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Revision as of 22:26, 30 May 2011 editEdward (talk | contribs)Administrators94,534 editsm link Current Protocols using Find link← Previous edit Latest revision as of 00:12, 15 September 2021 edit undoGraeme Bartlett (talk | contribs)Administrators250,258 edits remove wrong indexed values (duplicate) 
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{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 426629996
| Watchedfields = changed
⚫ | verifiedrevid = 431727176
| Name = | Name =
| ImageFile = Vince lactam.png | ImageFile = Vince lactam.png
| ImageFileL1 = Vince lactam 1S orientation 1.png | ImageFileL1 = Vince lactam 1S orientation 1.png
| ImageCaptionL1 = <!-- which optical isomer is this? must verify from lit refs --> | ImageCaptionL1 = <!-- which optical isomer is this? must verify from lit refs -->
| ImageFileR1 = Vince lactam 1R orientation 2.png | ImageFileR1 = Vince lactam 1R orientation 2.png
| ImageCaptionR1 = <!-- which optical isomer is this? must verify from lit refs --> | ImageCaptionR1 = <!-- which optical isomer is this? must verify from lit refs -->
| IUPACName = 2-Azabicyclohept-5-en-3-one | PIN = 2-Azabicyclohept-5-en-3-one
| SystematicName = | SystematicName =
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| 3DMet = | 3DMet =
| Abbreviations = | Abbreviations =
| ATCvet = | Beilstein =
| CASNo1 = 130931-83-8
⚫ | ATCCode_prefix =
| CASNo1_Ref = {{cascite|changed|CAS}}
⚫ | ATCCode_suffix =
| CASNo3 = 79200-56-9
⚫ | ATC_Supplemental =
| CASNo3_Ref = {{Cascite|changed|CAS}}
| Beilstein =
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | CASNo =
| CASNo_Ref = | ChEBI =
| PubChem3 = 2725037
| CASNos =
⚫ | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| CASOther =
⚫ | ChemSpiderID1 = 2007146
| ChEBI =
| PubChem1 = 2725037 | index1_label = (1S,4R)
| index3_label = (1R,4S)
⚫ | ChemSpiderID1 = 2007146
⚫ | PubChem1 = 11789150
| ChemSpiderID1_Comment=(1S,4R)
⚫ | ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}}
⚫ | SMILES1 = O=C1N2\C=C/1C2
⚫ | ChemSpiderID3 = 9963824
⚫ | StdInChI1=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m1/s1
⚫ | SMILES1 = O=C1N2\C=C/1C2
| StdInChI1_Comment=(1R,4S)
⚫ | InChI1_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey1 = DDUFYKNOXPZZIW-UHNVWZDZSA-N
⚫ | 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
| StdInChIKey1_Comment=(1R,4S)
| InChIKey1_Ref = {{stdinchicite|correct|chemspider}}
⚫ | PubChem = 11789150
⚫ | InChIKey1 = DDUFYKNOXPZZIW-CRCLSJGQSA-N
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | 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
⚫ | ChemSpiderID = 9963824
⚫ | InChIKey3 = DDUFYKNOXPZZIW-UHNVWZDZSA-N
| ChemSpiderID_Comment=(1R,4S)
| SMILES = O=C1N2\C=C/1C2 | SMILES3 = C12C=C1NC2=O
| EC_number1 = 627-840-6
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| EC_number3 = 418-530-1
⚫ | StdInChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1
| DTXSID3 = DTXSID10369337
| StdInChI_Comment=(1S,4R)
⚫ | Gmelin =
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | InChI =
⚫ | StdInChIKey = DDUFYKNOXPZZIW-CRCLSJGQSA-N
| KEGG_Ref = {{keggcite|correct|kegg}}
| StdInChIKey_Comment=(1S,4R)
| DrugBank =
| EC-number =
⚫ | EINECS =
| EINECSCASNO =
⚫ | Gmelin =
⚫ | InChI =
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG =
| MeSHName = | MeSHName =
| PubChem = | RTECS =
| RTECS = | UNNumber =
⚫ }}
| SMILES =
⚫ |Section2={{Chembox Properties
| UNNumber =
⚫ | AtmosphericOHRateConstant =
⚫ }}
| Appearance =
⚫ | Section2 = {{Chembox Properties
| BoilingPt =
⚫ | AtmosphericOHRateConstant =
| Appearance = | BoilingPt_notes =
| BoilingPt = | Density =
⚫ | C=6 | H=7 | N=1 | O=1
| Boiling_notes =
| Density = | HenryConstant =
⚫ | LogP =
⚫ | C=6 | H=7 | N=1 | O=1
| HenryConstant = | MeltingPt =
| LogP = | MeltingPt_notes =
| MeltingPt = | pKa =
| Melting_notes = | pKb =
| pKa = | Solubility =
| pKb = | SolubleOther =
| Solubility = | Solvent =
| SolubleOther = | VaporPressure =
}}
| Solvent =
|Section6={{Chembox Pharmacology
| VaporPressure =}}
⚫ | 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 lactam''' is the commercial name given to the ] γ-] 2-azabicyclohept-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).<ref>{{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= ] |volume= 80 |issue= 28 |pages= 40 }}</ref><ref>Holt-Tiffin, K. E. ''Chimica Oggi'' '''2009''', ''27'', 23-25.</ref> It is named after Robert Vince who has used the structural features of this molecule for the preparation of carbocyclic ]s.<ref>{{cite web |url= http://www.cdd.umn.edu/directory/vince/home.html |title= Robert Vince, Ph.D. |publisher= Center for Drug Design, ] }}</ref> Vince's work with this lactam eventually led to his synthesis of ].<ref>Daluge, S.; Vince, R. ''J. Org. Chem.'' '''1978''', ''43'', 2311-2320.</ref><ref>Vince, R.; Hua, M. ''"Synthesis of carbovir and abacavir from a carbocyclic precursor"'' ] in nucleic acid chemistry Ed. Beaucage, S. L. '''2006''', Chapter 14 Unit 14.4. ].</ref><ref>Vince, R. ''"A brief history of the development of Ziagen"'' ''Chemtracts'' '''2008''', ''21'', 127-134.</ref> '''Vince lactam'''<ref>Singh, R.; Vince, R. ''Chem. Rev.'' '''2012,''' ''112'' (8), pp 4642–4686."2-Azabicyclohept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics"</ref> is the commercial name given to the ] γ-] 2-azabicyclohept-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).<ref>{{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= ] |volume= 80 |issue= 28 |pages= 40 }}</ref><ref>Holt-Tiffin, K. E. ''Chimica Oggi'' '''2009''', ''27'', 23-25.</ref> It is named after ] who has used the structural features of this molecule for the preparation of ]s.<ref>{{cite web |url= http://www.cdd.umn.edu/Members/Vince/index.htm |title= Robert Vince, Ph.D. |publisher= Center for Drug Design, ] }}</ref> Vince's work with this lactam eventually led to his synthesis of ].<ref>Daluge, S.; Vince, R. ''J. Org. Chem.'' '''1978''', ''43'', 2311-2320.</ref><ref>Vince, R.; Hua, M. ''"Synthesis of carbovir and abacavir from a carbocyclic precursor"'' ] in nucleic acid chemistry Ed. Beaucage, S. L. '''2006''', Chapter 14 Unit 14.4. {{doi|10.1002/0471142700.nc1404s25}}.</ref><ref>Vince, R. ''"A brief history of the development of Ziagen"'' ''Chemtracts'' '''2008''', ''21'', 127-134.</ref> ] 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),<ref>Vince, R.; Daluge, S.; Brownell, J. ''J. Med. Chem.'' '''1986''', ''29'', 2400.</ref> carbocyclic Ara-A (II),<ref>Daluge, S.; Vince, R. ''J. Org. Chem.'', '''1978''', ''43'', 2311-2320.</ref> carbovir (III)<ref>Vince, R.; Hua, M. ''J. Med. Chem.'' '''1990''', ''33'', 17.</ref> and guanine as well as azaguanine carbocyclic derivatives (IV)<ref>Peterson, M. L.; Vince, R. ''J. Med. Chem.'' '''1990''', ''33'', 1214-1219.</ref> Vince lactam has been extensively used for the preparation of various carbocyclic nucleosides with medicinal applications in mind, including carbocyclic puromycin (I),<ref>Vince, R.; Daluge, S.; Brownell, J. ''J. Med. Chem.'' '''1986''', ''29'', 2400.</ref> carbocyclic Ara-A (II),<ref>Daluge, S.; Vince, R. ''J. Org. Chem.'', '''1978''', ''43'', 2311-2320.</ref> carbovir (III)<ref>Vince, R.; Hua, M. ''J. Med. Chem.'' '''1990''', ''33'', 17.</ref> and guanine as well as azaguanine carbocyclic derivatives (IV)<ref>Peterson, M. L.; Vince, R. ''J. Med. Chem.'' '''1990''', ''33'', 1214-1219.</ref>


] ]


Vince lactam is also an intermediate in the synthesis of various different nucleoside analogs such as difluoro guanosine derivatives (V),<ref>Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C. ''Tetrahedron Lett.'' '''1994''', ''35'', 5665-5668.</ref><ref>Toyota, A.; Aizawa, M.; Habutani, C.; Katagiri, N.; Kaneko, C. ''Tetrahedron'' '''1995''', ''36'', 8783-8798.</ref> carbocyclic oxanosine and related derivatives (VI),<ref>Saito, Y.; Nakamura, M.; Ohno, T.; Chaicharoenpong, C.; Ichikawa, E.; Yamamura, S.; Kato, K.; Umezawa, K. ''J. Antibiotics'' '''2000''', ''53'', 309-313.</ref> and precursors for azidocarbonucleosides (VII).<ref>Kiss, L.; Forro, E.; Sillanpaa, R.; Fulop, F. ''Synthesis'' '''2010''', 153-160.</ref> 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)<ref>Rommel, M.; Ernst, A.; Koert, U. ''Eur. J. Org. Chem.'' '''2007''', 4408-4430.</ref> and GABA-AT inhibitors (IX).<ref>Mineno, T.; Miller, M,. J. ''J. Org. Chem.'' '''2003''', ''68'', 6591-6596.</ref> Vince lactam is also an intermediate in the synthesis of various nucleoside analogs such as difluoro guanosine derivatives (V),<ref>Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C. ''Tetrahedron Lett.'' '''1994''', ''35'', 5665-5668.</ref><ref>Toyota, A.; Aizawa, M.; Habutani, C.; Katagiri, N.; Kaneko, C. ''Tetrahedron'' '''1995''', ''36'', 8783-8798.</ref> carbocyclic oxanosine and related derivatives (VI),<ref>Saito, Y.; Nakamura, M.; Ohno, T.; Chaicharoenpong, C.; Ichikawa, E.; Yamamura, S.; Kato, K.; Umezawa, K. ''J. Antibiotics'' '''2000''', ''53'', 309-313.</ref> and precursors for azidocarbonucleosides (VII).<ref>Kiss, L.; Forro, E.; Sillanpaa, R.; Fulop, F. ''Synthesis'' '''2010''', 153-160.</ref> 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)<ref>Rommel, M.; Ernst, A.; Koert, U. ''Eur. J. Org. Chem.'' '''2007''', 4408-4430.</ref> and GABA-AT inhibitors (IX).<ref>Mineno, T.; Miller, M,. J. ''J. Org. Chem.'' '''2003''', ''68'', 6591-6596.</ref>


] ]
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{{Reflist}} {{Reflist}}


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