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Molecules 2016, 21(1), 100; doi:10.3390/molecules21010100

Synthesis of Canthardin Sulfanilamides and Their Acid Anhydride Analogues via a Ring-Opening Reaction of Activated Aziridines and Their Associated Pharmacological Effects

1
School of Respiratory Therapy, Taipei Medical University, Taipei 11031, Taiwan
2
Chest Medicine Department, Shuang-Ho Hospital, Taipei Medical University, Taipei 11031, Taiwan
3
Gerontology Health Management, College of Nursing, Taipei Medical University, Taipei 11031, Taiwan
4
Department of Pharmaceutical Sciences, School of Pharmacy, Taipei Medical University, Taipei 11031, Taiwan
5
Department of Chemistry, Tam-Kang University, Danshui 25137, New Taipei City, Taiwan
*
Author to whom correspondence should be addressed.
Academic Editor: Wei-Zhu Zhong
Received: 3 December 2015 / Revised: 6 January 2016 / Accepted: 12 January 2016 / Published: 16 January 2016
(This article belongs to the Special Issue Drug Design and Discovery: Principles and Applications)
View Full-Text   |   Download PDF [1254 KB, uploaded 16 January 2016]   |  

Abstract

The cantharidinimide derivatives, 5ah, including sulfanilamides containing pyrimidyl, pyrazinyl, hydrogen, thiazolyl, and oxazolyl groups were synthesized. Modification of cantharidinimide by means of the reaction of activated aziridine ring opening led to the discovery of a novel class of antitumor compounds. The analogues 10ik, 11ln, 12op, and 16qs were obtained from treating cantharidinimide 6 and analogues (7, 8, and 13) with activated aziridines, which produced a series of ring-opened products including normal and abnormal types. Some of these compounds showed cytotoxic effects in vitro against HL-60, Hep3B, MCF7, and MDA-MB-231 cancer cells. The most potent cytostatic compound, N-cantharidinimido-sulfamethazine (5a), exhibited anti-HL-60 and anti-Hep3B cell activities. Two compounds 5g and 5h displayed slight effects on the Hep3B cell line, while the other compounds produced no response in these four cell lines. View Full-Text
Keywords: cantharidin; cantharidinimide; methylsulfanylaziridine cantharidin; cantharidinimide; methylsulfanylaziridine
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Chiang, L.-L.; Tseng, I.-J.; Lin, P.-Y.; Sheu, S.-Y.; Lin, C.-T.; Hsieh, Y.-H.; Lin, Y.-J.; Chen, H.-L.; Lin, M.-H. Synthesis of Canthardin Sulfanilamides and Their Acid Anhydride Analogues via a Ring-Opening Reaction of Activated Aziridines and Their Associated Pharmacological Effects. Molecules 2016, 21, 100.

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