Synthesis of [thiazolium‐2,2′‐14C2]‐SAR97276A from [14C]‐thiourea

Herbert, John M.; Strat, Franck Le; Oumeddour, Delphine G.; Passey, Stephen C.; Taylor, Keith T.; Whitehead, David M.

doi:10.1002/jlcr.1816

Cited by 4 publications

(2 citation statements)

References 3 publications

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“…12,13 The other precursor, compound 7 , was synthesized with little modification of the method described in the literature. 14 Acetyl butyrolactone 5 was chlorinated at room temperature using sulfuryl chloride followed by acid-catalyzed decarboxylation to afford 6 , which was further acetylated to give 7 . Intermediate compound 9 was prepared by reacting 4 and 7 with carbon disulfide followed by acid-catalyzed dehydration.…”

Section: Methodsmentioning

confidence: 99%

“… For pyrimidine precursor 4 , O -methylisourea bisulfate and ethoxymethylene malononitrile were reacted in the presence of sodium methoxide to give 3 . Nitrile intermediate 3 was then reduced to the corresponding amine by Raney nickel-catalyzed hydrogenation in the presence of ammonia to give 4 . , The other precursor, compound 7 , was synthesized with little modification of the method described in the literature . Acetyl butyrolactone 5 was chlorinated at room temperature using sulfuryl chloride followed by acid-catalyzed decarboxylation to afford 6 , which was further acetylated to give 7 .…”

Section: Experimental Proceduresmentioning

confidence: 99%

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Competence of Thiamin Diphosphate-Dependent Enzymes with 2′-Methoxythiamin Diphosphate Derived from Bacimethrin, a Naturally Occurring Thiamin Anti-vitamin

et al. 2016

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Bacimethrin (4-amino-5-hydroxymethyl-2-methoxypyrimidine), a natural product isolated from some bacteria, has been implicated as an inhibitor of bacterial and yeast growth, as well as in inhibition of thiamin biosynthesis. Given that thiamin biosynthetic enzymes could convert bacimethrin to 2′-methoxythiamin diphosphate (MeOThDP), it is important to evaluate the effect of this coenzyme analogue on thiamin diphosphate (ThDP)-dependent enzymes. The potential functions of MeOThDP were explored on five ThDP-dependent enzymes: the human and Escherichia coli pyruvate dehydrogenase complexes (PDHc-h and PDHc-ec, respectively), the E. coli 1-deoxy-d-xylulose 5-phosphate synthase (DXPS), and the human and E. coli 2-oxoglutarate dehydrogenase complexes (OGDHc-h and OGDHc-ec, respectively). Using several mechanistic tools (fluorescence, circular dichroism, kinetics, and mass spectrometry), it was demonstrated that MeOThDP binds in the active centers of ThDP-dependent enzymes, however, with a binding mode different from that of ThDP. While modest activities resulted from addition of MeOThDP to E. coli PDHc (6–11%) and DXPS (9–14%), suggesting that MeOThDP-derived covalent intermediates are converted to the corresponding products (albeit with rates slower than that with ThDP), remarkably strong activity (up to 75%) resulted upon addition of the coenzyme analogue to PDHc-h. With PDHc-ec and PDHc-h, the coenzyme analogue could support all reactions, including communication between components in the complex. No functional substitution of MeOThDP for ThDP was in evidence with either OGDH-h or OGDH-ec, shown to be due to tight binding of ThDP.

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Section: Methodsmentioning

confidence: 99%

Section: Experimental Proceduresmentioning

confidence: 99%

Competence of Thiamin Diphosphate-Dependent Enzymes with 2′-Methoxythiamin Diphosphate Derived from Bacimethrin, a Naturally Occurring Thiamin Anti-vitamin

et al. 2016

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Nanoparticles and Phage Display Selected Peptides for Imaging and Therapy of Cancer

Cutler

Chanda

Shukla

et al. 2012

Recent Results in Cancer Research

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Molecular imaging probes are a special class of pharmaceuticals that target specific biochemical signatures associated with disease and allow for noninvasive imaging on the molecular level. Because changes in biochemistry occur before diseases reach an advanced stage, molecular imaging probes make it possible to locate and stage disease, track the effectiveness of drugs, treat disease, monitor response, and select patients to allow for more personalized diagnosis and treatment of disease. Targeting agents radiolabeled with positron emitters are of interest due to their ability to quantitatively measure biodistribution and receptor expression to allow for optimal dose determinations. (68)Ga is a positron emitter, which allows for quantitative imaging through positron emission chromatography (PET). The availability of (68)Ga from a generator and its ability to form stable complexes with a variety of chelates hold promise for expanding PET utilization to facilities unable to afford their own cyclotron. Nanoparticles conjugated with various proteins and peptides derived from phage display that can be selectively targeted are being developed and evaluated for guided imaging and therapy. Herein we highlight some initial efforts in combining the enhanced selectivity of nanoparticles and peptides with (68)Ga for use as molecular imaging probes.

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Prostate tumor therapy advances in nuclear medicine: green nanotechnology toward the design of tumor specific radioactive gold nanoparticles

Katti

Khoobchandani

Thipe

et al. 2018

J Radioanal Nucl Chem

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Synthesis of [thiazolium‐2,2′‐¹⁴C₂]‐SAR97276A from [¹⁴C]‐thiourea

Cited by 4 publications

References 3 publications

Competence of Thiamin Diphosphate-Dependent Enzymes with 2′-Methoxythiamin Diphosphate Derived from Bacimethrin, a Naturally Occurring Thiamin Anti-vitamin

Competence of Thiamin Diphosphate-Dependent Enzymes with 2′-Methoxythiamin Diphosphate Derived from Bacimethrin, a Naturally Occurring Thiamin Anti-vitamin

Nanoparticles and Phage Display Selected Peptides for Imaging and Therapy of Cancer

Prostate tumor therapy advances in nuclear medicine: green nanotechnology toward the design of tumor specific radioactive gold nanoparticles

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