Allylic isothiouronium salts: The discovery of a novel class of thiourea analogues with antitumor activity.

Abstract

A series of 28 aryl- and alkyl-substituted isothiouronium salts were readily synthesized in high yields through the reaction of allylic bromides with thiourea, N-monosubstituted thioureas or thiosemicarbazide. The S-allylic isothiouronium salts substituted with aliphatic groups were found to be the most effective against leukemia cells. These compounds combine high antitumor activity and low toxicity toward non-tumoral cells, with selectivity index higher than 20 in some cases. Furthermore, the selected isothiouronium salts induced G2/M cell cycle arrest and cell death, possibly by apoptosis. Therefore, these compounds can be considered as a promising class of antitumor agents due to the potent cytostatic activity associated with high selectivity.

• Authors: Misael Ferreira, Laura Sartori Assunção, Adny Henrique Silva, Fabíola Branco Filippin-Monteiro, Tânia Beatriz Creczynski-Pasa, Marcus Mandolesi Sá
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 129 Pg. 151-158 (Mar 31 2017) ISSN: 1768-3254 [Electronic] France
• PMID: 28222315 (Publication Type: Journal Article)
• Copyright: Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Chemical References

• Antineoplastic Agents
• Isothiuronium
• Thiourea

Topics

• Antineoplastic Agents (chemical synthesis, pharmacology)
• Cell Cycle Checkpoints (drug effects)
• Cell Death (drug effects)
• Humans
• Isothiuronium (chemical synthesis, pharmacology)
• Structure-Activity Relationship
• Thiourea (analogs & derivatives)