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Bonjoch J.,Laboratori Of Quimica Organica | Diaba F.,Laboratori Of Quimica Organica | Bradshaw B.,Laboratori Of Quimica Organica
Synthesis | Year: 2011

This review highlights advances in the synthesis of morphan compounds from 1980 to the present day. 1 Introduction 2 Synthetic Approaches from Carbocyclic Compounds 2.1 Aminocyclization Processes Forming the C(1)-N Bond 2.1.1 From Amino Alkenes 2.1.2 From Amino Ketones 2.1.3 By Amine Alkylation 2.1.4 By Amino Conjugate Addition upon Enones 2.2 Aminocyclization Processes Forming the N-C(3) Bond 2.3 Cyclization Processes Forming the C(3)-C(4) Bond 2.4 Cyclization Processes Forming the C(4)-C(5) Bond 2.4.1 Aldol Reactions 2.4.2 Piperidine Ring Closure by a Heck Reaction 2.4.3 Alkenylation of Enolates 2.4.4 Radical Cyclizations 2.4.5 Miscellaneous Approaches 3 Synthetic Approaches from Piperidine Derivatives 3.1 Cyclization upon Iminium Ions Forming the C(1)-C(8) Bond 3.2 Cyclization Processes Forming the C(5)-C(6) Bond 3.3 Cyclization Processes Forming the C(6)-C(7) Bond 4 Cascade Processes 5 Rearrangements 6 Synthesis of 5-Phenylmorphans 7 Conclusions. © Georg Thieme Verlag Stuttgart.

Albert J.,University of Barcelona | Garcia S.,University of Barcelona | Granell J.,University of Barcelona | Llorca A.,University of Barcelona | And 10 more authors.
Journal of Organometallic Chemistry | Year: 2013

Treatment of benzophenone imine with the stoichiometric amount of Pd(OAc)2 in acetic acid at 60 °C produced the corresponding acetato-bridged five-membered ortho-cyclopalladated dimer [Pd{C 6H4CPhNH}(μ-OAc)]2 (1), which was isolated in pure form in a 79% yield. Reaction of 1 with an excess of LiCl in acetone gave rise to the corresponding chlorido-bridged cyclopalladated dimer [Pd{C 6H4CPhNH}(μ-Cl)]2 (2) in a 78% yield. Compounds 1-2 reacted with an excess of py-d5 or the stoichiometric amount of PPh3 to give the mononuclear compounds trans-N,L-[Pd{C 6H4CPhNH}(X)(L)] [3 (X = OAc, L = py-d5); 4 (X = Cl, L = py-d5); 5 (X = OAc, L = PPh3) and 6 (X = Cl, L = PPh3)]. Compounds 2-3 were prepared in CDCl3/py-d 5 solution and were studied by 1H NMR, but were not isolated. In contrast, compounds 5-6 were prepared in acetone and were isolated in pure form in 43 and 79% yields, respectively. Compounds 1, 2, 5 and 6 were characterized by elemental analyses, mass spectrometry, IR, NMR and electronic spectroscopy. Compounds 1, 2, 5 and 6 showed high antiproliferative activity against MDA-MB231 and MCF7 human breast cancer cell lines, especially, compounds 5-6. These two latter compounds presented greater antiproliferative activity than cisplatin and produced IC50 values in the range 1-5 μM. The interaction of compounds 1, 2, 5 and 6 with DNA was also studied by the DNA electrophoretic migration, DNA-ethidium bromide fluorescence quenching and viscometry techniques. © 2012 Elsevier B.V. All rights reserved.

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