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Synthesis of (S)-5-(1-aminoethyl)-2-(cyclohexylmethoxy)benzamide
Institution:1. EMAN Testing and Research Laboratory, Department of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia;2. Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia;3. Department of Pharmacology, School of Medical Sciences, Quest International University, Perak, Malaysia;4. Centre for Drug Research, Universiti Sains Malaysia, Penang, 11800, Malaysia;5. Institute for Research in Molecular Medicine (INFORMM), Universiti Sains Malaysia, Penang 11800, Malaysia;1. Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, Johannes Gutenberg University, Mainz 55128, Germany;2. Leipzig University, Institute of Organic Chemistry Johannisallee 29, 04103 Leipzig, Germany;1. Centre for Drug Research, Universiti Sains Malaysia, 11800, Minden, Penang, Malaysia;2. Department of Chemistry, College of Education for Women, University of Anbar, 31001, Ramadi, Anbar, Iraq;3. Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia;4. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800, Minden, Penang, Malaysia;1. School of Science and Technology, The University of New England, Armidale, NSW 2351, Australia;2. Department of Chemistry, College of Education for Pure Science, University of Anbar, Iraq;3. Discipline of Civil and Environmental Engineering, The University of New England, Armidale, NSW 2351, Australia;1. Department of Pharmaceutical Sciences, Medicinal Chemistry Section “Pietro Pratesi”, University of Milan, Via L. Mangiagalli 25, 20133, Milan, Italy;2. Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611-7200, USA;3. Department of Pharmacology and Therapeutics, University of Florida, P.O. Box 100267, Gainesville, FL 32610-0267, USA
Abstract:Three short syntheses of the title compound, a peptidomimetic for the Glu-Glu-Ile-NH2 portion of Ac-pTyr-Glu-Glu-Ile-NH2, a high affinity peptide for the Src SH2 domain, are described. The most efficient route produces the title compound in a final enantiopurity of 94% ee.
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