rac 2-Azabicyclo[2.2.1]hept-5-en-3-one

CAS: 49805-30-3

Ref. TR-A795200

Product Information

• Name: rac 2-Azabicyclo[2.2.1]hept-5-en-3-one
• Synonyms: 2-Azabicyclo[2.2.1]hept-5-en-3-one, (±)-2-Azabicyclo[2.2.1]hept-5-en-3-one, (±)-Vince lactam, 3-Azabicyclo[2.2.1]hept-5-en-2-one, Rac-Vince lactam, Vince lactam, Vince Lactam (GR39239X), 2-Azabicyclo[2,2,1]hept-5-en-3-one, Vince Lactam
• CAS: 49805-30-3

Description

Impurity Abacavir - In House Impurity
Applications rac 2-Azabicyclo[2.2.1]hept-5-en-3-one (Abacavir - In House Impurity) is a useful reagent in the synthesis of carbocyclic sugar amines, carbanucleosides, and carbocyclic dinucleotide analogues (1). rac 2-Azabicyclo[2.2.1]hept-5-en-3-one is also an intermediate of Abacavir (A104990), a carbocyclic 2'-deoxyguanosine nucleoside reverse transcriptase inhibitor and anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.
References (1) Slama, J.T., et al.: Biochemistry, 27, 183 (1988) (2) Jackson, A., et al.: Antivir Ther. 17, 19 (2012) (3) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)

• Brand: TRC

Chemical properties

• Molecular weight: 109.13
• Formula: C₆H₇NO
• InChI: 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
• InChI key: InChIKey=DDUFYKNOXPZZIW-CRCLSJGQSA-N
• SMILES: O=C1N[C@@H]2C=C[C@H]1C2