Abstract
Two easily accessible, natural occurring triterpenoids, betulinic and ursolic acid, were used as starting materials for the synthesis of novel cytotoxic agents. A set of 28 ethylenediamine-spacered carboxamides was prepared holding an additional substituent connected to the ethylenediamine group. The compounds were screened in SRB assays to evaluate their cytotoxic activity employing several human tumor cell lines. Betulinic acid-derived carboxamides 17–30 showed significantly higher cytotoxicity than their ursolic acid analogs 3–16. In particular, compounds 25 and 26 were highly cytotoxic, as indicated by EC50 values lower than 1 μM.
Highlights
During the last decade, significant progress has been made in the therapy of cancer, with several major breakthroughs recorded in recent years
Our own work in recent years has been focused on modifications of naturally occurring triterpenes, such as ursolic, oleanolic, glycyrrhetinic, betulinic, boswellic, platanic and maslinic acid, in which cytotoxic agents were synthesized for their cancer-fighting properties
The objective of this work was to improve the cytotoxic properties of the two triterpenoids, ursolic (UA) and betulinic acid (BA), by structural modification at the C-28 carbonyl moiety
Summary
Significant progress has been made in the therapy of cancer, with several major breakthroughs recorded in recent years. Despite the promising therapeutic benefits of immuno- or gene therapy, chemotherapy remains a key means of cancer treatment. Many natural products show a wide range of pharmacological properties, including antiviral, antimalarial, anti-inflammatory and antitumor activities. They are considered as ideal lead structures for the development of new bioactive substances. Triterpenes are a class of pharmacologically interesting natural products that exhibit cytotoxic properties among several other biological activities [2]. Our own work in recent years has been focused on modifications of naturally occurring triterpenes, such as ursolic, oleanolic, glycyrrhetinic, betulinic, boswellic, platanic and maslinic acid, in which cytotoxic agents were synthesized for their cancer-fighting properties
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