Synthesis and cytotoxic activity of psorospermin and acronycine analogues in the 3-propyloxy-acridin-9(10H)-one and -benzo[b]acridin-125H-one series

European Journal of Medicinal Chemistry
Sabrina BoutefnouchetMarie-Christine Lallemand

Abstract

In order to explore the structure-activity relationships in the acronycine and psorospermin series, simplified analogues of the highly cytotoxic (+/-)-(2R*,1'R*)-5-methoxy-11-methyl-2-(2-methyloxiran-2-yl)-1,2-dihydro-11H-furo[2,3-c]acridin-6-one and (+/-)-(2R*,1'R*)-5-methoxy-13-methyl-2-(2-methyloxiran-2-yl)-1,2-dihydro-13H-benzo[b]furo[3,2-h]-acridin-6-one lacking the fused furan ring, including 3-allyloxy-1-methoxy-10-methyl-acridin-9(10H)-one, 3-allyloxy-1-methoxy-5-methyl-benzo[b]acridin-12(5H)-one, the corresponding epoxides, and related dihydrodiol esters and diesters were prepared. Only the simplified oxirane compounds displayed significant antiproliferative activity compared to the parent compounds. The oxirane alkylating unit appears indispensible to observe significant antiproliferative activity in both series, but the presence of the angularly fused furan ring does not appear as a crucial structural requirement to observe significant cytotoxic activity.

References

Dec 13, 1969·Chemistry & Industry·J HlubucekW C Taylor
Mar 1, 1980·Journal of Natural Products·S M KupchanA T Sneden
May 1, 1996·The Journal of Pharmacy and Pharmacology·C N LinS J Won
Mar 15, 2001·European Journal of Medicinal Chemistry·B L WeiC N Lin
Jun 26, 2003·European Journal of Biochemistry·Marie-Hélène David-CordonnierChristian Bailly
Dec 31, 2003·Bioorganic & Medicinal Chemistry·Marie Hélène David-CordonnierChristian Bailly
Mar 18, 2008·European Journal of Medicinal Chemistry·Quyên DoHanh Dufat
Aug 7, 1948·Nature·G K HUGHES, F N LAHEY
Feb 5, 2009·Journal of Natural Products·Hung The NguyenFrançois Tillequin

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