Anandamide is part of the cannabinoid group and functions as a neurotransmitter. Anandamide plays a role in depression, pain, appetite, memory, and fertility. Since it is well documented that anandamide analog behaves as probes of the cannabinoid receptor, it is of great interest to find a new method of making new series of anandamide derivatives. Dennis Hall and his group recently reported a direct amidation process of carboxylic acid by ortho-iodo boronic acid. Using ortho-iodo boronic acid as a catalyst, we explore the amidation of arachidonic acid under microwave heating and synthesize anandamide derivatives in high yields.
References
[1]
Kozak, K.R., Prusakiewicz, J.J., Rowlinson, S.W., Prudhomme, D.R. and Marnett, L.J. (2003) Amino Acid Determinants in Cyclooxygenase-2 Oxygenation of the Endocannabinoid Anandamide. Biochemistry, 42, 9041-9049. https://doi.org/10.1021/bi034471k
[2]
Dossou, K.S.S., Devkota, K.P., Morton, C., Egan, J.M., Lu, G., Beutler, J.A., et al. (2013) Identification of CB1/CB2 Ligands from Zanthoxylumbungeanum. JournalofNaturalProducts, 76, 2060-2064. https://doi.org/10.1021/np400478c
[3]
Elsebai, M.F., Rempel, V., Schnakenburg, G., Kehraus, S., Müller, C.E. and König, G.M. (2011) Identification of a Potent and Selective Cannabinoid CB1 Receptor Antagonist from Auxarthronreticulatum. ACSMedicinalChemistryLetters, 2, 866-869. https://doi.org/10.1021/ml200183z
[4]
Fulp, A., Bortoff, K., Zhang, Y., Snyder, R., Fennell, T., Marusich, J.A., et al. (2013) Peripherally Selective Diphenyl Purine Antagonist of the CB1 Receptor. JournalofMedicinalChemistry, 56, 8066-8072. https://doi.org/10.1021/jm401129n
[5]
Palermo, G., Campomanes, P., Cavalli, A., Rothlisberger, U. and De Vivo, M. (2014) Anandamide Hydrolysis in FAAH Reveals a Dual Strategy for Efficient Enzyme-Assisted Amide Bond Cleavage via Nitrogen Inversion. TheJournalofPhysicalChemistryB, 119, 789-801. https://doi.org/10.1021/jp5052276
[6]
Ahn, K., McKinney, M.K. and Cravatt, B.F. (2008) Enzymatic Pathways That Regulate Endocannabinoid Signaling in the Nervous System. ChemicalReviews, 108, 1687-1707. https://doi.org/10.1021/cr0782067
[7]
Gernigon, N., Al-Zoubi, R.M. and Hall, D.G. (2012) Direct Amidation of Carboxylic Acids Catalyzed by Ortho-Iodo Arylboronic Acids: Catalyst Optimization, Scope, and Preliminary Mechanistic Study Supporting a Peculiar Halogen Acceleration Effect. TheJournalofOrganicChemistry, 77, 8386-8400. https://doi.org/10.1021/jo3013258
[8]
Montalbetti, C.A.G.N. and Falque, V. (2005) Amide Bond Formation and Peptide Coupling. Tetrahedron, 61, 10827-10852. https://doi.org/10.1016/j.tet.2005.08.031
[9]
Valeur, E. and Bradley, M. (2009) Amide Bond Formation: Beyond the Myth of Coupling Reagents. Chemical Society Reviews, 38, 606-631. https://doi.org/10.1039/b701677h