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. 2009 Apr 2;11(7):1575-8.
doi: 10.1021/ol900210h.

Synthesis and anticancer activity of new hydroxamic acid containing 1,4-benzodiazepines

Lawrence P Tardibono  1 , Marvin J Miller
Affiliations

Synthesis and anticancer activity of new hydroxamic acid containing 1,4-benzodiazepines

Lawrence P Tardibono et al. Org Lett. .

Abstract

By employing an intramolecular Pd(0)-mediated ring opening of an acylnitroso-derived cycloadduct, new hydroxamic acid containing benzodiazepines have been synthesized and have demonstrated biological activity in MCF-7 and PC-3 tumor cell lines. Subsequent N-O bond reduction of the hydroxamate has provided access to amide analogues for SAR studies. During the course of our syntheses, an intermediate oxazoline N-oxide was isolated and gave insight into the mechanism of the key Pd(0)-mediated reaction.

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Figures

Figure 1
Figure 1
Benzodiazepines with anti-cancer activity.
Figure 2
Figure 2
X-ray structure of 4 with thermal ellipsoids drawn at 50% probability.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
Scheme 6
Scheme 6
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