Discovery of a New Class of Polycyclic RSV Inhibitors

Bond, S; Draffan, Alistair G.; Lambert, John; Lim, Chae-Man; Lin, Bin; Luttick, Angela; Mitchell, James; Morton, Catherine; Nearn, Roland H.; Sanford, V

doi:10.1016/j.antiviral.2007.01.017

Cited by 5 publications

(3 citation statements)

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“…anticipated to be important in the drug discovery regimen. [34] We deduced from the above results that an intramolecular displacement of the hydroxyl group in 15 with a primary amine will provide easy access to 16 (Scheme 5). Initially, we attempted condensation of phthalic anhydride 12 with one equivalent of 1,2-diaminoethane thinking that the reaction will lead to the corresponding phthalimide with 2-aminoethane substitution on N(2).…”

Section: Chemistryselectmentioning

confidence: 96%

Facile and High‐Yielding Synthesis of C(3)‐Aminoisoindolinones Under Metal Catalyst‐Free Conditions

2022

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C(3)-Aminoisoindolinones have attracted the attention of medicinal chemists due to their unique and stable NÀ CÀ N substructure and possibilities for facile and scalable synthesis of combinatorial libraries. We discovered that para-toluenesulfonic acid (PTSA), an organic protic acid, efficiently catalyzes condensation of isoindolinone-3-ols with primary and secondary amines to furnish C(3) N-substituted isoindolinones in high yields. The NÀ C bond formation reaction is highly efficient and experimentally simple. The method replaces known transition metal catalysts involving Cu, Pt, Pd or Au. It works efficiently for both intra-and inter-molecular variants. Furthermore, it is amenable for synthesis of C(3)-aminoisoindolinones with free N(2) via photolytic deprotection of the 2-nitrobenzyl group. We have demonstrated application of the method for synthesis of a variety of medicinally relevant bicyclic and tricyclic C(3)-aminoisoindolinones.

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Section: Chemistryselectmentioning

confidence: 96%

Facile and High‐Yielding Synthesis of C(3)‐Aminoisoindolinones Under Metal Catalyst‐Free Conditions

2022

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“…Fluorescent compositions based on isoindolobenzimidazolone are described in the patent [132]. Additional data on the biological activity can be found in [133][134][135][136][137].…”

Section: Addendummentioning

confidence: 99%

11H-isoindolo[2,1-a]benzimidazoles (Review)

Lyaskovskyy

Voitenko

Ковтуненко

2007

Chem Heterocycl Compd

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“…BTA9881, was selected as a clinical candidate. The compound is orally bioavailable and has been shown to demonstrate favorable pharmacokinetics in phase I clinical trials (Bond, 2007). However, the clinical development of BTA9881 was stopped because the compound failed to develop an acceptable safety profile.…”

Section: Entry Inhibitorsmentioning

confidence: 99%