Synthesis and Chemical Reactivity of a 6-Me-3,2-Hydroxypyridinone Dithiazolide with Primary Amines: A route to New Hexadentate Chelators for Hard Metal(III) Ions

A hydroxypyridinone building block, bifunctionalized with thiazoline, has been prepared from orthogonally protected 2‐(3‐(benzyloxy)‐4‐(ethoxycarbonyl)‐6‐methyl‐2‐oxopyridin‐1(2H)‐yl) acetic acid. The reactivity of the dithiazolide has been explored with two primary amines, leading to the synthesis...

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Published inJournal of heterocyclic chemistry Vol. 53; no. 4; pp. 1065 - 1073
Main Authors Pailloux, Sylvie L., Nguyen, Sean, Zhou, Stephanie, Hom, Marisa E., Keyser, Michelle N., Smiles, Danil, Raymond, Kenneth N.
Format Journal Article
LanguageEnglish
Published HOBOKEN Blackwell Publishing Ltd 01.07.2016
Wiley
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RELAXIVITY MRI AGENTS
FAST WATER EXCHANGE
RELAXOMETRIC PROPERTIES
LUMINESCENCE
ALKYLATION
STABILITY
COMPLEXES
GENERATION
DERIVATIVES
BINDING
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Abstract A hydroxypyridinone building block, bifunctionalized with thiazoline, has been prepared from orthogonally protected 2‐(3‐(benzyloxy)‐4‐(ethoxycarbonyl)‐6‐methyl‐2‐oxopyridin‐1(2H)‐yl) acetic acid. The reactivity of the dithiazolide has been explored with two primary amines, leading to the synthesis and characterization of four new hexadentate ligands. Their complexes with selected hard trivalent ions pertinent to potential molecular imaging applications have been surveyed.
AbstractList A hydroxypyridinone building block, bifunctionalized with thiazoline, has been prepared from orthogonally protected 2-(3-(benzyloxy)-4-(ethoxycarbonyl)-6-methyl-2-oxopyridin-1(2H)-yl) acetic acid. The reactivity of the dithiazolide has been explored with two primary amines, leading to the synthesis and characterization of four new hexadentate ligands. Their complexes with selected hard trivalent ions pertinent to potential molecular imaging applications have been surveyed.
A hydroxypyridinone building block, bifunctionalized with thiazoline, has been prepared from orthogonally protected 2‐(3‐(benzyloxy)‐4‐(ethoxycarbonyl)‐6‐methyl‐2‐oxopyridin‐1(2 H )‐yl) acetic acid. The reactivity of the dithiazolide has been explored with two primary amines, leading to the synthesis and characterization of four new hexadentate ligands. Their complexes with selected hard trivalent ions pertinent to potential molecular imaging applications have been surveyed.
Author Smiles, Danil
Pailloux, Sylvie L.
Zhou, Stephanie
Nguyen, Sean
Keyser, Michelle N.
Hom, Marisa E.
Raymond, Kenneth N.
AuthorAffiliation a Department of Chemistry, University of California, Berkeley, California 94720-1460, Fax: 510-642-5324
AuthorAffiliation_xml – name: a Department of Chemistry, University of California, Berkeley, California 94720-1460, Fax: 510-642-5324
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  givenname: Kenneth N.
  surname: Raymond
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  email: raymond@socrates.berkeley.edu
  organization: Department of Chemistry, University of California, California, 94720-1460, USA, Berkeley
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Issue 4
Keywords RELAXIVITY MRI AGENTS
FAST WATER EXCHANGE
RELAXOMETRIC PROPERTIES
LUMINESCENCE
ALKYLATION
STABILITY
COMPLEXES
GENERATION
DERIVATIVES
BINDING
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Snippet A hydroxypyridinone building block, bifunctionalized with thiazoline, has been prepared from orthogonally protected...
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SubjectTerms Chemistry
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Title Synthesis and Chemical Reactivity of a 6-Me-3,2-Hydroxypyridinone Dithiazolide with Primary Amines: A route to New Hexadentate Chelators for Hard Metal(III) Ions
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