441287
(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one
≥98%
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About This Item
Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
Molecular Weight:
109.13
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Assay:
≥98%
Product Name
(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one, ≥98%
InChI
1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1
SMILES string
O=C1N[C@H]2C[C@@H]1C=C2
InChI key
DDUFYKNOXPZZIW-CRCLSJGQSA-N
assay
≥98%
optical activity
[α]20/D +565°, c = 1 in chloroform
optical purity
ee: 99% (HPLC)
mp
94-97 °C (lit.)
Quality Level
Related Categories
Application
This lactam and its antipode are precursors to the enantiomers of the carbocyclic nucleoside carbovir. It has been demonstrated that (-)-carbovir is a potent inhibitor of HIV-1 and based on clinical trials it could become an alternative to AZT. AZT is a trademark of The Wellcome Foundation Ltd.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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R Vince et al.
Journal of medicinal chemistry, 33(1), 17-21 (1990-01-01)
(+-)-cis-[4-[(2,5-Diamino-6-chloropyrimidinyl)amino]-2- cyclopentenyl]carbinol (5a) was synthesized from 2-amino-4,6-dichloropyrimidine and cis-4-(hydroxymethyl)cyclopentenylamine (2a) by subsequent preparation of the 5-[(4-chlorophenyl)azo] derivative of the resulting pyrimidine (3a) and reduction of the azo moiety with zinc and acetic acid. The carbocyclic analogue of 2',3'-didehydro-2',3'-dideoxy 2-amino-6-chloropurine (6a)
Handa, S. et al.
Journal of the Chemical Society. Perkin Transactions 1, 1885-1885 (1994)
Campbell, J.A. et al.
The Journal of Organic Chemistry, 60, 4602-4602 (1995)
E L White et al.
Biochemical and biophysical research communications, 161(2), 393-398 (1989-06-15)
Carbocylic 2',3'-didehydro-2',3'-dideoxyguanosine (Carbovir; NSC 614846) is an antiretroviral agent which may be useful in the treatment of AIDS. We have synthesized the 5'-triphosphate of Carbovir and examined its ability to inhibit human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (EC
Jung. M.E. Rhee, H.
The Journal of Organic Chemistry, 59, 4719-4719 (1994)
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