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Synthesis and anticancer activity of (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purines.
- Source :
-
ChemMedChem [ChemMedChem] 2008 Jan; Vol. 3 (1), pp. 127-35. - Publication Year :
- 2008
-
Abstract
- A series of eleven 2- and 6-substituted (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purine derivatives was obtained by applying a standard Mitsunobu protocol that led to a six-membered ring contraction from (R,S)-3,4-dihydro-2H-1,5-benzoxathiepin-3-ol via an episulfonium intermediate. The signal approximately delta=151 ppm, which corresponds to the C4' carbon atom, is unequivocal proof of the N9' regioisomer. The potential of the target molecules as anticancer agents is reflected in their activity against the MCF-7 cancer cell line. The most active compounds have IC(50) values of (6.18+/-1.70) and (8.97+/-0.83) microM. The results indicate that the anticancer activity for the most active compounds is correlated with their capacity to induce apoptosis.
- Subjects :
- Antineoplastic Agents chemical synthesis
Antineoplastic Agents therapeutic use
Breast Neoplasms drug therapy
Breast Neoplasms pathology
Cell Line, Tumor
Crystallography, X-Ray
Female
Heterocyclic Compounds chemistry
Humans
Inhibitory Concentration 50
Nitrogen chemistry
Oxathiins chemical synthesis
Oxathiins pharmacology
Purines chemical synthesis
Purines pharmacology
Stereoisomerism
Structure-Activity Relationship
Antineoplastic Agents pharmacology
Cell Proliferation drug effects
Oxathiins therapeutic use
Purines therapeutic use
Subjects
Details
- Language :
- English
- ISSN :
- 1860-7187
- Volume :
- 3
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- ChemMedChem
- Publication Type :
- Academic Journal
- Accession number :
- 18022976
- Full Text :
- https://doi.org/10.1002/cmdc.200700180