Lett.'' '''1994''', ''35'', 5665-5668.
  13. Toyota, A.; Aizawa, M.; Habutani, C.; Katagiri, N.; Kaneko, C. ''Tetrahedron'' '''1995''', ''36'', 8783-8798.
  14. Saito, Y.; Nakamura, M.; Ohno, T.; Chaicharoenpong, C.; Ichikawa, E.; Yamamura, S.; Kato, K.; Umezawa, K. ''J. Antibiotics'' '''2000''', ''53'', 309-313.
  15. Kiss, L.; Forro, E.; Sillanpaa, R.; Fulop, F. ''Synthesis'' '''2010''', 153-160.
  16. Rommel, M.; Ernst, A.; Koert, U. ''Eur. J. Org. Chem.'' '''2007''', 4408-4430.
  17. Mineno, T.; Miller, M,. J. ''J. Org. Chem.'' '''2003''', ''68'', 6591-6596.
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lactams nitrogen-heterocycles heterocyclic-compounds-with-2-rings
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