Literature DB >> 18181639

Cyclopropanecarboxylic acid esters as potential prodrugs with enhanced hydrolytic stability.

David M Bender1, Jeffrey A Peterson, James R McCarthy, Hakan Gunaydin, Yu Takano, K N Houk.   

Abstract

Esters of cyclopropanecarboxylic acid demonstrate a substantial increase in stability under both acid- and base-catalyzed hydrolytic conditions. Comparison of the stability of valacyclovir 13 with the cyclopropane analogue 14 shows that at 40 degrees C and pH 6 the half-life of 14 is >300 h while the value for 13 is 69.7 h. CBS-QB3 calculations on isodesmic reactions for transfer of groups from an alkane to an ester show that a cyclopropyl group provides hyperconjugative stabilization.

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Year:  2008        PMID： 18181639     DOI： 10.1021/ol702892e

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Selective esterase-ester pair for targeting small molecules with cellular specificity.

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2.  Design and synthesis of neuroprotective methylthiazoles and modification as NO-chimeras for neurodegenerative therapy.

Authors:  Zhihui Qin; Jia Luo; Lawren VandeVrede; Ehsan Tavassoli; Mauro Fa'; Andrew F Teich; Ottavio Arancio; Gregory R J Thatcher
Journal:  J Med Chem       Date:  2012-07-24       Impact factor: 7.446

3.  Univalent and bivalent ligands of butorphan: characteristics of the linking chain determine the affinity and potency of such opioid ligands.

Authors:  Michael Decker; Brian S Fulton; Bin Zhang; Brian I Knapp; Jean M Bidlack; John L Neumeyer
Journal:  J Med Chem       Date:  2009-12-10       Impact factor: 7.446

4.  Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging.

Authors:  Wen Chyan; Henry R Kilgore; Brian Gold; Ronald T Raines
Journal:  J Org Chem       Date:  2017-04-11       Impact factor: 4.354

5.  Increasing oral absorption of polar neuraminidase inhibitors: a prodrug transporter approach applied to oseltamivir analogue.

Authors:  Deepak Gupta; Sheeba Varghese Gupta; Arik Dahan; Yasuhiro Tsume; John Hilfinger; Kyung-Dall Lee; Gordon L Amidon
Journal:  Mol Pharm       Date:  2013-01-04       Impact factor: 4.939

6.  Ester-prodrugs of ethambutol control its antibacterial activity and provide rapid screening for mycobacterial hydrolase activity.

Authors:  Erik M Larsen; Dominique C Stephens; Nathan H Clarke; R Jeremy Johnson
Journal:  Bioorg Med Chem Lett       Date:  2017-08-30       Impact factor: 2.823

7.  Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system.

Authors:  J Pedroni; T Saget; P A Donets; N Cramer
Journal:  Chem Sci       Date:  2015-06-17       Impact factor: 9.825

8.  MOG analogues to explore the MCT2 pharmacophore, α-ketoglutarate biology and cellular effects of N-oxalylglycine.

Authors:  Natalie Bevan; Patrícia M Nunes; Louise Fets; Sebastien Campos; Mariana Silva Dos Santos; Emma Sherriff; James I MacRae; David House; Dimitrios Anastasiou
Journal:  Commun Biol       Date:  2022-08-26
  8 in total

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