Thiocamptothecin

The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Me...

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Bibliographic Details
Published in:Journal of medicinal chemistry 2008-05, Vol.51 (10), p.3040-3044
Main Authors: Samorì, Cristian, Guerrini, Andrea, Varchi, Greta, Zunino, Franco, Beretta, Giovanni Luca, Femoni, Cristina, Bombardelli, Ezio, Fontana, Gabriele, Battaglia, Arturo
Format: Article
Language:English
Subjects:
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Biological and medical sciences
Camptothecin - analogs & derivatives
Camptothecin - chemical synthesis
Camptothecin - chemistry
Camptothecin - pharmacology
Cell Line, Tumor
Crystallography, X-Ray
DNA Damage
DNA Topoisomerases, Type I - chemistry
General aspects
Humans
Medical sciences
Models, Molecular
Pharmacology. Drug treatments
Thiones - chemical synthesis
Thiones - chemistry
Thiones - pharmacology
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Summary:The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm8001982