Vince lactam
Names
Preferred IUPAC name
2-Azabicyclo[2.2.1]hept-5-en-3-one
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • (1S,4R): 627-840-6
  • (1R,4S): 418-530-1
  • (1S,4R): InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1 checkY
    Key: DDUFYKNOXPZZIW-CRCLSJGQSA-N checkY
  • (1R,4S): InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m1/s1
    Key: DDUFYKNOXPZZIW-UHNVWZDZSA-N
  • (1S,4R): O=C1N[C@@H]2\C=C/[C@H]1C2
  • (1R,4S): C1[C@H]2C=C[C@@H]1NC2=O
Properties
C6H7NO
Molar mass 109.128 g·mol−1
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H317, H318
P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P333+P313, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Vince lactam[1] 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).[2][3] It is named after Robert Vince who has used the structural features of this molecule for the preparation of carbocyclic nucleosides.[4] Vince's work with this lactam eventually led to his synthesis of abacavir.[5][6][7] 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),[8] carbocyclic Ara-A (II),[9] carbovir (III)[10] and guanine as well as azaguanine carbocyclic derivatives (IV)[11]

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),[12][13] carbocyclic oxanosine and related derivatives (VI),[14] and precursors for azidocarbonucleosides (VII).[15] 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)[16] and GABA-AT inhibitors (IX).[17]

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

References

  1. ↑ Singh, R.; Vince, R. Chem. Rev. 2012, 112 (8), pp 4642–4686."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. 80 (28): 40.
  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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