Abstract

The cantharidinimide derivatives, 5a-h, 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 10i-k, 11l-n, 12o-p, and 16q-s 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.

Original languageEnglish
Pages (from-to)100
JournalMolecules
Volume21
Issue number1
DOIs
Publication statusPublished - 2016

Fingerprint

Sulfanilamides
Aziridines
Anhydrides
anhydrides
cultured cells
Sulfamethazine
Cells
Pharmacology
analogs
multiple docking adapters
Cell Line
acids
Acids
rings
Cytostatic Agents
synthesis
Hydrogen
cancer
hydrogen
products

Keywords

  • Journal Article

Cite this

Synthesis of Canthardin Sulfanilamides and Their Acid Anhydride Analogues via a Ring-Opening Reaction of Activated Aziridines and Their Associated Pharmacological Effects. / Chiang, Ling-Ling; Tseng, Ing Jy; Lin, Pen-Yuan; Sheu, Shiow-Yunn; Lin, Ching Tung; Hsieh, Yun-Han; Lin, Yi-Jing; Chen, Hsiao-Ling; Lin, Mei-Hsiang.

In: Molecules, Vol. 21, No. 1, 2016, p. 100.

Research output: Contribution to journalArticle

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