- Title
- Norcantharimides, synthesis and anticancer activity: synthesis of new norcantharidin analogues and their anticancer evaluation
- Creator
- Hill, Timothy A.; Stewart, Scott G.; Ackland, Stephen P.; Gilbert, Jayne; Sauer, Benjamin; Sakoff, Jennette A.; McCluskey, Adam
- Relation
- Bioorganic and Medicinal Chemistry Vol. 15, Issue 18, p. 6126-6134
- Publisher Link
- http://dx.doi.org/10.1016/j.bmc.2007.06.034
- Publisher
- Pergamon
- Resource Type
- journal article
- Date
- 2007
- Description
- A range of amines was reacted with norcantharidin (2) to provide the corresponding norcantharimides (9–43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (20) which was amenable to epoxidation (mCPBA, 22) and subsequent ring opening (MeOH/H⁺; 23) or alternatively, osmylation (OsO₄/NMO; 24). These simple synthetic modifications of 2 facilitated the development of a novel series of norcantharimides displaying modest to good broad spectrum cytotoxicity against HT29 and SW480 (colorectal carcinoma); MCF-7 (breast adenocarcinoma); A2780 (ovarian carcinoma); H460 (lung carcinoma); A431 (epidermoid carcinoma); DU145 (prostate carcinoma); BE2-C (neuroblastoma); and SJ-G2 (glioblastoma). Analogues possessing a C₁₀, C₁₂ or C₁₄ alkyl chain or a C₁₂ linked bis-norcantharimide displayed the highest levels of cytotoxicity.
- Subject
- cantharidin; norcantharidin; norcantharimides; cytotoxicity; anticancer
- Identifier
- http://hdl.handle.net/1959.13/33619
- Identifier
- uon:3264
- Identifier
- ISSN:0968-0896
- Language
- eng
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