Vince lactam
Encyclopedia
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 nucleoside
s. Vince's work with this lactam eventually led to his synthesis of abacavir
.
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)
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).
Bicyclic molecule
A bicyclic molecule is a molecule that features two fused rings. Bicyclic molecules occur widely in organic and inorganic compounds.Fusion of the rings can occur in three ways:...
γ-lactam
Lactam
A lactam is a cyclic amide. Prefixes indicate how many carbon atoms are present in the ring: β-lactam , γ-lactam , δ-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 nucleoside
Nucleoside
Nucleosides are glycosylamines consisting of a nucleobase bound to a ribose or deoxyribose sugar via a beta-glycosidic linkage...
s. Vince's work with this lactam eventually led to his synthesis of abacavir
Abacavir
Abacavir is a nucleoside analog reverse transcriptase inhibitor used to treat HIV and AIDS. It is available under the trade name Ziagen and in the combination formulations Trizivir and Kivexa/Epzicom...
.
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)
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).