Syntheses of chiral fluorine analogs of hematoporphyrin

Authors
Omote, M Ando, A Sato, K Kumadaki, I
Citation
M. Omote et al., Syntheses of chiral fluorine analogs of hematoporphyrin, TETRAHEDRON, 57(38), 2001, pp. 8085-8094
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
38
Year of publication
2001
Pages
8085 - 8094
Database
ISI
SICI code
0040-4020(20010917)57:38<8085:SOCFAO>2.0.ZU;2-G
Abstract
Four chiral fluorine analogs of hematoporphyrin, (R,R)-, (R,S)-, (S,R)-, an d (S,S)-3,8-bis(2,2,2-trifluoro-1-hydroxyethyl)deuteroporphyrins, were synt hesized starting from pyrroles with a chiral 2,2,2-trifluoro-1-hydroxyethyl (TFHE) group. This chiral TFHE group was obtained by asymmetric reduction of a trifluoroacetyl group. Among these chiral analogs of hematoporphyrin, the (S,S)-isomer showed higher affinity for cancer cells than other stereoi somers. (C) 2001 Elsevier Science Ltd. All rights reserved.