Iodocyclisation of N-allyl ureas; a route to imidazolin-2-ones

Moody, Christopher J.; Hunt, Peter; Smith, C.W.

doi:10.3998/ark.5550190.0001.504

Cited by 4 publications

(1 citation statement)

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“…Thus, silver fluoride, which usually converts iodo to fluoro, instead gave rise to the hydroxy group in good yield. Iodo to hydroxy conversion has previously been reported using AgNO 3 or F 3 CCO 2 Ag on other small molecules. , Here, we report the use of AgF for this same conversion. This transformation provided a robust method for generation of 12 , which was previously generated in very low yield by treatment of 6 with NaOH .…”

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confidence: 60%

Leaving Groups Prolong the Duration of 20S Proteasome Inhibition and Enhance the Potency of Salinosporamides

et al. 2008

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Salinosporamide A ( 1 (NPI-0052)) is a potent, monochlorinated 20S proteasome inhibitor in clinical trials for the treatment of cancer. To elucidate the role of the chlorine leaving group (LG), we synthesized analogues with a range of LG potentials and determined their IC 50 values for inhibition of chymotrypsin-like (CT-L), trypsin-like (T-L), and caspase-like (C-L) activities of 20S proteasomes. Proteasome activity was also determined before and after attempted removal of the inhibitors by dialysis. Analogues bearing substituents with good LG potential exhibited the greatest potency and prolonged duration of proteasome inhibition, with no recovery after 24 h of dialysis. In contrast, activity was restored after

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Section: Resultssupporting

confidence: 60%

Leaving Groups Prolong the Duration of 20S Proteasome Inhibition and Enhance the Potency of Salinosporamides

et al. 2008

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An alternate route to the synthesis of imidazo[1,2‐a]quinolines using I₂‐NaI reagent

Upadhyay

Chandra

Singh

et al. 2011

Journal of Heterocyclic Chem

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Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

Antonova

Баранов

Кравченко

2015

Chem Heterocycl Comp

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Iodocyclisation of N-allyl ureas; a route to imidazolin-2-ones

Abstract: Dedicated to Professor AbstractTreatment of N-allyl ureas 7-9 with TMS triflate, followed by iodine in THF resulted in iodocyclisation to give the imidazolin-2-ones 10-12 in good yield.

Cited by 4 publications

References 6 publications

Leaving Groups Prolong the Duration of 20S Proteasome Inhibition and Enhance the Potency of Salinosporamides

Leaving Groups Prolong the Duration of 20S Proteasome Inhibition and Enhance the Potency of Salinosporamides

An alternate route to the synthesis of imidazo[1,2‐a]quinolines using I₂‐NaI reagent

Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

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Iodocyclisation of N-allyl ureas; a route to imidazolin-2-ones

Abstract: Dedicated to Professor AbstractTreatment of N-allyl ureas 7-9 with TMS triflate, followed by iodine in THF resulted in iodocyclisation to give the imidazolin-2-ones 10-12 in good yield.

Cited by 4 publications

References 6 publications

Leaving Groups Prolong the Duration of 20S Proteasome Inhibition and Enhance the Potency of Salinosporamides

Leaving Groups Prolong the Duration of 20S Proteasome Inhibition and Enhance the Potency of Salinosporamides

An alternate route to the synthesis of imidazo[1,2‐a]quinolines using I2‐NaI reagent

Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones

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An alternate route to the synthesis of imidazo[1,2‐a]quinolines using I₂‐NaI reagent