Vince lactam
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 431727176
| Name =
| ImageFile = Vince lactam.png
| ImageFileL1 = Vince lactam 1S orientation 1.png
| ImageCaptionL1 =
| ImageFileR1 = Vince lactam 1R orientation 2.png
| ImageCaptionR1 =
| PIN = 2-Azabicyclo[2.2.1]hept-5-en-3-one
| SystematicName =
| OtherNames =
|Section1={{Chembox Identifiers
| 3DMet =
| Abbreviations =
| Beilstein =
| CASNo1 = 130931-83-8
| CASNo1_Ref = {{cascite|changed|CAS}}
| CASNo3 = 79200-56-9
| CASNo3_Ref = {{Cascite|changed|CAS}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI =
| PubChem3 = 2725037
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 2007146
| index1_label = (1S,4R)
| index3_label = (1R,4S)
| PubChem1 = 11789150
| ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID3 = 9963824
| SMILES1 = O=C1N[C@@H]2\C=C/[C@H]1C2
| InChI1_Ref = {{stdinchicite|correct|chemspider}}
| InChI1 = 1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1
| InChIKey1_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey1 = DDUFYKNOXPZZIW-CRCLSJGQSA-N
| InChI3 =1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m1/s1
| InChIKey3 = DDUFYKNOXPZZIW-UHNVWZDZSA-N
| SMILES3 = C1[C@H]2C=C[C@@H]1NC2=O
| EC_number1 = 627-840-6
| EC_number3 = 418-530-1
| DTXSID3 = DTXSID10369337
| Gmelin =
| InChI =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
| MeSHName =
| RTECS =
| UNNumber =
}}
|Section2={{Chembox Properties
| AtmosphericOHRateConstant =
| Appearance =
| BoilingPt =
| BoilingPt_notes =
| Density =
| C=6 | H=7 | N=1 | O=1
| HenryConstant =
| LogP =
| MeltingPt =
| MeltingPt_notes =
| pKa =
| pKb =
| Solubility =
| SolubleOther =
| Solvent =
| VaporPressure =
}}
|Section6={{Chembox Pharmacology
| ATCvet =
| ATCCode_prefix =
| ATCCode_suffix =
| ATC_Supplemental =
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|317|318}}
| PPhrases = {{P-phrases|261|264|270|272|280|301+312|302+352|305+351+338|310|321|330|333+313|363|501}}
}}
}}
Vince lactamSingh, 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" 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).{{cite journal |url= http://pubs.acs.org/cen/coverstory/8128/8128finechemicals1a.html |title= Simplifying Syntheses Is Always A Key Goal |author= Rouhi, A. M. |date= July 14, 2003 |journal= C&EN |volume= 80 |issue= 28 |pages= 40 }}Holt-Tiffin, K. E. Chimica Oggi 2009, 27, 23-25. It is named after Robert Vince who has used the structural features of this molecule for the preparation of carbocyclic nucleosides.{{cite web |url= http://www.cdd.umn.edu/Members/Vince/index.htm |title= Robert Vince, Ph.D. |publisher= Center for Drug Design, University of Minnesota }} Vince's work with this lactam eventually led to his synthesis of abacavir.Daluge, S.; Vince, R. J. Org. Chem. 1978, 43, 2311-2320.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}}.Vince, R. "A brief history of the development of Ziagen" Chemtracts 2008, 21, 127-134. 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),Vince, R.; Daluge, S.; Brownell, J. J. Med. Chem. 1986, 29, 2400. carbocyclic Ara-A (II),Daluge, S.; Vince, R. J. Org. Chem., 1978, 43, 2311-2320. carbovir (III)Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17. and guanine as well as azaguanine carbocyclic derivatives (IV)Peterson, M. L.; Vince, R. J. Med. Chem. 1990, 33, 1214-1219.
File:Prepared Carbocyclic Nucleoside Analogs by Using Vince Lactam.JPG
Vince lactam is also an intermediate in the synthesis of various nucleoside analogs such as difluoro guanosine derivatives (V),Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C. Tetrahedron Lett. 1994, 35, 5665-5668.Toyota, A.; Aizawa, M.; Habutani, C.; Katagiri, N.; Kaneko, C. Tetrahedron 1995, 36, 8783-8798. carbocyclic oxanosine and related derivatives (VI),Saito, Y.; Nakamura, M.; Ohno, T.; Chaicharoenpong, C.; Ichikawa, E.; Yamamura, S.; Kato, K.; Umezawa, K. J. Antibiotics 2000, 53, 309-313. and precursors for azidocarbonucleosides (VII).Kiss, L.; Forro, E.; Sillanpaa, R.; Fulop, F. Synthesis 2010, 153-160. 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)Rommel, M.; Ernst, A.; Koert, U. Eur. J. Org. Chem. 2007, 4408-4430. and GABA-AT inhibitors (IX).Mineno, T.; Miller, M,. J. J. Org. Chem. 2003, 68, 6591-6596.
Prepared Nucleoside and non-nucleoside molecules with applications by using Vince Lactam
