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Synthesis of Canthardin Sulfanilamides and Their Acid Anhydride Analogues via a Ring-Opening Reaction of Activated Aziridines and Their Associated Pharmacological Effects.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2016 Jan 16; Vol. 21 (1), pp. 100. Date of Electronic Publication: 2016 Jan 16. - Publication Year :
- 2016
-
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.
- Subjects :
- Anhydrides chemical synthesis
Antineoplastic Agents pharmacology
Cantharidin analogs & derivatives
Cantharidin pharmacology
Cell Line, Tumor
Cell Survival drug effects
HL-60 Cells
Humans
Inhibitory Concentration 50
MCF-7 Cells
Oxazoles chemistry
Pyrazoles chemistry
Pyrimidines chemistry
Structure-Activity Relationship
Sulfanilamides chemical synthesis
Thiazoles chemistry
Anhydrides pharmacology
Antineoplastic Agents chemical synthesis
Aziridines chemistry
Cantharidin chemical synthesis
Sulfanilamides pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 21
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 26784163
- Full Text :
- https://doi.org/10.3390/molecules21010100