Synthesis and characterization of new
Bader A. Salameh
Kayed A. Abu-Saﬁeh
Sanaa R. A. Al-Kaabenah
Raed A. Al-Qawasmeh
Received: 20 January 2013 / Accepted: 5 March 2013 / Published online: 23 March 2013
Ó Springer Science+Business Media Dordrecht 2013
Abstract Thioglycosides derivatives of N-phenylmaleimide have been prepared
by the reaction of derivatives of 1-thio-
-maltose with 3,4-dichloro-N-phenylmaleimide. The reaction of 3,4-
dichloro-N-phenyl maleimide with sugar thiols (protected or unprotected) took
place by displacement of both chlorine atoms by sulﬁde nucleophile giving the
corresponding bis-thioglycoside products.
Keywords Thioglycosides Á Sugar thiols Á N-phenylmaleimide
The maleimide ring is presented in many bioactive compounds that have shown
anti-bacterial, anti-fungal, anti-hypertensive and anti-cancer activities . Many
naturally occurring anticancer compounds such as, staurosporine , rebeccamycin
, granulatimide and isogranulatimide , are in reality substituted maleimides.
The favorable biological activities of such compounds have justiﬁed a large number
of articles describing the syntheses and biological evaluations of these compounds
and their analogues [5–7].
Many structures of naturally occurring anti-cancer compounds that contain the
maleimide ring, or its structural related quinone ring, also contains sugar units (i.e.
anthracyclins [5, 8], rebeccamycin 1  and daunomycin 2 ), which are widely
believed to play a crucial role in the biological activity  of the above compounds.
B. A. Salameh (&) Á K. A. Abu-Saﬁeh Á S. R. A. Al-Kaabenah
Department of Chemistry, The Hashemite University, P.O. Box 150459, Zarqa 13115, Jordan
e-mail: email@example.com; firstname.lastname@example.org
R. A. Al-Qawasmeh
Department of Chemistry, The University of Jordan, Amman 11942, Jordan
Res Chem Intermed (2014) 40:3001–3009