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Bioorg Med Chem Lett. 2001 Dec 3;11(23):3015-7.

Cyclopenta[g]quinazoline-based antifolates: the effect of the chirality at the 6-position on the inhibition of thymidylate synthase (TS).

Author information

1
CRC Centre for Cancer Therapeutics at The Institute of Cancer Research, Chemistry Department, CRC Laboratory, 15 Cotswold Road, Sutton, Surrey SM2 5NG, UK. vassilio@icr.ac.uk

Abstract

Cyclopenta[g]quinazoline-based inhibitors of thymidylate synthase (TS) possess a chiral centre at the 6-position of the molecule. The effect of this chirality on the inhibition of TS was investigated by synthesising compounds 6S-1a-c, 6R-1a-c. It was shown, in particular with the diastereoisomers 6S-1c, 6R-1c, that the inhibitory activity against TS is mainly due to the 6S diastereoisomer rather than the 6R diastereoisomer, which is virtually inactive.

PMID:
11714600
DOI:
10.1016/s0960-894x(01)00612-6
[Indexed for MEDLINE]

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