Affiliation:
1. Université de Toulouse
2. CNRS
3. Institut de Pharmacologie et de Biologie Structurale
4. Université de Carthage
Abstract
A recently proposed "ethynylogation" pharmacochemical approach, first envisaged in the series of anticancer lipidic dialkynylcarbinols (DACs) H–C≡C–CH(OH)–C≡C–R at the levels of the H–C⋮ and ⋮C–R bonds for R = n-C12H25, is completed here at the level of the (HO)C–H bond. The so-devised mono-lipidic trialkynylcarbinol (TAC) target (HC≡C)2C(OH)–C≡CR and its bis-lipidic counterpart HC≡C–C(OH)(C≡CR)2 were synthesized in 4 steps and with 33 % and 23 % overall yield, respectively. Their antitumor cytotoxicity has been evaluated towards HCT116 cells: while the latter TAC is totally inactive, the former DAC-ethynylogous TAC still exhibits a significant toxicity with an IC50 of 10 µM.
Publisher
Taras Shevchenko National University of Kyiv
Reference28 articles.
1. Neumeyer J. Book Review of The Practice of Medicinal Chemistry. Third Edition The Practice of Medicinal Chemistry. Third Edition . Edited by Camille G. Wermuth . Academic Press/Elsevier, Amsterdam, The Netherlands. 2008. xxvi + 942 pp. 22 × 28.5 cm. ISBN 978-0-12-374194-3. $175.00.. Journal of Medicinal Chemistry 2008;51(22):7323-7323. https://doi.org/10.1021/jm801122c
2. Patrick GL. An Introduction to Medicinal Chemistry, Fifth Edition, Oxford University Press, 2013, 816.
3. Wermuth C, Ganellin C, Lindberg P, Mitscher L. Glossary of terms used in medicinal chemistry (IUPAC Recommendations 1998). Pure and Applied Chemistry 1998;70(5):1129–1143. https://doi.org/10.1351/pac199870051129
4. Cancer.gov [homepage on the Internet]. Bethesda, MD: NIH National Cancer Institute [updated August 18 2016]. Available from: https://www.cancer.gov/about-cancer/treatment/drugs
5. Andriamialisoa R, Langlois N, Langlois Y, Potier P. Composés antitumoraux du groupe de la vinblastine: nouvelle méthode de préparation. Tetrahedron 1980;36(20-21):3053-3060. https://doi.org/10.1016/0040-4020(80)88032-x
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