-transparent.png){kind=logo}
N-Acyl analogues 8, 9, and 12-26 of butitaxel (3) were prepared in one or two steps from amines 5 and 6 through Schotten-Baumann acylation. Seventeen novel analogues, consisting of aliphatic carbamates, alicyclic amides, and heteroaromatic amides, were synthesized. They were evaluated for their in vitro ability to stimulate the formation of microtubules, their cytotoxicity toward B16 melanoma cells, and their solubility in water. The most potent analogue found in this study was N-debenzoyl-N-(2-thenoyl)butitaxel (20), possessing ca. 2-fold better tubulin assembly properties and cytotoxic activity against B16 melanoma cells than paclitaxel. Compound 20 was ca. 25 times more water soluble than paclitaxel.
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
November 1993,
Journal of pharmaceutical sciences,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
May 1991,
Journal of medicinal chemistry,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
January 2000,
Bioorganic & medicinal chemistry letters,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
April 2010,
Bioorganic & medicinal chemistry letters,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
March 2000,
Current medicinal chemistry,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
September 1990,
Journal of medicinal chemistry,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
December 2006,
Journal of medicinal chemistry,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
August 1997,
Journal of medicinal chemistry,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
November 1977,
Journal of medicinal chemistry,
S M Ali, and
M Z Hoemann, and
J Aubé, and
G I Georg, and
L A Mitscher, and
L R Jayasinghe
March 2009,
ChemMedChem,
