Research ArticleOpen AccessGoogle Scholar indexed
Aminated (Cyclopropylmethyl)Phosphonates: Synthesis and Anti-Pancreatic Cancer Activity
Department of Chemistry and Chemical Technology, Faculty of Science and Technology, Al-Quds University, Jerusalem, Palestine
Department of Microbiology and Immunology, Al-Quds University, Jerusalem, Palestine
Department of Chemistry and Chemical Technology, Faculty of Science and Technology, Al-Quds University, Jerusalem, Palestine
Institut des Sciences Moleculaires de Marseille (iSm2), Aix-Marseille University, CNRS, Centrale Marseille, Marseille, France
Bio-Geo-Chem Laboratories, Ltd., Aliso Viejo, USA
- 1 Department of Chemistry and Chemical Technology, Faculty of Science and Technology, Al-Quds University, Jerusalem, Palestine
- 2 Department of Microbiology and Immunology, Al-Quds University, Jerusalem, Palestine
- 3 Department of Chemistry and Chemical Technology, Faculty of Science and Technology, Al-Quds University, Jerusalem, Palestine
- 4 Institut des Sciences Moleculaires de Marseille (iSm2), Aix-Marseille University, CNRS, Centrale Marseille, Marseille, France
- 5 Bio-Geo-Chem Laboratories, Ltd., Aliso Viejo, USA
International Journal of Organic Chemistry·Volume 13 (2023)·Pages 129–136·Published 5 December 2023·DOI10.4236/ijoc.2023.134010
Copy link · social · email
Abstract
Buoyed by the extensive research on the wide-range biological activities of aminophosphonates, a novel class of aminated (cyclopropylmethyl)phosphor-nates compounds was synthesized from diethyl ((1-(3-chloropropyl)cyclopropyl)methyl)phosphonate and various amines in the presence of Hunig’s base. Upon biological activity screening these compounds demonstrated encouraging anti-pancreatic cancer properties at low micromolar concentrations.
KeywordsPhosphonatesAminophosphonatesPancreatic CancerCancerCyclopropylphosphonates
- Moschidis, M.C. (1984) Phosphonolipids. Progress in Lipid Research, 23, 223-246. https://doi.org/10.1016/0163-7827(84)90012-2
- Hori, T. and Nozawa, Y. (1982) Phosphonolipids. New Comprehensive Biochemistry, 4, 95-128. https://doi.org/10.1016/S0167-7306(08)60007-1
- Mukhamedova, K.S. and Glushenkova, A.I. (2000) Natural Phosphonolipids. Chemistry of Natural Compounds, 36, 329-341. https://doi.org/10.1023/A:1002804409503
- Selvy, P.E., Lavieri, R.R., Lindsley, C.W. and Brown, H.A. (2011) Phospholipase, D: Enzymology, Functionality, and Chemical Modulation. Chemical Reviews, 111, 6064-6119. https://doi.org/10.1021/cr200296t
- Exton, J.H. (1997) Phospholipase D: Enzymology, Mechanisms of Regulation, and Function. Physiological Reviews, 77, 303-320. https://doi.org/10.1152/physrev.1997.77.2.303
- Jenkins, G.M. and Frohman, M.A. (2005) Phospholipase D: A Lipid Centric Review. Cellular and Molecular Life Sciences CMLS, 62, 2305-2316. https://doi.org/10.1007/s00018-005-5195-z
- Exton, J.H. (2002) Phospholipase D—Structure, Regulation and Function. In: Exton, J.H., Ed., Reviews of Physiology, Biochemistry and Pharmacology, Springer, Berlin, 1-94. https://doi.org/10.1007/BFb0116585
- Horsman, G.P. and Zechel, D.L. (2017) Phosphonate Biochemistry. Chemical Reviews, 117, 5704-5783. https://doi.org/10.1021/acs.chemrev.6b00536
- Hanuš, L.O., Levitsky, D.O., Shkrob, I. and Dembitsky, V.M. (2009) Plasmalogens, Fatty Acids and Alkyl Glyceryl Ethers of Marine and Freshwater Clams and Mussels. Food Chemistry, 116, 491-498. https://doi.org/10.1016/j.foodchem.2009.03.004
- Levitsky, D.O., Goldshlag, P. and Dembitsky, V.M. (2015) Profiling of Bioactive Lipids of the Wild Edible Land Snails of the Genus Helix. SDRP Journal of Food Science & Technology, 1, 1-10.
- Kostetsky, E.Y. and Velansky, P.V. (2009) Phospholipids of Sea Worms, Mollusks, and Arthropods. Russian Journal of Marine Biology, 35, 187-199. https://doi.org/10.1134/S1063074009030018
- Quinn, J.P., Kulakova, A.N., Cooley, N.A. and McGrath, J.W. (2007) New Ways to Break an Old Bond: The Bacterial Carbon-Phosphorus Hydrolases and Their Role in Biogeochemical Phosphorus Cycling. Environmental Microbiology, 9, 2392-2400. https://doi.org/10.1111/j.1462-2920.2007.01397.x
- Horiguchi, M. and Kandatstu, M. (1959) Isolation of 2-Aminoethane Phosphonic Acid from Rumen Protozoa. Nature, 184, 901-902. https://doi.org/10.1038/184901b0