A Convenient New Route to Tetradentate and Pentadentate Macrocyclic Tetraamide Ligands

Rorrer, Leonard C.; Hopkins, Stephen D.; Connors, Michele K.; Lee, Daniel W.; Smith, Matthew V.; Rhodes, and Hilary J.; Uffelman, Erich S.

doi:10.1021/ol990155f

Cited by 7 publications

(2 citation statements)

References 18 publications

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“…Amidopyridine macrocycle H 2 pydioneN 5 (Scheme ) and its analogues have been prepared previously, ,, but its complexation with transition metal ions has not been studied. We found that anhydrous iron(III) chloride readily reacts with H 2 pydioneN 5 at ambient temperature in the presence of 2 equiv of triethylamine, yielding an iron(III) complex with a doubly deprotonated ligand, [Fe(pydioneN 5 )Cl(H 2 O)].…”

Section: Resultsmentioning

confidence: 99%

A New High-Spin Iron(III) Complex with a Pentadentate Macrocyclic Amidopyridine Ligand: A Change from Slow Single-Ion Paramagnetic Relaxation to Long-Range Antiferromagnetic Order in a Hydrogen-Bonded Network

et al. 2004

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A new, stable iron(III) complex with a pentadentate amide-containing macrocyclic ligand was prepared and fully characterized. The complex adopted a pentagonal-bipyramidal geometry, where an equatorial plane is occupied by the pyridine nitrogen, two deprotonated amide nitrogens, and two secondary amines from the macrocycle, and two axial positions are available for monodentate ligand (chloride anion or solvent molecule) coordination. The rigid, planar iron-amide building blocks are linked in a three-dimensional network via a system of hydrogen bonds, with the shortest Fe-Fe separation of 8.02 A. The coordination of strongly electron-donating, negatively charged deprotonated amide groups resulted in expected stabilization of a high oxidation state of iron (the redox potential of the Fe(III)L/Fe(II)L couple, -0.57 V vs SCE). In contrast to the majority of the iron complexes with polydentate amide ligands, the pentagonal-bipyramidal geometry of the macrocyclic complex described in this work affords a high-spin configuration of the central metal ion (room-temperature magnetic moment is 5.84 micro(beta)). Variable-temperature iron-57 Mössbauer spectroscopy and ac and dc magnetization studies indicate slow paramagnetic relaxation and a crossover to long-range antiferromagnetic order at T < approximately 3.2 K.

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Section: Resultsmentioning

confidence: 99%

A New High-Spin Iron(III) Complex with a Pentadentate Macrocyclic Amidopyridine Ligand: A Change from Slow Single-Ion Paramagnetic Relaxation to Long-Range Antiferromagnetic Order in a Hydrogen-Bonded Network

et al. 2004

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“…Ethyl 4-aminocinnamate ester building blocks C , D , and E were obtained by condensation of ethyl 4-aminocinnamate with amino acid chlorides 18 , themselves obtained from commercially available amino acids using the procedure of Rorrer et al, as shown in Scheme . Fragment H was prepared in a similar fashion starting from α-methylcinnamic acid 19 via sequential protection of the acid function and reduction of the nitro group to give aniline 20 .…”

Section: Chemistrymentioning

confidence: 99%

Discovery of the First Thumb Pocket 1 NS5B Polymerase Inhibitor (BILB 1941) with Demonstrated Antiviral Activity in Patients Chronically Infected with Genotype 1 Hepatitis C Virus (HCV)

et al. 2012

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Combinations of direct acting antivirals (DAAs) that have the potential to suppress emergence of resistant virus and that can be used in interferon-sparing regimens represent a preferred option for the treatment of chronic HCV infection. We have discovered allosteric (thumb pocket 1) non-nucleoside inhibitors of HCV NS5B polymerase that inhibit replication in replicon systems. Herein, we report the late-stage optimization of indole-based inhibitors, which began with the identification of a metabolic liability common to many previously reported inhibitors in this series. By use of parallel synthesis techniques, a sparse matrix of inhibitors was generated that provided a collection of inhibitors satisfying potency criteria and displaying improved in vitro ADME profiles. "Cassette" screening for oral absorption in rat provided a short list of potential development candidates. Further evaluation led to the discovery of the first thumb pocket 1 NS5B inhibitor (BILB 1941) that demonstrated antiviral activity in patients chronically infected with genotype 1 HCV.

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ChemInform Abstract: A Convenient New Route to Tetradentate and Pentadentate Macrocyclic Tetraamide Ligands.

et al. 2000

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A Convenient New Route to Tetradentate and Pentadentate Macrocyclic Tetraamide Ligands

Cited by 7 publications

References 18 publications

A New High-Spin Iron(III) Complex with a Pentadentate Macrocyclic Amidopyridine Ligand: A Change from Slow Single-Ion Paramagnetic Relaxation to Long-Range Antiferromagnetic Order in a Hydrogen-Bonded Network

A New High-Spin Iron(III) Complex with a Pentadentate Macrocyclic Amidopyridine Ligand: A Change from Slow Single-Ion Paramagnetic Relaxation to Long-Range Antiferromagnetic Order in a Hydrogen-Bonded Network

Discovery of the First Thumb Pocket 1 NS5B Polymerase Inhibitor (BILB 1941) with Demonstrated Antiviral Activity in Patients Chronically Infected with Genotype 1 Hepatitis C Virus (HCV)

ChemInform Abstract: A Convenient New Route to Tetradentate and Pentadentate Macrocyclic Tetraamide Ligands.

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