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Chemical compound From Wikipedia, the free encyclopedia
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.
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Names | |||
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Preferred IUPAC name
2-Azabicyclo[2.2.1]hept-5-en-3-one | |||
Identifiers | |||
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3D model (JSmol) |
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ChemSpider | |||
EC Number |
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CompTox Dashboard (EPA) |
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Properties | |||
C6H7NO | |||
Molar mass | 109.128 g·mol−1 | ||
Hazards | |||
GHS labelling: | |||
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).
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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]
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]
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