HOMEPRODUCTSCOMPANYCONTACTFAQResearchDictionaryPharmaSign Up FREE or Login

Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues.

Abstract
Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC50 = 5.70 ± 0.21 and 8.50 ± 1.18 mg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.
AuthorsMuhammad Nadeem Akhtar, Seema Zareen, Swee Keong Yeap, Wan Yong Ho, Kong Mun Lo, Aurangzeb Hasan, Noorjahan Banu Alitheen
JournalMolecules (Basel, Switzerland) (Molecules) Vol. 18 Issue 8 Pg. 10042-55 (Aug 20 2013) ISSN: 1420-3049 [Electronic] Switzerland
PMID23966087 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Aldehydes
  • Anthraquinones
  • nordamnacanthal
  • damnacanthal
Topics
  • Aldehydes (chemistry, pharmacology)
  • Anthraquinones (chemistry, pharmacology)
  • Cell Line, Tumor
  • Cell Survival (drug effects)
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure

Join CureHunter, for free Research Interface BASIC access!

Take advantage of free CureHunter research engine access to explore the best drug and treatment options for any disease. Find out why thousands of doctors, pharma researchers and patient activists around the world use CureHunter every day.
Realize the full power of the drug-disease research graph!


Choose Username:
Email:
Password:
Verify Password:
Enter Code Shown: