Arene Chromium and Manganese Tricarbonyl Analogs of the PCP Receptor Ligands 5-Methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (MK-801) and 10,5-(Iminomethano)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (IDDC)

• Published in: Journal of organic chemistry Vol. 59; no. 6; pp. 1492 - 1498
• Main Authors: Gee, Kyle R, Lu, Yixin, Barmettler, Peter, Rhodes, Michael R, Reddy, N. Laxma, Fischer, James B, Cotter, Ronald E, Weber, Eckard, Keana, John F. W
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.03.1994; Amer Chemical Soc
• Subjects: Carbonyl and nitrosyl metals; Chemistry; Chemistry, Organic; Exact sciences and technology; Inorganic chemistry and origins of life; Physical Sciences; Preparations and properties; Science & Technology; NEUROTRANSMISSION; ANTAGONIST; Iron Organic compounds; Nitrogen heterocycle; Chromium Carbonyl Complexes; Manganese Carbonyl Complexes; Organic ligand; Reaction mechanism; Transition metal Carbonyl Complexes; Tetracyclic compound; Exchange reaction; Metallocene
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo00085a042

Chromium tricarbonyl complexes of MK-801 (2), IDDC (4), and 3-Cl-IDDC (10) were prepared by arene exchange with benzenechromium tricarbonyl. The resulting complexes retained binding affinity for the PCP receptor, as reflected by IC50 values relative to [H-3]-2. A manganese tricarbonyl analog 28 of 4 was synthesized in which the D ring of 4 was replaced with cyclopentadienylmanganese tricarbonyl. However, 28 showed significantly diminished binding affinity for the PCP receptor, relative to 4. Attempts to prepare a ferrocene analog of 4 in which the A or D rings were replaced with ferrocene failed, due to a very stable carbocation formed in the last step of the synthetic route; the novel alcohols 25 and 29 were formed instead.