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441287

Sigma-Aldrich

(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:
130931-83-8
Molecular Weight:
109.13
MDL number:
MFCD00211275
UNSPSC Code:
12352005
PubChem Substance ID:
24867650
NACRES:
NA.22

Quality Level

200

assay

≥98%

optical activity

[α]20/D +565°, c = 1 in chloroform

optical purity

ee: 99% (HPLC)

mp

94-97 °C (lit.)

SMILES string

O=C1N[C@H]2C[C@@H]1C=C2

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

InChI key

DDUFYKNOXPZZIW-CRCLSJGQSA-N

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
Handa, S. et al.
Journal of the Chemical Society. Perkin Transactions 1, 1885-1885 (1994)
Evans, C.T. et al.
Journal of the Chemical Society. Perkin Transactions 1, 589-589 (1992)
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