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Synthesis, Experimental and Density Functional Theory (DFT) Studies on Solubility of Camptothecin Derivatives

1
Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung 40201, Taiwan
2
Department of Medical Education, Chung Shan Medical University Hospital, Taichung 40201, Taiwan
3
Master Program for Pharmaceutical Manufacture, China Medical University, Taichung 40402, Taiwan
4
School of Pharmacy, China Medical University, Taichung 40402, Taiwan
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(12), 3170; https://doi.org/10.3390/molecules23123170
Received: 7 November 2018 / Revised: 27 November 2018 / Accepted: 30 November 2018 / Published: 1 December 2018
Two camptothecin derivatives, 10-cyclohexyl-7-methyl-20(S)-camptothecin and 7-methyl-10-morpholino-20(S)-camptothecin, were synthesized and their differences in solubility were investigated using four chosen solvent systems. Based on our results, 10-cyclohexyl-7-methyl-20(S)-camptothecin exhibited higher solubilities than 7-methyl-10-morpholino-20(S)-camptothecin in polar aprotic solvents. However, these two camptothecin derivatives did not exhibit apparent differences in solubility between 5% dimethyl sulfoxide (DMSO)/95% normal saline co-solvent system and 5% dimethylacetamide (DMAC)/95% normal saline co-solvent system. To rationalize their differences in solubility, we also tried to perform a DFT-B3LYP study to investigate their interaction with one water molecule. View Full-Text
Keywords: acid-catalyzed; condensation; camptothecin; solubility; DFT acid-catalyzed; condensation; camptothecin; solubility; DFT
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MDPI and ACS Style

Lai, C.-H.; Chang, C.-C.; Weng, Y.-L.; Chuang, T.-H. Synthesis, Experimental and Density Functional Theory (DFT) Studies on Solubility of Camptothecin Derivatives. Molecules 2018, 23, 3170.

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