Premium
Efficient synthesis of cytotoxic quinones: 2‐Acetyl‐4 H ,9 H ‐naphtho[2,3‐ b ]furan‐4,9‐dione ( 6 ) and (±)‐2‐(1‐hydroxyethyl)‐4 H ,9 H ‐naphtho[2,3‐ b ]furan‐4,9‐dione ( 7 )
Author(s) -
Lopes Cláudio C.,
Lopes Rosangela S. C.,
Pinto Antonio V.,
Costa Paulo R. R.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210274
Subject(s) - bignoniaceae , chemistry , furan , phthalic anhydride , bark (sound) , yield (engineering) , cytotoxic t cell , ethanol , stereochemistry , organic chemistry , traditional medicine , in vitro , biochemistry , medicine , physics , materials science , acoustics , metallurgy , catalysis
From the ethanol extract of the stem bark of Tabebuia cassinoides (Lam.) DC (Bignoniaceae), Kingston and Rao [1] isolated two new furonaphthoquinones 6 and 7 that showed activity in KB cell culture assay (ED 50 1.0 and 2.0 μg/ml, respectively). These values may be significant since lapachol, which has an ED 50 value of 4.4 μg/ml in the same assay, showed sufficient in vivo activity to reach clinical trial at the National Cancer Institute of the United States. The syntheses of these compounds ( 6 and 7 ) were realized in 36% overall yield starting from furan and phthalic anhydride.