Potential inhibitors of nucleotide biosynthesis. 1. Nitrosoureidonucleosides. 2

Ja, Montgomery; Hj, Thomas; Rw, Brockman; Gp, Wheeler

doi:10.1021/jm00134a011

Cited by 20 publications

(20 citation statements)

References 2 publications

(2 reference statements)

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“…Diphenylphosphorylazide, previously applied in the synthesis of uridine-5′-carboxylic acid amides, resulted in low yields. 43 Therefore, we examined a series of coupling reagents based on 1-hydroxybenzotriazole, which have been described in the literature as powerful tools for amide synthesis. 44 Among these, benzotriazol-1-yl-oxy-trispyrrolidinophosphonium hexafluorophosphate (PyBOP) had been successfully applied to the preparation of adenosine-5′-carboxamides.…”

Section: Synthesesmentioning

confidence: 99%

Selective Nucleoside Triphosphate Diphosphohydrolase-2 (NTPDase2) Inhibitors: Nucleotide Mimetics Derived from Uridine-5′-carboxamide

et al. 2008

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Ecto-nucleoside triphosphate diphosphohydrolases (E-NTPDases, subtypes 1, 2, 3, 8 of NTPDases) dephosphorylate nucleoside tri-and diphosphates to the corresponding di-and monophosphates. In the present study we synthesized adenine and uracil nucleotide mimetics, in which the phosphate residues were replaced by phosphonic acid esters attached to the nucleoside at the 5′-position by amide linkers. Among the synthesized uridine derivatives, we identified the first potent and selective inhibitors of human NTPDase2. The most potent compound was 19a (PSB-6426), which was a competitive inhibitor of NTPDase2 exhibiting a K i value of 8.2 μM and selectivity versus other NTPDases. It was inactive toward uracil nucleotide-activated P2Y 2 , P2Y 4 , and P2Y 6 receptor subtypes. Compound 19a was chemically and metabolically highly stable. In contrast to the few known (unselective) NTPDase inhibitors, 19a is an uncharged molecule and may be perorally bioavailable. NTPDase2 inhibitors have potential as novel cardioprotective drugs for the treatment of stroke and for cancer therapy.

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Section: Synthesesmentioning

confidence: 99%

Selective Nucleoside Triphosphate Diphosphohydrolase-2 (NTPDase2) Inhibitors: Nucleotide Mimetics Derived from Uridine-5′-carboxamide

et al. 2008

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“…IR spectra were recorded on a Research Series FT-IR using KBr disks in the range 4000-500 cm À1 . The compounds [Pd(CH 3 )Cl-(COD)] [52], 1-(2-aminoethyl)-3-ethylurea [53] and N-(n-propyl)-2-pyridylmethanimine (PyPr) [54] were synthesised according to previously reported procedures.…”

Section: General Proceduresmentioning

confidence: 99%

Palladium complexes containing ligands with hydrogen-bonding functionalities. Reactivity and catalytic studies with CO and olefins

Owen

Burkill

Vilar

et al. 2005

Journal of Organometallic Chemistry

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“…The positioning of the nitrosourea group at either the 3‘- or 5‘-positions required a series of protection and deprotection steps. A rationale for the synthesis of the N -nitrosoureido nucleosides was their potential as active, site-directed irreversible enzyme inhibitors. , The N -methylnitrosoureido function was chosen 532 because it would be expected to have greater carbamoylating activity than the N -(chloroethyl)nitrosoureido moiety. It was thought 532 that the 3‘-deoxy-3‘- N -methylnitrosoureido nucleosides could either inhibit the nucleotide-metabolizing enzymes or be phosphorylated to the corresponding nucleotides which could act as enzyme inhibitors.…”

Section: F Nucleoside Analogsmentioning

confidence: 99%